Hamptons Outdoor Activities on the Water
Most search results for outdoor activities Hamptons list the beaches, the trails, and the open sky. The hiking is fine. The biking is fine. But the best outdoor day in the Hamptons happens on the water. That is where the seals show up. That is where the sun sets behind the Greenport waterfront. And that is where you can drop a line and pull dinner out of the bay.
Charters in The Hamptons is a family-run charter company based at 63 Menantic Road on Shelter Island. We organize water-based outdoor activities across the East End. That includes boat charters, fishing trips, sunset cruises, eco tours, and water sports. Call us at (631) 251-1777 to plan your day on the water.
Boat-Based Outdoor Activities We Organize
Our outdoor activities are organized around the things only the water makes possible. We do not run hiking trips, vineyard tours, or land-based excursions. We do run the activities the East End is actually famous for.
Yacht and Boat Charters
Private charter is the headline activity. Our Hamptons boat charter rentals range from center consoles for half-day runs to our 57' and 62' Pershing yachts for full-day group outings. A captain handles the navigation. You handle the cooler and the playlist.
Sightseeing and Eco Tours
Our Hamptons boat tours run along the Greenport waterfront and past Bug Light at the entrance to Greenport Harbor. They also run through the back creeks bordering the Mashomack Preserve on Shelter Island. The preserve covers more than 2,000 acres of tidal creeks, woodlands, and salt marsh. The best views of it are from a boat.
Our Shelter Island eco tours focus on the quiet side of the island. Think herons, osprey nests, and slow-water coves you cannot reach by road or trail.
Fishing Charters
Our Hamptons fishing charters cover the Peconic Bay, Gardiners Bay, and the waters off Montauk. Striped bass, fluke, porgy, and bluefish are the regulars. All trips are run by USCG-licensed captains who know which spots are producing this week.
Water Sports — Jet Skis, Paddleboards, Kayaks
Our water sports equipment rentals cover the gear most people want for an active outdoor day. That includes paddleboards, kayaks, and jet skis. Members of our seasonal charter program get priority on rentals during peak summer weekends.
Sunset Cruises and Evening Adventures
The Hamptons sunset is the activity. Our Hamptons sunset cruises run on the calmer water as the day cools. Sightlines stretch back toward the Greenport waterfront, the North Fork wineries, and the open Peconic Bay. Sunset cruises are also the most-booked outing on our calendar. Book ahead for August weekends.
Why the Water Is The Hamptons' Best Outdoor Playground
When people search outdoor activities Hamptons, they usually picture sand and trails. Most of the famous spots are on the water. Shelter Island sits in the middle of the East End, between the North and South Forks of Long Island. From a boat anchored off the Mashomack Preserve, you can see both forks, the Peconic Bay, and on a clear day, Bug Light.
The South Fork has the famous beaches: Cooper's Beach in Southampton and the Hither Hills coast in Montauk. The North Fork has the wineries and Greenport. The water connects all of it. A day on the water can mix it all. A swim stop near Cooper's Beach. Lunch at a Sag Harbor restaurant dock. A sunset run back through the Greenport waterfront.
Why Plan Your Outdoor Day With Us
We are not the only operator on the East End. We are the one based in the middle of it, with the captains and fleet to back it up.
Our fleet includes 26+ vessels including 57' and 62' Pershing yachts. That is more than enough variety to match the right boat to your group size and your outdoor plan. All captains hold USCG (US Coast Guard) licenses, which is the trust signal you should look for in any captained outdoor experience.
Pickup is available at Greenport and Sag Harbor, with departures from our Shelter Island home base. If you are staying on the North Fork, we meet you at the Greenport dock. If you are on the South Fork, we meet you at Sag Harbor. You are not driving to a strange marina on vacation.
We are family-run by cousins who grew up in the marina business. The captain who picks you up at the Greenport dock has probably known this water since middle school. That local knowledge is the part most outdoor tour companies cannot bottle.
Where We Run Outdoor Activities
Our outdoor activities cover the full East End from our Shelter Island base. That includes Shelter Island, Greenport, Sag Harbor, Montauk, the North Fork, and Fishers Island. Need a useful local starting point? The town's Things to Do page lists the public beaches, town landings, and seasonal access points worth knowing about.
Plan Your Day on the Water
Call (631) 251-1777 or email captain@chartersinthehamptons.com to plan a Hamptons outdoor day on the water. We are based at 63 Menantic Road, Shelter Island, NY 11964.
Hamptons Tour Operator FAQs
What outdoor activities are in the Hamptons? The headline outdoor activities are beaches, hiking trails, vineyards, golf, and water sports. We focus on the water-based options. That includes charters, fishing, sunset cruises, eco tours, and rentals like paddleboards and jet skis. Call (631) 251-1777 to plan an on-water day.
What is there to do on the water in The Hamptons? Most popular: private boat charters, fishing trips, sunset cruises, eco tours through the back creeks, and water sports like paddleboarding and jet skiing. We run all of these from our Shelter Island base, with custom pickup at Greenport and Sag Harbor.
What are the best things to do in the Hamptons in summer? Summer in the Hamptons is built around the water. A typical great day starts with a morning swim at a beach like Cooper's Beach. The afternoon is a boat charter through Shelter Island Sound. The evening is a sunset cruise toward the Greenport waterfront. Dinner is at a Sag Harbor restaurant reached by boat dock.
Is the Hamptons good for outdoor activities? Yes. The Hamptons has some of the best beaches in the Northeast. It has the protected Mashomack Preserve on Shelter Island. And it has miles of bay and ocean coastline for water sports. The catch: the best of it is on the water, not from a parking lot.
What outdoor activities can you do on Shelter Island? On Shelter Island, the standouts are walking the Mashomack Preserve trails and beach time at Crescent Beach or Wades Beach. Water-based options include boat charters, sunset cruises, eco tours, and paddleboarding through the back creeks. Our base at 63 Menantic Road is the home dock for the on-water portion.
What's the best beach in The Hamptons? Cooper's Beach in Southampton is consistently ranked as one of the best beaches in the country. Hither Hills in Montauk is the favorite for surfers. On Shelter Island itself, Crescent Beach is the local favorite. Our charters can include beach-day stops along the route.
Can you go hiking and boating in the Hamptons? Yes. The Mashomack Preserve on Shelter Island has more than 10 miles of marked trails for hiking. The surrounding waters are some of the best in the region for boating. We do not run hiking trips, but our eco tours run along the preserve's coastline so you can see it from the water.
Do you offer outdoor activity pickup at Greenport? Yes. Pickup is available at Greenport and Sag Harbor for all of our outdoor activities. That includes charters, fishing trips, sunset cruises, and eco tours. North Fork visitors typically meet the boat at the Greenport dock, which is the closest pickup point to downtown Greenport and the North Fork wineries.
