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Beyond Boston

Sightseeing Day Sail around Boston Harbor

Recommended by 94% of travelers
Badge of Excellence
Boston, USA
High interest
Booked 5+ times today.
  • 1 hour 30 minutes to 2 hours (approx.)
  • Mobile ticket
  • Offered in: English

Why travelers loved this

4.8
·
· Susan_H ·
Sep 2026
It was way more than I expected. The ship was beautiful as was the weather. The crew members were fun, knowledgeable, and very helpful. Seeing Boston from the harbor was a whole new experience. The airplanes went right over us. I have already told a lot of my friends and family.
· Joy_C ·
Aug 2026
Our day sail on the Adirondack II around Boston Harbor was outstanding. The boat itself is stunning. Huge shout out to the crew, Claire and Charlie. From hoisting the sails to making sure we were comfortable, they did their jobs well. Captain Eric was a real professional and made the sail even better. Kudos to the captain and crew. Highly recommend sailing about Adirondack II!

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

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

Kathleen_S
We have a beautiful experience. The crew were helpful and engaging. Loved the time with friends. Enjoy your experience.

Reviews

4.8
based on 647 reviews
Total reviews and rating from Viator & Tripadvisor
Sort by: Most insightful

Beautiful sailboat to...

Laurie_M, Sep 2026
Beautiful sailboat to view the Boston Harbour. . Crew was attentive and friendly Beautiful scenery and knowledgeable staff

Beautiful sailing Boston!

Susan_H, Sep 2026
It was way more than I expected. The ship was beautiful as was the weather. The crew members were fun, knowledgeable, and very helpful. Seeing Boston from the harbor was a whole new experience. The airplanes went right over us. I have already told a lot of my friends and family.

Beautiful sail boat,...

Walter_F, Sep 2026
Beautiful sail boat, friendly service. Claire was a great host. Very entertaining to see them masterfully operating the sails.

A Lovely Afternoon Sail

Karen_W, Sep 2026
It was a pleasant 90 minute sail in the Boston Harbor with a seemingly cohesive team that all enjoy their jobs. It wasn’t a newsy historical tour but welcome banter of landmarks and some interesting Boston fun facts. I’d recommend taking the time to visit the harbor area & taking this cruise. My only suggestion is that the name of the vessel be identified & the need to secure actual tickets prior to boarding are required. This would be a Viator issue and not the sail line’s issue.

Great experience

Roger_F, Aug 2026
Very easy and great experience. Board right behind Boston Harbor Hotel. Very nice 90 min sail and Kira and Andrew were excellent and very knowledgeable.

Great crew and experience!

Aaron_K, Aug 2026
The crew was amazing. Friendly and informed and accommodating. Snacks might have been nice to have along with the drink options.

Beautiful sailing

COLLEEN_C, Aug 2026
The best sailing experience ever!! The female crew was FANTASTIC. Very interactive and always operating with safety first! We have done sailing in Newport and other areas, this was one of the best experiences we had! We will be back…..

Our day sail on the...

Joy_C, Aug 2026
Our day sail on the Adirondack II around Boston Harbor was outstanding. The boat itself is stunning. Huge shout out to the crew, Claire and Charlie. From hoisting the sails to making sure we were comfortable, they did their jobs well. Captain Eric was a real professional and made the sail even better. Kudos to the captain and crew. Highly recommend sailing about Adirondack II!

Just do it! You can’t go wrong

Susan_D, Aug 2026
This is so relaxing and well done. You can get beverages on board and crew is very knowledgeable. Highly recommend!!

We went on a so-so...

Ns_C, Aug 2026
We went on a so-so weather day, so it wasn't crowded at all. The tour was lots of fun, and the crew was very helpful and personable. I would have liked to have a few announcements about what we were seeing, but if you ask the crew, they would tell you.

Great experience!

Emily_R, Aug 2026
Cannot recommend this experience enough! The boat and views were beautiful, but the crew was what really made the experience great! Michael, Charlie, and John were so helpful and friendly, and made the experience so much fun! Thank you for the great afternoon!

Oolala

Crystal_B, Aug 2026
This whole vibe was just Oolala. You just get on the boat and feel the breeze and look at the skylines all around you. Don’t over think it, just go on the boat ride.

The Sailing Docents of Boston Harbor

Soren_J, Aug 2026
Captain & crew are excellent sailors with such knowledge of Boston Harbor’s history that you could call them the Sailing Docents of Boston Harbor. Remarkably, the Adirondack II is the exact same two-masted schooner my wife and I enjoyed as guests about 11 years ago in Newport.

Great family activity

Dean_L, Aug 2026
The crew was very helpful and knowledgeable. They do sell beverages on the ship but you are able to bring your own onto the ship too.

Sailing the Harbor!

Julia_L, Aug 2026
It was great being on the water and seeing Boston Harbor in a unique way. The Captain and crew were very informative and personable.

Beautiful serene couple...

Philip_R, Aug 2026
Beautiful serene couple of hours boating in the Harbor on a beautiful boat, the Adirondack II. Captain Eric and crew were great.!! Highly recommend.

Great cruise! Very chill...

Jennifer_O, Aug 2026
Great cruise! Very chill and relaxing. Crew was super friendly. Highly recommend. Suitable for all ages.

Wonderful time spent...

Lukasz_S, Aug 2026
Wonderful time spent sailing, totally relaxing and totally fun. One of the best things we did in Boston.

It's all about the crew!!

Karl_G, Aug 2026
Great day! Great way to see the harbor. No doubt the best crew out there...Charlie, Eric and Big Dawg!!

It was a fun and relaxing...

Andrea_W, Aug 2026
It was a fun and relaxing tour of the harbor. The crew was engaging and the whole experience was fun.

Beautiful views and experience!

Becca_H, Aug 2026
Captain and crew are so knowledgeable & fun to talk to on the tour! You will learn so much about Boston, the harbor, and sailing. Just ask! The views are amazing & seeing the harbor islands from a tall ship is such a fun experience. We loved being able to feel the ocean as we sailed.

Boston Bay Sailing

Sandy_S, Aug 2026
The boat ride is so relaxing. We loved the oysters and adult beverages that were served. The crew was attentive but chill. We would absolutely do this again.

Sail on the Adirondack!

Sean_G, Jul 2026
Wonderful experience, great for families. The crew was outstanding, funny, and if you have a young child they may even be able to captain the boat!

Great first sailboat ride!

Tanya_B, Jul 2026
We absolutely loved this sailing trip and would do it again! Our weather was perfect which absolutley helped! Terez was our captain and did great. Alex and Charlie were great and had lots of great information about the area and history. It was our first trip on a sail boat and very memorable.

A beautiful day on the water

James_W, Jul 2026
Great job, friendly staff, great captain. E has a bottle of champagne and enjoyed the water and the sun. The staff was super friendly and recommended a great lunch spot.

Wonderful Summer afternoon

Stephanie_V, Jul 2026
I had a terrible migraine- but the sail was still so relaxing and wonderful. My mother has never been to Boston, or even on a sailboat so the fact that she was impressed and had a good time was the high point for me. We came from Texas so, being out in the sun in late July is not something we get to enjoy regularly lol - 2 very enthusiastic thumbs up 10/10 would recommend

We had a fantastic time...

Eileen_G, Jul 2026
We had a fantastic time on this Boston Harbor Sail Tour. The crew was very enthusiastic and knowledgeable about the Boston area. We highly recommend this tour!

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++++++++++
Member Pricing
From

$51.71

per person
Was $54.44(-5%)

up to 24 hours before the experience starts (local time)

Book ahead!
On average, this is booked 18 days in advance.

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