Boston’s waterfront is one of the city’s most compelling features. With its historic ships, soaring skyline, and shimmering harbor, seeing Boston from the water offers a fresh perspective on this bustling hub. If you’re visiting, boat tours aren’t just a way to relax—they’re a chance to see iconic landmarks like the USS Constitution, Old North Church, and the Charlestown Navy Yard from a different angle. One of our favorites is the Harbor Champagne Sunset Sail from Rowes Wharf, which combines a classic sailboat experience with the magic of Boston’s sunset reflections. These cruises give you a peaceful way to unwind while soaking in the city’s beauty.
Whether it’s a quick harbor hop or an elegant dinner cruise, Boston offers a variety of water-based experiences. From romantic sunset sails to lively buffet dinners, there’s a tour for every interest. Our list highlights the most memorable options, helping you find the best fit for your schedule and budget.
Quick Overview
Boston’s boat tours range from guided sunset cruises and historic tall ship sails to luxury dinner cruises and in-depth sightseeing adventures. Many tours include live narration, offering insights into Boston’s landmarks, while others focus on the sheer pleasure of sailing. Prices vary from around $29 for a short narrated cruise to over $169 for a small-group tour with hotel pickup. For a full list of options, including classic tall ship cruises and Harbor Buffet Lunch or Dinner, check below.
1. Boston: Harbor Champagne Sunset Sail from Rowes Wharf
For about $82 per person, this classic sailboat takes you out into Boston Harbor at sunset. The two-hour trip offers stunning views of Boston’s waterfront landmarks like the Custom House and Seaport District. What makes this cruise stand out is the chance to enjoy champagne, wine, beer, and soft drinks—all available for purchase—as you gently sail into the evening. The crew is friendly and eager to answer questions about Boston’s sights, making it a relaxed yet scenic experience. It’s perfect for romantics or anyone wanting a peaceful break while taking in the city’s beauty. The boat’s vintage charm adds to the ambiance, making the entire experience feel special.
Bottom Line: A romantic, elegant way to experience Boston’s harbor at sunset. Be sure to arrive early for the best sunset views.
2. Boston: Boston Harbor Sunset Cruise
At just $31, this 1.5-hour guided sunset cruise offers a straightforward way to enjoy Boston’s skyline as the sun dips low. It’s one of the most affordable options and includes views of the USS Constitution and other landmark ships. The cruise is well-rated, with 829 reviews praising its stunning scenery and lively onboard bar. It’s a good pick if you’re looking for a quick, relaxed boat ride with a focus on scenery and a casual atmosphere. The onboard bar makes it easy to sip your favorite drink while watching the city lights flicker on.
Bottom Line: An affordable, no-fuss sunset cruise that offers great views and a laid-back vibe, perfect for a short evening outing.
3. Boston Harbor Sunset Cruise
This 2-hour cruise, costing around $54.45, takes you past Old North Church, Charlestown Navy Yard, and the Leonard P. Zakim Bunker Hill Memorial Bridge. Unique to this experience is the chance to listen to the cannon fire of the USS Constitution at sunset—an authentic and memorable Boston tradition. You can choose to be on the open-air deck or stay inside, with drinks, snacks, and water available for purchase. The reviews highlight the beautiful views and the chance to see Boston’s waterfront from the water. It’s an ideal trip for those who want a relaxed, scenic evening with a touch of history.
Bottom Line: A peaceful way to enjoy Boston’s sunset with the added thrill of the USS Constitution’s cannon shot.
4. Classic Tall Ship Sightseeing Cruise of Boston Harbor
For around $35, the 90-minute tall ship cruise aboard the schooner Liberty Star is a favorite for its authentic sailing experience. Departing midday, it offers views of Boston’s skyline from the water while giving you a chance to learn about sailing from experienced crew members. The open deck space allows for social distancing and plenty of sunshine. Many visitors appreciate the informative commentary from the captain, making it both relaxing and educational. You can bring your own lunch, and drinks are available onboard, adding to the leisurely vibe. This cruise suits families and those eager to see Boston from a traditional sailing vessel.
Bottom Line: An excellent, family-friendly option for experiencing Boston’s harbor on a classic schooner with personal touches from the crew.
5. Boston: Downtown Harbor Sailing Cruise
At $67, this cruise offers a chance to sail past Inner Harbor Islands like the Moakley Federal Courthouse and New England Aquarium on the Adirondack III or IV schooners. It’s a relaxing, scenic trip designed for those who want a smooth, comfortable ride. The crew is available to answer questions, adding an informative layer to the experience. This cruise is ideal if you want a shorter but quality sailing tour with a focus on iconic Boston sights from the water.
Bottom Line: A good pick for those wanting a comfortable, scenic sail with easy access to popular waterfront attractions.
6. Sightseeing Day Sail around Boston Harbor
For around $66, this replica pilot schooner offers a daytime adventure with several departure options. It’s perfect for those who want to combine a sailing experience with the opportunity to visit Spectacle Island, Fort Independence, and Castle Island. The boat is open and airy, and the captain provides commentary about the passing landmarks. Many reviews mention the friendly crew and the chance to ask questions while enjoying the scenic views of Boston’s coast. Bring a packed lunch to enjoy during the voyage or purchase snacks on board.
Bottom Line: A versatile day trip combining sailing with visits to Boston’s seaside attractions.
7. Sunset Sailing Cruise on a Tall Ship in Boston Harbor
This $68 cruise on the 67-foot Liberty Star is a fantastic way to see Boston from a traditional tall ship at sunset. Departing from Fan Pier Marina, you’ll enjoy views of Fort Independence, East Boston, and Charlestown Navy Yard. You’re encouraged to grab a line if you want to help with the sails or just relax and enjoy the ride. Many appreciate the authentic sailing experience, and the cost makes it accessible for most travelers seeking a unique perspective. It’s particularly suited for those who enjoy hands-on sailing or want a romantic evening on the water.
Bottom Line: A charming choice for those seeking a classic, hands-on sailing experience with beautiful sunset views.
8. Boston: City Cruises Sunset Skyline Cruise with Commentary
For $55, this 1.5-hour cruise combines spectacular sunset views with narration about Boston’s key sights. You’ll see the USS Constitution firing her cannon and learn about Boston’s skyline and history from an expert guide. Many reviews praise the informative commentary and the stunning sunset scenery, making it a balanced mix of sightseeing and relaxation. It’s a solid choice for travelers wanting a guided experience that blends history with scenic beauty.
Bottom Line: An engaging, scenic cruise that pairs beautiful views with knowledgeable narration.
9. 90-Minute Boston Harbor Sunset Sightseeing Cruise
Costing about $56, this 1.5-hour boat ride offers spectacular sunset views and the chance to see the USS Constitution’s sunset cannon. Many reviewers mention the relaxing atmosphere and the informative narration that details Boston’s sights. The seasonal operation from May to September limits availability but makes the sunset ritual even more special. The cruise is a great budget-friendly option for a romantic evening or quick sightseeing.
Bottom Line: A well-rated, affordable sunset cruise that’s perfect for a relaxed, scenic end to the day.
10. Boston: Tall Ship Harbor Sail
This simple, 1.5-hour sail on the schooner Liberty Star is perfect for a casual harbor cruise. The focus is on relaxing and taking in the stunning city skyline and waterfront views. The experience is informal but engaging, with options to buy drinks and enjoy the fresh air. It’s ideal for travelers looking for a laid-back, scenic ride without elaborate commentary or formalities.
Bottom Line: A no-fuss, relaxing harbor cruise for fans of sailing and city views.
11. Best of Boston Small Group Tour w/Boat Cruise
This small-group tour, costing $169, combines a minivan city tour with a harbor cruise. It visits Harvard University, the Bunker Hill Monument, and the Tea Party site, finishing with a boat ride along Boston’s skyline. Limited to just seven people, it offers a more personalized experience. Many praise the guide’s knowledge and the seamless combination of land and water sightseeing, making it ideal for visitors wanting depth without rushing.
Bottom Line: A comprehensive, intimate tour suited for history and culture enthusiasts.
12. City Cruises Boston: Harbor Buffet Lunch or Dinner Cruise
Priced at $89, this buffet cruise on the Spirit of Boston lasts 2-3 hours and includes live music, dancing, and panoramic harbor views. You’ll enjoy a buffet meal served by servers while cruising past landmarks like the USS Constitution. This is perfect for those wanting a full dining experience combined with sightseeing and entertainment.
Bottom Line: A lively, relaxed cruise for food, music, and scenic views combined in one package.
13. Boston: New England Harbor Cruise
At about $46 for 1 to 1.5 hours, this moderately narrated cruise highlights Bunker Hill, the USS Cassin Young, and Fort Independence. It’s a good choice for travelers wanting a compact but informative tour that offers good photo opportunities of Boston’s skyline and waterside attractions. The focus is on visual storytelling with a relaxed pace.
Bottom Line: An accessible, scenic cruise for a quick and informative harbor overview.
14. Boston: Salem by Boat – Witch Trials & Walking Tour
This full-day tour ($129) combines maritime legend with Salem’s witch trial history. The boat ride is part of a broader exploration, including museums and walking tours. It’s perfect for history buffs and fans of pirates and witchcraft alike. The tour includes visits to Salem Witch Museum or Pirates Museum and plenty of free time to explore Salem on your own.
Bottom Line: For those interested in Salem’s dark past, this day trip offers a deep dive combined with a water journey.
15. Boston Harbor Sightseeing Cruise
This lightly narrated 1.5-hour cruise at about $46 offers a relaxed way to enjoy Boston’s landmarks like the USS Constitution and Spectacle Island. It’s perfect for photographers wanting a different perspective on Boston’s harbor and its islands. The cruise’s casual atmosphere makes it suitable for families or travelers looking for a short, scenic escape.
Bottom Line: A friendly, scenic cruise ideal for capturing memorable photos of Boston’s waterfront.
16. Narrated Sunset Cruise of Boston Harbor
For around $29, this budget-friendly 90-minute sunset cruise combines live narration with views of the Old North Church, USS Constitution, and Boston’s skyline. It’s a great choice for history and scenery lovers who want a relaxed, guided experience. Many reviews mention the informative commentary and the beautiful sunset scenery, making it an excellent value.
Bottom Line: An affordable, well-rated option for those who want to learn about Boston’s history while watching the sun go down.
How to Choose the Right Boston Boat Tour
When selecting your perfect boat experience, consider your budget, how much sailing you want, and whether you prefer guided narration or a more relaxed, self-guided cruise. If you’re looking for a romantic sunset, the Harbor Champagne Sunset Sail or Sunset Tall Ship Cruise are excellent choices. For a family adventure or history enthusiast, the Classic Tall Ship Sail or Small Group Tour with Boat offer engaging experiences. Budget travelers might favor the Boston Harbor Sunset Cruise or the Narrated Sunset Harbor Cruise, both offering great views at affordable prices.
Booking early, especially for popular sunset and dinner cruises, guarantees a spot and the best seats. Consider the season—most cruises operate from spring through early fall, with sunset cruises especially stunning during summer months. Think about your interests—whether scenic views, historical narration, or a lively dinner—and you’ll find the perfect water adventure.
In summary, Boston provides a rich lineup of boat tours—from romantic sunset sails to informative sightseeing and family-friendly schooner rides. For a relaxed evening, the Harbor Champagne Sunset Sail stands out, while history buffs will enjoy the Tall Ship Harbor Sail. For a mix of land and water exploration, the Best of Boston Small Group Tour offers a comprehensive experience. No matter your choice, early booking is recommended to secure the best times and spots on these memorable water journeys.