Sightseeing Day Sail around Boston Harbor

Recommended by 94% of travelers

Badge of Excellence

Boston, USA

Very popular!

5+ bookings in the past 6 hours.

1 hour 30 minutes to 2 hours (approx.)
Mobile ticket
Offered in: English

Why travelers loved this

4.8

· Adelete_B ·

Jul 2026

We had a great time the crew and the captain were great. I will definitely do it again. We love boston

· mma2450carole ·

Jul 2026

Wonderful sail around the Boston Harbor. Oysters shucked in front of you and good selection of beverages. Crew were delightful and knowledgeable about the area. First time on a sailboat for us and truly enjoyed the experience.

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Overview

See Boston Harbor’s sights from the water on this day sail aboard a replica of a pilot schooner. Step aboard the boat and sail off through the harbor, bound for Spectacle Island, Fort Independence, Castle Island, and Long Island. Snap photos of Boston's coast from the water and feel free to ask the captain or crew questions about the passing landmarks.

Choice of several departure times to fit your schedule departures throughout the day
Water cooler available to fill your reusable bottles
Choose between from two duration lengths
Card-only bar on board the boat serves wine, beer, and soft drinks

What's Included

Duration: Choose between a 1.5 or 2 hour sailing experience
This is not a narrated tour, but the crew is available to answer questions on the sights & landmarks

Beverages are not included, but are available for purchase by credit card only.
Gratuities (recommended for the captain and crew)
Food (guests are welcome to bring their own snack aboard)

Meeting and Pickup

Meeting point

Classic Harbor Line Boston
60 Rowes Wharf, Boston, MA 02110, USA
The boat departs from Rowes Wharf, directly behind the Boston Harbor Hotel, located at (for GPS) 400 Atlantic Avenue, Boston (02110). Check-in at Rowes Wharf is located in the Ferry Terminal, a climate controlled public space, located on the wharf only steps away from our dock. If guests are lost or running late, please call us at 617-951-2460.

End point

This activity ends back at the meeting point.

Itinerary

Classic Harbor Line Boston MA Day Tours (Pass By)

Fan Pier (Pass By)

Boston Harbor Islands State Park (Pass By)

Additional Info

Confirmation will be received at time of booking
Not wheelchair accessible
Service animals allowed
Near public transportation
Most travelers can participate
Children must be accompanied by an adult
Minimum drinking age is 21 years. Coolers and outside alcoholic beverages are not permitted

Dress for the weather - it's often cooler on the water
Please let us know in advance if assistance is required for boarding
Only animals that perform a manual task to assist a person are permitted aboard. Emotional support animals and pets are not permitted
Plan to arrive at the ticket booth 15-30 minutes prior to the departure time. The meeting point is located directly behind the Boston Harbor Hotel in the Ferry Terminal just steps away from the dock. Boarding begins 5 minutes prior to the scheduled departure time.
This experience will be aboard Schooner Adirondack III or Schooner Adirondack IV
Large group bookings are not permitted. Multiple bookings are subject to added fees or cancellation by operator
This tour/activity will have a maximum of 80 travelers

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Cancellation Policy

You can cancel up to 24 hours in advance of the experience for a full refund.

Traveler Photos

Gallery picture 1 (from a traveler's review)

Gallery picture 2 (from a traveler's review)

Gallery picture 3 (from a traveler's review)

Gallery picture 4 (from a traveler's review)

Gallery picture 5 (from a traveler's review)

Featured review

Jose_G

We had an incredible time on the Sightseeing Day Sail around Boston Harbor with Classic Harbor Line. From start to finish, the experience was smooth, relaxing, and absolutely beautiful. The crew was friendly and welcoming, and our captain was fantastic—knowledgeable, personable, and clearly passionate about sailing. The views of the city skyline and historic landmarks from the water were stunning, and the boat itself was elegant and comfortable, offering the perfect balance of adventure and tranquility. It was the perfect way to see Boston from a new perspective and enjoy a peaceful day on the water. Highly recommend to anyone visiting or living in the city—this was a perfect experience!

Reviews

4.8

based on 591 reviews

Total reviews and rating from Viator & Tripadvisor

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Sort by: Most insightful

A different view of Boston!

Jim_R, Jul 2026

While the weather wasn't the best, very cloudy, windy and wet and limited where we could go, we had a good time chatting with the crew, who were very knowledgeable about the area, and we meet some fun new people!

The perfect day

Ann_L, Jul 2026

We had a wonderful day filled with sun and breeze! The captain and crew were wonderful and going around the harbor was relaxing and romantic.

Great sailing

Logan_B, Jul 2026

Excellent experience and service. Would sail again. Crew was knowledgeable and friendly. A++++++++++

My family and I had a...

Kasey_H, Jul 2026

My family and I had a great time! They were visiting from Florida, first time on a sail boat and the crew was very kind, informative, and all around amazing. We will definitely be back!

Fun family sail

Alissa_B, Jul 2026

Sail boats lean, if you don't like the boat tipping go on a catamaran or a motor yacht. This sail on Adirondack II was awesome! Great captain and crew, saw a lot of Boston Harbor. I would definitely sail with them again!

Great time

Adelete_B, Jul 2026

We had a great time the crew and the captain were great. I will definitely do it again. We love boston

An Awesome Sailing Tour

Judith_S, Jul 2026

They will be allowed to steer the ship if they want. It was the highlight of my trip to Boston. I got a great recommendation for a place to try clam chowder and it was very good.

Afternoon sail with oysters, shrimp and drinks.

mma2450carole, Jul 2026

Cool break on the hottest day

James_S, Jul 2026

Eric and the crew did a great job of making us feel at home. They even let my 11 year old take the steering wheel as we navigated the Harbor. The cool breeze was a great break on a 90+ degree day. Thanks for such a great time.

A beautiful way to see...

Beth_C, Jun 2026

A beautiful way to see the city from another point of view! We were on the adirondakII with Capt Michael, Mike and Keira. They did a fabulous job!

Mediocre tour at best, boring sail.

Luis_S, Jun 2026

Boring. Just zig zags in front of city. Guides do not explain anything only offer drinks and expect tip afterwards. They should give some history presentation or talk about the architecture. Seats are hard and uncomfortable.

Response from Host, Jun 2026

Luis, thank you for booking a sail with us and taking some time to provide your valuable feedback. We are sorry to hear that this experience was not as lively or as entertaining as you had hoped. The excitement and speed of the sailing portion can vary from slow and relaxing to thrilling, but unfortunately we don't have much control over that aspect. The route can also vary significantly depending on the wind of the day. We appreciate your thoughts about adding narration and do encourage our guests to ask the crew all about the area if they want. We hope you will get the chance to join us for a more exciting sail in more favorable conditions. - Classic Harbor Line Boston

Trashy Drunks Ahoy!

Holly_S, Jun 2026

A few days prior to this sailing adventure, we had been sailing with a different group. On this trip, there were two groups of people who got drunk (which was fine) and were yelling over the noise of other people and the wind (this was not enjoyable). On the other sailing, the captain and mates educated us about the areas we were sailing near. This trip did not because it was so loud we wouldn't have heard them anyway. Some of the drunk people also left their trash and it blew onto me, getting my shorts wet. This trip was such a disappointment.

Response from Host, Jun 2026

Holly, thank you for booking a cruise with us and taking some time to provide your valuable feedback. We are sorry to hear that this experience was negatively affected by the noise and debris from the other groups. We will let our crews know to keep a closer eye on these aspects and to step in if they can help in these situations. We hope to be able to provide you with a better experience on another occasion. - Classic Harbor Line Boston

Schooner cruise

Jeanne_N, Jun 2026

An absolute fantastic trip. The crew were amazing, patient, even with a small child running up and down the deck without parental supervision. The child climbed onto the side where there were only ropes preventing him from going overboard! Again, no parents watching over them. We decided last-minute to get tickets and we are so glad we did. Changing gusts of winds from nothing to full sails, it was all handled extremely well. I will definitely be returning!

Went with me and my two...

Kenneth_L, Jun 2026

Went with me and my two children (20 and 10). A lot of fun. Fun trip and beautiful traveling. Crew was extremely friendly.

I really enjoyed the...

Lynn_D, Jun 2026

I really enjoyed the voyage around the Harbour. The crew was informative and friendly and helpful. It was a wonderful experience.

It was a lovely afternoon...

Jody_H, Jun 2026

It was a lovely afternoon on the water. The crew was friendly, professional and helpful. Would definitely recommend

It was such a beautiful...

Dan_T, Jun 2026

It was such a beautiful and relaxing adventure! Amazing way to see the city, highly recommend to all!

Very cool experience

crystal_r, Jun 2026

First of all I have never been on a sail boat before it was incredible to watch the crew manage the sails and keep us moving along at quite a clip. Also almost as impressive was how they managed to keep us all topped up on drinks at the same time. It was a very cool experience and I'm very glad I did it. Well worth it and I would definitely recommend if your looking for something a little different to do while your in the city.

Great trip!

Steve_J, Jun 2026

Wonderful tour of the harbor. Great crew and a very nice afternoon. Gavin’s my Drinks onboard was a nice touch as well. Just a very nice relaxing cruise.

Fun trip around the...

Brenda_M, Jun 2026

Fun trip around the Harbor. Not crowded and the staff was very knowledgeable. Eric the captain was great!

Wonderful sailing tour of...

Timothy_J, May 2026

Wonderful sailing tour of Boston Harbor. Very cool way to see the harbor. The Adirondak II crew was informative, welcoming and attentive. Though the tour was not narrated, the crew was great at pointing highlights, names of the harbor islands and their histories.

Don't think twice :D

Ashley_D, May 2026

We had a great time and highly recommend! We were a group of six and had the best afternoon; the crew was friendly, knowledgeable and attentive. The boat is gorgeous and on a beautiful day, there's no way to beat it.

A very nice sail.

jihanshareef, May 2026

The captain was incredible. Crew was awesome. They provided blankets which came in handy because it was a chilly day. You won’t be sorry if you book them.

Great Boston Harbor Sail

Makram_S, May 2026

The Sail boat was awesome ! It was so beautiful to be out on the water and really experience what it was like to be on a sail boat! The captain Anna was very awesome! Charlie, Alex, and Mike the deck hands were enthusiastic, friendly, fun! They offered to take lots of pics and kept the drinks comming!

Highly recommend

Maria_C, May 2026

Beautiful experience with an amazing crew! It was my first time on a sail boat and the crew made me feel so safe! It was a great way to see the Boston Harbor!