11. Guided kayak tour of Gloucester Harbor and Annisquam River
5.0· 1 reviews· 6 hoursFour-hour guided kayak tour from Boston — paddle past historic sites, spot Wicked Tuna boats, and collect sea glass on Ten Pound Island with free time for dinner in Gloucester.
22. Whale watching trip to Stellwagen Bank Marine Sanctuary from Gloucester
4.9· 2170 reviews· 4 hoursThree to four hours from Gloucester Harbour — see seals, birds, and whales in their natural habitat aboard the spacious Privateer IV with comfortable seating.
“The experience was incredible. We witnessed numerous whales, and the crew provided excellent service. We had a fantastic time and would highly recommend it to everyone. Go enjoy it!”— Donald_H
33. Cape Ann self-guided driving tour in Gloucester and Rockport
4.1· 103 reviewsThis narrated driving tour allows you to explore the coastline, beaches, and lighthouses of Cape Ann at your own pace.
“This tour was incredibly user-friendly, allowing us to discover stunning scenery that we would have missed otherwise.”— Leslie_N
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