Adventure you will never forget

Provincetown Harbor

Schooners in Provincetown Harbor

A schooner is a type of sailing ship, as defined by its rig configuration. Typically it has two or more masts, the foremast being slightly shorter than the mainmast. Pronounced /ˈskuːnər/, the schooner first developed off the coast of North America in the early 1700s, originally for fishing and local trade purposes. The name may be related to a Scots language word meaning to skip over water, or to skip stones.

Sailing in Provincetown Harbor

Sailing in Provincetown Harbor


For more information about businesses listed below simply click on the business name.



Dog Gone Sailing Charters

 Pet Friendly  Kid Friendly  Waterfront  Weddings

Sailing charter business that Sails from May 15 till October 15. We love and take dogs. Sailing charters are Sunrise to/and sunset including shrimp sail 1.5-2 hours,1/2 day and full/day are private. We take up to 6 passengers. The Captain can marry you and bury your beloved. Flexible and love to make request and special events happen for you.
P.O. Box 722, MacMillan Pier slip #8, Provincetown, MA 02657

Flyer’s Boat Rental & Boat Shop, Inc.

 Pet Friendly  Kid Friendly  Waterfront  Fishing  Parking  Professional Services  Weddings

Boat rentals from luxury pontoon boats, skiffs, small sail boats to kayaks and paddle boards.

Moorings with launch service, Long Point Shuttle to tip of the Cape, sailing lessons, seal tours in high season, parties and cruises.

Hold special events on the water: sunset cruises, weddings, memorial services or fun parties. Boats hold from 2 to 39 passengers.

Flyer’s has been a working boatyard for more than 66 years, with experience in repairs on vessels and their engines ranging from 80ft wooden fishing draggers to 6ft fiberglass dinghies.

We also offer mechanical services and winter small boat storage.

P.O. Box 561, 131A Commercial Street, Provincetown, MA, 02657

Hindu Charters

 Pet Friendly  Waterfront

The Schooner Hindu was built in 1925, and has been sailing out of MacMillan Pier in Provincetown since 1946. Hailing from an era of form and function, she is a living ambassador of American maritime history.

Join us for an hour and a half family friendly day sail, or a gorgeous two hour sunset sail around the Cape’s protected Bay with a salty breeze in your hair and a setting sun in the sky. Bring your dog(s) with you and let our Admiral Finnegan, the Nautidog, show them the ropes! You can help the crew raise sail, or just sit back and relax with a picnic and enjoy unforgettable views of Long Point, the Provincetown monument, and the bend of the Cape.

Come see why generations of people support the Schooner Hindu in Provincetown MA and Key West Fl.

We also offer private charters for any occasion.

Join us for a timeless experience by booking online, or by calling us. We look forward to sailing with you! BYOB and picnic!

MacMillan Pier 10W, PO Box 404, Provincetown, MA, 02657

Impossible Dream

 Waterfront  Handicapped Accessible

A universally accessible catamaran Impossible Dream

The Impossible Dream, a universally accessible catamaran

The Impossible Dream, a universally accessible catamaran, is dedicated to raising awareness of barrier-free design and improving the quality of life for people with disabilities. Since 2015, the Impossible Dream has sailed more than 30,000 miles along the Eastern Seaboard of North America. Each summer we provide FREE sailing trips for groups of wheelchair users and people with various life-changing illnesses and disabilities.

When not sailing the East Coast, the Impossible Dream is based at Shake-A-Leg Miami, one of the most accessible community boating centers in the world. From this home base, we continue to introduce those with disabilities, their families, and our community to the joy of sailing. We work year-round to provide people with disabilities a new way to improve their quality of life.

MacMillan Pier, Provincetown, MA, 02657
Text GIVE or DONATE to: 305 680-3627

Moment Sailing Adventures

 Kid Friendly  Waterfront  Weddings

Moment Sailing Adventures is outer Cape Cod’s only choice for deluxe private captained sailing day charters.

We offer Day sails and day, weekend, and destination sails aboard the 47′ “Moment” departing from Provincetown, Cape Cod.

During the summer months, take a 2, 4, or 6 hour day sail around Provincetown Harbor and Cape Cod Bay. Experience wildlife, beaches, lighthouses, and sunsets of this New England gem. Moment takes up to six guests maximum. We welcome friends, family, and couples for birthdays, proposals, weddings, honeymoons, vacations and more!

For the more adventurous, take a two day overnight sailing trip with four guests to Plymouth and Wellfleet. For even more time on the water, increase your charter additional days to include destinations such as Boston, Marblehead, Plymouth, Nantucket, Martha’s Vineyard, New Bedford, Cuttyhunk and many more!

131 Commercial Street, Provincetown, MA, 02657

Provincetown Yacht Club

 Waterfront

The Provincetown Yacht Club welcomes new members- both sailors and power boaters. Our members hail from 10 States. Although the majority spend the season in P’Town, forty percent live in Truro and several in Wellfleet.

The club sponsors sailboat races, Racing Seminars, Spring Vineyard Social, “Open Sails,” Raft Up Parties, a Sunset sail on the Schooner Hindu or Bloodhound, a Dune Buggy Sunset Tour and more.

We host races every Saturday at 1 PM from mid June through mid September. It’s a mixed fleet composed of keel boats from twenty to forty feet, several Rhodes nineteens, and cat boats. All are welcome. The New England PHRF handicap system is used so everyone has a chance to win. The races are held in the harbor outside of the breakwater, between Beach Point and Long Point. Courses range from one to five miles in length depending on the wind. Every race is exciting and competitive. Visiting sailboats and crew members are always welcome and there may be opportunities to crew from week to week. Club members are available to assist inexperienced racers.
Family, individual and junior memberships (Under 18) are available.

Interested boaters can find details on membership at: Provincetownyachtclub.org, or email us at: [email protected]. We hope to see you out on the water!”

“Like” us on Facebook: https://www.facebook.com/ProvincetownYachtClub/.

P.O. Box 909, Provincetown, MA, 02657

West End Racing Children’s Community Sailing (WERCCS)

 Kid Friendly  Waterfront

Sailing program for children ages 8 – 14. We provide low-cost, affordable instruction in sailing and sailboat racing in a fun and safe environment to children in Provincetown and Truro.

The West End Racing Children’s Community Sailing (WERCCS) non-profit organization offers children’s sailing program for ages 8-14 providing lessons and equipment for a seasonal registration fee of $100.

The program is open to both residents and visitors from Provincetown and Truro. There will be a program instructor and assistant instructors on duty at all times. Regular hours are 9-noon and 1-4 pm weekdays in July and August varying with the weather and tides.

Children must be able to swim unassisted for a distance of 100 feet. Parents/guardians must register children in person at the WERCCS.

83 Commercial Street, Provincetown, MA, 02657