Sag Harbor Travel Guide

Where to Weekend: Sag Harbor Makes a Great Chill-Weather Getaway

All Photos Courtesy Of James O'Brien

For urban dwellers deprived of star-saturated skies, easily accessible beaches, and Dickensian-level quaintness, Sag Harbor provides a perfect two-day reprieve from city life.

Don’t let that old-fashioned charm fool you, though: there is ample opportunity in the Long Island village to indulge during your weekend away, whether on local wine and beer, or oysters and other delectables. You don’t have to wait until summer, either: in fall and early winter the crowds disperse, the skies take on a cinereal blue, and fireplaces crackle in bed and breakfast lobbies.

DAY1

Beets, Beer, and Baron’s Cove 

Arrive at the hotel Friday night (we love Baron’s Cove) in time for dinner, or ease stress levels and opt for an early-morning drive on Saturday, when you’re likely to miss traffic.

Dine at the hotel’s restaurant (reservations recommended), to try Chef Jay Lippin’s seasonally-shifting menu—think candy-striped beet salad, Peconic gold oysters, and steak frites. Pair with a beer or glass of wine from the Tavern menu. See what packages the hotel has to offer for dining credit during your stay.

Oysters at Baron’s Cove
DAY2

Booze, Books, and Burrata

Grab breakfast at your hotel, then wander to the adjacent harbor and marvel at yachts and subtle lapping waves. Later, walk or bike to Main Street for gourmet pizza and wine at Sag Pizza. White-tiled and sun-drenched, the classically modern eatery has an open-concept kitchen where you can watch creations like pies with farm eggs and mecox cheese come to life in a brick oven. A glass of red pairs nicely in the afternoon.

Sag Pizza

Stroll along Main Street as far as the marina, stopping in at Harbor Books and Dobra Tea Shop where you can pick up a copy of Colson Whitehead’s Sag Harbor, which takes a look at the village in the mid-1980s from the perspective of two African American brothers.

Ready for a drink? Go for pre-dinner cocktails at the American Hotel to get a sense of whaling-era Sag Harbor. Opened in 1846, this spot was a hangout for politicians and cigar aficionados, and the interior remains relatively unchanged.

American Hotel

Check in and unwind at Baron’s Cove; hopefully, you’ll catch some early evening live entertainment in the nautical-chic lounge.

 

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Oktoberfest at Baron’s Cove

Take an evening stroll but skip the downtown scene. If you’re really curious about what the locals are up to after sunset, drop in for a beer at The Corner Bar, seemingly the one remaining stronghold for locals-approved drinking dens. Alternatively, you can grab some champagne for your room at the Sag Harbor Liquor Store, or warm up in the lobby lounge with cocktails by the fire.

 

DAY3

Bakeries, Bikes, and Bordeaux

The next morning, borrow a bike from Baron’s Cove and ride to Grindstone Coffee & Donuts for a quick and easy breakfast, or the local-loved Jack’s Stir Brew for coffee and pastries. Continue your bike ride over the bridge and take in views of the bay.

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Grindstone Coffee and Donuts

If you’re driving, return your bikes and check out of the hotel. If you’re car-less, keep the bikes to get to these nearby locales: Get produce to take home from Basalm Farms in Amagansett, then bike to the LongHouse Reserve Sculpture Garden and wander through impressive contemporary sculptures (including one by Yoko Ono!) and bucolic wonderlands.

Later, bike or drive to Wölffer Estate Vineyard (less than 10 minutes) to marvel at the vineyard and vast, rustic tasting room while nibbling charcuterie and sipping their light and refreshing rosé cider.

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WHERE TO STAY

Make Baron’s Cove your home for the weekend, where luxury is balanced with comfort and warm hospitality. Totally worth the splurge, it feels more like your own personal hideaway rather than a 67-room resort when you wake up with the sun bouncing off the harbor and through the skylight into your lofted suite, complete with a balcony. From breakfast, lunch, and dinner served in the open and opulent upstairs dining room, to live entertainment (nightly in summer), and various events like Oktoberfest and Restaurant Week in the lounge, you could spend at least half your vacation just on the property and not get bored.

 

 

 

WHEN TO GO

In summer and early fall, wade in the outdoor pool at Baron’s Cove or dine on the patio. Complimentary bikes can get you around the Hamptons, but you can also walk just a few minutes to Main Street’s shops, bars, and restaurants, and to the local jitney stop (check to see what travel credits they are offering to guests). In winter, cozy up by the fireplace and marvel at Christmas decorations and revel in the lack of other tourists during Sag Harbor’s off-season.

 

GETTING THERE

By car: Sag Harbor is slightly over a two-hour drive from Manhattan without traffic (which you should expect on a Friday afternoon or evening) via 495 West. By public transportation: For the 55 percent of New Yorkers without cars, it’s also accessible via the Long Island Railroad (you will need to get a cab or take the Hampton Hopper from the train station—Bridgehampton is the closest), or better yet, the Hampton Jitney (tickets are $29 each way if purchased in advance online).