A great long weekend: Basking in the island's real high season
In-the-know visitors – and locals – tend to agree that fall is the best time of year to head to Nantucket. The crowds have abated (but the vibe remains lively), the water is still warm, and the whole island seems to take on a magical golden hue. Plus, you can score deals at swanky hotels and get prime-time dinner reservations with relative ease, though be sure to call ahead, since some places close in October.
Getting There: Cape Air (866-227-3247; http://www.capeair.com) offers direct flights to Nantucket from Boston starting at around $310 round trip and super-fast puddle jumps from Hyannis for $112. For those who prefer to go by sea, there’s the Steamship Authority (508-495-3278; http://www.steamship-authority.com) and the Hy-Line (800-492-8082; http://www.hy-linecruises.com), both of which offer fast ferry (about one hour) and slow boat (about two hours) options from Hyannis (round trip $33 to $75).
Friday: If you go in mid-October or later, book a tee time at Sankaty Head Golf Club (508-257-6655; http://www.sankatyheadgc.com) in Siasconset. It’s uber-private all summer, but nonmembers can play starting in October. Have dinner in the candlelit American Seasons (508-228-7111; http://www.americanseasons.com) in downtown Nantucket. Start with a fall cocktail like a cranberry Old-Fashioned or a Drunk Pumpkin (Nantucket’s own Triple Eight vodka infused with sugar pumpkin from Bartlett’s Farm and brown-sugar simple syrup), then order a bottle from the restaurant’s well-edited all-American wine list. Treat yourself to a luxurious room complete with sumptuous organic sheets at the White Elephant (508-228-2500; http://www.whiteelephanthotel.com) or, heck, even the super-fancy Wauwinet (508-228-0145; http://www.wauwinet.com) on the east side of the island. Fall rates are a fraction of what you’d pay in midsummer – and even lower in October than they are in September. For an unheard-of-on-Nantucket bargain, try the Jared Coffin House (800-248-2405; http://www.jaredcoffinhouse.com), where rooms start at $125 per night in October.
Saturday: Start the day with a trail run or ramble through Sanford Farm, Ram Pasture, and The Woods, a group of adjacent properties protected by the Nantucket Conservation Foundation (508-228-2884; http://www.nantucketconservation.com) on the south side of the island; the “Ocean Walk” route there is a 6-mile excursion from Madaket Road out to the Atlantic and back. Then pick your favorite beach – think
Sunday: Have breakfast at Black-Eyed Susan’s (508-325-0308; http://www.black-eyedsusans.com) without waiting in summer’s out-the-door line – they don’t take credit cards – then stroll around town and hunt for late-season sales at boutiques like the new-this-year Milly & Grace (508-901-5051; 2 Washington Street). Before you hop on a flight or ferry, grab a Nantucket Red cupcake from Sweet Seasons at American Seasons or a Turkey Terrific sandwich from Provisions (508-228-3258; 3 Harbor Square) and savor the flavor of fall on Nantucket for a little longer.
For more great long weekend travel ideas, please visit boston.com/magazine