An hour-long flight or a seven-hour drive, Nantucket is more accessible than you might think. Lobster rolls, boat rides, biking through quaint towns…Nantucket really is the picture of New England charm. And though it’s sure to be full of people on Labor Day weekend, the crowd is relaxed and low key. Grab an AirBnB near the water or, if you’re feeling like splurging a bit, stay at one of the cottages at The White Elephant, just steps from the beach. If The White Elephant is sold out or its price tag is too steep for you, snag a room at Jared Coffin House.
It’s a mere four-hour drive to Manchester, Vermont, and here you’ll find The Equinox Golf Resort & Spa, a well-known luxury resort. If Equinox isn’t quite your style, there’s the Woodstock Inn & Resort in Woodstock, Vermont. From either base, you can spend your days hiking, canoeing, fishing, or playing tennis or golf. This is the perfect place if you’re looking for a quiet, calm getaway away from the bustle of the city.
Only four-and-a-half hours away by car, The Finger Lakes in upstate New York have something for everyone, whether it’s hiking, swimming under a waterfall, or wine tasting that you’re after. Check out Ravines Wine Cellars or Sheldrake Point Winery for wine tastings with views over lakes, or take advantage of the natural beauty and head out for a kayak or canoe ride. Either way, there are plenty of things to do on and off the water to keep you busy.
Shelter Island is nestled between the South Fork of Long Island and the wine country of the North Fork, and it’s the perfect in-between spot. It’s only three hours away from Penn Station by train, but if you stay at the gorgeous Chequit, you’ll feel like you’re a world away from the city. Shelter Island itself is only 11.5 square miles, so spend your time exploring and admiring the Victorian architecture. Alternatively, check out vineyards, rent bikes, or explore the lavender fields for a picture-perfect weekend.
Though it may seem crazy to go all the way down to Bermuda for a weekend, it’s really just a two-hour flight away. And if you catch an evening flight on Friday, you’ll have three full days to soak up the sun and the water. This beach paradise has everything you’d expect in a tropical getaway, from scuba diving to beachfront shopping to lounging on the beach. hough this getaway isn’t the most wallet-friendly, you’ll be amazed that a mere two-hour flight can land you in the tropics.