Choose your trip length, interests, and pace to build a flexible Gloucester itinerary. Add other destinations, compare experiences, and reserve time for travel between stops.
Plan my Gloucester trip →Explore more in Massachusetts.
Browse these experiences as a starting point. The planner considers your interests, pace, and published schedules when building your days.
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 …
Approx. 240 minutesView on Viator →
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…
Approx. 240 minutesView on Viator →
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 driv…
Approx. 180 minutesView on Viator →
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’…
Approx. 90 minutesView on Viator →
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…
Approx. 480 minutesView on Viator →
Get the full Massachusetts experience with this combo of walking and driving tours around Boston! You’ll find ten tours in one app - all highly entertaining, thoroughly researched…
Approx. 2880 minutesView on Viator →Start with the number of days you have, then choose an unhurried, balanced, or fuller pace. Review the suggested route before generating your daily plan. Transport allowances are estimates; confirm services and meeting points before booking.
Save your trip with or without an account, share a read-only link, or download a PDF with booking and map links.