Boston is best known for its baked beans, Boston Red Sox, Fenway Park, The Boston Marathon, and universities – not the things that attract lovers in droves.
However, when one digs a little deeper below the surface, one realizes that Boston is the best city in America for young couples.
Young and old couples, visitors, and locals love spending their Valentine’s Day in the capital of Massachusetts state.
If you adore your sweetheart (and we don’t doubt it!), you will want to spoil them with all the romantic surprises Boston offers.
Plan ahead of time, for many lovers will be flocking to Boston to celebrate the most romantic day of the year – 14 February 2025.
Check out our pick for the city’s most romantic Valentine’s Day itinerary.
Top Boston Valentine’s Day Tickets
# Martha’s Vineyard
# 5-hour Small-Group Food & History Tour
# Boston Trolley tour
Table of Contents
Things to do on Valentine’s Day in Boston
Here are our recommended 12 romantic things for your Valentine’s Day week in Boston.
You only need to bring your boyfriend or girlfriend along.
Explore Martha’s Vineyard
The 12-hour Martha’s Vineyard day trip is an award-winning romantic outing for couples in love.
You board an air-conditioned Mini Coach from Boston to Cape Cod, from where you get on a cruise to Martha’s Vineyard.
Once you reach, you can spend hours exploring at your leisure or upgrade to the narrated Island Tour, which includes stops at Edgartown and Gay Head Cliffs.
Book This TourGet romantic on a dinner cruise
This Boston Harbor cruise includes an all-you-can-eat buffet, live entertainment, and dancing.
Watch the sunset, then stroll beneath the stars to take in the beauty of the illuminated Boston skyline at night, or head to the ship’s dance floor for music and fun.
Bring that special someone for an evening to remember this Valentine’s Day.
Book This CruiseIf you prefer a slightly longer experience, opt for the Boston Odyssey Dinner Cruise.
If you have some other romantic activity planned for the evening of 14 February, check out the Boston Lunch Cruise.
Enjoy a Boston sunset cruise
A sunset cruise lets you enjoy the beautiful Boston architecture and landmarks from the best vantage point.
Even as you glide over the waters, you will watch the sun slowly go down, painting the sky in many colors.
You can have snacks and beverages from the onboard bar while enjoying the spectacular views.
If you and your partner love to laze around, this is an ideal way to spend Valentine’s Day together.
| Sunset Cruise | Cost |
|---|---|
| Harbor Sunset Yacht Cruise | US$47 |
| 2-hour Boston Harbor Sunset Cruise | US$49 |
| Champagne Sunset Sail from Rowes Wharf | US$71 |
Go in search of Boston’s best food
Elders have said, “The way to his heart is through his stomach,” and the same can be said for the way to her heart, too!
That is why one of the best ways to celebrate Valentine’s Day 2025 in Boston is to go on a food tour.
On these tours, a local food expert helps you experience the food and culture of the city.
If you and your lover are food connoisseurs, we recommend you opt for one of the numerous tours.
Go around on the Boston Trolley tour
The Boston Trolley tour is an excellent way to explore the city.
You can board these Trolleys, get down at any attraction on the loop, and get back on the Trolley once you are done exploring.
Couples who want to stretch their romantic celebration can opt for the Platinum ticket, which gets you two days of unlimited trolley boarding.
Book This TourIf you want the experience to be more elaborate, check out this tour, which includes a 90-minute harbor cruise.
Get frightened on a night tour of Boston
If you and your spouse prefer nighttime romance amongst the glittering lights, try this “frightening” tour aboard the Trolley of the Doomed.
The Trolley roams around Boston’s haunted streets and burial grounds, and you discover some of the city’s deepest, darkest secrets.
This activity is perfect if you have already planned something romantic for the day and are looking for a wild adventure for the night.
Book This TourGo pub crawling with your loved one
Image: Bostoncrawling.com
If you love beer or pub-hopping, the Boston History Tour & Pub Crawl is the best way to celebrate Valentine’s Day with the person you love.
You and your boyfriend (or girlfriend!) will discover the best of Boston’s hops and history on a pub crawl.
This tour is open only for 21+ year-olds, and couples must show a valid ID to join.
Your tour ends at the pickup location, after which you can hop into any pub and continue your romance.
Book This TourFeel like a student at Harvard University
Harvard is America’s oldest university and is located 10 km from Boston.
During the Hahvahd University Tour (yes, that’s what it’s called!), you see Harvard through the eyes of a student.
The 70-minute student-led walking tour of Harvard’s campus is funny and educational.
Book This TourGet lovey-dovey on a cycle tour
If you love cycling, you and your partner can discover Boston’s top attractions on this comprehensive guided bike tour.
The cycling tour goes to places where the other tours can’t, so you get to see each community’s unique character and charm up close.
Book This TourDo the unusual – learn Boston’s history
Actors posing at Boston Tea Party Ship and Museum.
Boston is a historic city with so many stories to be learned under the calm exterior.
Learning a city’s history may not be the traditional way to celebrate Valentine’s Day in Boston, but why not if you and your partner are curious?
On a self-guided tour of the Boston Tea Party Ships and Museum, you can relive the most important event leading up to the American Revolution.
Or you can be part of the Revolutionary Story Tour and see all the important sites of the American Revolution. This tour of Boston’s famous Freedom Trail is 3 hours long.
If you want a quick overview of Boston’s contribution to present-day American freedom, try out the 90-minute tour with a costumed guide.
Get sporty at Boston Fenway Park
If you or your lover is either a Boston Red Sox fan or just a plain sports lover, Boston Fenway Park is a great place to visit on 14 February 2025.
During this tour, you will explore the historic grounds of Fenway Park, “America’s Most Beloved Ballpark,” home to the Boston Red Sox.
A local expert guide will narrate the fables of this 109-year-old Boston monument’s fables, which will make you fall in love with the Boston Red Sox all over again.
Book This TourHold Hands on this Walking Tour
Spend quality time with your loved one on this 2.5-hour guided walking tour, where you and your partner will stroll along the historic path, enjoying the city’s rich past and charm.
This comprehensive tour ensures you’ll experience 16 official historic sites along the Freedom Trail, such as the Golden Dome of the Massachusetts State House and the the poignant sites of the Bloody Massacre.
Visit the resting places of famous patriots like Paul Revere, John Hancock, and Samuel Adams, a reminder of your enduring bonds.
This is one of the best ways to spend Valentine’s Day in Boston.
Book This TourBoston Go City Pass for more attractions
What can be more romantic than not worrying about the cost and roaming around Boston freely?
Imaginative romantic couples go for a Discount Pass, which helps them get more out of less during Valentine’s Day week.
The Boston All-Inclusive Go City Pass helps tourists and locals see must-see attractions yet saves lots of money.
Get This PassSo, how do you and your love plan to celebrate Valentine’s Day 2025 in Boston?
Book ahead before your options run out – after all, it is yet another way of showing that you care.
Additional Reading
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