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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  Whale Watching

Hi! We would like to welcome you to join us June – October on our historic wooden sailing vessels for a fun and timeless tradition. On board the elegant 1874 designed Cutter Bloodhound, and locals favorite Schooner Hindu (1925), we will pass by the Long Point Lighthouse, look for seals in the cove, and circle houseboats, all while getting the best view of Provincetown.

You’ll get a chance to help our crew raise or brail a sail! We offer hour and a half family friendly day sails, 2 hour sunset sails, and 4 hour whale watch sails, as well as private charters.

With room for everyone to sit down comfortably, the Schooner Hindu sails with up to 46 guests; the Cutter Bloodhound with up to 34.

Pack a picnic, and a bottle of wine, or whatever you’d most enjoy eating and drinking while on your sail with us, and let our crew entertain you with their local knowledge, and sailing expertise.

Did we mention we are dog friendly?! Call to book today!

Slip 10w MacMillan Pier, 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 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 for up to six guests. Experience wildlife, beaches, lighthouses, and sunsets of this New England gem. We welcome friends, family, and couples for birthdays, proposals, weddings, honeymoons, vacations and more!

15 MacMillian Wharf, Provincetown, MA, 02657

Project Valor Sailing Inc.

 Waterfront

VALOR Dutch-built Lemsteraak 38 feet in length and judged one of the most beautiful wooden boats

VALOR… one of the most beautiful wooden boats in America.

VALOR is a celebrated Dutch-built Lemsteraak, 38 feet in length, and judged one of the most beautiful wooden boats in America. Her mission is to honor and remember the service of all United States Veterans, especially those disabled in service to the nation.

She sails as a proven therapeutic methodology and adventure, establishing life-long connections and fellowships.

ALL members of the Veteran Community and their assistants sail free of charge. We heartily invite you to join us in this noble tribute and program. Welcome!

Commodore Adam R. Howard
United States Navy – Service Connected Disabled Veteran

37 Bradford Street Extension – Unit 20A, 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