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