Nantucket, MA

From White Plains: 6.5 hours (incl. 2-hour ferry ride)

Skip the summer gridlock and visit this preppy paradise in the fall, when outdoor activities rule. Take a guided bird/nature walk at the Linda Loring Nature Foundation, to see glorious autumn wildflowers, the unique sand-plane grassland, and myriad birds. A two-hour cycle with Nantucket Bike Tours includes sights like the Brant Point Lighthouse, Steps Beach, and the spectacular mansions of the coveted Cliff neighborhood before ending up at Cisco Brewery. Kids will adore the Nantucket Critter Cruise, a one-hour boat trip that lets them try their hand at fishing while checking out briny critters hauled up from the deep.

Fall is also festival season on the island: a TED Talk-like gathering called The Nantucket Project takes place Sept 14–17; the Nantucket Arts Festival (Sept 30–Oct 9) combines visual, musical, theatrical, and other fine arts; and the Nantucket Conservation Foundation’s Cranberry Festival in early October offers all things cranberry.

Nantucket has more than its fair share of amazing food, too. The whole family will love breakfast at Black-Eyed Susan’s and quite possibly the best ice cream ever at The Juice Bar. Make time for an adults-only dinner at Dune, to sample Chef Michael Getter’s ridiculously fresh seasonal cuisine, and/or Cru, a see-and-be-seen waterfront hotspot with the island’s best raw bar. Don’t leave Nantucket without browsing the quaint downtown cobblestone streets and visiting The Whaling Museum for a fascinating look at the island’s history.

STAY: The Nantucket Hotel + Resort

Set foot in the lobby of The Nantucket Hotel + Resort, and you’re reassured that kid-friendly and upscale luxury can happily coexist. Your children will get an official welcome from the hotel’s mechanical whale (a nod to the island’s whaling history), while you are greeted warmly by the pampering staff. Ideally located within walking distance to everything and decorated in a modern nautical style, the hotel’s 42 guestrooms (including one- to four-bedroom suites) ooze preppy chic. Amenities include two outdoor heated pools; Breeze restaurant; and The Nantucket Club & Spa, which includes a kids’ activity area (babysitting services, too!), plus fitness/yoga classes and massage treatments. At some point during your stay, be sure to sip a craft cocktail (we fell in love with the ACK Breeze, featuring local muddled blueberries) next to a firepit on the darling front porch. From $250/night; www.thenantuckethotel.com

Luxe Tip: The long trip to Nantucket can be a deterrent, but luckily there’s a splurge that is 100% worth the cost: Tradewind Aviation runs daily scheduled shuttle service from HPN to the island through early December. The eight-seat Pilatus PC-12s get you to Nantucket in just about an hour — and you get to skip all the vacation-ruining inconveniences of driving or flying commercial. One-way flights from $585