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Cape Cod, Martha’s Vineyard and Nantucket Boating & Watersports

Cape Cod and the Islands have some of the best boating and watersports activities on the East Coast. Whether you like to sail, powerboat, kayak, windsurf, paddle board or canoe, you will find it all here on Cape Cod, Martha’s Vineyard and Nantucket.


Sailing Lessons


South East Sailing School
115 Walnut Ave., West Barnstable / 
(508) 420-1144
Sailing lessons on Lewis Bay and Hyannisport. Group and individual.

Wianno Yacht Club
101 Bridge St., Osterville 
(508) 428-2232

Junior sailing programs for kids and private sailing instruction for adults by appointment. 


Lower Cape  

Cape Sail
Saquatucket Harbor, Mass. Rt. 28, Harwich 
(508) 896-2730

Small boat instruction in Brewster and Harwich Port. Open Memorial Day to early October.

Arey’s Pond Boat Yard Sailing School
Arey’s Ln., South Orleans 
(508) 255-0994
Private and group lessons. Summer sailing program.

Chequessett Yacht & Country Club
Chequessett Neck Rd., Wellfleet 
(508) 349-0198
Open early July through the end of August. Junior sailing clinics and private lessons for adults.

Flyer’s Boat Yard
131A Commercial St., Provincetown 
(508) 487-0898, (800) 750-0898

From mid-May to mid-October, Beginner and intermediate levels.


Boat Rentals

Upper Cape

Waquoit Kayak Company
Mass. Rt. 28, East Falmouth
(508) 548-9722

Sailboat rentals by the day or 5 days.

Mid Cape  

Cape Cod Waterway Boat Rentals
Mass. Rt. 28, Dennisport 
(508) 398-0080
Manual or electric paddleboats, canoes, and kayaks. Open May through October.


Lower Cape  

Cape Sail
Mass. Rt. 28, Saquatucket Harbor, Harwich 
(508) 896-2730

Lessons and charters.

Jack’s Boat Rental
Mass.Rt. 6A, Nickerson State Park, Brewster 
(508) 896-8556

Sunfish, sailboards, sea-cycles, pedal boats, canoes, and kayaks on Flax pond or Gull Pond in Wellfleet.

Wellfleet Marine
Town Pier, Wellfleet 
(508) 349-2233
From mid-June to mid-October, larger sailboats our of Wellfleet harbor.

Flyer’s Boat Yard
131A Commercial St., Provincetown 
(508) 487-0898, (800) 750-0898

Power boats and sailboats. Mid-May to mid-October.




Force 5 Watersports
37 Main St. 
(508) 228-0700 Jetties Beach Rd. 
(508) 228-5358
Windsurfing, kayaking, and sailing lessons. Open May through October. Rentals.

Nantucket Harbor Sail
Swain's Wharf
(508) 228-0424
Sailboat rentals in season.

Sea Nantucket Kayak Rentals
Washington St. Ext
(508) 228-7499
Rentals, lessons, and guided tours. In season.

Nantucket Boat Rental
Slip 1 Boat Basin at the end of Main St.
(508) 325-1001
Power boat rentals.


 Canoe and Kayak Tours and Rentals


Upper Cape

Cape Cod Kayak
North Falmouth 
(508) 540-9377

Kayak rentals and tours.

Cape Cod Coastal Canoe & Kayak
Falmouth & Cape-Wide 
(508) 564-4051

Canoe and kayak tours. No rentals.

Waquoit Kayak Company
Edwards Boatyard, State Rt. 28, East Falmouth 
(508) 548-9722

Canoe and Kayak rentals and tours.

Sea Crest Resort
Falmouth on Buzzards Bay
(508) 540-9400.

Ripple Creek Kayak at the Red Jacket Beach Motor Inn
(508) 776-9036
Kayak rentals and lessons.


Mid Cape

Eastern Mountain Sports
1513 Mass. Rt. 132, Centerville 
(508) 362-8690

Open year-round. Kayak equipment and tours.

Cape Cod Waterway Boat Rentals
Mass. Rt. 28, Dennisport 
(508) 398-0080
Canoe and kayak rentals. Open May through mid-September. 

Sea Sports Inc. 
195-D Ridgewood Ave (Rte. 28) Hyannis, MA 02601 (508) 790-1217


Lower Cape

Explore Cape Cod
South Orleans
(508) 240-1211 

Daily kayak tours at Nauset.

Cape Cod Museum of Natural History
Mass. Rt. 6A, Brewster 
(508) 896-3867
Kayak tours led by naturalist. Open April through October. 

Goose Hummock Shop
Mass. Rt. 6A, Town Cove, Orleans 
(508) 255-2620

Kayak sales, rentals and tours.

Audubon Society Wellfleet Bay Wildlife Sanctuary
U.S. Rt. 6, Wellfleet 
(508) 349-2615
Guided canoe trips April through the end of October.  

Jack’s Boat Rental
U.S. Rt. 6, Wellfleet 
(508) 349-9808

Guided kayak tours. Open Memorial Day through Columbus Day weekend.

Off the Coast Kayak
Whaler’s Wharf, Provincetown 

Guided tours and rental boats. Open from the end of May through the summer months.


Surfing and Windsurfing

The Atlantic beaches along the Cape Cod National Seashore cater to the surfing crowd, and the calmer waters and steady winds of Nantucket and Vineyard Sounds are great for windsurfing. 

Upper Cape  

Cape Sailboards
661-D Main St., Falmouth 
(508) 540-8800
Sailing gear, boards, repairs. Open March to December. 


Mid Cape

Boarding House Surf Shop
302 Main St., Hyannis 
(508) 778-4080
Year-round. Surfing, skateboarding, and snowboarding supplies and repairs.

Sound Sailboards
223 Barnstable Rd., Hyannis 
(508) 771-3388
Sailing/surfing sales. Lessons. Open from April through December, seven days a week. 


Lower Cape

Monomoy Sail and Cycle
275 Mass. Rt. 28, Chatham 
(508) 945-0811
Sailboard rentals.

Nauset Sports
Mass. Rt. 6A, Orleans 
(508) 255-4742
Windsurfing and surfing equipment. Open year-round.

The Pump House Surf Company
9 Cranberry Highway (Mass Rt. 6A), Orleans 
(508) 240-2226
Surf shop, repairs, rentals and lessons. Open 7 days from May until October, and weekends only from October to December. Closed Jan to March.

Jasper’s Surf Shop
U.S. Rt. 6, Eastham 
(508) 255-2662
Surfing equipment. Repairs in summer only.  

Jack’s Boat Rental
Gull Pond, Wellfleet
(508) 349-9808

Surfing, windsurfing, canoe and kayak rentals.


Jet Skiing

Not everyone are fans of the noise and speed of powered miniboats, like Jet Skis or Waverunners. In fact, Provincetown has banned the use of them in their harbor. Be sure to check with the local harbormasters or the rental company to find out where you can use powered Jet Skis or Waverunners.


Upper Cape

Cape Cod Windsurfing Academy & Watersports Rentals
134 Menauhant Rd., Falmouth Heights 
(508) 495-0008
Jet-Skis kayaks and windsurfing board rentals.


Mid Cape

Cape Cod Para-Sail and Jet-Ski Hyannis Marine
Arlington St., Hyannis 
(508) 760-6710
Parasailing tours, Jet Ski and boat rentals.

Rick’s Rollers
240 Lower County Rd., Dennisport
(508) 760-6747
Jet Ski and in-line skate rentals.


Lower Cape

Offshore Watersports
Chatham Fish Pier, Aunt Lydia’s Cove, Chatham 
(508) 945-5700
Jet Ski rentals.

Mad Maxines
131A Commercial St., Provincetown 
(508) 487-9480
Waverunners rentals.



Diving off of Cape Cod is popular on the Cape, especially on the Cape Cod Bay side, particularly at Corporation Beach in Dennis and Sandwich’s Town Beach, which are considered safer and better for divers because the current is light and the rocky bottom is interesting. Consult the staff at local dive shops for suitable areas and current conditions for diving.  


Upper Cape

Aquarius Diving Center
3239 Cranberry Hwy, Buzzards Bay 
(508) 759-3483
Scuba lessons, sales, and service, charter diving and dive travel arrangements. Open year-round.

Aqua Center
2 Freezer Rd., Sandwich 
(508) 888-3444
Diving sails, rentals and lessons.


Mid Cape 

East Coast Divers
237 Falmouth Rd., Hyannis 
(508) 775-1185
Scuba lessons, equipment, service and repair.

Sea Sports
195 D Ridgewood Ave., Hyannis 
(508) 790-1217
Scuba diving, snorkeling supplies. Open year-round.