A Weekend in Sag Harbor – Small Town Charm & Seaside Elegance
Looking for the perfect seaside escape? Sag Harbor is where celebrities go “to get away from it all.” Pack your celebrity-approved oversized sunglasses and get ready to cruise Sag Harbor’s waterways in style.
Located on Long Island’s interior south fork, Sag Harbor, with its chic vibe and coastal charm, is recognized as a playground for the rich and famous. Yet this renowned whaling village still retains its small town appeal. Overlooking the beautiful Shelter Island, Sag Harbor still bares the architectural evidence of its whaling glory days, while the stylish beach décor and welcoming atmosphere provide a relaxed haven for sea lovers, history buffs, and beach-goers alike.
Sag Harbor’s calm waters are the perfect place for sailing, cruising, sightseeing, and fishing. Live concerts, plays, gallery openings, and performances abound year-round. Check the Sag Harbor events calendar for upcoming art and music festivals.
With a past steeped in whaling and maritime history, Sag Harbor is infused with nautical fare and attractions. Ocean lovers will delight at the wealth of opportunity to experience seafaring culture—from museum exhibits, to boating excursions and cruises.
Main Street, the major artery through town, anchors the famous Long Wharf Harbor, often referred to as the “Million Dollar Harbor” due to the value of the boats that dock here.
Sag Harbor is exceptionally pedestrian friendly. Visitors will enjoy wandering the myriad of eclectic restaurants and shops, where everything from surf gear and beachwear to art galleries and book stores is easily within reach. Celebrity sightings along Main Street are a common occurrence.
History buffs won’t want to miss the Sag Harbor Whaling & Historical Museum, declared a National Treasure in 1998. Built in 1845, the museum was originally the home of Benjamin Huntting II, a leading citizen of Sag Harbor and owner of various whaling ships. The home was later occupied by well-known philanthropist Russell Sage, and subsequently purchased by the Masonic Lodge before becoming recognized as a certified National Treasure. Check the Sag Harbor Whaling & Historical Museum calendar for a list of upcoming events.
Beaches & Parks
Elizabeth A. Morton National Wildlife Refuge features remarkably diverse habitats. With sandy and rocky beaches outlying the peninsula, this 187-acre refuge consists of fields, ponds, salt marshes, and upland forests. The habitats are used by a variety of wildlife including white-tailed deer, eastern chipmunk, painted turtles, green frogs, songbirds and osprey.
Havens Beach is commonly rated as one of the most scenic beaches in Long Island. It features a playground and jungle gym for the kids, stunning views of the yachts in the harbor, as well as gazebos and BBQ grills.
Foster Memorial Beach, commonly known as Long Beach, is slightly rockier than Havens Beach but provides an excellent opportunity for shell hunting along the shore.
Shelter Island & Mashomack Preserve
Shelter Island is a unique island community within easy reach of New York City and the world-famous Hamptons. The jewel of Shelter Island is the 2,039-acre Mashomack Preserve, which comprises approximately one third of the Island’s land mass.
This natural area encompasses diverse habitats and protects one of the densest populations of breeding ospreys on the east coast. Mashomack also harbors a number of rare plants and nesting populations of other endangered birds. With its combination of interweaving tidal creeks, woodlands, fields, and coastline, Mashomack Preserve provides unparalleled scenic beauty as well as a diverse habitat for protected wildlife.
Sightseeing Cruises – the perfect way to spend a day on the water!
For picturesque views of Sag Harbor from the water, take a cruise along the river, or explore Shelter Island‘s 17 miles of shoreline, which provide plenty of opportunity for boating and sailing year-round.
Hop aboard a passenger boat for a public tour, or rent your own a private yacht! As you navigate these pristine waters, you will experience the beauty of Sag Harbor’s depths. You may even catch a glimpse of sea lions tanning, or a group of brown pelicans gliding low over the waves. Admire the glamorous luxury yachts as you cruise past Shelter Island’s Yacht Basin and enjoy close-up views of gorgeous waterfront resorts.
At the end of a fun-filled day on the water, satisfy your summer craving for ice-cream with a famous homemade cone at Big Olaf’s Ice Cream Shop, favorited by locals and visitors alike.
Reserve your Sag Harbor luxury boating adventure today!
Boatsetter has fleets of private boats, licensed captains, and a variety of sailing options available to help you embark on your Sag Harbor getaway. Whether you’re looking for a private cruise, a luxury yacht, or a sightseeing tour along the Peconic River, Boatsetter has you covered. Reserve today, then pack a chic wide-brimmed hat and get ready to experience all that Sag Harbor has to offer!