• Camden, ME

Camden is the quintessential New England town, so picturesque that it has literally been the poster child for the region in movies such as “Carousel” and “Peyton Place.” Stroll through the historic downtown to see why—with its tall church steeples and 19th-century architecture, Camden oozes historical charm. Plus, it offers plenty to do. Take a classic sail around the harbor, fish off the coast, or spend time sightseeing at the town’s classic lighthouse or signature seal statue.

• Lola 41 - Nantucket

This buzzy sushi restaurant only takes same-day reservations, so call right at 4 p.m. or pay them a visit in person to secure a table or a spot at the sushi bar. It’s decidedly trendy by Nantucket standards, but the sushi is out of this world.

• Cru - Nantucket

One of my favorite lobster rolls on the island comes from this exquisitely decorated oyster bar on Straight Wharf. Make reservations well in advance or be prepared to wait with a glass (or two) of rosé on their outdoor patio or at the bar in the front room. It’s definitely a splurge for lunch or dinner, but the chic nautical interior and waterfront views are worth every penny.

• Toppers - Nantucket
• BOARDING HOUSE - Nantucket

I love a lively group dinner outside on the Boarding House patio. Located in the heart of downtown on the corner of Federal and India Street, it’s a perfect spot for people-watching and a plate of their lobster spaghetti.

• BRANT POINT GRILL - Nantucket

If you’re looking for an Instagram opportunity alongside your meal, head to this restaurant located outside the White Elephant for its sweeping views of Nantucket Harbor. Don’t leave without trying a bite of their famous lobster mac and cheese.

• BROTHERHOOD OF THIEVES - Nantucket

A casual, family-friendly spot for burgers and lobster rolls. The downstairs interior has the feel of an old whaling bar and is a cozy spot to sit by the fire on a rainy night, but if it’s warm out we always ask to sit in the outdoor patio to the left of the main entrance. It’s a no-frills hangout where no one will rush you out of your seats, plus it’s a two-minute walk down the street to cult favorite Juice Bar for ice cream.

• THE CHANTICLEER - Nantucket

An insanely charming little bistro where Will and I had our rehearsal dinner (and where my parents had theirs 31 years before us!). If you’re looking for a romantic spot outside the hustle and bustle of town, head to ‘Sconset for a splurge-worthy meal in The Chanticleer’s rose garden. The chapel where we were married is just across the street!

• CLUB CAR - Nantucket

This Nantucket classic has been given a light and bright new look and is a centrally located spot for a last-minute reservation in town. Come with friends and order a variety of small plates for the table, then stay for a rowdy evening gathered around the piano in front.

• GALLEY BEACH - Nantucket

If you’re willing to overlook the $25 cocktails and mediocre service in favor of the island’s best sunset, Galley Beach is a must for pre-dinner cocktails with your toes in the sand. Make dinner reservations in advance or scope out a firepit a couple hours before sunset. Call ahead on weekends to make sure it’s not closed for a wedding or rehearsal dinner.

• GREYDON HOUSE - Nantucket

A newcomer to the downtown restaurant scene and one we love for a leisurely weekend brunch or group dinner. The decor is as stunning as the exterior and the cocktails served in copper pineapples have Instagram app written all over them.

• MILLIE'S - Nantucket

If you’re looking for casual Baja fare like fish tacos and lobster quesadillas, Millie’s is the place. Make it a beach day in Madaket with snacks from Millie’s Market or kid-friendly fare from the takeout window, or take an Uber out in time to enjoy the killer sunset with an infamous Madaket Mystery in hand. I may be biased as my cousins and siblings worked here for many summers, but it’s the perfect spot when you’re ready for a break from fancier dining options in town. They also have a food truck parked at Cisco Brewers!

• PROPRIETORS - Nantucket

An eclectic spot in town that’s a favorite for dinner with girlfriends. Order a bottle of rosé and a variety of shareable plates – and don’t leave without trying the fried broccoli!

• THE SUMMER HOUSE - Nantucket

Go for lunch downstairs at the Beachside Bistro (where we had our wedding reception!) or make dinner reservations at the main restaurant up top and stay for cocktails in the piano bar (where we had our after party!).

• VENTUNO - Nantucket

Hands down the best Italian food on the island and lovely service to boot. Enjoy a cocktail in the “back bar” (outdoor patio) or the wine bar upstairs. We love the ricotta and honey crostini to start, and you can’t go wrong with any of the pastas.

• BLACK-EYED SUSAN'S - Nantucket

A Nantucket institution with a wait time to match. Get here early for the best pancakes you’ll ever have. Cash only!

• DOWNYFLAKE - Nantucket

The best mornings start with a donut run to Downyflake. Located near the mid-island Stop & Shop, the diner has a family-friendly retro vibe, but we usually pick up a box of cinnamon sugar donuts and enjoy them at home. Cash only!

• ISLAND KITCHEN - Nantucket

We love eating outside at Island Kitchen, which always seems to accommodate our large group. You can’t go wrong with the avocado toast, breakfast burrito, or eggs Benedict.

• LEMON PRESS - Nantucket

Now located on Main Street, Lemon Press is a go-to for acai bowls, avocado toast, breakfast sandwiches, and smoothies.

• MET ON MAIN - Nantucket

My favorite brunch spot in town, both for the food and the decor. You have to get an order of buttermilk biscuits with honey-maple butter – I literally dream about them in the winter. And is it weird to say go check out the wallpaper in the bathroom? It’s my favorite.

• 45 SURFSIDE - Nantucket

A pretty bakery and café with ample indoor and outdoor seating. A go-to spot for grabbing an iced coffee and a croissant en route to Surfside Beach.

• ESPRESSO TO GO - Nantucket

A local favorite, Espresso To Go has a location on Old South Road and a sister location called Fast Forward on Orange Street in town. We love walking the dogs here and enjoying our coffee underneath their bright yellow umbrellas.

• HANDLEBAR CAFÉ - Nantucket

If you’re looking for a barista who really knows his stuff, this is the place for you. The service is delightful, there’s a water bowl out front for pups, and the back garden is a hidden treasure.

• ISLAND COFFEE - Nantucket

Steps off of the Steamship Authority ferry is this tiny coffee counter on Broad Street. It’s been known to save me when I’m racing to catch an early boat, but I’ll make a detour anytime for their out-of-this-world corn muffins.

• 'SCONSET MARKET - Nantucket

This isn’t so much a coffee shop as the only bakery and grocery store on this side of the island, but they happen to serve my favorite iced coffee on the island. My entire life I’ve insisted on sneaking out of church a few minutes early to get in line for their blueberry muffins, which are the most divine sugar-filled confections in the entire world and sell out like clockwork every weekend morning. We may or may not have placed an order for two dozen the morning of our wedding!

• BARTLETT'S FARM - Nantucket

A family-run farm near Cisco Brewers with a market filled with beach picnic fare. Their legendary tomatoes pop up on menus all over the island. They also have a darling flower and produce truck on Main Street every morning!

• OATH PIZZA - Nantucket

A create-your-own-pizza counter located on Straight Wharf next to the Hyline ferry dock. The line is always out the door but I swear the pizza is worth the wait! The outdoor seating on the water makes for a very affordable meal with a view.

• PROVISIONS - Nantucket

A beloved sandwich shop on Straight Wharf famous for its Thanksgiving-inspired Turkey Terrific.

• SOMETHING NATURAL - Nantucket

A sandwich shop on Cliff Road with grab-and-go food for the beach or outdoor picnic tables for a casual outdoor lunch. Don’t miss their homemade chocolate chip cookies!

• SUSHI BY YOSHI - Nantucket

We love ordering sushi from this little spot in town and driving out to eat on the beach at Brant Point Lighthouse.

• BRANT POINT LIGHTHOUSE - Nantucket

The closest lighthouse to town and a great spot to catch both sunrise and sunset. Grab an ice cream cone from Juice Bar and walk down to the lighthouse to dip your toes in the water and wave to passing ferries.

• CISCO BREWERS - Nantucket

A brewery, distillery, and winery with three separate bars for each. With several food trucks, live music, and puppies everywhere, it’s easy to spend the whole day.

• GREAT POINT LIGHTHOUSE - Nantucket

Rent a Jeep with an oversand vehicle permit, stop to let air out of the tires, and make the nearly two-hour drive out to Great Point. We drove out for the sunrise and had the place to ourselves!

• JUICE BAR - Nantucket

The best ice cream on Nantucket and quite possibly anywhere. The line often stretches around the block, but the smell of homemade waffle cones is always enough to keep me waiting. I’ve ordered the cookie dough for at least twenty years now and it’s never once disappointed!

• RENT BIKES OR VESPAS - Nantucket

Head to Nantucket Bike Shop on Broad Street and rent a bike or Vespa for the day. The island has incredible bike paths leading out of town to Surfside Beach and all the way to ‘Sconset, but it’s also fun to rent a Vespa and cruise over the cobblestones more comfortably.

• SAILING ON THE ENDEAVOR - Nantucket

We love this sailboat charter so much we took some of our engagement pictures on it! Book a spot on one of the four daily departures or rent out the boat for a 90-minute private charter with family and friends. Bring your own food and beverages and say hi to Captain Jim for us!

• SANKATY LIGHTHOUSE - Nantucket

At the end of Baxter Road where my family’s original home was sits our favorite lighthouse on the island. We took our engagement and wedding pictures here and had my parents recreate theirs from 31 years prior!

• 'SCONSET BLUFF WALK - Nantucket

An only-on-Nantucket experience, the ‘Sconset Bluff Walk is a public walking path that takes you from the village of Siasconset almost all the way out to Sankaty Lighthouse through the backyards of some of the island’s most exquisite homes. To get to the start of the walk, turn right after 21 Front Street and make a quick left.

• WHALING MUSEUM - Nantucket

If you get stuck with a rainy day during your visit, spend an afternoon at the Whaling Museum in town to learn about the history of Nantucket. Bonus: you’ll be just across the street from an ice cream cone at Juice Bar!

• 28 CENTRE POINTE - Nantucket

If I could decorate my home from just one boutique on the island, this would be it. You’ll find gorgeous furnishings, decorative items, and hostess gifts by the likes of Amanda Lindroth, Kate Spade, and Oomph – so consider this a warning that you’ll want to buy (or at least Instagram) one of everything.

• CJ LAING - Nantucket

CJ has a primary location in town and a tiny boutique out in ‘Sconset, both of which carry an assortment of preppy-meets-bohemian clothing and accessories. Think Rebecca de Ravenel bon-bons, straw tote bags, and striped maxi dresses set against grasscloth walls and white floors… yes please.

• FLOWERS ON CHESTNUT - Nantucket

I worked three days a week at Flowers on Chestnut and three days a week at Ralph Lauren the summer I turned sixteen, so this flower shop always brings back fond memories of one of my favorite childhood summers. Their fresh flower assortment is unparalleled, while the gift shop upstairs carries pretty candles, coffee table books, and throw pillows.

• IN THE PINK - Nantucket

My cousin worked in this store for six or seven summers and I can’t walk inside without thinking of our first jobs on the island! This Lilly Pulitzer signature store is located at the bottom of Main Street and is always a colorful oasis on an overcast day.

• LION'S PAW - Nantucket

A dreamy decor spot on Main Street with beautiful artwork, home furnishings, and hostess gifts.

• MILLY & GRACE - Nantucket

A girly boutique just off Main Street where you’ll find clothing, accessories, home decor, and quite possibly the friendliest sales associates on the island. The owner’s sister Caroline planned our wedding – be sure to check out Milly & Grace Weddings if you’re a Nantucket bride-to-be!

• PETER BEATON HAT STUDIO - Nantucket

My Grandy’s signature hat is the ‘Sconset Stroller and she buys a new one every summer or two in this tiny studio attached to the owner’s home in town. If you’re willing to splurge on a stylish souvenir, pick out your hat, customize it with a wide assortment of grosgrain ribbons, and carry it out in one of their instantly recognizable black and white striped hat boxes. I also dream about the day I can dress my future children in their monogrammed swimsuits and rainboots!

• RALPH LAUREN - Nantucket

One of a small handful of brand names on the island and one that feels right at home on Main Street. I always stop to admire the elaborate window displays, which are always decked out for holiday weekends.

• SKINNY DIP - Nantucket

A collective concept store on Old South Wharf that features brands including ACK v. Hamps artwork, Harding Lane needlepoint accessories, and Solid & Striped swimwear.

• SOUTHERN TIDE - Nantucket

This preppy Southern brand has made its way to New England and into its own storefront on Main Street. It’s a go-to of mine for dressing the men in my life, but I’ve found several cute things for myself as well!

• VINEYARD VINES - Nantucket

Named after nearby Martha’s Vineyard, Vineyard Vines has a new home on Straight Wharf with preppy clothes and accessories for men, women, and children.

• Castello Di Borghese - Cutchogue, NY

Soak up the history at Castello Di Borghese, the oldest Bordeaux vineyard on the North Fork of Long Island. The 100-acre farm is well known for its expansive collection of Bordeaux and gives history tours at the vineyard for guests to learn about the area and its rich past. The winery also draws a huge art crowd with a gallery in the tasting room that offers regular art shows featuring local artists.

• Channing Daughters - Bridgehampton, NY

Tucked away in the picturesque East End in Bridgehampton, Channing Daughters is well known for having a wide array of whites, rosé, reds, orange or skin contact, pet nat and sparkling wine. The vineyard also features a sculpture garden that draws guests to roam through the vineyard and enjoy Walter Channing’s artwork, including a massive 40-foot rocket.

• Wölffer Estate - Sagaponack, NY

Established in 1987, Christian Wölffer started Wölffer Estates as a small operation; today that little dream has turned into the largest vineyard in the heart of the Hamptons. Wölffer has an expansive collection of delicious rosés, and has created a pink gin using their famed rosé as the gin base. The winery also has an outstanding summer program, including events like yoga in the vines, music, and special wine-paired chef dinners at the estate.

• Island Coffee Roasters - Nantucket, MA
• Provisions - Nantucket, MA
• Skinny Dip - Nantucket, MA
• Walk around and shop at the south wharf - Nantucket, MA
• Downtown - Nantucket, MA

-Murray’s Toggery Shop and Nantucket Looms on Main Street -Isobel and Cleo and Toujours Midi on Centre Street -Nantucket Bookworks on Broad Street

• Grab a milkshake at the old-school Nantucket Pharmacy on Main before resting up at the hotel - Nantucket, MA
• Jetties Beach and Steps Beach - Nantucket, MA

A quick bike ride from town (you can rent bikes from several shops close to he hotel).

• Galley Beach - Nantucket, MA

A classic Nantucket waterfront restaurant. Sit outside on the wooden deck overlooking the boats coming into the harbor while sipping a cold glass of rosé. Enjoy local fare like pernod-scented escargot with melted leeks, tomato garlic-butter, and pimenton pastry; and truffle-butter-poached two-pound lobster with local corn from Nantucket’s own Bartlett’s Farm.

• Black Eyed Susan’s - Nantucket, MA
• Cisco Beach - Nantucket, MA
• Bartlett's Farm - Nantucket, MA
• Cisco Brewers - Nantucket, MA

Nantucket’s finest craft beer (they also make wine, cider, and various liquors). The brewery is very dog-friendly, and there is usually a raw bar (167 Raw) and a couple food trucks—we like the overstuffed lobster roll from Millie’s.

• Sayle's - Nantucket, MA

Order the fried bay scallops and a cup of clam chowder and eat out on the deck (or down on the harbor beach) while watching the boats bob up and down at their moorings.

• Straight Wharf - Nantucket, MA
• Petticoat Bakery - Nantucket, MA

The best spinach and cheese croissant you'll ever eat, and a refreshing iced coffee

• Siasconset - Nantucket, MA

Head east out of town, toward the rotary and down Milestone road. Take in the sights—windswept trees, lighthouses in the distance, stretches of pristine golf courses. Your first stop: Siasconset (referred to as Sconset by most). This historic little village is its own designated town on the island, and is known for its distinct, hydrangea-clad white homes on the steep cliffs overlooking the ocean. When you arrive, check out Sconset Market and pop into Claudette’s for a sandwich—you can't go wrong with the meatloaf. After you’ve had your fill of exploring the narrow streets and the beach, make your way to the edge of Sconset to look at Sankaty Head Light, the iconic red and white lighthouse on the eastern edge of the island.

• Explore the east side - Nantucket, MA

Next, head down Poplis Road, past elegant homes with widow walks and lazy dirt roads that lead to the waterfront. If you're traveling with little ones, Quidnet Beach is a good stop to make—more often than not, it's very quiet, not busy, and an ideal beach combing spot. Spend an hour or so soaking up the sun, walking the shoreline, and perhaps spotting some seals. This beach is conveniently located right next to Sesachaha pond, which is a perfect swimming hole for little ones. (There is a small parking lot here, but parking along the road is perfectly acceptable, too.) Take the afternoon to explore the island by car or hole up on the shore. If you're looking for places that are great swimming spots and more likely to have a crowd, check out Surfside, Nobadeer, or Fisherman's beaches. Just before the sun goes down, drive west out to Madaket beach for a sunset walk.

• The Nautilus - Nantucket, MA

(make sure you call ahead for a reservation, especially on weekends). Some must-try small plates: to start, order the tuna poke, and for sharing, ask for the Peking duck feast, which serves up to four people.

• Club Car - Nantucket, MA
• Do a lobster bake - Maine
• Try clear clam chowder, clam cakes, and Narragansett beer - RI
• Art Cliff Diner (Vineyard Haven)

For a much better-than-average diner breakfast, check out Art Cliff, a family-friendly restaurant that can get very crowded on weekend mornings. Get there early to snag a seat and some delicious pancakes and waffles.

• Rosewater Market & Takeaway (Edgartown)

I love this little market and café for breakfast and lunch. It’s easy to order and take food to go or eat there, the food is good, the coffee and tea drinks are great, and they have a cute home shop too. Go for the breakfast jammie or the breakfast bowl.

• Mocha Mott’s (Vineyard Haven & Oak Bluffs)

Not much to say about this locals-favorite besides that it’s a classic coffee shop that always delivers a solid dose of caffeine when you need it.

• Espresso Love (Edgartown)

Despite what the name tells you, Espresso Love is more than just a coffee shop. It serves great breakfast sandwiches and bowls along with all the regular coffee shop favorites you (espresso) love.

• Backdoor Donuts (Oak Bluffs)

The donuts are excellent and if you don’t get an apple fritter from Backdoor, you aren’t living. The not-so-secret secret behind this local-favorite is that they sell hot and fresh donuts for the night crowd from, you guessed it, the back door until 1 am. That’s when you really want to get one!

• Black Dog Tavern (Vineyard Haven)

The Black Dog is a tourist hot-spot but my dad loves going there for the tradition of it, so we always go for at least one breakfast. The pancakes are incredible!

• State Road (West Tisbury)

We used to go here for dinner but found the service to be not-so-great so we started going for brunch and have had better luck. Our family-favorite is the Limpopo pastry which is basically just a giant sugar-coated donut hole but even better.

• Scottish Bakehouse (Vineyard Haven)

This dog and kid-friendly coffee shop and bakehouse have a big lawn and picnic tables to eat on. It’s not fancy but the food is really good, especially the pastries.

• Rosewater Market & Takeaway (Edgartown)

For lunch here, I like any of the prepared food (great kale salads) and the Italian sub. They have a big selection of healthy-ish beach snacks too.

• The Net Result (Vineyard Haven)

It’s half fish market and half takeout but they make great lobster rolls, stuffies, mussels, crabcakes, and even sushi.

• Waterside Market (Vineyard Haven)

Another great sandwich spot right in the center of Vineyard Haven. We usually grab their sandwiches and to-go salads for our ferry home if we’re traveling out of VH. They have a good kids menu and outside seating which makes it a great kid-friendly lunch spot.

• 7a Foods (West Tisbury)

If you’re going to Long Point Beach or anywhere near West Tisbury, stop by 7a for delicious sandwiches to go. The Liz Lemon, chicken salad, and pulled pork are my personal favorites.

• The Atlantic (Edgartown)

This bustling restaurant in Edgartown is definitely tourist-heavy but for good reason. It’s right on the water with great views and the lunch menu is awesome. We try to go once a trip for lobster rolls and fried oyster rolls. It’s also fun to go here late-night for drinks and dancing. It randomly turns into a club of sorts and is a great time.

• Edgartown Meat and Fish Market (Edgartown)

This is a great little gourmet shop where you can pick up salads and sandwiches for the beach. It’s right near State Beach, making it super convenient. The chicken salad is excellent!

• The Port Hunter (Edgartown)

Anel and I like to have one date night when we’re on family vacations, and we almost always choose The Port Hunter because the food and drinks are amazing and the vibe is young, cool, and vivacious. Don’t skip the buffalo Brussels!

• Atria (Edgartown)

The food here is great, but you definitely want to try and sit outside if you can. The gardens are beautiful. We like to go here for grown-ups only meals.

• The Covington (Edgartown)

This new(ish) restaurant has gotten mixed reviews for some reason, but I personally love it. It’s a very veggie-f0rward farm-to-table spot right in the heart of Edgartown with really interesting dishes. I’d recommend it for dinner with a group of girls who like to share food so you can try multiple things.

• Beach Road (Vineyard Haven)

This fish-focused restaurant, the sister restaurant to State Road down the street, is as beautiful as it is delicious. Don’t miss the clams linguini and the fried chicken!

• 19 Raw Oyster Bar (Edgartown)

19 Raw is one of our favorite restaurants on the island and it’s kid-friendly too! Make an early reservation for outside and your little ones can run around if they get antsy. Obviously, get oysters which are the star of the show here, but the various crudos also delicious. As are the smoked house bluefish deviled eggs. You really can’t go wrong. If you like fish, this is the restaurant for you.

• Nomans (Oak Bluffs)

Check out this Oak Bluffs based restaurant for breakfast, lunch, or dinner (they have one menu that they serve all day) and enjoy cocktails, tons of craft beers, small bites, and lawn games in the sun. The lawn and patio are pet-friendly so you can bring your pup too.

• Woods (Lambert’s Cove)

My dad and his wife got engaged at the Lambert’s Cove Inn so they like to take us back there every summer or two. Last year they completely renovated the restaurant and it is beautiful. Explore the grounds and gardens before you eat and enjoy a tasty farm-to-table meal in a gorgeous setting.

• Grace Church Lobster Rolls (Vineyard Haven)

Every Friday in the summer, you can get lobster rolls at Grace Church between 4-7pm. We pick up the lobster salad and the buns separately and make them at home for dinner or save them for beach lunch the day after. They’re phenomenal and worth the wait in line!

• Ben & Bills (Edgartown)

There is a lot of debate on the island about what the best ice cream is, including within my family. Half of us vote for Ben & Bills and half of us vote for Mad Martha’s. This summer we also learned that they make epic ice cream cakes. My dad and his wife got Amalia an ice cream cake for her birthday and it was beautiful and delicious.

• Mad Martha’s (Vineyard Haven, Edgartown, Oak Bluffs)

A Martha’s Vineyard staple! Mad Martha’s is a must if you’re on the island for the first time. There is one in each town so you can’t miss it. The peppermint flavor is a family-favorite what I always got as a kid.

• The Scoop Shack (Edgartown)

The Scoop Shack is my personal favorite ice cream shop because they also make snow cones (dairy-free) and soft-serve frozen yogurt so there is something for everyone. And Amalia loves their funfetti cake batter flavor that has sprinkles already mixed in.

• State Beach (Edgartown & Oak Bluffs)

Out of all the MV beaches, State Beach is our favorite because you can park right next to the path and the walk to the beach is short and easy. The waves are tiny and the sand is really nice and clean. They also have a lifeguard stand which is nice if you’re bringing kids.

• Long Point Beach (Vineyard Haven)

The parking can be tough here so go either early in the morning or you have to call in the afternoon to see if they’re free after the lunch rush. It’s worth a visit though, because not only is it a giant wildlife refuge, but they have a beautiful beach plus a lagoon where you can paddleboard and little kids can easily play in the water with no waves.

• Rent bikes - Martha's Vineyard

There are a ton of bike-rental spots on Martha’s Vineyard but if you’re in Edgartown, go to Wheel Happy, a cute bike shop owned by my friend’s dad!

• Beach House (Vineyard Haven)

This is maybe my favorite store on the island. It’s packed full of beautiful handmade table linens and throw pillows, home goods that you might find in a beach house, and a great assortment of hostess gifts.

• Katydid (Edgartown)

I love their selection of dresses, tunics, tops, and summery women’s clothing and some baby gifts too.

• Nell (Edgartown)

This beautiful little boutique carries a beautifully curated collection of upscale women’s clothing.

• Backwater Trading Co. (Edgartown)

This store is half men and half women’s clothing with an outdoor focus, but it has a cool vibe and carries a lot of sustainable brands.

• Soft As a Grape (Vineyard Haven)

This is the best shop to buy tourist tees, tanks, sweatshirts, sweatpants, and hats. Their selection is on point.

• Edgartown Books (Edgartown)

We love bringing Amalia here to play and read on the window seat they have in the kids’ section. The store is right downtown and has a really good selection of (adult) books and some great kids ones too.

• Rainy Day (Vineyard Haven)

Anel calls this the “hoarder store” because it carries such a random assortment of gifts, toys, and clothing, but we all love it and there is something for everyone. The toy section is awesome and can keep your kids occupied for a few minutes while you shop.

• Le Roux Kitchen (Vineyard Haven)

A beautiful home store with great gifts too.

• Bunch of Grapes Bookstore (Vineyard Haven)

Fun fact: my family saw Obama in here once. Sadly, I was not with them and I missed it! But Obama-sightings or not, it’s a great bookstore if you’re looking for a last-minute beach read or anything else.

• Portland Head Lighthouse - Portland, ME

The Portland Head Lighthouse in Cape Elizabeth’s Fort Williams Park dates back to 1791, making it the oldest lighthouse in Maine; the museum in the former Lighthouse Keeper’s quarters holds maritime artifacts, documents, navigational tools and models.

• Eventide - Portland
• Izakaya Minato - Portland
• Rose Foods - Portland

Recommend the bagels

• Drifters Wife - Portland
• Acadia National Park, Maine

Acadia National Park is an essential stop on any Maine road trip, but you can—and should—visit the park even if you're not already in the area. Those photogenic lighthouses and sunrises atop Cadillac Mountain are certainly worth traveling for.

• Matunuck Oyster Bar - Rhode Island
• The Schoodic Peninsula in Acadia National Park - Maine
• Woodstock, Vermont

Woodstock in the summer is my absolute favorite. The temperatures are gorgeous, in the 70s and 80s, the sun is shining and there are so many options no matter what type of adventure you seek. The beautiful, quaint village of Woodstock has lovely choices for dining and shopping. Check out our favorite shops, Woody’s and F.H. Gillingham and Sons. Take a stroll to get coffee at Abracadabra, eat breakfast at Mon Vert, lunch at the Village Butcher, ice cream at Woodstock Scoops and dinner at Mangalitsa. Swim down by the Ottaquechee River at one of the sandy access points (ask a local for help finding the secret spots) or venture to the Kedron Pond in South Woodstock or Silver Lake in Barnard. Hike Mt. Tom or mountain bike Mt. Peg and pack a picnic for the top. Enjoy outdoor music concerts at Artistree, East End Park or Feast and Field in Barnard. Look out for The Woodstock Guide for more insider scoop coming this June! Check out 15 Things to Do in Manchester, VT This Summer for a fun day trip from Woodstock or another Vermont getaway.

• Newport, Rhode Island

Newport is the perfect summer getaway with all things sand, sea, shopping and dining. Spend the day at Third Beach or walk along the Cliff Walk and enjoy beautiful views of the ocean and Gilded Age mansions. Grab breakfast at Belle’s Cafe with views of Newport harbor and don’t miss drinks on the lawn at Castle Hill. If you’re looking to shop check out The Little Chateau and Kristen Coates. Check out Jess’s comprehensive Newport Guide for more on where to stay, what to eat, drink and do during your trip. Jess also recently wrote, 15 of the Best Things to Do in Newport, RI this Summer and What To Do With Kids in Newport, RI. Narragansett and Block Island are other fun day trips and weekend getaways in Rhode Island.

• OGUNQUIT, MAINE

Last summer, we had our first family vacation with our 8 week old baby in Ogunquit, Maine. It was such a lovely getaway. Maine during the summer is like the perfect combination of Vermont adventure and Rhode Island ocean. Ogunquit is a touristy town, but very charming and has wonderful options for shopping and dining. The beach is gorgeous white sand and has a beautiful inlet that is great for little ones to play and also protects you on those windy days. We had dinner outside on the street at The Front Porch, a charming little piano bar and enjoyed the music and people watching. Ice cream at Sweet Pea’s is a must!

• ACADIA NATIONAL PARK- BAR HARBOR, MAINE

Acadia National Park is one of the most beautiful places and full of choose your adventure options. You can camp, hike, bike, canoe, kayak, stand up paddle board and so much more! We rented bikes and took a shuttle to the park from Bar Harbor. The paths are pristine and the scenery is gorgeous. This is a trip that could be both family friendly or more challenging for adult groups. Be sure to book your stay early because this is a popular destination! Other fun Maine destinations include Portland (for the city seekers) and Kennebunkport for a more small town, family beach vacation vibe.

• LAKE WINNIPESAUKEE, NEW HAMPSHIRE

I grew up going to Lake Winnipesaukee in the summer and it brings back such warm, lovely, nostalgic childhood feels. I can still hear the peaceful sound of the loons early in the morning. We used to go with a few families from our town and rent houses next to each other along the lake. It was so fun having friends my age to play with and the adults were happy not to have to entertain us and from what I remember had a blast themselves! Lake Winnipesaukee, or “The Smile of the Great Spirit” is the largest lake in New Hampshire overlooking the White Mountain range. The lake is surrounded by many diverse towns each with their own fun niche and spirit. Weirs Beach is known for it’s boardwalk, arcades, waterslide, activity center and public beach- basically it is heaven for kids. Meredith is an old mill village with an array of antique galleries. Wolfeboro is a quaint town with a historic Main Street. Fireworks, concerts and other events are sprinkled throughout the summer adding to Winnipesaukee’s fun and charm. Swimming, biking, fishing and boating are all accessible during your vacation at Lake Winnipesaukee!

• CHATHAM, MASSACHUSETTS

I recently went to Chatham for the second time for a girls bachelorette weekend. The first time I went was a family vacation. Chatham is such a beautiful ocean town and has so much to offer for family, friend and couple getaways. The Chatham Bars Inn is a gorgeous inn overlooking Chatham Bars and is a great option for your stay or stop in for a drink or meal and enjoy the outdoor seating on the beach with yard games and a bonfire. The shopping in downtown Chatham is perfect for souvineers and clothes as well as dining. Our dinner at Bluefins Sushi & Sake Bar was delicious and we had fun dancing and drinking at The Chatham Squire afterwards. Our favorite shop was The Fisherman’s Daughter. During my first trip to Chatham we did a fishing day trip with Chatham Fishing Charters. It was so fun and we all had an exciting reel in and big catch to celebrate! Beware: if you get seasick like me, all the dramamine in the world will not prevent you from getting sick in the deep seas off Chatham.

• PORTSMOUTH, NEW HAMPSHIRE

On our way back from Ogunquit last summer we stopped in Portsmouth for a few hours and it was not nearly enough time! Portsmouth is a fun destination because city meets beach and you get the best of both worlds. We checked out some of the shops in downtown and had lunch at the Portsmouth Brewery. We hit up one of the local beaches and enjoyed a quick dip in the chilly water, which was so refreshing on a 95 degree day. A few close beach options include: Long Sands Beach, Great Island Common, Hampton Beach, Wallis Sands State Beach and Jenness State Beach. When we go back we want to check out Portsmouth Farmers Market, Market Square, Strawberry Banke Museum, Moffatt-Ladd House & Garden and who doesn’t love a good ghost and trolley tour.

• MARTHA’S VINEYARD, MASSACHUSETTS

My sister travelled to Martha’s Vineyard last summer with her husband and 2-year-old and it was a perfect getaway for their family. They absolutely adored Edgartown. Edgartown Books is a sweet little bookshop. Behind the Bookstore, literally located behind Edgartown Books, is a true gem serving al fresco dining for breakfast, lunch and dinner. My sister recommended the yummy breakfast, delicious coffee and even mentioned an iced coffee, soft serve float option which is always our favorite. Their website also mentions spicy cocktails and dinner under the stars. Sold! Morning Glory Farm was another favorite spot and Bad Martha for outdoor seating, live music, yummy snacks and pizza. The swimming was especially perfect for a toddler with quiet beaches protected from the usual rough waters.

• THE BERKSHIRES, MASSACHUSETTS

Located in Western Mass., the Berkshires has been on my travel bucket list for a while now! There is so much to do for a fun-filled adventurous vacation including hiking and biking in the mountains, an excellent foodie scene, shopping, concerts, museums and historic gardens. Check out all the fun things to do and plan your next trip to the Berkshires here! Here are a few bucket list items for the Berkshires: Tanglewood Concerts, Monument Mountain and Hancock Shaker Village. The Berkshires is known for having an amazing farm to table food scene. Check out some recommendations here!

• WHITE MOUNTAINS, NEW HAMPSHIRE

A trip to the White Mountains in New Hampshire is the perfect getaway for outdoor enthusiasts. Take a Zip Line Tour, experience Flume Gorge, hike Falling Waters Trail, ride the Cannon Mountain Aerial Tramway, have a drink or stay at Mount Washington Hotel, climb Mount Washington or ride the Cog Railway or Auto Road and bike Franconia Notch. Adventure awaits you at every turn in the White Mountains!

• Dinner at Cloudland Farm - Woodstock, VT

Dinner at Cloudland Farm is at the very top of my summer bucket list for Woodstock. Get a true farm to table experience and dine outdoors overlooking rolling hills and mountains. The menu is a 3-course pre-fixe that changes daily, featuring ingredients grown at Cloudland Farm and other local organic farms. It’s BYOB and reservations are required so be sure to plan ahead.

• Visit Sugarbush Farm - Woodstock, VT

Sugarbush Farm is a local farm we know and love in Woodstock. Most well known for their mouth watering cheese and maple syrup production. Visit the farm in the spring (March and April) to get an up close and personal look at the sugaring process and visit all year round to sample cheese and maple syrup, walk the nature trail, meet the farm animals, picnic and enjoy the view!

• Market on the Green - Woodstock, VT

Woodstock’s weekly Farmer’s Market from June-October, Market on the Green is a must if you’re in town on Wednesdays in the summer. You’ll find everything from free face painting and live music to locally made shaved ice and wood fired pizzas. Lots of local farmers have stands too so you can stock up on fresh produce, cheese and more. Bring an appetite! Every Wednesday 3-6pm all summer.

• Marsh Billings Rockefeller National Historical Park - Woodstock, VT

The Marsh – Billings – Rockefeller National Park is a wonderful testament to the beauty of conservation and stewardship. The village of Woodstock takes pride in this flourishing national park including pristine walking and hiking trails, kids programming and mansion tours. Walk through trails of sugar maples and 400 year old hemlock trees. Take a stroll to the Pogue and notice the stillness of the water and reflection of the trees. It is dog friendly (on leash). Map of the Park. Hiking Trails.

• Billings Farm and Museum - Woodstock, VT

Just a short stroll from the village of Woodstock, Billings Farm and Museum is both a working dairy farm and history museum. Educational exhibits, interactive programs and events, a gift shop, farmhouse cafe (with ice cream and snacks), activities and demonstrations and small movie theater– Billings Farm is a wonderful resource that the whole family will enjoy. They have events going all summer long, check the calendar to see what’s happening while you’re in town. The Sunflower House is a must see in the late summer months.

• Ice Cream at The White Cottage - Woodstock, VT

Situated along the Ottaquechee River, The White Cottage is the perfect spot to cool down on a hot summer day in Woodstock. Get ice cream or burgers and onion rings and then grab yourself a picnic table overlooking the Ottaquechee River. Very kid friendly, this is a great spot to bring the whole family. Bring your bathing suits and river shoes!

• Mount Tom - Woodstock, VT

Go for a hike at Mount Tom and explore the trails along the way as you approach the summit where you’ll find stunning views of Woodstock village. There are a few different trail options to hike to the top. We like Faulkner trail which is wooded and provides decent shade for most of the walk. You can also take the access road through Marsh Billlings Rockefeller National Park, stop at the Pogue and continue to South Peak. This is paved and you could bring a stroller.

• Quechee Gorge - Woodstock, VT

Known as “Vermont’s Little Grand Canyon” and located in Quechee, Vermont, the focal point of the Quechee State Park is Vermont’s deepest gorge, formed by glacial activity approximately 13,000 years ago. Visitors can look down at the Ottauquechee River, flowing 165 feet below viewing points along Route 4. There’s several camping sites located within the park (open seasonally) along with a snack bar and gift shop. There are numerous hiking trails and spots for a picnic. Pets are also allowed.

• Silver Lake State Park

Silver Lake State Park is a must see year round but it’s particularly fun in the summer months. It has a sandy swimming area, picnic grounds, and camping area. It’s a very short drive from Woodstock and is popular for swimming, paddling and fishing. Pets are not permitted on the sandy beach or designated swimming area but are allowed elsewhere throughout the park. A very family friendly destination, there is a large grassy area by the beach with a great playground. There is also a snack bar, restrooms, changing rooms, and boat and canoe rentals. Stop by the Barnard General Store and pick up lunch to go or grab ice cream after a day at the lake.

• Golf at Woodstock Country Club - Woodstock, VT

Head to the Woodstock Country Club located just outside of Woodstock Village for a beautiful and challenging course that includes a restaurant, pro shop, driving range and putting green. Golf Magazine named the Woodstock Country Club one of the top 100 golf resorts.

• Woodstock Inn Spa - Woodstock, VT

If you’re ready for some pampering there is no better place than the Woodstock Inn spa. Recognized by Forbes Four Star Award for Spas, the Woodstock Inn Spa has incredible treatments and amenities. Lounge in the relaxation room, enjoy the outdoor sauna, spa and pool (seasonal) and take a eucalyptus steam in the beautifully appointed dressing rooms. The estheticians and massage therapists provide unique, calming and beneficial treatments. We love the Tata Harper facial!

• Shopping in Woodstock Village - Woodstock, VT

One of my favorite things about the village in Woodstock is how easy and manageable it is. Park right in downtown Woodstock and walk around to shop the small boutiques, book store, art galleries and more. A few personal favorites are Woody’s Mercantile, Clover Gift Shop, Yankee Bookstore, and F.H. Gillingham and Sons.

• Baxter State Park & Allagash Wilderness Waterway (Maine)

Maine's sparsely inhabited North Woods offers a wild and rugged escape for more than 25 million people living in New England and eastern Canada. The region covers roughly 3.5 million acres -- more water and woods than Yellowstone and Yosemite combined. Baxter State Park and the Allagash Wilderness Waterway are the region's premier parks. With only about 65,000 visitors each year -- mostly in the summer months -- the two state reserves deliver on getting away from it all. Baxter boasts Maine's highest peak, 5,269-foot (1,606 meters) Mount Katahdin, and the northern terminus of the Appalachian Trail, while Allagash provides a 92-mile (148-kilometer) corridor of wild rivers and lakes that Henry David Thoreau extolled in an 1864 travel story about his own paddle through the North Woods. Related content22 of the USA's most underrated destinations Just passing through: Reserve a room at the rustic Big Moose Cabins or other digs in Millinocket and drive into Baxter State Park for day hikes. Deep dive: Join a weeklong guided paddle along the Allagash Wilderness Waterway with Maine Trails Guide Service. Best time: June to early October More info: Baxter State Park and Allagash Wilderness Waterway

• Madison, CT

Christy’s for breakfast– We remembered their giant pancakes from our last trip and the kids loved them! They split a strawberry chocolate pancake (they’re giant).

The Wharf at The Madison Beach Hotel for dinner– The house was only a two minute walk from the hotel so the first night we decided to keep things easy and head over for dinner. Hotel restaurants can be meh but this one is awesome. We overlooked the water and enjoyed crab cakes, lobster cobb salads, mussels, and pasta for the kids. They had a fantastic zero-proof mocktail menu too which I always appreciate.

RJ Julia’s Bookstore– The way I love this bookstore. We spent almost an hour perusing both the kid and adult sections of one of the best bookstores I’ve ever been to. Don’t worry, I definitely plugged my book and they said to reach out when it drops.

Ashley’s Ice Cream– They are voted best ice cream in Connecticut for good reason! They have some amazing dairy free options too. I went with coffee oreo. 10/10.

Grand Apizza– There are so many great food options in Madison, but we just wanted to keep things easy and low key for the kids. The goal was zero meltdowns and we somehow succeeded! The pizza at Grand’s was next level New-Haven style pizza. We finished three smalls between the four of us. It was fantastic!

Lobster Landing– Anel picked up lobster rolls here for lunch the first day and they were just as good as we remembered them from the last trip. At some point we had heard they were the best rated in all of CT and I get that. Don’t expect anything fancy, it’s a bunch of benches outside with lobster rolls wrapped in tin foil, but they’ll blow your mind.

The Lobster Pound– We had been to this spot in Guilford with friends a few years ago and loved their lobster rolls so decided to hit it up again for lunch on our way home. It’s basically a big dock where they serve (hot) lobster rolls, hot dogs, cole slaw, and clam chowder. The kids can run around and it’s super low key.