Top Gloucester Adventure Tours

Explore the stunning Gloucester Harbor and Annisquam River on a guided kayak tour from Boston. Paddle past historic landmarks, catch a glimpse of the famous Wicked Tuna boats, and even hunt for sea glass on Ten Pound Island. This adventure is perfect for both seasoned kayakers and beginners, blending sightseeing with relaxation. Enjoy free time for dinner in Gloucester before returning to Boston via a private van shuttle. - Guided 4-hour kayak tour suitable for all skill levels - Visit Ten Pound Island for the best sea glass collecting - Spot Wicked Tuna boats while paddling through the harbor - Includes transportation from Boston and free time for dinner