Boat Rentals and 
Water Sports

If you're in the mood to do a little sailing, motoring, kayaking, jet skiing or parasailing upon the waves, and you've got some prior experience, Cape Cod has it all. There are several rental outfits across the Cape to help you out, and some of them are listed below.


Upper Cape

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


Waquoit's offers sailboat rentals. Here is your opportunity to rent a 13-foot sailboat for $95 per day or $395 for five days, or an 11-foot sailboat for $75 per day or $295 for five days. Discover and enjoy Waquoit Bay and its many beautiful rivers and ponds at the helm of an Escape sailboat.

Mid Cape

Cape Cod Waterway Boat Rentals

Mass. Rt. 28, Dennisport• (508) 398-0080

You can rent manually powered and electric paddleboats, canoes, and kayaks here, and, since it is located right on Swan River, between Swan Pond and Nantucket Sound, renters can enjoy a variety of nearby Cape waters. The shop is open from May through October, and rentals are flexible in terms or hours, days, or weeks.

Cape Sail
Saquatucket Harbor, Rte. 28, Harwich• (508) 896-2730

Looking for a great Cape sailing experience? Cape Sail offers a range of opportunities from congenial captained charters to hands-on learning expeditions. Experience offshore Cape Cod on a three-hour private charter, or a more adventurous overnight trip to Nantucket. Trips of other durations can be arranged. Captain Bob Rice shares his 35 years of sailing and teaching experience on his 35-foot boat, the Southern Cross, or in smaller day sailers. Charters are available for a three-hour trip. Lessons are also available as a six-hour course for two people. Reservations are needed for all charters, trips, and lessons.

Jack's Boat Rental
Nickerson State Park, Rte 6A, Brewster• (508) 896-8556

Almost nothing beats sailing on Flax Pond on a warm summer day, and Jack's Boat Rentals is the place for one-stop shopping. It's all here: Sunfish, sailboards, seacycles, pedal boats, canoes, kayaks, boogie boards and more.  Jack's also offers windsurfing and sailing lessons. Jack's has other locations at Gull Pond in Wellfleet, (508) 349-7553, and a retail shop on U.S. Rt. 6 in Wellfleet, (508) 349-9808.

Howie's Kayaks, 
109 Main Street, West Dennis• (508) 398-0060

Howie's Kayaks is one of the Bass River's largest sources for kayak rental and sales. Located  on Route 28 just a third of a mile from the Bass River Bridge, our location at the Windmill Plaza is central enough to be perfect for launching your paddling expedition and convenient enough for the Kayak shopper. 

Dennis Parasail and Jet Ski
377 Setucket Rd, Dennis• (508) 385-8359 
8 MacMillan Wharf, Provincetown• (508) 487-8359 

Let the professionals at Dennis Parasail take you higher than ever before!  Your adventure begins with an exhilarating speed boat ride in Cape Cod Bay out to our flight area offshore.  They will outfit you in a harness and life jacket and clip you into the parachute and you’ll begin your gentle, dry ascent to a maximum hight of up to 300 feet over the Bay and Dennis coastline!

Gold Coast Parasailing
1 South Shore Dr, S. Yarmouth• (
508) 398-7245

Gold Coast Parasailing and Jet Ski has been offering top of the line watersports on Cape Cod in Massachusetts for over 15 years. They offer watersports such as parasailing, wave runner rentals, banana boat rides, segway rentals, kayaks, and more!  Open from Memorial Day through Labor Day.  Reservations are highly recommended!

Outermost Adventure
83 Seagull Road, Chatham• (508) 945-5858

You haven’t truly experienced the beauty of Cape Cod until you have seen it from the water, and the Chatham waterways are among the Cape’s most scenic. The captains at Outermost Adventures (at Outermost Harbor Marine) offer a nice selection of tours and shuttles. They’ll take you to the limited access areas of highly acclaimed South Beach and Monomoy Island for shorebird and seal watching or on a scenic Stage Harbor Cruise to see Chatham at its most picturesque. Free parking and easy “dry dock” boarding.

Pirate's Adventures
Ocean St. Dock, Hyannis• (508) 394-9100

Pirate Adventures is pure fantasy - an old-fashioned, swash buckling adventure your children will remember for years to come. With costumed pirate actors, painted faces and sailor sashes, the little mates aboard the pirate ship "Sea Gypsy" cast off on a pirate adventure. There's underwater treasure to find and a secret map that leads you there. But before the crew gets to pull up the booty, the crew may have to fire the water cannons in order to save the ship and capture the treasure. There is lots of fun to be had, as the crew sings sea chanteys, takes the time-honored oath of loyal sailors, participates in storytelling and a gang effort to find the treasure. This popular adventure runs frequent trips from the Ocean Street Docks in Hyannis and Town Cove, next to the Goose Hummock, in Orleans beginning late June and running through Labor Day.

Osprey Sea Kayak Adventures
South Orleans• (508) 240-1211

Osprey offers daily half day kayak tours both in the morning and the afternoon. Since 1998, their professional guides have introduced thousands each season to kayaking in a safe, fun, and comfortable manner.

Cape Cod Power Boat Rentals
130 Pleasant Street, Bass River• (508) 398-2256

Rents power boats on Bass River with ocean access.  Can also be reached at (800) 699-2256.


Lower Cape


Wellfleet Marine
Town Pier, Wellfleet• (508) 349-2233

From mid-June to mid-October, Wellfleet Marine rents (by the hour or day) Stur-Dee Cat 14-foot sailboats, 14-foot skiffs (with 6-horsepower motors), 19-foot Rhodes sloops, and 21-foot MacGregor sloops for use in Wellfleet Harbor.

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

Since opening its doors in 1965, Flyer's has satisfied the needs of all kinds of boaters since it has one of the largest rental fleets on the Cape. Here they offer powerboats (ranging from 8- to 90-horsepower) and sailboats from a Sunfish to a 27-foot Irwin. There is a two-hour minimum on rentals, with options for renting by the day or week. Flyer's also rents fishing equipment and is open 8 AM to 6 PM from mid-May to mid-October.  They will deliver.