Sightseeing Day Sail around Boston Harbor
Overview
Choose between either a 1.5 or 2-hour sail around Boston Harbor aboard one of our beautiful schooner Adirondack sailboats! These classic boats are reminiscent of the sailboats from the 1890s. Sail past the seaport district, Castle Island, Fort Independence, Spectacle Island, and Long Island with Long Island Head Light. Great for families and friends who want to sail and see the sights of Boston from the water!
Within minutes of leaving the dock, guests will forget the distractions of life on land and experience the joy of a leisurely sail. Sit back and relax as the crew raises sail and provides beverage service. Drinks are available for purchase by credit card only. Guests are welcome to bring a picnic onboard.
The knowledgeable captain and crew are always ready to answer questions about the sights and history of Boston Harbor and its surrounding areas. From interesting facts to old-time legends, the maritime world of Boston has many great stories to offer.
What's Included
- This is not a narrated tour, but the crew is available to answer questions on the sights & landmarks
- Duration: Choose between a 1.5 or 2 hour sailing experience
- 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 Location
60 Rowes Wharf
Boston, MA 02110, USA
Detailed check-in instructions, including the exact address, are provided with your booking confirmation.
This activity ends back at the meeting point.
What To Expect
Book Online
Safe & secure Easy breezy Hassle‑free
Classic Harbor Line Boston MA Day Tours (pass by)
Fan Pier (pass by)
Boston Harbor Islands State Park (pass by)
Additional Info
- Confirmation is instant and will be received at time of booking
- Service animals allowed
- Public transportation options are available nearby
- Suitable for all physical fitness levels
- 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 52 travelers
Frequently Asked Questions (9)
Q: Will I get seasick on Sightseeing Day Sail around Boston Harbor?
Cancellation Policy
Still have questions?
We're here to help.
Activity code: C-5985P14
Traveler Photos
Reviews
Average 4.82 out of 5 stars based on 654 traveler reviews collected by Cool Shore Excursions and partner sites such as Cool Destinations and TripAdvisor
Additional Info
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Frequently Asked Questions (9)
The answers provided below were previously given in response to questions from Cool Shore Excursions customers.
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If you have any doubts about becoming seasick on the water, we recommend taking a Dramamine® Motion Sickness Relief tablet the night before your trip. Some people recommend taking it the night before your cruise and then again that morning so you will not feel so drowsy.
Feb 2023- For a full refund, you must cancel at least 24 hours before the tour start time.
- If you cancel less than 24 hours before the tour start time, the amount you paid will not be refunded.
- Any changes made less than 24 hours before the tour start time will not be accepted.
- Cut-off times are based on the tour local time (EST).
- This tour requires a minimum number of travelers. If it’s canceled because the minimum isn’t met, you’ll be offered a different date/experience or a full refund.
- This is not a narrated tour, but the crew is available to answer questions on the sights & landmarks.
- Duration: Choose between a 1.5 or 2 hour sailing experience.
- 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).
This tour requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.
Apr 2025There is no minimum age for this tour, so bring your wee one along for an adventure. This tour requires at least one adult to accompany children..
Apr 2025If a date or time is not listed on the calendar, it’s sold out or unavailable for another reason. Support cannot assist further if a date or time is not on the calendar.
If you find a date and time that works for you, book it NOW because things always sell out at this time of year.
Apr 2025Accessibility information for the Sightseeing Day Sail around Boston Harbor is as follows:
- Service animals allowed
- Public transportation options are available nearby
- Suitable for all physical fitness levels
Detailed check-in instructions – including meeting point address, Google map, and parking information – for Sightseeing Day Sail around Boston Harbor will be included in your confirmation email from Cool Shore Excursions. Please be sure to double and triple check your email address is correct at checkout so this important email makes its way to you!
Mar 2024Once your refund is processed, it usually shows on your card statement within 5–10 business days. The exact timing depends on your bank or card issuer.
Want it sooner? When you cancel, choose Receive a refund to my wallet instead. The credit is in your Wallet straight away and is applied automatically at checkout on your next booking when you’re signed in with the same email. You can see your balance any time in My Wallet.
If you paid part of your booking with Wallet credit, that part always goes back to your Wallet. Trip protection isn’t refundable.
Oct 2026What's Included
- This is not a narrated tour, but the crew is available to answer questions on the sights & landmarks
- Duration: Choose between a 1.5 or 2 hour sailing experience
- 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)
Additional Info
- Confirmation is instant and will be received at time of booking
- Service animals allowed
- Public transportation options are available nearby
- Suitable for all physical fitness levels
- 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 52 travelers
