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Give yourself the best chance of seeing whales in the wild on this half-day boat tour from Gloucester to the Stellwagen Bank National Marine Sanctuary. Hop on a high-speed catamaran that gets to and from the whales in the least amount of time possible. Once there, look out for humpback and fin whales, plus Atlantic white-sided dolphins and harbor porpoises with the help of a naturalist guide. The on-board galley offers hot meals, snacks and beverages for purchase during the trip.

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 history, architecture, and innovation. Wander through its grand halls, secret passageways, and oceanfront grounds at your own pace. What You’ll Experience Roam through the breathtaking halls, medieval artifacts, and hidden chambers of this one-of-a-kind seaside castle. See its towering stone archways, gothic-style rooms, and original furnishings. Step onto the castle’s terraces for stunning panoramic views of the Atlantic Ocean and Gloucester’s rocky coastline. Learn about Hammond’s groundbreaking work in radio and remote-control technology through interactive exhibits and displays. Each Trip includes The Weekend Commuter Rail Pass, so your travels don’t need to end when the tour ends! The Weekend Pass is valid on ALL Commuter Rail Lines all weekend!

Explore the stunning Gloucester Harbor and Annisquam River on a guided kayak tour from Boston. Paddle past historic landmarks, catch a glimpse of the famous Wicked Tuna boats, and even hunt for sea glass on Ten Pound Island. This adventure is perfect for both seasoned kayakers and beginners, blending sightseeing with relaxation. Enjoy free time for dinner in Gloucester before returning to Boston via a private van shuttle. - Guided 4-hour kayak tour suitable for all skill levels - Visit Ten Pound Island for the best sea glass collecting - Spot Wicked Tuna boats while paddling through the harbor - Includes transportation from Boston and free time for dinner