Top Gloucester Tours, Sightseeing & Cruises

Enrich your New England road trip with a self-guided audio tour of Cape Ann that you can listen to as you drive. Filled with evocative tales and historic information, the tour will lead 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.

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.

Explore Boston, Cambridge, Salem, Cape Ann, and more! This package covers Boston's iconic Freedom Trail (Old North Church, Faneuil Hall, & more), Harvard University, the Harborwalk, Salem Witch Trails, and a scenic waterfront drive near Cape Ann. This is the ultimate "must-do" package for a Boston and New England trip. This self-guided tour allows you to explore Boston’s historic wonders with maximum flexibility and value. Purchase one tour per car. Everyone can listen at the same time! After booking, you can check your email before downloading the Tour Guide App by Action, enter your unique password, and access your tour. The preceding steps require good internet/wifi access. Simply follow the audio instructions and the route from there. This is not an entrance ticket. Check opening hours before your visit. New, extra validity — now, it’s yours for an entire year! Use multiple times over multiple trips!

Explore some of the best spots for fall foliage on the East Coast, including Acadia, Shenandoah, and Great Smoky Mountains national parks, Kancamagus Highway, Blue Ridge Parkway, Bar Harbor, Newport, Salem, and the Freedom Trail, with this self-guided driving tour. Enjoy the flexibility to travel at your own pace, with hands-free functionality, turn-by-turn directions, and offline access. Includes full itineraries, travel tips, audio guide, and text.