top of page
IMG_0520 copy.jpg

About Chick

Chick Stapleton - Owner of ISK

Chick Stapleton founded Island Spirit Kayak in her hometown on the island of Martha’s Vineyard in 2000.   After graduating Boston University she worked as a bartender at Lola’s by night and as a kayak instructor by day. Starting with just three kayaks, she lead groups of two until she could afford another kayak, then another. Her dream of being Julie from the Love Boat combined with a passion for paddling made introducing others to the beauty of the Vineyard from the water, the perfect combination.

On the off seasons she completed guide certifications and traveled the world working for other kayak companies. After completing her BCU certification in Nova Scotia, she guided for Scotia Kayaking on Cape Breton. Wilderness camping and kayaking with huge pods of whales was their specialty. She was capsized by a pilot whale off Chetticamp while guiding a tour, encountered bears and moose while camping, and had an all-in situation from a rogue wave off the cliffs in a no land zone. t was an extreme and amazing experience.

After another summer building Island Spirit Kayak by day and bartending by night she decided to get her feet wet in the Indian Ocean. Dave Williams, an expatriate white water guru and owner of the very successful Paddle Asia took her under his wing for a winter. She assisted in kayak tours all around Thailand including Phang Nga, Phuket, Trang, Koh Yao Noi & Khao Sok. For an amazing article written about kayaking Khao Sok, encountering gibbons and underwater cave diving where Chick was one of the leaders, click hereIt was an extreme and amazing experience.

 By 2004 Chick was working full time as a kayak guide with a fleet of more than 45 kayaks, two trailers and 4 other guides. Next winter she drove to San Francisco to lead tours and certify guides in the Point Reyes area for Blue Waters Kayak, California Canoe & Kayak, and Sea Trek. She also had the opportunity to train and play with the Golden Gate Breakers canoe polo team and compete in National Events.

In 2006, Cape Cod Life voted Chick among Cape Cod’s top 20 most intriguing people. While planning her next winter of kayaking in Laos & Myanmar, she stumbled upon Tyler Stapleton at a Blues Traveler concert at the Hot Tin Roof. It was love at first sight and the one time sailor is now a successfully converted kayaker. After a few winters of “settling down” and living on Vieques, Puerto Rico, they are now married and have two future Island Spirit Kayak guides, Collin and Kian.

In 2018 Island Spirit Kayak is entering into its 18th year in business. They could not be more passionate and thankful for all they have to offer, with a team of 14 full time fabulous staff and their kayak location on State Beach. Chick is now an Executive Member of the Board of Directors for Friends of Sengekontacket Pond, dedicated to the preservation of Sengekontacket Pond and its barrier beaches. The Stapleton family lives on the Vineyard year round in their home in Oak Bluffs.

IMG_0358 copy.jpg
Recent Awards and Honors
  • BCU (British Canoe Union): 3 Star, Coastal Adventures Sea-Kayaking School, Tangier, Nova Scotia: 2001

  • AESKO (Association of Eastern Canadian Sea Kayaking Outfitters): Instructor Training, Coastal Adventures Sea-Kayaking School, Tangier, Nova Scotia: 2001

  • CRCA (Canadian Recreation Canoe Association): Level 3, Coastal Adventures Sea-Kayaking School, Tangier, Nova Scotia: 2001

  • ACA LEVEL 3 – Coastal Kayaking, Wild River Outfitters Touring Company, Virginia Beach, Virginia: 2002

  • Wilderness Guide Paddle Asia: Phuket, THAILAND: 2003

  • Greenland Skills Training, Walden Pond, MA 2000, Walden Qajaq Society (pond scum), Instructor: Cheri Perry (Greenland Qajaq Games Gold Medalist)

  • TIPS– (Training for Intervention ProcedureS)

  • Heart Saver CPR– Emergency Cardiac Care and Child First Responder

  • Basic Wilderness First Aid– SOLO

  • Advanced Open Water/Archaeology Diver– PADI

  • New York Times: 2009 Ten things not to miss on Martha’s Vineyard, Island Spirit Kayak.

  • Cape Cod Life: 2009 Best Kid’s Activity, Island Spirit Kayak.

  • U.S. Small Business Administration  2007 Massachusetts Young Entrepreneur of the Year, awarded by Massachusetts Governor Duvall Patrick

  • Cape Cod Life, 2006 Cape Cod’s top 20 most intriguing people.

  • Boston University, School of Hospitality Administration, Bachelor of Science, May 2000 Major: Hotel, Restaurant, and Hospitality Management

  • Sydney Olympic Committee Internship Program, ‘99-’00

  • Martha’s Vineyard Regional High School, Graduated May 1996

bottom of page