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Romantic Things to Do in Boston

Romantic Things to Do in Boston

Known for fantastic food, walkable neighborhoods, and easy proximity to other New England attractions, Boston is an ideal destination for an adventure with your sweetheart. Here are some ways to get romantic in the waterfront city.

Sail on Boston Harbor

Nothing says romance quite like a sailing excursion on Boston Harbor. Hop on a clipper ship, sails and all, or opt for a pilot schooner to savor views of top sights such as the Boston Harbor Hotel, New England Aquarium, and Mystic Tobin Bridge. 

Taste Food, Wine, and Chocolate

It’s been said that the way to the heart is through the stomach, so take your significant other on a gastronomic adventure around Boston. If you have a sweet tooth, join a chocolate tour; for a more elevated culinary option, consider a food and wine tasting in the lovely Back Bay neighborhood. 

Take a Sunset Dinner Cruise

For skyline views and a romantic evening on Boston Harbor, book a cocktail or sunset dinner cruise. Tours typically offer a buffet, a live DJ, and drinks, so dine in style and dance all night with your special someone.

Enjoy the New England Foliage

New England is known for its colorful autumn leaves, so don’t miss the chance to take your partner along on a fall foliage journey along the winding roads of the White Mountains. Tours usually leave from Boston, and include hotel drop-off.

Spend a Day in Martha’s Vineyard

A short ride from Boston, you’ll find the quaint island paradise of Martha’s Vineyard, a scenic stretch of coastline just south of Cape Cod. Stroll through the island’s charming villages, check out the pastel-colored cottages, and explore the waterfront. If you’re there in summer, hang out on the beach and take a quick dip in the Atlantic.

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Free Cancellation:Get a full refund up to 24 hours in advance on most experiences.See Details

7 Tours and Activities | All Boston Tours

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Martha's Vineyard Day Trip from Boston with Optional Island Tour (Small Group)

Martha's Vineyard Day Trip from Boston with Optional Island Tour (Small Group)

star-4.5
Join Boston's only award-winning, original, Martha's Vineyard Day Trip! Leave the trouble of driving to someone else and enjoy a day trip to Martha’s Vineyard from Boston. Then, take a short cruise to Martha's Vineyard then enjoy free time to explore or upgrade to add an island tour. Complimentary snacks, bottled water, island guidebooks and a discount card with island perks are provided during the drive.
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  • 12 hours
  • Free Cancellation
  • Taking safety measures
From
$105.00
From
$105.00
Taking safety measures

Boston's North End Secret Food Walking Tour w/ Private Tour Option

Boston's North End Secret Food Walking Tour w/ Private Tour Option

star-5
Get to know Boston through its food on this small-group walking tour limited to 12 people. With a guide, you sample seafood, Italian dishes, and other fare as you explore the city's North End neighborhood. Along the way, learn about the history of the area.
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  • 3 hours
  • Taking safety measures
From
$221.20
From
$221.20
Taking safety measures

Boston to New Hampshire Fall Foliage White Mountains Day Trip

Boston to New Hampshire Fall Foliage White Mountains Day Trip

star-5
New England is renowned for having some of the most beautiful fall foliage in the country—and this seamless, full-day tour from Boston makes it easy to discover the region’s vibrant scenery. Following morning pickup from your Boston hotel, travel to New Hampshire’s White Mountains, and stop for photography breaks along the Kancamagus Highway. Following lunch in charming North Conway (own expense), continue the seasonal sightseeing as you journey to the storied Mount Washington Hotel. At the end of the day, return to your Boston hotel.
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  • 12 hours
  • Free Cancellation
  • Taking safety measures
From
$125.00
From
$125.00
Taking safety measures

5-Hour Private Chauffeur Service from Boston

5-Hour Private Chauffeur Service from Boston

Travel in style! Our service puts a vehicle and chauffeur at your disposal, valid for any destination(s) from your pick up point in Boston. Prices are quoted for five hours of service. Additional hours will be billed to you directly for a total amount minus the value of this voucher.
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  • 5 hours
  • Free Cancellation
From
$457.80
per group
From
$457.80
per group

Spirit of Boston Sunset Dinner Cruise with Buffet

Spirit of Boston Sunset Dinner Cruise with Buffet

star-4.5
Try a unique alternative to a typical night out in downtown Boston on an exciting dinner cruise along the city’s waterfront. This expedition on Boston Harbor features an all-you-can-eat buffet meal with live entertainment and dancing. Watch the sunset, then take a stroll under the stars and enjoy the view of the illuminated Boston skyline at night or head to the dance floor for music and fun inside the ship’s nightclub. Bring that special someone or a whole group of friends for a night to remember.
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  • 2 hours 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$104.67
From
$104.67
Taking safety measures

Cocktails & Cannoli: Boston's North End Dessert Tour

Cocktails & Cannoli: Boston's North End Dessert Tour

star-5
As a small local business we can only take booking larger than 2 guests directly on our website: www.cocktailsandcannoli.com For last minute bookings, private and custom tours, please contact us at 617-744-9896 (text is fastest) BUT FIRST, DESSERT! Do dessert before dinner when you join us for Cocktails & Cannoli, an all inclusive North End Boston food tour. Skip the infamous lines to taste delicious drinks and classic cannoli, and sample the best sweets the North End has to offer. Not to mention the Paul Revere House and Old North Church along the way! To top it all off, our local tour guides will sprinkle in fascinating historic knowledge, fun cultural facts, and culinary tidbits.
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  • 2 hours 30 minutes
  • Taking safety measures
From
$79.00
From
$79.00
Taking safety measures

Boston's Emerald Necklace Guided Bicycle Tour

Boston's Emerald Necklace Guided Bicycle Tour

star-4.5
Discover Boston’s fall beauty on this guided, 4-hour, small-group bike tour around the North End of the city. Explore the historic Emerald Necklace, a 1,100-acre chain of parks linked by parkways and waterways in Boston and Brookline. Visit the shaded boulevard on Commonwealth Avenue, the shores of Jamaica Pond, and the popular, winding paths of the Arnold Arboretum of Harvard University. Also, see the Rose Kennedy Greenway, Boston’s newest public park; the famous Charles River Esplanade; the Boston Common and Public Garden and much more.
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  • 4 hours
  • Free Cancellation
  • Taking safety measures
From
$89.00
From
$89.00
Taking safety measures