Boston is a city with a very rich history and is filled with tons of culture. After all, it’s known as one of the country’s oldest cities and happens to be the capital of Massachusetts. Some notable historical events include the Boston Tea Party, the Battle of Bunker Hill, as well as the Siege of Boston. With all that history, it makes for a great place to live and/or visit. Even more so around a special day like Valentine’s Day!
Enjoy Valentine’s Day Dinner on Boston Harbor
Treat your special Valentine to something extraordinary on Valentine’s Day. City Cruises Boston has the perfect romantic outing, where you can kick back and relax on a luxurious yacht. The Boston Valentine’s Day Signature Dinner Cruise is a wonderful way to show your Valentine all the romance you can fit into an evening cruise around Boston Harbor. It is two glorious hours on the water, so be sure to dress in your semi-formal attire and get ready for an amazing Valentine’s dinner you will never forget.
This exhilarating evening on the water will include dancing to the music from a live DJ, delectable and creative cocktails available from the cash bar, and a chef-designed signature buffet menu along with Boston’s breathtaking views. You will be greeted by warm, welcoming, and hospitable staff who will ensure you have an amazing time.
The buffet menu includes Caesar Salad and Caprese Salad. Main courses feature Coriander Crusted Salmon and Root Vegetable Fricassee, while Garlic Mashed Potatoes and Seasonal Vegetables complement your main course. Enjoy cakes, brownies, and seasonal fruit for dessert. Unlimited coffee, tea, and iced tea are available as well as a guaranteed table for your party.
The cruise has extras and upgrades available for a more customized experience. Available packages include:
Silver Package:
- Glass of champagne/sparkling wine
- Single rose, per couple
Gold Package:
- Glass of champagne/sparkling wine
- Single rose, per couple
- Guaranteed window seat
Platinum Package:
- Romance package (bottle of Mumm) [or equivalent]
- 1/2 dozen roses and logoed flutes
- Guaranteed window seat
Fun Things to Do in Boston on Valentine’s Day 2026
Join ZEST The Collective for Open Hearts: A Valentine’s Day Cacao Journey, February 14 from 1:00 –3:30 pm, with Carla L. This heart-opening experience invites you to explore the magic of cacao through delicious treats, connection, and a Reiki-infused sound bath. Whether you join solo or with a loved one, you’ll be welcomed into a warm, cozy space to celebrate love, presence, and community. Don’t miss this unique Valentine’s Day experience!
Join Formaggio Kitchen at Kendall on February 7 from 7:30 pm – 9:00 pm for French Bistro Classic: Wine and Cheese, a romantic pre–Valentine’s experience led by Justin. Explore the timeless pairings that define Parisian bistro culture as you taste velvety reds, crisp whites, and expertly selected cheeses that capture the charm of France’s vineyards and cafés. Whether you attend with a partner, a friend, or simply a love for life’s pleasures, this elegant tasting promises an evening of rich flavors and classic French romance.
Join Seven Hills Pasta Co. on February 13 from 6:00 – 7:30 pm at Canopy by Hilton Boston Downtown for a fun and flavorful Valentine’s Day pasta class—perfect for a date night. Learn to make fresh pasta from scratch, shaping dough into forms like gnocchetti, orecchiette, and farfalle while exploring the culinary traditions behind each style. After the hands-on lesson, enjoy a farm-to-table pasta dish featuring either ossobuco beef bolognese or fresh pesto, along with one complimentary glass of wine (cash bar available). This relaxed yet informative evening ensures you go home with new skills, delicious tastes, and a memorable start to Valentine’s weekend.
Other Unique Valentine’s Day Options in Boston
Bring your date for a night of ice skating at The Boston Common Frog Pond. Whether you are a longtime ice skater or a beginner, this is a great place to enjoy Valentine’s Day. You can try skating lessons here, including private or group lessons. Skates and lockers are available to rent. Hang tightly onto your partner as you glide across the ice. Later, you can head over to the Frog Pond Café, which has sandwiches, salads, snacks, and beverages. Ice skating runs from November to March.
Get romantic at Carrie Nation Restaurant and Cocktail Club, a speakeasy in downtown Boston that is sure to make your Valentine’s Day just a bit spicy for you and your date. Here you will find yourself feeling like you are back in the 1920s during the time of prohibition. They have various food menus as well as cocktails to quench your desire for a drink in a bygone era. “And though the main dining spaces are charming and inviting, slip along the bar to a corridor just beyond, making your way to the red velvet curtain and get ready to get raided,” according to their website. “Make sure to have a twenty-spot, secret handshake or password, and find yourself in Boston’s Original Speakeasy.”
Book Your Boston Valentine’s Day with City Cruises
Boston is such a great town with so much to do; it’s easy to see how it’s a top Valentine’s Day destination. Even with all there is to do, nothing beats a day on the water. So, book your Valentine’s Day with City Cruises in Boston, and you won’t go wrong. You and your Valentine won’t want to miss the romance on the water.
FAQs – Celebrating Valentine’s Day 2026 in Boston
What is included in a Valentine’s Day dinner cruise?
A Valentine’s Day dinner cruise includes a delicious multi-course meal, live or DJ entertainment, and incredible views of Boston Harbor and its skyline. The atmosphere is designed for romance, with private tables available for couples.
Can dietary preferences or restrictions be accommodated?
Yes, City Cruises can accommodate dietary needs such as vegetarian, vegan, and gluten-free options. Please mention your requirements when booking or notify us in advance of your experience.
What is the dress code for Valentine’s Day cruises?
The dress code is typically smart casual to semi-formal. Many guests enjoy dressing up to enhance the romantic experience.
What Boston landmarks will we see during the cruise?
During the cruise, you’ll take in views of Boston’s iconic landmarks, including the USS Constitution, Bunker Hill Monument, Boston Tea Party Ships, and the shimmering city skyline.
What happens if the weather is bad on Valentine’s Day?
City Cruises operates rain or shine. The vessels are equipped with climate-controlled indoor spaces to keep guests comfortable regardless of the weather.
How far in advance should I book a Valentine’s Day cruise?
It’s recommended to book at least a month in advance, as Valentine’s Day is a popular holiday and cruises tend to sell out quickly.
Can I reserve a private table for two?
Yes, private tables are available to ensure a romantic and intimate experience. Early reservations are encouraged to secure the best seating.
Does City Cruises offer special packages for proposals or other celebrations?
Yes, City Cruises offers customizable packages for proposals or special celebrations. Contact their team to arrange added touches such as flowers, champagne, or a dedicated moment for your event.
Original Post Date: December 15, 2023