Living in Sag Harbor places you in one of the most charming corners of the Hamptons. With its boating culture, historic charm, and access to fine dining and shopping, it offers a lifestyle that's both relaxed and sophisticated. Yet part of the appeal of owning property in Sag Harbor is how conveniently located it is to other attractive destinations. Whether you’re looking for a quick beach escape, a taste of wine country, or a walk through history, there are many weekend trips from Sag Harbor worth taking.
Each destination offers something unique, allowing you to change the pace without losing touch with luxury and comfort.
Montauk, NY: A Coastal Experience at the Edge of Long Island
Just about an hour from Sag Harbor, Montauk draws those who love wide beaches, fresh seafood, and outdoor adventure. It's a fitting option for a weekend retreat that remains close to home but feels worlds away.
From early morning surfing to sunset dinners by the water, Montauk has something to offer every type of traveler.
- Visit the iconic Montauk Point Lighthouse, the oldest in New York State
- Spend an afternoon fishing or take a charter boat for a deep-sea experience
- Dine at local seafood spots like Duryea’s or Harvest on Fort Pond
Whether you're visiting in summer or the quieter shoulder seasons, Montauk gives you the freedom to recharge.
Greenport, NY: A North Fork Favorite for Wine and Waterfront
Reachable by ferry through Shelter Island, Greenport is a historic harbor village on Long Island’s North Fork. Known for its walkable downtown and coastal views, it’s a destination that blends small-town charm with refined attractions.
Enjoy time by the water or explore the wine trail that winds through the nearby countryside.
- Tour the East End Seaport Museum or take a harbor cruise
- Sample wines at vineyards like Kontokosta, One Woman, or Sparkling Pointe
- Stroll through Mitchell Park or visit local galleries and boutiques
Greenport makes a great weekend trip for those who want to slow down while still enjoying high-quality food and wine.
Shelter Island, NY: Peaceful Luxury Between the Forks
Only a short ferry ride from Sag Harbor, Shelter Island offers a restful alternative to the busier parts of the Hamptons. It’s perfect for low-key weekends centered on nature, art, and coastal views.
Popular activities include kayaking, hiking, and enjoying meals outdoors at one of the island’s quiet, upscale spots.
- Hike through Mashomack Preserve, a 2,000+ acre nature area
- Relax at Crescent Beach or take a paddleboard out on Coecles Harbor
- Dine at The Rams Head Inn for classic Long Island cuisine
Shelter Island is a fitting choice if you're looking for close proximity paired with tranquility.
Mystic, CT: Maritime Heritage and Coastal Appeal
A drive and ferry ride away, Mystic is one of Connecticut’s most popular destinations for a short getaway. It's known for maritime history, local seafood, and well-preserved architecture.
Explore everything from historic ships to coastal trails during your visit.
- Tour the Mystic Seaport Museum with its restored 19th-century village
- Visit the Mystic Aquarium or take a walk along the riverfront
- Try local favorites like oysters at Red 36 or a lobster roll from Ford’s
For anyone who enjoys the charm of coastal New England, Mystic delivers both culture and comfort.
Hudson Valley, NY: Art, History, and Rolling Countryside
About three hours from Sag Harbor, the Hudson Valley presents a scenic contrast to coastal living. It’s known for farm-to-table dining, vineyard tours, and cultural landmarks.
The area suits those looking for wide open spaces, historic homes, and access to the arts.
Visit Dia Beacon or Storm King Art Center for large-scale contemporary works. Stop at local wineries like Millbrook Vineyards or Benmarl Winery. Tour historic estates like the Vanderbilt Mansion or Franklin D. Roosevelt’s home.
The Hudson Valley makes a thoughtful escape for anyone seeking refined relaxation in a more rural setting.
East Hampton, NY: Culture and Convenience Close to Home
Just a 20-minute drive from Sag Harbor, East Hampton is an excellent option for a quick overnight stay or day trip. It's home to some of the most upscale shopping and fine dining on Long Island’s East End.
It's also a cultural destination with historical sites and artist residences.
Tour the Pollock-Krasner House in nearby Springs. Shop at designer boutiques and independent stores along Newtown Lane. Book dinner at Nick & Toni’s or 1770 House for a top dining experience.
East Hampton provides a seamless mix of culture, cuisine, and coastal leisure.
Port Jefferson, NY: A North Shore Village with Historic Character
Port Jefferson, located on Long Island’s northern shore, offers a family-friendly environment with maritime flavor. It’s easily accessible by car from Sag Harbor in under two hours.
Spend your weekend walking through town, enjoying the harbor views, and taking in local performances.
Attend a show at Theatre Three, a local performing arts center. Walk along the marina or book a harbor tour. Dine at waterfront restaurants like Danfords or The Fifth Season.
With its combination of scenic beauty and small-town warmth, Port Jefferson is well-suited for a relaxing trip.
Quogue, NY: Beachfront Simplicity in the Hamptons
Located just west of Southampton, Quogue offers an intimate beach town setting that retains the charm of Old Long Island. It’s known for quiet beaches and historic homes, making it a quiet counterpart to more developed parts of the South Fork.
Walk through the Quogue Historic District with its classic architecture. Visit the Quogue Wildlife Refuge for nature trails and birdwatching. Enjoy an uncrowded beach day away from the summer rush.
For those seeking privacy and subtle luxury, Quogue is an ideal destination.
Cedar Point County Park, NY: Nature Just Minutes Away
Only a short drive from Sag Harbor, Cedar Point County Park offers an easy escape for a day trip focused on the outdoors.
With access to walking trails and water views, it’s a great choice for anyone who enjoys fresh air and coastal scenery.
Hike the trail to the historic Cedar Island Lighthouse. Plan a picnic or camp overnight under the stars. Enjoy kayaking or paddleboarding in the bay.
It’s close enough to make the most of your weekend while still feeling like a break from the everyday routine.
Contact Michael Petersohn
For those looking to make Sag Harbor their full-time residence or vacation home base, Michael Petersohn offers the guidance you need to make the right move. His local knowledge and dedication to client success make him the right partner for buying or selling in this exceptional community.
Michael has extensive experience helping buyers navigate the Hamptons market and assisting sellers with strategic marketing and pricing. Whether you're upgrading, downsizing, or searching for a second home, he provides the clarity and professionalism that turn goals into results.
Reach out to Michael Petersohn today to explore current listings and personalized opportunities in Sag Harbor and beyond.
