Top Massachusetts Kayaking Tours

RideAway Adventures has been awarded the best tours on Cape Cod 12 years in a row. We have the only fully ACA certified guide staff on Cape Cod. Our tours stay at low numbers so that it is a fun and unique experience for every participant. Our equipment is always top of the line and this area is perfect for all levels of kayakers.

RideAway Adventures has been awarded the best tours on Cape Cod 12 years in a row. We have the only fully ACA certified guide staff on Cape Cod. Our tours are small and intimate so that it is a fun and unique experience for every participant. Our equipment is always top of the line and this area is perfect for all levels of kayakers. RideAway Adventures is the highest rated outdoor company on Cape Cod and we are committed to creating ocean ambassadors through education and active environmental awareness.

Why You’ll Love This Tour: Seamless & Stress-Free – Round-trip transportation from Boston is included. Great for Nature Lovers & Outdoor Enthusiasts – A fun, low-key adventure in a protected coastal habitat. Beginner-Friendly – Easy-to-navigate waters and expert guides make this a stress-free introduction to kayaking. Breathtaking & Off-the-Beaten-Path – Discover a lesser-seen side of the North Shore’s iconic Crane Estate.

Unlike typical kayak tours, North of Boston Island Lighthouse Tour is a refined, personalized coastal experience. Your expertly trained guides combine deep knowledge of local history, wildlife, and island landscapes with the freedom to tailor each outing to the day’s conditions and your group’s interests. Expect a relaxed pace, intimate storytelling, and exclusive moments among iconic lighthouses and pristine island scenery—no scripts, no crowds, just a truly elevated adventure.

Join our wonderful, professionally trained guides for an unforgettable evening adventure designed to beautifully wrap up your day. From the moment you set out, our knowledgeable guides are there to ensure your safety, comfort, and confidence on the water. More than just expert paddlers, they are passionate storytellers and local experts who bring the surroundings to life. As you glide across calm waters under the changing colors of the sunset, they will share fascinating insights about the islands, marine life, local ecosystem, and natural wonders you encounter along the way. Whether you’re spotting wildlife, learning about the area’s history, or simply soaking in the peaceful atmosphere, our guides make sure the experience is engaging, educational, and truly memorable.

Families can enjoy a unique pirate-themed adventure on the serene waters of Cape Cod. This 2-hour journey invites young explorers aged 8 and up to paddle, engage in a lively water cannon battle against a rogue pirate, and uncover hidden treasures. Expert guides ensure safety while igniting excitement with interactive storytelling and teamwork. It's the perfect way to enjoy a day out of the water, all while connecting with nature and creating lasting memories together. Adventurers 2-7 are welcome to accompany an adult on their paddleboard.