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Boston’s Best Weekend Getaways

You can enjoy a lot of winter activities in the city, but sometimes you just want to get away, enjoy the fresh air, and explore quaint little towns. Plan your next summer getaway with car service at Logan Airport guide to the top summer getaways. Here are some day trips from Boston if you can’t make it for the whole weekend. Once you’re back in the city, visit some of Boston’s most beautiful museums, catch some live music, eat at some of the hippest restaurants and get back into the swing of things.

Nantucket Island

Summers on Nantucket are magical. The Whale (38 Main St, 508-825-5897) located right on downtown Nantucket’s cobblestone main street. If the weather is nice, the back patio of The Whale is also a great place to eat.

Hotel Pippa (5 Chestnut St, 508-228-5300) offers guests complimentary breakfast before they set out for the day at the contemporary boutique hotel. With the assistance of Hotel Pippa’s team, guests can book a variety of island activities, from fishing expeditions to cooking classes. Guests can relax on Hotel Pippa’s cozy patio when the day is over. 

Travelers can attend a new fall festival in early October at The Harvest Fair (220 Milestone Rd), which takes place October 1-2. Island Fairs and Cranberry Festivals have been held separately for most of history. However, in 2022, the events will merge into one large evental.

Newport, RI

Visiting Newport, RI is like taking a trip back in time, home to the famous Newport Mansions, great waterfront restaurants, shopping, and plenty of outdoor activities.

It’s best to book a table on the deck overlooking the wharf around sunset at The Mooring Seafood Kitchen & Bar (1 Sayers Wharf 401-486-2260). 

Check out Castle Hill Inn (590 Ocean Ave, 888-466-1355), an ideal spot for a romantic getaway in Newport. 

It is a must to tour at least three Newport Mansions, but we recommend saving The Breakers for the last. After exploring the Cliff Walk, you can take in the breathtaking views of Newport. Last but not least, a sail around Newport harbor cannot be missed, so book the Adirondack II for an afternoon or evening cocktail sail.

Woodstock, VT

The perfect New England fall getaway town, Woodstock offers visitors the opportunity to stroll through the town square, visit local farms, museums, and browse all the local shops.

You may want to visit Worthy Kitchen (442 Woodstock Rd, 802-457-7281) for farm-to-table comfort food and local craft beer.

If you want to be centrally located to everything in town, stay at the Woodstock Inn & Resort (14 The Green, 888-338-2745), which is located directly on the town square. The Inn offers a world-class, LEED-certified spa and is walking distance to tons of shops and restaurants.

Free cheese and maple syrup tastings are available at Sugarbush Farm (591 Sugarbush Farm Rd, 802-457-1757). During the fall, you have to visit Sleepy Hollow Farm (3429 Cloudland Rd South, Woodstock, VT 05091) for a ride out to see the fall foliage. You can also take a stroll around the farm grounds. It is privately owned, but you are free to view the farm from the road. You will probably share the road with other photographers and leaf peepers who are enjoying the beautiful fall colors.

Provincetown, MA (PTown)

On a car services Boston it takes 90 minutes to get to Provincetown from Boston by ferry, and it offers plenty of bars, restaurants, and activities.

You can enjoy beach front dining at The Canteen (508 487-3800) which also has lobster rolls and frosé.

Located on 698 Commercial Street, 508-487-1711, the Harbor Hotel Provincetown’s retro-glam style and modern amenities make it an ideal place for a weekend away. They even allow pets!

Take a dune tour with Art’s Dune Tours and experience the thrill of dune driving while learning about the history behind the artist shacks and how this area joined the Cape Cod National Seashore.

Watch Hill, RI

The watch hill merry-go-round is the oldest continuously functioning merry-go-round in the country, and Taylor Swift vacations here, so why shouldn’t you? This small town is just over two hours from Boston, and it’s walkable.

Just a short walk from the beach, Olympia Tea Room (74 Bay Street 401-348-8211) is an institution. 

The Ocean House (1 Bluff Avenue 855-678-0364) and the Watch Hill Inn (38-44 Bay Street 855-677-7686) are two clear winners when it comes to where to stay. This Ocean House has its own private beach, a seasonal Mexican restaurant by Chef Dantón Valle, croquet courts, and multiple dining options. A convenient location on Bay Street overlooking the harbor, the Watch Hill Inn offers a comfortable stay near the shops and restaurants.

Spend the day shopping or heading to the beach after visiting the Watch Hill Lighthouse.

Kennebunkport, ME

With quaint shops, restaurants, and a charming seaside town, Kennebunkport is just an hour and a half from Boston. 

For outdoor seating and live music, visit Old Vines Wine Bar (173 Port Road (207) 967-2310). They offer small snacks and shareables, as well as a wide selection of wines and craft cocktails. A trip to Kennebunkport wouldn’t be complete without visiting The Clam Shack (2 Western Ave 207.967.3321), 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.

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Taking a picture of Nubble Light is a must-do whenever you are in Kennebunkport.

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