All Gloucester Tours & Excursions in 2026

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

Get the best chance of seeing whales off the coast of Gloucester, Massachusetts, by booking this half-day whale-watch cruise. Your experienced captain and crew know the whales’ feeding and swimming patterns and keep close tabs on where they’re hanging out. Spread out on the deck of the boat and enjoy being out in the open air while you find whales, then get ready to snap photos of breaching, spouts, and tail slaps.

Experience a unique Himalayan Salt Cave on Main Street in beautiful Gloucester, MA. Enjoy a 30-minute session in a zero gravity chair with salt air from our halotherapy generator. Revive Wellness LLC is a newly built wellness facility with state-of-the-art treatments. Please wear comfortable clothing and bring socks. Socks are available onsite for purchase. Note: No refunds for cancellations made less than 24 hours in advance.

Experience ultimate relaxation and rejuvenation with our Hydrotherapy Massage Bed. Let the soothing water therapy and gentle massage techniques melt away stress and tension, leaving you feeling refreshed and revitalized.

Enjoy a full-body table massage designed to melt away stress and ease muscle tension. Perfect for total relaxation and rejuvenation.

Looking for a day trip from Boston by train? Step inside a medieval-style castle on the New England coast! The Hammond Castle Museum, built in the 1920s by eccentric inventor John Hays Hammond Jr., is a stunning mix of history, architecture, and innovation. Wander through its grand halls, secret passageways, and oceanfront grounds at your own pace. What You’ll Experience Roam through the breathtaking halls, medieval artifacts, and hidden chambers of this one-of-a-kind seaside castle. See its towering stone archways, gothic-style rooms, and original furnishings. Step onto the castle’s terraces for stunning panoramic views of the Atlantic Ocean and Gloucester’s rocky coastline. Learn about Hammond’s groundbreaking work in radio and remote-control technology through interactive exhibits and displays. Each Trip includes The Weekend Commuter Rail Pass, so your travels don’t need to end when the tour ends! The Weekend Pass is valid on ALL Commuter Rail Lines all weekend!

Give yourself the best chance of seeing whales in the wild on this half-day boat tour from Gloucester to the Stellwagen Bank National Marine Sanctuary. Hop on a high-speed catamaran that gets to and from the whales in the least amount of time possible. Once there, look out for humpback and fin whales, plus Atlantic white-sided dolphins and harbor porpoises with the help of a naturalist guide. The on-board galley offers hot meals, snacks and beverages for purchase during the trip.

Enjoy complete flexibility and explore the parts of Massachusetts that most interest you with this collection of self-guided walking and driving tours. Receive 10 different itineraries and choose the day and time to use any of them. Use offline with GPS and learn about each place as you travel through.

Discover Boston, Salem, and Cape Ann with maximum flexibility using this self-guided audio tour. Location-based narration shares colorful local history as you explore—it’s all at your own pace, which means you can stop and start the guide as you pause to take photos, eat lunch, or take breaks. Since the self-guided tour uses offline maps, it even works without cell service or WiFi.