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Weekend in Sag Harbor - hero
Jamie Ditaranto

How to Do a Weekend in Sag Harbor, New York

Before I even left for my weekend away, just dropping the line “I’m going to the Hamptons,” felt like admitting that I am secretly a movie star. After all, the region that defines the forked point on the eastern end of Long Island is associated with wealthy socialites and celebrities retreating from the crowds of the city for the solitude of their seaside mansion. However, you don’t need to be in the market for a multimillion dollar home to enjoy the natural beauty of the Hamptons that draws so many to find respite on the water.

Among its grassy marshes and bays, the Hamptons is made up of many different enclaves, from the celebrity-dense Southampton to the surfing haven of Montauk. But for travelers looking to partake in a more down-to-earth version of the Hamptons, look no further than Sag Harbor—the Hamptons village famously referred to as “the Unhamptons.”

Along Main Street, Sag Harbor is trimmed with independent shops all the way down to the water, where a windmill commemorating former mayor and author John Steinbeck who spent the last years of his life in Sag Harbor, marks the entrance to the Long Wharf Marina. Beyond the marina, are the many bays, inlets, and islands that make up the Hamptons. With Sag Harbor right in the middle of it all, it’s the perfect launching-off point for a weekend spent lounging on the beach, gawking at mansions, and indulging in fresh seafood. If you’re planning a getaway to the Hamptons, here’s how to do a weekend in Sag Harbor.

[viator_tour destination=”687″ type=”3-mod” tours=”3857NYCHAM,7030P15,67464P3″]

The Hotel 

Weekend in sag harbor
Jamie Ditaranto

Overlooking the bay, Baron’s Cove is a hotel that modestly knits together the subtle style of a Hamptons summer home with the relaxed feel of a New England backyard. Each room features a front porch set with a picnic table and chairs, and at the center of every guest-to-guest conversation, are the plush cloud-like beds set in trim white rooms. But what makes this hotel great for a weekend stay are the plenty of amenities to be taken advantage of, such as the saltwater pool, tennis courts, complimentary bike rentals, and free beach shuttle bus. 


Weekend in sag harbor
Jamie Ditaranto

If you’re coming from the city, you’ll need to catch “the jitney.” For those who are unfamiliar, the jitney is the catch-all term for the buses that run routes from Manhattan to the Hamptons. There are a handful of different companies you can use, but I recommend the super comfortable Hampton Ambassador, which leaves from Manhattan from 11:30 a.m. to 8:30 p.m., and has excellent Wi-Fi. The ride lasts anywhere between two and three hours depending on traffic, so on your first night in Sag Harbor, plan for a relaxed evening and indulge in dinner either at your hotel or venture a short way down the road for fresh seafood at The Bell & Anchor. Before bed, you can grab a nightcap at the Baron’s Cove lobby cocktail bar, best enjoyed while sitting next to the fireplace on the terrace.


Weekend in sag harbor
Jamie Ditaranto

 Take your time to enjoy a peaceful morning, either by walking down to town for a quick breakfast at Grindstone Coffee and Donuts or by ordering room service to your personal front porch. Once you refuel, it’s time to launch off and enjoy the Hamptons on the water. If you’re feeling adventurous, you can sign up for wakesurfing or waterskiing with Global Boarding. If you want a more relaxing ride, take the water taxi to Sunset Beach or rent or charter a boat. You can use websites like Discover Boating to find and compare last-minute options like Sailacat Sailing Charters or Sag Harbor Charters. Once you’ve got your boat, you can cruise around the Hamptons admiring the larger-than-life ho

mes and hopping from town to town. If you’re in the mood for oysters, make a stop on the North Fork in Greenport to explore the town and check out Little Creek Oyster Farm & Market, a cozy shack where you can shuck your own fresh-caught oysters and try the local beer.

Make sure to get back to town in time to try and grab a table at the Dock House, one of the most popular restaurants in town, famous for its lobster rolls and sunset views.

Behind the Scenes Look at Island Creek Oysters


Weekend in sag harbor
Jamie Ditaranto

If you wake up on your last day in Sag Harbor in the mood for brunch, you can try the menus at Wolffer Kitchen or the Market Yard Grille at the American Hotel before checking out of your hotel. When you head back is up to you: You can decide to get home early or make the most of your day by booking a later jitney. There’s always the option to store your bags at the front desk and take some time to explore the town by browsing the shelves at Harbor Books or checking out the latest fashions at designer Donna Karan’s boutique Urban Zen. If you’re in need of a quick a bite before the bus, stop in for a burger at the local-favorite LT Burger. Another way to spend your extended afternoon is by taking advantage of Baron Cove’s free shuttle and heading to Long Beach to clock in some more time on the water.


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 Jamie Ditaranto visited Sag Harbor courtesy of Discover Boating. Follow her on Twitter @jamieditaranto.

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