How to Plan the Perfect Trip to Sag Harbor, New York

Between its beautiful beaches, tony shops, and buzzy bars and restaurants, it’s no surprise the Hamptons is considered among America’s most popular summer travel destinations. While the destination has earned a reputation for its sometimes-stuffy, seen-and-be-seen vibe, there are some more low-key spots worth exploring. Take Sag Harbor, for example: Part of both Southampton and East Hampton, this unincorporated village is most famous for its whaling history and laid-back atmosphere. According to Fora co-founder and travel advisor Henley Vazquez, “Sag Harbor is a charming town packed with a ton of character.” Plus, she says, “It has deep historic connections that offer a real sense of place and a down-to-earth vibe.” 

Sag Harbor also makes a great jumping-off point for exploring the rest of the Hamptons, along with nearby Shelter Island. The North Fork, known for its fantastic culinary scene and ample wineries, is about an hour away, while Montauk is approximately 35 minutes away by car. Another reason to visit Sag Harbor? The beaches. Unlike other Hamptons hotspots like East Hampton or Sagaponack, which are located on the ocean, the stretches of sand found in Sag Harbor are situated along the bay  — meaning the waters are much calmer.

Ultimately, just about anyone, from families to couples to groups of friends, will appreciate Sag Harbor’s small-town feel. Ahead, we’re rounding up everything you need to know — from hotel recommendations to transportation tips — to help you plan a spectacular Sag Harbor getaway. 

Best Hotels in Sag Harbor 

Baron’s Cove

Vazquez describes Baron’s Cove as “a renovated and rehabbed motel [with] retro vibes.” The hotel attracts all sorts of travelers — from hip couples to young families — for its upscale amenities such as a sparkling swimming pool, seasonal beach service, an on-site tennis court, and complimentary bike rentals so you can explore Sag Harbor in style. The all-day restaurant, which serves up seafood staples like lobster rolls and local oysters, is especially noteworthy, as is the lively lounge area with indoor and outdoor seating. Take your pick of 67 rooms and suites done up in whites, grays, and blues in homage to Sag Harbor’s nautical history and waterfront locale. For a worth-it splurge, consider one of the accommodations with private gardens or decks. 

The American Hotel

Dating back to 1846, The American Hotel “offers a great sense of history as well as comfortable rooms right in the middle of town,” says Vazquez. The quaint property is ideally situated in the heart of Sag Harbor. Each of its eight rooms is outfitted with turn-of-the-century art and furniture along with double whirlpool bathtubs — making it an ideal choice for those craving a more intimate stay. The on-site restaurant, famous for its French-American fare and spectacular wine list, is also not to be missed.

Best Things to Do in Sag Harbor

Main Street 

Dating back to 1745, Main Street serves as Sag Harbor’s central hub. The picturesque nine-block stretch is teeming with eclectic shopping and dining offerings — but more on those later. Additionally, you can easily spend an entire afternoon here popping in and out of stores and people-watching, stopping for coffee, cocktails, and snacks along the way. 

The Beach

Sag Harbor is home to several serene stretches of sand, including the beloved Havens Beach. The calm waters make it a popular pick amongst families. The mile-long Foster Memorial Beach is another excellent option. Meanwhile, Windmill Beach is just steps from Main Street, and Circle Beach is a great place to watch the sunset.

Bay Street Theater

According to Vazquez, a visit to Bay Street Theater is an absolute must. “In the summer, they also offer kids camps, giving families another reason to love the theater; parents can relax while their children are entertained!”  Additionally, the venue often hosts concerts, workshops, masterclasses, and more, so be sure to check the events calendar. 

Elizabeth Alexandra Morton National Wildlife Refuge

This 187-acre wildlife refuge is a popular spot for hiking and  — you guessed it — spotting wildlife such as white-tailed deer, turkeys, songbirds, and turtles. Spend the morning walking along the 1.2-mile-long Wild Birds Nature Trail, which winds through wooded areas and the beach. Visitors can also stroll nearly two miles on the beach along Jessup’s Neck Peninsula. 

Sag Harbor Whaling & Historical Museum

History buffs can learn more about the destination’s fascinating whaling history at the Sag Harbor Whaling & Historical Museum. Housed inside an 1845-era building right on Main Street, the museum is home to a vast collection of historical objects along with more contemporary exhibits. 

Best Shopping in Sag Harbor 

Thriftknd

Thriftknd — which gets its name from its owner, Brittany Rivkind — offers an array of vintage and pre-owned apparel and accessories to suit every style. But that’s not all: The shop also sells fun items like cheeky greeting cards, colorful planners, and even locally made dog treats.

Bloom

“Bloom is a fabulous little antique and furniture store,” says Vazquez. “It’s perfect for anyone looking to furnish their dream Hamptons house or take a piece of the Hamptons back home.” Expect a specially curated selection of beachy-chic hostess gifts, tableware, and accessories. 

Sag Harbor Books

Established in May 2019, this lovely little independent bookstore is a fairly new addition to the neighborhood. Literary lovers will appreciate the wide variety of reading materials, ranging from splashy coffee table books to beach reads and beyond. Plus, says Vazquez, “The whale logo on their storefront is a nice nod to ‘Moby Dick.’” 

Sylvester & Co. Modern General

Helmed by designer and artist Lynda Sylvester, Sylvester & Co. Modern General is the chicest general store we’ve ever seen — which, given its Sag Harbor locale, is no surprise. Shoppers can find (pretty much) anything, including bespoke furnishings, colorful pickleball paddles, stylish barware, artisanal soap, baby clothes, and gourmet chocolates. Before checking out, grab a cold brew at the on-site coffee bar — where you’ll encounter a much shorter line than Jack’s Stir Brew, which is just a few steps away.

Best Restaurants in Sag Harbor 

Le Bilbouquet

If you’re looking for an over-the-top lunch scene, Vazquez recommends heading straight to Le Bilbouquet. The French eatery, best known for its iconic Upper East Side flagship location, attracts well-heeled locals and travelers alike. Come for the signature Cajun chicken or tuna tartare – best enjoyed with a glass of rosé, of course — and stay for the harbor views and people-watching opportunities. If you’re lucky, you may be able to spot a celeb or two. 

Tutto Il Giorno

For excellent Italian cuisine, look no further than Tutto Il Giorno, which Vazquez describes as a “Sag Harbor staple” thanks to its fun vibe and killer pasta dishes (do yourself a favor and order the rigatoni with spicy sausage). Try snagging a table outdoors, where you’ll be surrounded by lush greenery, blooming hydrangeas, and twinkling lights — setting the scene for a picture-perfect meal. 

Grindstone Coffee & Donuts

Start your mornings at Grindstone Coffee & Donuts, which offers an ever-changing daily selection of small-batch brioche and cake donuts (flavors run the gamut from lemon poppy seed to strawberry glazed to churro). Bonus: All glazes and fillings are made in-house with locally sourced organic ingredients. Pair your pastry with a classic hot or iced coffee, or, for something sweet, opt for a mocha or honey lavender latte. 

Lulu Kitchen & Bar

Wood-fired cooking is on full display at the Mediterranean-inspired Lulu Kitchen & Bar. The restaurant boasts a cozy ambiance, making it the ideal date night spot. Diners can feast on mouthwatering menu items such as extravagant seafood towers, wood-fired pizzas, steak tartare, and, last but not least, the signature heirloom cauliflower served with spicy grapes, yogurt, Aleppo pepper, roasted sesame seeds, and balsamic glaze. Wash it all down with a specialty cocktail – you can’t go wrong with the daiquiri —  and save room for dessert (the strawberry sundae and profiteroles are two of our favorites). 

Best Time to Visit Sag Harbor 

The best time to visit Sag Harbor is between May and October, which overlaps with the destination's peak season (though parts of May and September, along with October, are considered shoulder seasons). During this time, travelers can enjoy warm, sunny weather (read: plenty of beach days and al fresco meals). Also, it's worth noting that some shops, restaurants, and hotels are only open seasonally.

However, that’s not to say you have to visit in the summer to have a great time. Moreover, Vazquez notes that “Sag Harbor is really a year-round destination" and that visiting outside of June, July, or August is "when you will find it to be the most charming.” For example, Vazquez tells Travel + Leisure that “even though it might be chilly,” Sag Harbor is “a cozy spot around the winter holidays.” Additionally, keep in mind that during the off-season, you’ll be able to enjoy fewer crowds and lower prices — a win-win, in our book.

How to Get There

“The ideal way to travel to Sag Harbor is by car because you will want your car to get around once you arrive,” says Vazquez. No car? No problem. From New York City, hop on the Hampton Jitney, which will drop you off right on Main Street; just note that the schedule varies depending on the season. You can also take the Long Island Railroad to Bridgehampton, a 10-minute Uber ride away. 

Travelers hoping to avoid the traffic and the crowds altogether can splurge on a quick 40-minute helicopter ride from Manhattan to East Hampton (a nine-minute drive from Sag Harbor) with Blade. Lastly, Long Island MacArthur Airport in Islip is about 55 miles away, followed by John F. Kennedy International Airport and LaGuardia International Airport, which are both around 93 miles away.  

How to Get Around

Once you’re in Sag Harbor, getting around is relatively easy, considering its small size and walkability. However, if you want to explore the surrounding towns and villages, renting a car is best. (Fortunately, companies like Hertz and Enterprise have several locations throughout the Hamptons.) While taxis and ride-share services are available, they’re not cheap — and the cost can add up quickly.