Top Gloucester Outdoor Activities

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 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 Museum and picturesque Halibut Point State Park. Learn about the granite industry's fascinating past and the artistic legacy of local painters like Fitz Henry Lane while enjoying stunning views along Route 127 and 127A. This tour allows you to explore at your own pace, making it perfect for families and history enthusiasts alike. - Self-guided tour covering 25 miles of scenic coastline - Visit historical sites like Hammond Castle and Eastern Point Lighthouse - Flexible pacing allows for stops at beaches, museums, and trails - Family-friendly, suitable for all ages and no 4WD required

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.

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 Gloucester Harbor and rugged Cape Ann coastline in a relaxed atmosphere. This sailing experience is perfect for families, couples, and small celebrations, providing ample space to unwind and explore at your own pace. - Experience Gloucester's coastline from a spacious 36-foot catamaran - Tailored trips for special occasions like birthdays and proposals