15 best weekend getaways from Boston

Nantucket is the quintessential weekend spot for New Englanders looking to get away from it all. The fastest way for Bostonians to get to the island is via Cape Air. Hop on one of the many daily shuttle flights and after the brief 45-minute (door-to-door including boarding and all) flight, you will be 30 miles off the coast of Cape Cod, but a world away.

Eat at: Sister Ship (29 Centre St, Nantucket, MA 02554) is the coolest kid on the block right now. Expect lots of fresh takes on classic flavors and the insider secret is that it turns into a night club on Friday and Saturday nights.

Stay at: The Federal Suite at Faraway Nantucket (29 Centre St, Nantucket, MA 02554) is the most luxurious home away from home, without the hassle of a vacation rental. This standalone suite offers its own private entrance, three bedrooms, chef’s kitchen, wet bar and outdoor patio. It is perfect for a family or group of friends for an extended stay, the Federal Suite sleeps six.

Must do: A trip to Nantucket can be whatever you want it to be. Spend all day reading a book at Steps Beach, dance the night away at the Chicken Box and somehow make it up in the morning for brunch at Or the Whale, following by an afternoon shopping at the Vault and Murray’s.

Leave the car at home because Provincetown is just a 90-minute ferry ride from Boston. With lots of fun bars, great restaurants, and plenty to do Ptown is one of our top weekend getaways from Boston for a reason.

Eat at: The Canteen (225 Commercial Street 508 487-3800) has beach front dining, an incredible lobster roll, and frosé. What more could you need?

Stay at: The Harbor Hotel Provincetown's (698 Commercial St, 508-487-1711) retro-glam style and modern amenities makes it exactly what you want on a weekend away. Plus they’re pet friendly!

Must do: Enjoy off roading on a dune tour. Stop by Art’s Dune Tours for an exhilarating ride through the dunes, the team gives you a full history of the area, from how it joined the Cape Cod National Seashore to the history behind the artist shacks.

Just an hour and a half from Boston, Kennebunkport is the quaint seaside town you’ve been dreaming of. There is a little something for everyone in Kennebunkport (you may even spot the Bush family!). 

Eat at: Stop by Old Vines Wine Bar (173 Port Road (207) 967-2310) for outdoor seating and live music, their menu is filled with small snacks and sharables plates. However, the wine list and craft cocktails are the real draw. And no trip to Kennebunkport is complete without a stop at The Clam Shack (2 Western Ave 207.967.3321), they’ve been serving fresh seafood since 1968!

Stay at: The Boathouse (21 Ocean Ave; 207-967-8225) brushes up against the Kennebunk River, which is easily viewed from your room’s oversized windows.

Must do: Visit Nubble Light. If you went to Kennebunkport for the weekend and didn’t take a picture of the famous lighthouse, did you really go?

Step back in time with a weekend getaway to Newport, RI. Home to the famed Newport Mansions, Newport is also packed full of waterfront dining, shopping, and plenty of options for getting outside and staying active.

Eat at: The Mooring Seafood Kitchen & Bar (1 Sayers Wharf 401-846-2260) pro-tip is to reserve a table around sunset on their deck overlooking the wharf. 

Stay at: The Vanderbilt (41 Mary St 833-242-8850) is conveniently located downtown just steps away from the action on Thames Street. If you’re looking for a more quiet getaway check in at Castle Hill Inn (590 Ocean Ave 888-466-1355), the views cannot be beat. 

Must do: Touring the Newport Mansions is a must, we recommend doing at least three. But save The Breakers for last as it is the most impressive! Afterwards, stroll along the Cliff Walk for world class views. Last, no trip to Newport is complete without a sail around the harbor, book an afternoon sail or an evening cocktail sail on the Adirondack II.

Home to Mystic Pizza and the Mystic Aquarium, this small coastal village, which is actually officially part of Stonington CT, is a great weekend getaway from Boston. 

Eat at: Mystic Pizza (56 West Main St. 860-536-3700) is worth a visit. But if you’re not in the pizza mood checkout Red 36 Bar & Grill (2 Washington Street 860-536-3604) for waterfront dining, fresh seafood and great cocktails.

Stay at: Stonecroft Country Inn Bed and Breakfast (515 Pumpkin Hill Road 860-744-5868) is the quaint B&B that summer weekend getaway dreams sometimes require.  

Must do: Go brewery hopping. Mystic and Stonington are home to a handful of great local breweries including Barley Head Brewery, Bank & Bridge Brewing and Beer’d Brewing Co. Not into beer? There are also a bunch of great vineyards and wineries in the area.

A little further afield, Bar Harbor is almost five hours from Boston by car so be sure to make the most of your weekend in Bar Harbor and add on a trip to Acadia National Park, the only national park in New England

Eat at: The Travelin Lobster (1569 ME-102 207-288-8028), have the lobster roll you won’t regret it.

Stay at: The Bar Harbor Grand Hotel (269 Main Street 207-288-5226) is a replica of the historic Rodick House, convenient to both downtown and Acadia. This hotel is the perfect spot to relax and unwind after a day of hiking.

Must do: Make the most of your weekend in Bar Harbor by doing a tour of Acadia National Park. Thsi is the most approachable way to see the park if you’re not a big hiker and want to see all the major landmarks in a short period of time. (The classic tour is only 2.5 hours leaving you plenty of time to explore on your own!)

Martha's Vineyard is just a short ferry ride from Cape Cod that drops travelers right in either Edgartown, Oak Bluffs or Vineyard Haven for convenient access to shops, hotels and restaurants. Enjoy amazing beaches, see the Edgartown Lighthouse or take a ride to Island Alpacas for a truly one-of-a-kind experience.

Eat at: Visit Back Door Donuts (1-11 Kennebec Ave 508-693-3688) for the ultimate late-night snack, these donuts are worth waiting in line.  

Stay at: The Harbor View Hotel (131 N Water St 877-624-7992) cannot be beat. So many things including amazing views, sumptuous accommodations, complimentary bikes and the Mercedes-Benz Drive Program make it a luxurious home away from home. 

Must do: Whether using complimentary bikes provided by a hotel or renting bikes for the weekend, bikes are one of the best ways to explore the island. Martha’s Vineyard offers over 40 miles of trails and roadways through its scenic towns and along its coast.

Taylor Swift vacations in Watch Hill, why shouldn’t you? Just over two hours from Boston this small town is walkable and is home to the oldest continuously operating merry-go-round in the country.

Eat at: Olympia Tea Room (74 Bay Street 401-348-8211) is an institution. Just a short walk from the beach the simple menu has been keeping guests happy for over 100 years. 

Stay at: There are two clear winners when it comes to where to stay, the Ocean House (1 Bluff Avenue 855-678-0364) or the Watch Hill Inn (38-44 Bay Street 855-677-7686). The Ocean House boasts its own private beach, multiple onsite dining options including Dalia, a new seasonal Coastal Mexican venue by Chef Dantón Valle, and croquet courts. The Watch Hill Inn is right on Bay St overlooking the harbor, and is convenient to all the shops.

Must do: Walk down to the Watch Hill Lighthouse, then spend the day shopping along Bay Street or head to the beach.

In need of fresh air? The Berkshires have you covered with museums, concerts, legendary authors' homes, botanical gardens, hiking and whitewater rafting.

Eat at: Methuselah Bar and Lounge (391 North St, Pittsfield; 413-347-2888) is focused on organic wines and craft beers, pairing them with funky, reimagined American fare, tacos and Korean-inspired dishes. Nudel: Comfort & Craft (37 Church St. 413-551-7183) post-pandemic this Berkshires favorite has been doing “pop-ups” that allows them to change their menu every few months to focus on fresh seasonal ingredients! 

Stay at: Seven Hills Inn (40 Plunkett St 413-637-0060) the former Gilded Age mansion offers 57 guest rooms, stunning gardens and an outdoor pool.

Must do: Be adventurous at Catamount Mountain Resort (Route 23 413-528-1262) go on a zipline tour, spend the day in the adventure park, or go on a scenic chairlift ride!

Located just 13 miles offshore, Block Island is a great alternative to Nantucket or Martha’s Vineyard, it is a bit quieter and more relaxed. Good news for our nature lovers, 40% of the island is conservation land, accessible only by bike or foot.

Eat at: Poor People’s Pub (33 Ocean Ave 401-466-8533) offers casual local seafood, burgers, pizza and more. They’re conveniently located by the Old Harbor Block Island Ferry and offer outdoor seating! Before heading back to the ferry, grab gourmet sandwiches from Three Sisters (443 Old Town Rd; 401-466-9661).

Stay at: Spring House (1401 Ocean Ave; 732-776-6700), the island’s oldest hotel, entices with Adirondacks and a wraparound veranda overlooking the water. 

Must do: Go horseback riding on the beach. Visit Rustic Rides Horse Farm, the offer both beach rides and trail rides, a great way to see the island!

Charming brownstones, bucket list worthy restaurants and ocean views? Portland is a great idea any time of year but especially in the summertime when you can take advantage of everything happening on the waterfront. Be prepared to eat all weekend long, Portland is a foodie’s paradise.

Eat at: You really can’t go wrong but three spots to get you started: Duckfat (43 Middle St; 207-774-8080) for fries, poutine and a milkshake when you're hungover the next day. Central Provisions (404 Fore St; 207-805-1085) for the locavore meal of the moment. And you must try Highroller Lobster Co (104 Exchange St. 207-536-1623)!

Stay at: Conveniently located in the Old Port, The Press Hotel (119 Exchange St; 800-971-2000) is the former home of the Portland Press-Herald and carries on the print tradition with newspapered walls, letterpress carpeting and leather desk chairs. Be sure to check out their amazing art collection.

Must do: Tour Casco Bay! Experience Portland on the water as you visit all the islands throughout Casco Bay.

New England is awash with winter resort towns, but we most love those areas that celebrate four-season recreation. Come summer, Stowe swaps out skiing for hiking, golfing, mountain biking and kayaking. Bonuses include swimming hole visits and scenic drives up the squiggly Auto Toll Road.

Eat at: Plate (91 Main St; 802-253-2691) combines California cuisine with Vermont-sourced ingredients. Take the gondola up to Cliff House (5781 Mountain Rd; 802-253-3665) and enjoy a bottle of wine on the outside deck before hiking down afterward.

Stay at: Spruce Peak (7412 Mountain Rd; 802-253-3560) manages to feel homey and warm (also dog-friendly!), despite its luxury amenities. Added perk: It's also dog friendly, so your canine companions can come stay on vacay.

Donation-based outdoor concerts, art galleries, riverside farm-to-table dining and a bookstore that serves beer and wine—all an hour’s distance from Boston.

Eat at: Moxy (106 Penhollow St; 603-319-8178) from James Beard nominee Matt Louis does American tapas like you’ve never seen (i.e. pork belly bites and mini red hots).

Stay at: Ale House Inn (121 Bow St; 603-431-7760), a former brewery with brick-walled rooms, in-room iPads and a complimentary bottle of Smuttynose upon check-in. 

When did our southern neighbor become so grown up? Providence is now a bonafide go-to destination, thanks to its WaterFire performances, concerts and serious dining scene. “Creative Capital” indeed.

Eat at: CAV Restaurant (14 Imperial Pl, 401-751-9164) is part-eatery, part-antiques shop, serving its bistro bites in a truly stunning setting. Drinks at The Dorrance (60 Dorrance St; 401-521-6000) will transport you back to the Roaring Twenties.

Stay at: The Dean Hotel (122 Fountain St; 401-455-3326), a 51-room boutique, has brought a new level of hipsterdom to the downtown area. 

The Cape is a no-brainer, but where to stake your claim? We’ve long migrated towards the inimitable charms of Chatham, where the homes will make you drool, the town center is walkable and crammed with cute boutiques, and the seafood is hauled in just offshore. 

Eat at: Impudent Oyster (15 Chatham Bars Ave, 508-945-3545) offers innovative spins on classic seafood dishes and a lively bar inside a former church.

Stay at: Chatham Bars Inn (297 Shore Rd; 508-776-6700) is the ne plus ultra of Cape retreats for good reason: The cabana’d beach alone earns the resort its mythic reputation—and justifies the indulgence.