watch hill rhode island

48 Hours in Watch Hill, Rhode Island

Want to vacation like Taylor Swift? You've come to the right place.

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Watch Hill, to many, is the one of the best alternatives to the Hamptons. A three-hour drive from New York City (without the stultifying Long Island Expressway traffic) and two hours from Boston, this quiet, little coastal town is the perfect place to chill out, work out and step back in time. While Watch Hill has been a beloved getaway since the days of Clark Gable and Jean Harlow, it's Taylor Swift who's bringing attention to the destination these days. Her annual Fourth of July parties and $17.75 million dollar home occasionally land the town in celebrity news—and all over Instagram. But for the most part, this seaside retreat treasures its low profile.

Where to Stay
There really is only one place to say in Watch Hill and that’s Ocean House. A beautiful Victorian-era inn set on the beach, the original hotel was built in 1868. In 2010, it re-opened after an extensive renovation that recreated the original structure with modern amenities. The five-star property features traditional hotel rooms as well as suites and cottages, perfect for when you’re traveling with a crowd. The Ocean House is an all-inclusive resort, so gratuities are included and amenities such as snacks and sparkling water are provided in all rooms. The resort features a beautiful, private, white sand beach with cabana service. And there’s an indoor pool that overlooks the ocean as well as a pair of on-site restaurants. Serious movie buffs might recognize the hotel and its tournament-level croquet lawn, as they were featured in the 1916 Douglas Fairbanks movie, American Aristocracy.

Day 1
Start your the morning with a smoothie in your room and then head to the beach for a surfing lesson. Watch Hill is an ideal place to learn how to surf because the beach has a soft sand bottom as opposed to sharp rocks or reef. While this particular coastline is mild enough that you can surf all day, wave conditions are typically cleaner in the morning or early evening. Come back to the hotel for an early lunch at the Verandah Raw Bar, which is adjacent to the pool and overlooks the Atlantic Ocean. The spot features a traditional New England raw bar with oysters, clams and crab claws as well as a daily offering of ceviche and chowders. After lunch, take a leisurely walk down to the Watch Hill lighthouse. The watch tower has been a beacon for ships since 1745 and Thomas Jefferson signed the order to build the lighthouse in 1806. You’ll pass Taylor Swift's house along the way. You'll know it's hers because there’s a sign that says, “No Trespassing. I Knew You Were Trouble When You Walked In.”

Come late afternoon, set sail in one of Ocean House’s three boats. You can charter a motor boat, fishing boat, or a sailboat, complete with a captain, for a two-hour stretch. If you want a more active end to your day, sign up for a Full Moon party, a regular Saturday night sunset stand-up paddle board party organized by Paddle Surf Rhode Island.

Day 2
Sleep in a little bit or wake up early to take a private paddle board yoga class. Either way, you'll next want to check out the Sunday jazz brunch at Seasons, the Ocean House’s main farm-to-table restaurant. Tables in the front room offer direct views of the ocean and the brunch features the usual breakfast suspects, with an added emphasis on seafood in the form of a raw bar, fisherman’s stew and jerk shrimp skewers. Save room for dessert and walk into town for ice cream at the historic (seriously, it's been around since 1887) St. Claire Annex ice cream shop. Once you get your cone, take a peek at the Flying Horses Carousel, the oldest continuously operating carousel in the United States. In the afternoon, change into your whites for a game of croquet or squash in town. Then borrow one of the Ocean House's four Mercedes convertibles for a sunset drive into nearby Newport, Rhode Island or Mystic, Connecticut.