New York to Nantucket = 1 hour
For every popped-collar blue blood swanning about this tony enclave, there’s a pleb-friendly local willing to cut a deal. Charming B&B Union Street Inn (from $169; 7 Union St.; unioninn.com) posts reduced rates ten days in advance, while some midweek rooms at the 167-year-old Jared Coffin House (29 Broad St.; jaredcoffinhouse.com) dip as low as $125. Dodge the overpriced, ornery cabbies by hitching a lift on the Wave shuttle ($1 to $2; nrtawave.com) or renting a hybrid bike from Young’s (day rates start at $25; 6 Broad St.; 508-228-1151). Early risers can dig into a stack of cranberry pancakes ($6) at the venerable Downyflake (18 Sparks Ave.; 508-228-4533); late sleepers can savor a $25 prix fixe lunch at Topper’s in the ritzy Wauwinet hotel (120 Wauwinet Rd.; 508-228-8768). Hike the ram pastures near old Sanford Farm (nantucketconservation.org) or observe ospreys and northern harriers at the Linda Loring Nature Foundation (10 Eel Point Rd.; llnf.org)—all gratis—or pay a visit to the Nantucket Dreamland theater (17 S. Water St.; 508-228-1784), which has reopened after a $30 million overhaul and sells select tickets for $10 and up. The property tour at Cisco Brewers ($20; 5 Bartlett Farm Rd.; 508-325-5929) includes live music and tastings of house quaffs like Whale’s Tale Pale Ale. Grab a six-pack to go before boarding the friendship sloop Endeavor (Slip 1015, Straight Wharf; 508-228-5585), whose 90-minute BYO sunset sails start at $50. For authentic souvenirs, skip the seaside shopping loop and raid the town dump’s Take It or Leave It pile instead (188 Madaket Rd.; 508-228-4283). Because, yes: Rich people’s trash really is better.