Boston, Massachusetts is surrounded by quaint New England towns, picturesque natural beauty, and plenty of romantic attractions. Whether you’re relaxing in a beach house in Martha’s Vineyard, indulging in fresh-caught Maine lobster by the sea, or escaping to a rustic New Hampshire mountain cabin, you’re sure to enjoy your romantic weekend getaway. Stay at one of numerous Boston vacation rentals, or venture to one of the many available accommodations in neighboring states. Here are seven of the most romantic weekend getaway spots near Boston.
1. Nantucket, Massachusetts
Located a bit less than four hours south of Boston, Nantucket is a lovely island that’s known for its fantastic restaurants, eclectic shops, and cobblestone roads. Rent bicycles and explore the area’s scenic beaches together; Surfside Beach, Jetties Beach, and Dionis Beach are all fantastic choices. Take a tour of the historic Sankaty Head Light lighthouse, and enjoy a stunning view from the top. Visit the Loines Observatory and enjoy stargazing like you’ve never experienced. Pack a picnic, go to Endeavour Sailing Excursions, and spend the day sailing the gorgeous Nantucket Sound. For dinner, enjoy seasonal American cuisine by candlelight at American Seasons, an elegant restaurant with over 500 different wines available. While you’re in Nantucket, be sure to stop by Straight Wharf Restaurant, where you can enjoy some exquisite seafood from the comfort of the restaurant’s rustic waterfront outdoor porch.
2. Oak Bluffs, Massachusetts
Martha’s Vineyard is one of the most popular vacation destinations in the country, and the island is less than three hours away from Boston. Whether you’re interested in treating yourselves to luxurious vacation rentals or just unwinding in a quaint, vibrantly-colored gingerbread cottage, Oak Bluffs is one of the most charming Martha’s Vineyard towns. Enjoy a sunset stroll on the ultra-fine sand at Inkwell Beach, and then enjoy a cup of coffee and a scone at Mocha Mott’s, a favorite spot among the locals. Constructed in 1876, the Flying Horses Carousel is one of the area’s most famous attractions. The gingerbread cottages at the Oak Bluffs Campground are must-see attractions, even if you don’t stay in one. Ocean Park is a wonderful place for an outdoor picnic on the well-groomed grass, or visit the historic single-screen Strand Theater to see a movie. Be sure to stop by Martha’s Vineyard Chowder Company for some authentic New England clam chowder in an upscale-yet-casual setting.
3. Portland, Maine
The great thing about New England is that you can visit a variety of states without driving too far. Portland, Maine is less than two hours from Boston, and it gives you a brand new environment to explore. Portland is one of the best vacation destinations for couples who enjoy the finer things in life, boasting an exceptional food and beer scene. While you’re in Maine, you must have at least one lobster dinner, so visit Street & Cos, a rustic bistro nestled in a cobblestone alley. Enjoy a relaxing day exploring over 17,000 works of art at the Portland Museum of Art, and then take a tour of the historic Portland Observatory, where you can enjoy a beautiful view of the city. Experience Portland’s thriving culinary scene by taking one of the Maine Foodie Tours. A local takes you and your sweetheart to some of the best eateries, giving you a sample of the finest locally sourced ingredients prepared by world-class chefs. Maine Foodie Tours also offers cooking classes that are perfect for couples.
4. Portsmouth, New Hampshire
Portsmouth is a welcoming coastal city that has plenty to see and do, from scenic parks and gardens to museums and water parks. Take in the city with one of the most classic dates: dinner and a show. The Music Hall is a must-visit attraction. Constructed in 1878, this historic venue regularly hosts a variety of performances, from comedians to magicians to concerts to films. When it comes to restaurants, Portsmouth’s upbeat downtown area has no shortage of options. The Wellington Room and Mombo are both fine choices if you want American fare in an elegant atmosphere. Or, head to Bridge Street Bistrot & Wine Bar for traditional French cuisine by candlelight. Black Trumpet Bistro is another great choice for food, featuring an eclectic menu and a cozy, romantic dining room. There’s a lively wine bar upstairs if you feel like indulging after your meal.
5. Stockbridge, Massachusetts
Stockbridge is a lovely town in the bucolic Berkshires region. You can spend your entire visit exploring Stockbridge, or branch out to the other many Berkshire towns nearby, such as Lee, Lenox, and Great Barrington. Visitors and residents often say that the charming town looks like a Norman Rockwell painting, and that’s unsurprising considering Stockbridge was the artist’s hometown. Be sure to stop by the Norman Rockwell Museum to view a wonderful collection of his works. Wander around the picturesque Berkshire Botanical Garden, a beautiful public garden that was founded in 1924. Stop by Nejaime’s Wine Cellar for some fantastic wine, cheese, bread, and other picnic foods. For dinner, enjoy a delicious meal made with love from local ingredients at Once Upon a Table, a cozy, romantic eatery tucked away in an alley.
6. North Conway, New Hampshire
Home to the majestic White Mountains, North Conway is the ideal getaway if you want to escape to sleepy mountain cabin vacation rentals, and it’s less than three hours from Boston. Board the Conway Scenic Railroad, and enjoy watching the gorgeous nature fly by as you dine in a beautiful restaurant car. During autumn, the Kancamagus Highway is one of the country’s best spots for viewing fall foliage, so take a drive or explore the rural area by foot. On a clear day, head to the Mount Washington Observatory Weather Discovery Center for a breathtaking view of the area’s natural beauty. When it’s time for dinner, you can’t beat a molto delizioso meal for two at Cresh’s Italian Country Kitchen.
7. Providence, Rhode Island
Located roughly an hour from Boston, Providence is a vibrant Rhode Island city that’s packed with vacation rentals, from quiet suburban homes to luxury downtown lofts. The riverfront is modeled after Venice, Italy, and La Gondola offers incredibly romantic Venetian gondola boat rides paddled by captains in traditional striped shirts and straw hats. Providence boasts plenty of fantastic dining options. The Dorrance, located in the heart of downtown Providence, offers one of the best dining environments, featuring a luxurious palace-like setting that includes high ceilings, ornate decorations, and elegant white curtains. The New England cuisine is wonderful, and the wait-staff is the best around. For something a bit more casual, head to New Rivers for exquisite homemade cuisine in a lovely home-style setting. After dinner, take a stroll through the nearby Waterplace Park, where you can enjoy charming bridges and walkways along the water.
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