Cape Cod Charter Sailing Links
Every charter boat on cape cod listed!

Provided as a Public Service

(Rentals, Bareboats, and Sailing Schools at bottom)

If you want to take your dog, call Dog Gone Charters or Hindu in P-Town!

6 passenger Charters and Lessons
Larger Schooners and Yacht Charters- up to 141' carrying up to 49 passengers
Hourly, Daily or Weekly Rentals

Sailing Schools


  • Try different sailboats: 6 passenger or larger Schooners
  • Avoid driving in Cape Cod traffic: Find something close to your hotel!

This is the class of smaller uninspected passenger vessels requiring the captain to have a Coast Guard OUPV license (Operator of Uninspected Passenger Vessels), otherwise known as a "6 pack" license.

6 passenger charters are more private with only your family or a few other people onboard, on smaller vessels up to about 50'.  They are often for a half or full day or you can book for overnights, and usually more expensive.  They sometimes include food and drinks.

Cape Cod Catamaran
-Wellfleet Harbor
30' Discover Catamaran

6 passengers
4 hr Morning or Afternoon Cruise: $110/person-$550 private
2 hr Sunset Cruise: $75/person-$400 private

Wellfleet partner.

Cape Cod Sailing School-Cataumet (on Buzzards Bay-part of Bourne).  Kingman Marina at Red Rock Harbor, home of famous Chart Room bar and restaurant.
Various 30-40' sloops

6 passengers
2hr minimum: $100/hr,

Cape Sail (Harwich)-Saquatucket Harbor, Route 28 in Harwichport.
35' Southern Cross Cutter
6 passengers
3hrs: $110/person
Lessons: $95/hr: additional persons at $55/hr

Cape Cod Maritime Museum, Historic Catboat Sarah-Hyannis
1886 Crosby catboat replica
Adults $36, Children (3-17) $18

Captain Curley Sailing
19' O'Day Mariner
6 passengers
Eric Hansen (aka Captain Curley) is a former employee and manager for Outer Cape Sailing.  In 2016 he duplicated
Outer Cape Sailing and went into business in the same harbor.

Dog Gone Charters-Provincetown Harbor
30' Island Packet. Bring your dog.  Description from captain:
We motor out of fairway out of respect for the many charter fishing, whale watch vessels and traffic of transients, but
sails are up just on the other side of the breakwater and Hindu often puts sails up before breakwater if Joshua at helm.
On our tours there is an array of wildlife we point out to passengers and a rich history of our Province lands.
6 passengers
Half day: $330
1.5-2hr = $40/person

Moment Sailing Adventures-Provincetown
Tartan 34' or Stevens 47' sloop
6 passengers
2hr: $349-$499 to 8hrs: $949-1099

Postcard Harbor Tours-
Wellfleet Harbor
18' Marshall Sanderling Catboat
6 passengers
3hrs:  $50-$75/person
Wellfleet partner.

Schooner Tyrone-Chatham, Stage Harbor
1939 75' Crocker Schooner
6 passengers
2hrs: $400 minimum, $200/hr, plus $50 pier fees

Selkie Charters-Hyannis Harbor
42' Irwin Center Cockpit
6 passengers
1/2 day: $450, full day $900

Storm Petrel Charters
-North Falmouth, Fiddler Cove
48' Cutter
6 passengers
1/2 day: $600, full day $900


This is the class for larger Coast Guard Inspected Vessels and the Captain is required to have a USCG Master license
 at the rated tonnage for the vessel such as 50 or 100 tons.  Tonnage is a cargo volume measurement, not a
weight measure which is called displacement.
  Coast Guard Inspected doesn't just mean the boat is inspected annually
for safety.  It is designed and built to strict Coast Guard safety requirements due to the large number of passengers
they carry, including waterproof bulkheads, built-in fire extinguishers, fireproof construction materials, etc.

Sailing on a big schooner or catboat is a pleasant, nostalgic adventure, reminiscent of the sailing days of yore,
and is often the least expensive family option.

Down Cape Sailing Charters-Chatham, Pleasant Bay
33' daysailer: 1966 Glander Tavana
12 passengers
1 1/2 hrs: $75/adult, $30/child

Kalmar Nyckel-Tall Ship
-Provincetown (July 18-29)
1625 Dutch 200 tonne Pinnace-141' including bowsprit
49 passengers
3 hrs: $60 adults, $40 Ages 17 & under

La Liberte
-Falmouth, Vineyard Sound
74' Schooner
49 passengers
2-3 hrs: $25-$40 adults, $15-$20 children

Schooner Bay Lady II-Provincetown Harbor
70' schooner sails in Cape Cod Bay.
41 passengers
2 hrs: $28-$33

Schooner Hindu-
Provincetown Harbor (July-Sept)
1925 William H. Hand Schooner, 79' including bowsprit
35 passengers
1.5-2hrs: $20-$50

HOURLY AND DAILY RENTALS: Take the boat out by yourself.

Bay Sails Marine
(Wellfleet-Rt 6)
Sunfish or Rhodes 19 rentals

Chatham Sailboat Rentals
(Chatham-Ridgevale Beach)
Hobie Cat, sunfish, SUP rentals

Down Cape Boat Rentals
(Chatham-Pleasant Bay-Wequassett Resort and Golf Club) Hobie Cat
and Daysailor rentals

Flyer's Boatyard
Sailboat rentals and ferry to Long Point

Iggy Biggy Rentals (West Yarmouth-Englewood beach)
Sunfish rentals
Jack's Boat Rentals (Wellfleet and Brewster)
Small sailboat and kayak rentals, delivered or in Nickerson State Park Ponds in Brewster

Wellfleet Marine (Wellfleet Harbor)
Sailboat and powerboat rentals in Wellfleet Harbor

WEEKLY BAREBOAT RENTALS: Charter a Yacht for a week or more.
Swift Yacht Charters and Villas, LLC
30-54' Bareboat sloops in Cape Cod and Rhode Island area.

Compass Point Yacht Charters


US Sailing list of Schools. Click on state or put in zip code.
ASA list of Schools
RYA Yachtmaster Training

Q. What is the difference between US Sailing and ASA (American Sailing Association) you ask?

A.  US Sailing is a non-profit organization designated by Congress as the official rule making body for
sailing in the US and runs the Olympic team.  They are mainly focussed on racing and
Olympic development starting with small boat certification (<20'). 
They also have a cruising program, and training from keel boats up to cruising yachts.  US Sailing
was created by some sailing schools that were not satisfied with the training being offered by ASA at
the time.  US Sailing training is more rigorous.

ASA is a for profit organization dedicated to marketing sailing for its member organizations, and
mainly focussed on Cruising training starting with keelboat Certification.  They don't have any focus
on small boats or racing.  ASA was created as a professional training body based on the Canadian
Sailing Association.  The quality standards of ASA are much improved since competition from US
Sailing.  There are many more ASA Schools than US Sailing Schools.

RYA Yachtmaster is internationally recognized as among the best training for amateur and
professional skippers.

Tracey Sailing School-ASA Certified Instruction for keelboats, catamarans, powerboats, celestial
and coastal navigation

  Outer Cape Sailing, PO Box 1936, Wellfleet, MA 02667