3 Best Sights in Nantucket Town, Nantucket

This association maintains an assortment of venerable properties in town. A $25 pass gets you into all of the association's sites, including the glorious Whaling Museum and Hadwen House: historic properties including the Oldest House, Old Mill, Old Gaol, Greater Light are free for all visitors. Reserve in advance for the 60-minute Historic Downtown walking tour ( $25), which departs Monday through Saturday, late May–early September.

Surfside Beach, accessible via the Surfside Bike Path (3 miles) or by shuttle bus, is the island's most popular surf beach. This wide strand of sand comes fully equipped with conveniences. It draws teens and young adults as well as families and is great for kite flying and, after 5 pm, surf casting. Amenities: food and drink; lifeguards; parking (fee); showers; toilets. Best for: surfing; swimming; walking.

With exhibits that include a fully rigged whaleboat and a skeleton of a 46-foot sperm whale, this must-see museum—a complex that includes a restored 1846 spermaceti candle factory—offers a crash course in the island's colorful history. Items on display include harpoons and other whale-hunting implements; portraits of whaling captains and their wives (a few of whom went whaling as well); the South Seas curiosities they brought home; a large collection of sailors' crafts; a full-size tryworks once used to process whale oil; and the original 16-foot-high 1850 lens from Sankaty Head Lighthouse. The museum also offers a rotating gallery with new exhibits each season, a fine art gallery, and a world-class scrimshaw collection. The Children's Discovery Room provides interactive learning opportunities. Be sure to climb—or take the wheelchair-accessible elevator—up to Tucker's Roofwalk for a view of the harbor.