Circle Long Island by Boat: A Different Adventure Every Day
Did you know a boat trip around Long Island is about 250 nautical miles and can be completed in less than two weeks? If you’re a local boater who plans a big adventure to Block Island each summer, change things up and take an engaging and entertaining backyard boat vacation with the fun itinerary of harbor-side stopovers we’ve planned for you.
You can start this trip from any harbor and reverse our directions as necessary, depending on your starting point. While your pauses may vary, the idea is to visit as many of Long Island’s appealing harbors and enjoy as many local attractions as possible.
Picture yourself gliding by Jay Gatsby’s great dock as you navigate through Manhasset Bay and arrive at Port Washington, a boat-friendly village. There are plenty of shops to engage you; the Jeanne Rimsky Theater entertains with folk, cabaret, Broadway, rock, and children’s performances. When you get hungry, there are dozens of restaurants to choose from, including Butler’s Flat, Louie’s, La Motta’s at Manhasset Bay Marina, La Parma, and La Piccola Liguria (leave some room for Ralph’s Ices). Need provisions? The village has mini markets, delis, and a supermarket.
There are 10 transient moorings available free for 48 hours on weekdays and 24 hours on weekends, and a free water taxi to the dock. Transient docking is available at Manhasset Bay Marina (closest to the village), Brewer Capri Marina, and Toms Point Marina. If you prefer to stay at anchor, Leeds Pond is just northeast of the village dock — the water taxi picks up from this area as well.
If you’re leaving Port Washington early on Sunday, take a trip to North Hempstead Town Beach, located at the southern part of Hempstead Harbor. The trip is eight nautical miles from Port Washington. Drop anchor at the beach by 1:00 pm to enjoy live music from the band shell facing the water (the schedule is at www.northhempsteadny.gov/summer). There is a concession stand on the beach for refreshments, but you can’t stay overnight.
Trip note: You will pass Execution Rocks Lighthouse just off Sands Point traveling from Port Washington to Hempstead Harbor. Construction was completed in 1849 although it was not lit until 1850.
Town Dock: Main Street, Port Washington 516-767-4622
Bay Constable: Monitors marine channels 9 and 16
Walk-in medical care: City MD 516-829-2273
Laundry: Port Washington Super Laundromat 516-918-9003
Pumpout: Brewer Yacht Yard, Town Dock, or hail the pumpout boat on VHF channel 9
Your next destination is Oyster Bay Harbor from which both Cold Spring Harbor and Oyster Bay are accessible. It is 20 nautical miles from Manhasset Bay (15 from Hempstead Harbor). Cold Spring Harbor, known for its vibrant whaling history, is a quaint village with specialty shops. The Whaling Museum & Education Center is a short walk from the harbor and the Cold Spring Harbor Fish Hatchery & Aquarium is a brief cab ride away. Restaurants include Grasso’s, Harbor Mist, Sandbar, and Sweetie Pie’s on Main. There’s also a deli for picnics in the park or for replenishing the pantry.
H & M Powles Marina in Cold Spring Harbor offers transient moorings for boats 30 feet or smaller. Larger boats should head to Oyster Bay Marina for transient moorings and launch service. To stay at anchor, continue past the marina to West Harbor.
If you opt to explore Oyster Bay, its main streets — where Teddy Roosevelt strolled — are a few blocks from the water. Make a stop into Nobman’s Hardware (circa 1910) and check out restaurants including Spinnakers, Café Al Dente, The Homestead, Wild Honey, and Canterbury’s Oyster Bar and Grill. The Waterfront Center offers kids’ activities and public sails on the oldest oyster sloop in North America, Christeen. Roosevelt’s home, Sagamore Hill, is a short cab ride from town, as is the 15-acre Theodore Roosevelt Sanctuary & Audubon Center.
Oyster Bay Constable: 516-677-5350
Walk-in medical care: Northwell-Health Go Health Urgent Care (516) 537-9061
Laundry: Oyster Bay Laundromat 516-922-9103
Pumpout: Oyster Bay Sagamore Yacht Club, or hail the pumpout boat VHF channel 9
Trip note: Walls Wharf restaurant is approximately 1.3 nautical miles west of the entrance to Oyster Bay Harbor. This restaurant has three transient moorings on the Long Island Sound available for hungry boaters with an inflatable aboard.
The next stop on your journey around Long Island is Northport Village, where the early 1900s trolley tracks are still visible along Main Street. Northport is less than 15 nautical miles from Oyster Bay.
After entering Huntington Harbor, turn east into Northport Bay to get to the village fixed-pier dock — it’s identifiable by the gazebo at its northernmost end. Just north of the town dock is Seymour’s (dating back to 1923), which offers transient moorings, launch service, fuel, and related marine services. Further south in the harbor is Britannia Yachting Center, which has floating docks, a swimming pool, restaurants, fuel, and marine services and supplies.
This bustling village is a great destination. Spend a day strolling in and out of Main Street and Woodbine Avenue shops and ice cream parlors, and take the kids to the two waterfront parks (one features swings and slides). The whole family will enjoy entertainment at the John Engeman Theater, which runs a regular schedule of Broadway and children’s shows. The village is also pup-friendly, with a scenic dog park and merchants who set out water bowls and occasional treats.
There are plenty of restaurants in Northport, many with outdoor dining. These include Maroni’s, Main Street Café, Rockin’ Fish, Bistro 44, 7T8, Ritz Café, and the Sweet Shop. You can also pick up picnic treats from the Copenhagen Bakery or Organically Yours, a great choice for vegans and vegetarians.
If you prefer to stay at anchor, head to Lloyd Harbor — the entrance to this harbor is opposite the entrance to Northport Harbor (the harbormaster will direct you). Be sure to check out the beautiful Huntington Lighthouse, built in 1912. Lloyd Harbor is very close to Huntington Harbor where you will find fuel and restaurants (the main village is not along the water).
Northport Harbor Master 631-261-7520
Walk-in medical care: Medi Center 631-757-5400
Laundry: Northport Laundromat 631-262-1330
Pumpout: Woodbine Marina, Britannia Yachting Center, or hail the pumpout boat VHF channel 9
Port Jefferson is 23 nautical miles from Northport. You will pass the Eaton’s Neck Coast Guard Station, Smithtown Bay, and Stony Brook on your way to this fun stopover. Port Jefferson is one of the larger waterfront villages on the north shore, with a wide variety of retailers and lots of restaurants within walking distance. Shoppers can buy jewelry, art, pet food and supplies, clothing, souvenirs and more, and then cool off with ice cream or bubble tea. Delicious eateries include the Steamroom, Z-Pita, Tommy’s Place, Pasta Pasta, Ruvo, Kimi, Wave at Danfords, and Burger Bistro. Your dog is welcome to dine along with you outdoors at that restaurant as well as other places in this Fido-friendly village. If you’re picnicking, take out from
Tiger Lily Café, an eatery catering to vegans, vegetarians, and non-plant eaters.
Kids will enjoy the Maritime Explorium in the historic Shipyard Building and playing in the park. Theatre Three features concerts, plays, and children’s entertainment.
Transient boaters may stay at Danfords (a lovely waterside hotel with docks), the public marina, the Port Jefferson Yacht Club, or Port Jefferson Launch and Water Taxi. Pirates Cove, at the eastern entrance of Port Jefferson, is an ideal spot for spending the night at anchor.
Port Jeff Harbormaster: 631-473-3052
Walk-in medical care: Cooper MD Urgent Health Care Center 631-938-1518
Laundry: Port Jeff Station Laundromat 631-331-0060
Pumpout: Hail via VHF channel 73
Mattituck is the last harbor on the north shore before you make the cut through Plum Gut towards the Peconic. From Mattituck to Greenport takes three nautical miles as you travel south between Orient Point and Plum Island to Gardiners Bay. This is home to the waterside Old Mill Inn restaurant and Strong’s Water Club and Marina. The marina offers a resort experience for boats up to 75 feet, a saltwater pool, and Pace’s Dockside restaurant. It’s a great place to refuel, have a meal, or spend the night.
The next stop is Greenport, a popular destination for boaters. There is ample docking at the town docks adjacent to Claudio’s, Mitchell Park Marina, Preston’s Marina, Brewer Yacht Yard Greenport, and Brewer Sterling Harbor Marina. Nassau Point on the southern side of Shelter Island is a great spot to drop anchor and stay the night.
Village streets are lined with shops, restaurants, art galleries, and other interesting places such as the Railroad Museum with its displays of artifacts, photographs, and other bits of Long Island’s railroad history. Mitchell Park, featuring an antique carousel with a beautiful water view, has plenty of space for kids to romp and occasional performances on the lawn. The view of boats and water provide a nice backdrop for dining at Claudio’s, or walk over to Billy’s By the Bay Restaurant & Tiki Bar, Front Street Station, or Lucharitos Taqueria & Tequila Bar for lunch or dinner. After you finish touring Greenport, take the ferry across to beautiful Shelter Island and rent bicycles to explore.
Greenport Harbormaster: 631-877-2200, option 1
Walk-in medical care: HRH Care Health Center at Greenport 631-477-2678
Laundry: Greenport Laundromat 631-477-1994
Pumpout: Brewer Yacht Yard or hail the pumpout boat VHF channel 9
Your next destination is Sag Harbor, a place that packs a lot into two square miles. This leg runs about 13 nautical miles around Shelter Island to Sag Harbor.
The 300-year-old village has multiple art galleries, shops, the Bay Street Theater featuring both live theater and events, the Sag Harbor Whaling Museum, and restaurants for every taste including Page, Sen, The Bell & Anchor, and Il Capuccino Restaurant.
Transient space may be available at the Sag Harbor Village Marina, the Waterfront Marina, Malloys Sag Harbor Cove Marina, Sag Harbor Yacht Club, and the Mill Creek.
Sag Harbor Harbormaster: 631- 725-2368
Walk-in medical care: Sag Harbor Medical Walk-In 631-808-3337
Laundry: Sag Harbor Lauderette 631-725-7257
Pumpout: Sag Harbor dock
Trip Note: Getting to Sag Harbor by boat requires concentration to avoid hazards. From Gardiners Bay, head south of Shelter Island — the channel turns north of Cedar Point and south of Mashomack Point into Northwest Harbor. The channel takes you past Barcelona Point, turns west towards North Haven Peninsula, and then turns south to Sag Harbor. There are many boulders outside the Barcelona Point Channel and a group of rocks locally known as “Gull Island,” so stay in the channel.
Before entering the Shinnecock canal to destinations along the south shore, stop off in Riverhead, 17 nautical miles from Sag Harbor. Visit the Long Island Aquarium, an entertaining family spot with a 20,000-gallon coral reef display tank, Amazon rainforest and parrots, sea lions, sharks, and seals. Riverhead boasts a wide variety of restaurant choices including Jerry and the Mermaid, Turkuaz Grill, Seaside Grill, Tweeds Restaurant, Haiku, Farm Country Kitchen, PeraBell Food Bar East, or for a decidedly different kind of dock and dine, boat up to the waterfront McDonald’s just a short distance from the aquarium!
Transient space in Riverhead is available at Treasure Cove Marina and Lighthouse Marina.
Bay Constable: 631-466-0877
Walk-in medical care: HRC Health Care Center 631-574-2580
Laundry: Riverside Laundromat 631-369-1701
Pumpout: Riverhead town dock
Your next leg around the island takes you through the Shinnecock Canal towards Ocean Beach. This is an experience that every boater should have, but note that the waters can be challenging. We have tips and techniques on our website and suggest you learn about the area and boating through locks before undertaking this adventure.
The distance from Riverhead to Ocean Beach is 48 nautical miles using the inside route via Shinnecock, Moriches, Bellport, and Great South Bay to Fire Island. Alternately, you can head south from the Shinnecock Bay to the Atlantic Ocean, turn west into Fire Island Inlet, and then head east to Fire Island — a trip of slightly over 64 nautical miles.
The next destination is Ocean Beach on Fire Island — a place with little red wagons, bicycles, bare feet, and no cars. Enjoy the beautiful ocean and bay beaches, restaurants including Flynn’s and Matthew’s Seafood House, hotels, bed and breakfasts, nightlife, and art shows. Be sure to bring flying bug repellent.
Ocean Beach Marina has transient slips as does Flynn’s and The Inn Between.
Dock Master: 631-583-5940
Seaview community Doctor 631-583-5286
Pumpout Atlantique Beach 631-583-8610 or Captree Boat Basin 631-669-6464
Trip note: Depending on conditions, the ocean route may be quicker. You can maintain a faster speed and you won’t have to deal with winding channels and low tide areas throughout the route.
Next, head to Tobay Beach, a generally quieter place than Fire Island. The trip from Ocean Beach to Tobay Beach is approximately five nautical miles. You can swim or simply hang out on either the bay or the ocean beach, then dine at a restaurant overlooking the bay. There’s a general store, an outdoor shower, and a large kiddie park. The wildlife sanctuary’s creeks, dunes, salt marshes, and fresh and salt water ponds are a refuge for migratory waterfowl and shore birds.
Pumpout: TOBAY Beach Boat Basin 516-624-6180
Trip Note: The marina at Tobay boat basin is a 150-slip, transient-only marina that is open to both residents and non-residents (non-residents can use the facility on non-holiday weekdays on a first-come, first-served basis, so time your trip accordingly). If you decide to anchor offshore, you will need to pay a beach use fee to come ashore.
Zachs Bay at Jones Beach State Park is almost halfway between Tobay and Freeport. Zachs Bay to Freeport is seven nautical miles. There are no facilities here, but it is a favorite anchorage for many western south shore boaters to drop anchor. At the western part of Jones Beach State Park is the Theodore Roosevelt Nature Center — kids love the indoor and outside interactive marine habitat exhibits and the butterfly garden. There are transient slips available at the west end of the basin by the U.S. Coast Guard station.
Pumpout: West End Boat Basin
Freeport, famous for its Nautical Mile, is a boat-friendly, family-friendly village. This leg runs about seven nautical miles from Zachs Bay to Freeport.
The Village of Freeport has transient floating dock slips on Woodcleft Canal. Many dining spots are on the water, including River House Grille, Otto’s, Tropix on the Mile, Rachel’s, Nawlin’s, and Pier 95. For a change of pace, have a barbeque at John J. Randall Park.
To complete the trip back to the north shore, head into the Atlantic Ocean through Jones Inlet. Head west past Brooklyn, under the Verrazano Bridge, past the Statue of Liberty and Governors Island into the East River through Hells Gate and back into the Long Island Sound. Or maybe you’ll extend this glorious trip one more night by staying in New York City!
Bay Constable: 516-897-4100
Walk-in medical care: Advantage Care Health Centers 516-686-4400
Laundry: Five Star Laundromat 516-210-2358
Pumpout: Freeport Bay Marina, Guy Lombardo Marina
Freeport to Port Washington will run 50 nautical miles.
Check out docking and dining options along your exciting adventure!