9 Romantic Getaways from Boston: Best Trips for Couples

As romantic as it can be to grab a cannoli and walk hand-in-hand down cobblestone streets through Boston’s North End, sometimes you just need to get away. Maybe you’re dreaming of waking up to the sound of the surf crashing against the beach, or ocean views. Or, you want to go on a hike to appreciate New England fall colors.

If you need a little help planning a romantic getaway, here are nine couples getaways from Boston.

• Best for touring history, getting outdoors, and great food - Lenox, Massachusetts
• Best for a luxury oceanside getaway - Newport, Rhode Island
• Best for queer couples who love art - Provincetown

• Best for classic New England summer weekend trip - Martha’s Vineyard
• Best for partners who want entertainment options - Portland, Maine
• Bet for romantic sunsets, picnics, and beaches - Nantucket

• Best for big city lovers - New York City
• Best for history and nature lovers - North Conway, New Hampshire
• Best for winter getaway - Stowe, Vermont

There are so many options for weekend getaways for couples from Boston that it can feel overwhelming to narrow it down. It's helpful to ask yourself what kind of weekend getaway you want — a day at the beach, or a spa day — then scroll through this list. You'll be sure to find the perfect romantic day trip.

• ‌Perfect for:‌ Touring history, getting outdoors, and great food
• ‌Highlights of‌ ‌Lenox‌‌:‌
  • Gilded Age mansions
  • Biking, kayaking, and hiking
  • Candlelight dinners

Lenox is roughly a two hour drive from Boston, a straight shot on I-90.

Nestled in the heart of the Berkshires, the charming small town of Lenox is a great spot to reconnect with your partner. Stay at a historic inn, Hampton Terrace Inn, built in 1897, and enjoy its elegant, well-appointed rooms and outdoor pool. Tour Ventfort Hall, a Gilded Age mansion, and imagine living together in another time.

Rent a bike or kayak and head out into the beautiful fall foliage for quality time with no screens and no distractions. At the end of the day, enjoy a candlelight dinner at one of the town’s great restaurants such as Bistro Zinc or Cafe Boulud at Blantyre. You’ll return from your couples getaway from Boston refreshed and reconnected.

• ‌Perfect for:‌ A luxury oceanside getaway
• ‌Highlights of‌ ‌Newport‌‌:‌
  • Cliff Walk
  • Newport Mansions
  • Visit a luxury spa

Newport is an hour drive from Boston with no traffic. Take I-93 South.

Once you arrive in Newport, stretch your legs along the Cliff Walk. Drink in ocean views before being captivated by the Gilded Age mansions that line the National Recreation Trail. Check into a boutique hotel like Gilded‌,‌ a unique stay where colorful, modern decor mixes with classic touches. The next day, you can explore the historic downtown, rent a sailboat and head out on the harbor, or tour the Newport Mansions and wander through the beautiful gardens. Top off your weekend getaway with a visit to one of Newport’s luxury spas, such as The Vanderbilt or The Bodhi Spa.

• ‌Perfect for:‌ Queer couples who love art
• ‌Highlights of‌ ‌Provincetown‌‌:‌
  • Whale watching
  • Art galleries
  • Provincetown Art Association and Museum

The easiest way to get to Provincetown from Boston is to hop on a ferry! Ferries run from the Seaport, it takes about an hour and a half to get to P-town and fares are $100 and up. Not only will you avoid weekend traffic down to the Cape, you’ll enjoy the scenic trip.

If you’re a member of the LGBTQ community, you’ve heard of Provincetown (or “P-town”). This Cape Cod town has been a welcoming haven for gay and lesbian couples for more than 50 years. Commercial Street, the main street, features five plus art galleries where you can find something to hang above the mantelpiece. Spend some time at the Provincetown Art Association and Museum appreciating the artistic gifts of Cape Cod residents, many of whom contributed to the town becoming a hub of LGBTQ activity.

If you left the kids with the grandparents, stay at “adults only” The Brass Key guesthouse and truly get a break from the hubbub of children. Guest rooms have private balconies that overlook the outdoor pool and grounds, fireplaces, and jacuzzi tubs.

After drinking in the town’s picturesque charm on day one, spend the next relaxing at one of its beautiful beaches, or go on a whale watching tour.

These romantic getaways from Boston immerse you in a classic New England summer, give you entertainment options, and great restaurants to dine by candlelight.

• ‌Perfect for:‌ A classic New England summer weekend trip
• ‌Highlights of‌ ‌Martha’s Vineyard‌‌:‌
  • Edgartown Lighthouse
  • Boutique hotels, no chains
  • Beaches and small towns

First you’ll have to drive down MA-3 South, then hop on a ferry.

Martha’s Vineyard is perhaps one of the best weekend getaways from Boston. It’s the perfect romantic getaway from Boston. The island has gorgeous beaches, quaint small towns, and great restaurants for a romantic night out. Visit the Edgartown Lighthouse — the views of Edgartown Harbor, Chappaquiddick, and Cape Cod will leave you breathless.

Martha’s Vineyard retains an old world charm in part because it keeps out chains, whether that is fast food restaurants or hotels. You’ll have your pick of boutique and luxury hotels like The Mansion House Spa, built in 1794 this Victorian lady has gorgeous wrap-around porches, ocean views, and an on-site full spa where you can indulge in a couples massage.

• ‌Perfect for:‌ Partners who want entertainment options
• ‌Highlights of‌ ‌Portland‌‌,‌ ‌Maine‌‌:‌
  • Portland Symphony Orchestra
  • Craft breweries
  • Romantic bed and breakfasts

Portland is close to a two hour drive north of Boston up 1-495 N. Amtrak offers train service from North Station if you don’t need a car in town.

Portland is a great town if you want to go with the flow on your romantic weekend but have lots of options. Sometimes you don’t want to make a plan, but just hop in the car, show up and figure it out.

If it’s a warm night, sit outside at one of its 30 craft breweries and enjoy a cold one. If you want to dress up for a night on the town, get swept away by the music of The Portland Symphony Orchestra or the grace of the dancers at the Portland Ballet.

Craving both exercise and to connect with nature? Head out on the water of Casco Bay. There are kayak and stand up paddeboard rentals available, or you can book a tour. You can also drive further up the coast to Bar Harbor and enjoy a day of hiking at Acadia National Park.

Stay at a romantic bed and breakfast like The Chadwick Bed and Breakfast. Comfortable and elegant rooms each have a unique charm. Art galleries, museums, shops, and restaurants are all within walking distance.

• ‌Perfect for:‌ Romantic sunsets, picnics, and beaches
• ‌Highlights of‌ ‌Nantucket‌‌:‌
  • Beautiful sunsets and lighthouses
  • Whale watching or cruises
  • Excellent seafood restaurants

It’s a 3-hour drive down MA3- South and then a ferry to the island.

A Nantucket sunset is not to be missed. Watch the sky light up with pinks, reds, and golds, spilling romance over ocean waves and just try resisting being swept away by romance. Bring a picnic basket and sit out under the stars on the grounds of Brant Point Lighthouse as part of your romantic weekend getaway. Book a whale watching cruise or head out on a sleek schooner for a day on the water if the weather is nice.

Spend a day at the beach and frolicking in the ocean before dining at The Ships Inn Restaurant, located in a historic whaling captain’s mansion two blocks from the historic main street. Or book a reservation at the Straight Wharf Restaurant and sip wine while watching boats come and go in the harbor.

Stay at luxury hotel The Wauwinet and walk down to the private beach for a sunset stroll.

On a three or four-day weekend it’s possible to roam a big farther afield. Hop on a flight or drive a bit further to take in a Broadway show or

• ‌Perfect for:‌ Big city lovers
• ‌Highlights of‌ ‌New York‌ ‌City:‌
  • Broadway
  • World-class art museums
  • Restaurants for foodies

Most major airlines run hourly flights down to NYC. At an hour and a half on a plane, it’s not bad. If you prefer train travel, Amtrak has service from South Station.

Catching a weekend flight to New York City puts you right in the heart of Broadway, world-class art museums like the Metropolitan Museum of Art and the Guggenheim, great restaurants, and romantic strolls through Central Park.

Foodies will find romantic experiences at the Manhatta Restaurant with fabulous city views and an evolving menu, or dine at Le Rock in Rockefeller Plaza for a taste of old world glamor. Cuddle up in one of their leather banquettes while sipping a cocktail. NYC is a classic weekend getaway for couples from Boston for a reason — you can’t go wrong in the Big Apple.

• ‌Perfect for:‌ History and nature lovers
• ‌Highlights of North Conway:‌
  • Cross-country skiing, mountain biking, and hiking in the White Mountains
  • Walk across the Saco Covered Bridge
  • Russell-Colbath Homestead

Drive up 1-95N.

The historic sites of North Conway include the Saco River Covered Bridge, one of New England’s famous covered bridges. Walk across hand in hand and stop for a kiss by the water. Up the road from the bridge, pop into the Russell-Colbath Homestead and learn about domestic life in the 19th century.

A day of hiking in the nearby White Mountains, part of the Appalachian Trail, will take you away from the city’s hustle and bustle. Go cross-country skiing in the winter, mountain biking in the summer, or visit Mount Washington, the Northeast’s highest peak, in any season.

North Conway is a year-round destination. If you visit for cross-country skiing or hiking be sure and book a room at the Golden Gables Inn, where you can soak your aches away in the on-site hot tub.

• ‌Perfect for:‌ A winter getaway
• ‌Highlights of Stowe:‌
  • Skiing and cross-country skiing
  • Outdoor ice skating
  • Spa at Spruce Peak

Stowe is a 3-hour drive up I-93N.

Spend a day on the slopes or cross-country skiing trails with your sweetie in Stowe, Vermont. Enjoy uninterrupted conversation on the ski lift, or take a break for a romantic meal in front of the fireplace at the Tipsy Trout. Take a shuttle to Spruce Peak Village and ice skate hand-in-hand on the outdoor rink.

After a day of outdoor activity, enjoy a dip in the outdoor heated pool or the hot tubs at the Spa at Spruce Peak. Book a facial or a couples massage to unwind. You’ll return to the city relaxed and reconnected.

As great as it is to live in Boston, sometimes it’s hard to connect with your partner in the midst of work, errands, and the city’s noise. Book one of these romantic weekend getaways for some quality time with the one you love.