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You could join the spectators who flock to southeastern Massachusetts every summer for the Buzzards Bay Regatta (Aug. 1 to 3 this year; www.buzzardsbayregatta.com), with 450 boats and 1,200 sailors competing. Or you could paddle a kayak on the bay, a designated Estuary of National Significance, and experience its beauty firsthand. Osprey Sea Kayak Adventures (508-636-0300; www.ospreyseakayak.com), based in Westport, Mass., offers a variety of guided tours (from $49), including the Westport River, Sunset and Moonlight tours 鈥� even a six-hour excursion combining kayaking with wine-tasting and dinner. You can also New Bedford (www.newbedford-ma.gov), the famous whaling port where Herman Melville set the early scenes of 鈥淢oby Dick.鈥� Worth a visit: the New Bedford Whaling Museum ($10), the Greek Revival Rotch-Jones-Duff House and Garden Museum ($5), and the 13-block New Bedford Whaling National Historical Park on the waterfront (www.nps.gov/nebe).