Massachusetts is home to quaint and charming New England towns, as well as larger modern cities, giving visitors the best of both worlds. Whether you’re relaxing on a beach in Cape Cod or visiting Boston’s world-class museums, entertainment venues, and restaurants, Massachusetts is packed with romantic destinations for you to explore with your travel companion. There are plenty of vacation rentals in Massachusetts — from rustic cabins to luxury mansions — and many are just minutes from the best attractions in the state. Here are eight of the most scenic towns and cities to enjoy during a romantic weekend.
1. Martha’s Vineyard
Martha’s Vineyard is an exclusive island community just south of Cape Cod. It’s one of the state’s most luxurious vacation destinations, perfect when you and your sweetheart really want to go all out. Menemsha Beach boasts some of the most beautiful sunsets New England has to offer. Martha’s Vineyard is known for its incredible eateries. When you’re in the mood for a decadent Italian feast for two, head to Chesca’s – reserve a table on the porch if the weather allows it. The State Road restaurant is another wonderful place to eat, offering delectable modern American cuisine served in a rustic chic dining room or outside on the cozy outdoor patio area. With virtually no light pollution, Martha’s Vineyard has some of the finest stargazing Massachusetts has to offer. The Edgartown Lighthouse at dusk is a particularly romantic setting for admiring the twinkling night sky.
Nantucket is an island haven that’s one of Massachusetts’ most popular vacation destinations for couples. It’s known for its exquisite eateries, eclectic boutique shops, and charming downtown area with cobblestone roads. Visit the small shops in downtown Nantucket, and stop by Nantucket Country Antiques and Val Maitino Antiques to pick up some treasures to remember your trip. Nantucket has some gorgeous beaches, including Madaket Beach, Surfside Beach, and Dionis Beach. Explore the beach on foot, or rent bicycles for a delightful adventure. If you feel like sailing on the harbor, visit Island Boat Rental. For dinner, head to Brant Point Grill, and get a table overlooking the scenic harbor. The restaurant boasts some of the area’s finest fresh-caught local seafood, including plump lobsters and decadent New England clam chowder.
Massachusetts’ capital city has plenty of vacation rentals available, from luxury downtown lofts to cozy rowhomes. Take a Boston Chocolate Tour and sate your sweet tooth while you learn about the city’s many historical attractions. When the weather is pleasant, visit Gondola di Venezia to board a luxurious 36-foot Venetian gondola crafted in Venice and enjoy a relaxing private cruise down the Charles River with a complimentary basket of cheese and chocolates. Take a stroll down Newbury Street, home to a variety of luxury shops, and then stop in Bella Sante Boston Day Spa for a couples massage. The New England Aquarium is one of the most popular Boston date spots, boasting thousands of aquatic creatures, a 3-D IMAX theater, and other exhibits and attractions. For dinner, head to Mamma Mia in the North End for a classic Italian dinner in a romantic setting.
4. The Berkshires
The Berkshires are dotted with a variety of charming villages and towns. Pack a picnic, and head to Stockton to visit the famous Berkshire Botanical Garden – it contains over 3,000 species and varieties of plants spanning 15 acres. For a bucolic day trip, head to Sweet Brook Farm in Williamstown in the Northern Berkshires. Visit the herd of alpacas, and stop by the country store for some fresh maple syrup and other goodies. Check the calendar at the Mahaiwe Performing Arts Center, and enjoy an evening of cinema, dance, live music, or other performances. For dinner, enjoy some outstanding American comfort food in a cozy, tucked-away alley restaurant at Once Upon a Table in Stockbridge.
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Located just a half-hour northwest of Boston, Lexington is a historic town with that classic New England feel and close proximity to the big city. Visit the historic Wilson Farm for a relaxing day indulging in farm-fresh baked bread, candies, and other treats. The scenic farm has a wonderful market full of local foods, gifts, and more. Check the schedule beforehand, as the farm hosts events such as cooking classes and tours. Treat yourself and your travel companion to a luxurious day of pampering at the Bella Sante day spa. For dinner, enjoy exquisite French cuisine at Tres Petite Creperie, or if you’re feeling decadent, swing by The Bancroft for some steak or lobster.
Salem is a historic town less than an hour’s drive north of Boston. The city is famous for its late 17th century witch trials, and the Salem Witch Museum is one of its most popular attractions. Salem is also known for its exceptional 17th and 18th century architecture, including the famous House of the Seven Gables, making it one of the most popular spots to look for vacation rentals in Massachusetts. This vibrant city has plenty of non-spooky romantic attractions too, including some wonderful romantic spots. Take a boat to Bakers Island Light Station, a picturesque lighthouse with plenty of history. Salem Willows Park is a fantastic place to spend a day; it’s an oceanfront amusement park, arcade, and picnic area. While you’re in Salem, enjoy a delicious Italian meal at Bella Verona, an intimate trattoria with exquisite cuisine, an extensive wine and beer list, and delectable homemade cannolis.
Plymouth is a historic coastal town that’s about an hour south of Boston. Founded in 1620, it was the first Pilgrim settlement, making it one of the best vacation destinations for couples who enjoy American history. Visit the Plymouth Bay Winery to taste some excellent wines with pairing recommendations. Enjoy a full-service dinner cruise or whale watching at Pilgrim Belle Cruises. Take a romantic hand-in-hand stroll along the scenic Town Brook at Elder Brewster Gardens. Patrizia’s is a great spot to enjoy some delicious Italian cuisine by candlelight in an elegant dining room, or sit on the outdoor waterfront patio if the the weather allows.
Rockport is a small town roughly 40 miles northeast of Boston. It’s known for its pebbled beaches, historic lighthouses, and wooded hiking paths. Shalin Liu Performance Center is a breathtaking building that’s designed to showcase chamber music, and the acoustics are unparalleled. The floor-to-ceiling stage backdrop provides an incredible view of the beautiful Rockport Harbor. The venue hosts classical, jazz, folk, world, and pop music concerts, as well as films and other performances. Rockport is a great place for a classic dinner-and-a-movie date. Visit the old-fashioned Little Art Cinema for a film, and then stop by Cheryl’s By the Bay for a unique dining experience. The seafood is fresh and delicious, and the dining room has an enchanting atmosphere thanks to twinkling lights shimmering overhead.
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