Top Gloucester Tours, Sightseeing & Cruises

Enrich your New England road trip with a private self-guided audio tour of Cape Ann that you can listen to as you drive. Filled with evocative tales and historic information, the tour leads you on a scenic loop between Gloucester and Rockport, highlighting the region’s top landmarks and attractions. The convenient app-based guide allows you to travel at your own pace and stop whenever you wish.

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.

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