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Explore the beauty of Gloucester Harbor and the Annisquam River on this unforgettable guided kayak tour. Take in stunning coastal views in Massachusetts, paddle past historic landmarks, and even visit the best sea glass collecting beach on the North Shore. Whether you’re a seasoned paddler or new to kayaking, this adventure offers a perfect mix of sightseeing, history, and relaxation.
🚣♂️ Guided Kayak Tour – Glide through Gloucester Harbor, taking in breathtaking views of the coastline, fishing boats, and historic landmarks.
🏝 Sea Glass Collecting on Ten Pound Island – Stop at one of the best sea glass collecting beaches on the North Shore and hunt for colorful treasures along the shore.
🐟 See the Famous Wicked Tuna Boats – As you paddle through Gloucester, keep an eye out for the fishing vessels featured on the hit show Wicked Tuna!
🌉 Explore the Annisquam River (Tide Dependent!!) – If the tide allows venture into this picturesque tidal river, known for its tranquil waters, scenic marshlands, and historic waterfront homes.
🏙 Dog Bar & Skyline Views – Pass by Dog Bar, a well-known breakwater protecting the harbor, where on a clear day, you may even catch a glimpse of the Boston skyline in the distance.
🍽 Free Time for Dinner – After your kayaking adventure, enjoy some free time in town to grab dinner at one of Gloucester’s great local restaurants before we pick you up.
🚐 Return Shuttle & Train to Boston – After dinner, our private van will bring you back to the station for a smooth and easy ride home.
✅ A perfect mix of adventure, history, and relaxation
✅ Sea glass collecting on a secluded island beach
✅ Chance to see famous fishing boats & historic landmarks
✅ Seamless transportation with rail & shuttle included
✅ Time to explore Gloucester and enjoy a meal before heading home
Arrive to North Station to catch the 12:30pm Rockport line train to Gloucester
Your train to Gloucester departs
Arrival at Gloucester Station, when you exit the station our private van will be waiting for you
Arrival by van to the starting point of the tour
Enjoy your Harbor Kayak with an ACA Certified Kayak Instructor
Time on your own to explore Gloucester and grab a bit to eat
Board the bus back to the station
( you may depart from the Gloucester or Ipswich train station depending on our tour schedule for that day)
Your train back to boston departs
Arrival back to Boston
We will also send these details along via email with more information on how to get to/from North Station upon booking. Your train ticket will be emailed to you 48 hours in advance of the trip.
