The 11 best things to do in Gloucester (2026)

The ranked list

1. 

   1. Whale Watching Trips to Stellwagen Bank Marine Sanctuary. Guaranteed sightings!

   Outty Ranking92

   Guaranteed Sightings! 7 Seas Whale Watch is located in the heart of historic downtown Gloucester, MA and in one of the busiest parts of Gloucester harbor. As soon as you board the Privateer you will be surrounded by the. 90+ Club at 92/100, 4.9/5 from 2,324 traveler reviews, 4h from $45, free cancellation, an Outty 90+ Club member.

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2. 

   2. Whale Watching Tour in Gloucester

   Outty Ranking91

   You are guaranteed whale sightings on this whale watching tour out to Stellwagen Bank, a national marine preserve about 12 miles off the coast of Gloucester deemed one of the "Top 5 Whale Watching Destinations in the Wor. 90+ Club at 91/100, 4.8/5 from 4,741 traveler reviews, 4h from $48, free cancellation, an Outty 90+ Club member.

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3. 

   3. Haunted Harborwalk - Ghost Tour of Historic Downtown Gloucester

   Outty Ranking69

   Where History and Hauntings Cross Paths Haunted Harborwalk is a 90-minute guided ghost tour through the historic downtown of Gloucester, Massachusetts, with glimpses of the harbor’s edge. Wander old streets and hidden al. Solid Choice at 69/100, 5.0/5 from 40 traveler reviews, 1.5h from $35, free cancellation.

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4. 

   4. Boston App-Guided Audio Tour Bundle: Freedom Trail and More

   Outty Ranking59

   Explore Boston, Cambridge, Salem, Cape Ann, and more! This package covers Boston's iconic Freedom Trail (Old North Church, Faneuil Hall, & more), the Harborwalk, Salem Witch Trails, and a scenic waterfront drive near Cap. Worth a Look at 59/100, 4.4/5 from 5 traveler reviews, 6h from $25, free cancellation.

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5. 

   5. Cape Ann Self-Guided Driving Tour in Gloucester and Rockport

   Outty Ranking58

   Recommended: Purchase one tour per car, not per person. Everyone listens together! Discover the natural beauty of New England’s most picturesque coastline with this narrated driving tour. Hear the tragic tale of the Pe. Worth a Look at 58/100, 4.1/5 from 112 traveler reviews, 2h from $17, free cancellation.

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6. 

   6. Cape Ann Self Guided Driving Tour Audio/GPS Gloucester, Rockport

   Outty Ranking57

   Explore the coastline of Gloucester and Rockport, Massachusetts, with this self-guided GPS audio driving tour of Cape Ann. Discover the rich history of Cape Ann as you visit iconic sites like the medieval Hammond Castle. Worth a Look at 57/100, 4.0/5 from 2 traveler reviews, 2h from $12, free cancellation.

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7. 

   7. Self Guided Day Tour of Hammond Castle Museum from Boston

   Outty Ranking51

   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 h. Worth a Look at 51/100, 5.0/5 from 2 traveler reviews, 2h from $80, free cancellation.

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8. 

   8. Private Sailing Catamaran Charter in Gloucester

   Outty Ranking42

   Set sail on a private catamaran adventure aboard the Fountaine Pajot Mahe 36 Evolution, designed to accommodate up to 6 guests or more with prior arrangement). Captained by the knowledgeable Capt. Lu, enjoy the scenic Gl. Worth a Look at 42/100, 3h from $950, free cancellation.

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9. 

   9. Salt Cave Halotherapy

   Outty Ranking33

   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 we. Worth a Look at 33/100, 0.5h from $44.

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10. 

    10. Hydromassage Bed Gloucester Massachusetts

    Outty Ranking32

    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. Worth a Look at 32/100, 0.3h from $49.

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11. 

    11. Relaxing Gloucester Day Spa Private Activity

    Outty Ranking32

    Enjoy a full-body table massage designed to melt away stress and ease muscle tension. Perfect for total relaxation and rejuvenation. Worth a Look at 32/100, 0.5h from $49.

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