10 Boat Tours & Water Sports in Wellfleet That You Shouldn't Miss

March 14, 2022 Terina Blouin

Wellfleet is a town in Barnstable County, Massachusetts, United States, and is located halfway between the "tip" and "elbow" of Cape Cod. The town had a population of 2,750 at the 2010 census, which swells nearly sixfold during the summer. A total of 70% of the town's land area is in protection, and nearly half of it is part of the Cape Cod National Seashore. Wellfleet is famous for its eponymous oysters, which are celebrated in the annual October Wellfleet OysterFest.
Restaurants in Wellfleet

1. Billingsgate Charters

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5.0 based on 116 reviews

Billingsgate Charters

Lobster Charters, Sport Fishing Charters, and Combo Charters - Affordable Family Fun! We also sell fresh lobsters right off the boat at a great price!

2. Fun Seekers

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5.0 based on 32 reviews

Fun Seekers

Fun Seekers is your first choice on Cape Cod for water sports fun. We provide daily instruction and tours in Surfing, Kite surfing, Windsurfing, and Stand Up Paddle boarding. We operate from May to October and have been providing lifetime memories since 1992. Our qualified, patient, energetic instructors will provide a fun learning atmosphere for students of all ages.

3. Cape Side Surf School

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5.0 based on 8 reviews

Cape Side Surf School

15 years experience teaching families how to surf on Cape Cod. CPR certified, sliding you into waves with Safety & Stoke. Live the Ultimate dream vacation by sliding waves with friends, family and the ever growing tribe of Cape Side Surf School wave riders.. It's our pleasure to be your guides in the water here on Cape Cod Andy & Ryan

4. Captain Curley's Sailing Charters

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5.0 based on 142 reviews

Captain Curley's Sailing Charters

Captain “Curley" has been taking guests on Jeremy Point outings and sight seeing tours of Wellfleet Harbor since 2013. Some of his more memorable experiences have been finding live scallop in the tidal pools off of Jeremy Point, seeing a dolphin cruising the harbor waters, and viewing the impressive cloud formations and weather patterns unique to the Cape. However, it's the guests that make each outing a unique and enjoyable experience each trip. Everyday experiences such as finding pristine shells, seeing seals play, and swimming in the ocean continues to bring joy and a satisfaction day after day. In 2016 Curley introduced his new old boat. A 1969 classic 19 foot O'day Mariner “Tomoka.” Originally named after William McCoy's prohibition rumrunner of the same name. She has a sharp looking dark blue hull and beautiful teak trim. Sure to be an eye pleaser as we beach on Jeremy Point this summer.

5. Gala VI

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5.0 based on 6 reviews

Gala VI

Sailing tours of beautiful, historic Wellfleet Harbor on a classic, traditional Cape Cod catboat. Hours and availability may change-call or e-mail to check availability on any particular date/time. NOTE ON RATES: Quoted rate is a median figure. Rates for 1 or 2 persons $65/person; for 3 or more (up to 6), $50/person. For moonlight cruises or landing on Jeremy Point/Billingsgate Island or Great Island, add $10/person to above rates.

6. Captain Ramon Sportfishing

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5.0 based on 1 reviews

Captain Ramon Sportfishing

Sportfishing charters on Cape Cod Bay. Comfortable 28' Grady-White sport fishing boat. All tackle and bait supplied. Kids welcome. Bass, Blues and Tuna our specialty. Call for sailing schedule.

7. Cape Cod Catamaran

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5.0 based on 18 reviews

Cape Cod Catamaran

Sail in comfort on the Wellfleet catamaran Discovery and experience Cape Cod without the crowds. Enjoy the peace and beauty of the bay, Billingsgate Island & Jeremy Point, do some beachcombing or just kick back and relax as our experienced captain navigates the local waters. Visit capecodcatamaran.com to book your trip!

8. Wellfleet Charters

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5.0 based on 21 reviews

Wellfleet Charters

Kevin Coakley has been fishing the Cape for over forty years and has been a licensed captain for the past thirty. We have a 32’ Holland (downeast style) which runs out of Wellfleet Harbor. The "Molly Sue" is a spacious vessel (6 people Max) which includes a head and enclosed cockpit. We specializes in a light tackle (fly fishing upon request) casting/jigging and trolling for blues and bass. Combine some fishing with hauling a few lobster pots for a true vacation experience...

9. Cape Cod Boating Adventures

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5.0 based on 6 reviews

Cape Cod Boating Adventures

Comfort and fun is within reach for any family or group of friends. Cape Cod Boating Adventures will customize your trip for you. Whether you are looking for a variety of activities to please the whole group or just want to cruise in comfort for a leisurely day, we can tailor your trip to fit your needs. Some people choose to picnic aboard and some prefer to be dropped off at a harbor where you can eat at a local restaurant and then use our two-way radio to call us back and continue your trip.

10. Silva Surf Lessons

Brandon Silva, a Wellfleet native, has been teaching surf lessons for over 10 years. For him, surfing is not just a sport but a way of life.

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