Circling Long Island
An engaging and entertaining summer boat vacation is practically at your doorstep. A trip around Long Island is 250 nautical miles (which is not much more than visiting Block Island), and it can be completed in less than two weeks. While your pauses may vary, we’ve put together a fun itinerary of harbor-side stopovers. You can start this trip from any harbor and reverse our directions, depending on your starting point.
Think of Great Gatsby as you navigate through Manhasset Bay, then arrive at a village that is very boat friendly! Visitors will find plenty of places to shop for clothing, antiques, shoes, books, toys, jewelry, and music. The Jeanne Rimsky Theater features musical styles as varied as folk, cabaret, Broadway, and rock, and presents shows for children. When you’re hungry, there are over 40 restaurants to choose from, including Louie’s, La Mottas at Manhasset Bay Marina, La Parma, and La Piccola Liguria (leave some room for Ralph’s Ices). If you want to pick up more provisions, the village has mini markets, delis, and a supermarket, too.
There are 10 transient moorings available free for 48 hours on weekdays (24 on weekends), and a free water taxi to the dock. Transient docking is available at Manhasset Bay Marina (closest to the village and a short walk to restaurants and other services) and Capri Marina. If you prefer to stay at anchor, Leed’s Pond is just northeast of the village dock, and the water taxi picks up from this area as well.
If you’re leaving Port Washington early on a Sunday, make a quick side trip to North Hempstead Town Beach, located at the southern part of Hempstead Harbor. Drop anchor at the beach by 1:00 pm and be entertained with live music from the band shell facing the water (this summer’s concert schedule series begins July 4 and continues through August 31). While this is not a place to spend the night, it is an entertaining afternoon! There is a small concession stand on the beach for refreshments.
The trip from Port Washington to the Town Beach is eight nautical miles from Port Washington.
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.
Your next destination is Oyster Bay Harbor; both Cold Spring Harbor and Oyster Bay are accessible from here. Cold Spring Harbor is a quaint village known for its vibrant whaling history. Specialty shops include Say L Vie, Harbor Hounds, Pashley Children’s Boutique, and Heritage Candle and Home. The village is home to the Cold Spring Harbor Whaling Museum and the Cold Spring Harbor Fish Hatchery, well worth visiting, is a short cab ride away. Restaurants include Grasso’s, Harbor Mist, Sweetie Pie’s on Main, and there’s a deli for picnics in the park or for replenishing the pantry.
H & M Marina in Cold Spring Harbor offers transient moorings for boats 30’ 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.
Oyster Bay’s main street is a just a few blocks from the water. Restaurants include Jack Halyards, Luce, Café Al Dente,and Canterbury Aile. Leave time to explore the shops including Nobman’s Hardware (circa 1910), The Chocolate Lady, Bernstein’s Home Center, and Buckingham’s Variety shop. The Waterfront Center offers kids’ activities and public sails on the oldest Oyster Sloop in North America, the Christeen. Theodore Roosevelt’s home, Sagamore Hill, is a short cab ride from town, as is the 15-acre Theodore Roosevelt Sanctuary & Audubon Center.
It is 20 nm from Manhasset Bay or 15 nm from Hempstead Harbor direct to Oyster Bay Harbor.
Trip note: Approximately 1.28 nautical miles west of the entrance to Oyster Bay Harbor is the Walls Wharf restaurant. This restaurant has three transient moorings on the Long Island Sound available for boaters who get hungry along the way, provided you have an inflatable to get to the beach.
The next break in your round-LI journey is Northport Village, where you can spot the early 1900s trolley tracks running along Main Street. This bustling village is a great destination to spend a day strolling Main Street and Woodbine Avenue (the village is pup-friendly, and has a scenic dog park if your pooch has come along). There are many restaurants, including Maroni’s, Main Street Café, Bistro 44, Original Kasper’s of Northport, Ritz Café, and The Sweet Shop. Nina’s Pizza is a short walk past the main strip. Pick up picnic treats or eat in at the Copenhagen Bakery, Organically Yours (a great choice for vegans and vegetarians), and the local deli.
Northport is fun for kids, with two waterfront parks (one features swings and slides) and fun stores to explore. The whole family will enjoy entertainment at the John Engeman Theater, which runs a regular schedule of Broadway and children’s shows.
There’s lots of transient space in Northport. After entering Huntington Harbor, turn east into Northport Bay to get to the Village town dock (a fixed pier), which is easily identifiable by the gazebo at its most northern 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, a restaurant, fuel, and marine services and supplies. Head to Lloyd Harbor to stay at anchor (the harbormaster will direct you); the entrance to this harbor is opposite the entrance to Northport Harbor. Lloyd Harbor is also very close to Huntington Harbor, where you will find restaurants and fuel.
Northport is just less than 15 nautical miles from Oyster Bay.
You’ll really enjoy a stopover in the Village of Port Jefferson, one of the larger waterfront villages on the north shore, with its wide variety of retailers and restaurants. Shoppers will find jewelry, art, pet food and supplies, clothing, and souvenirs. Cool off with ice cream or bubble tea, and visit delicious eateries including The Steamroom, Z-Pita, Tommy’s Place, Pasta Pasta, Ruvo, Wave at Danfords, and Burger Bistro (your dog is welcome to dine along with you outdoors).
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, or the Setauket Yacht Club. Pirates Cove, at the eastern entrance of Port Jefferson, is an ideal spot for those who want to spend the night at anchor.
Port Jefferson is 23 nautical miles from Northport. You will pass the Eaton’s Neck Coast Guard Station, Smithtown Bay, and Stony Brook.
Trip note: Mattituck is the last harbor on the north shore before you’ll make the cut through Plum Gut towards the next destination. It’s a great place to refuel, have a meal, or spend the night if conditions don’t allow you to travel.
Our next stop is Greenport, another popular destination for Long Island boaters. The 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, with plenty of space for kids to romp, features an antique carousel with a beautiful water view. After some spinning, everyone will be ready for ice cream or a sit-down meal. The view of boats and water provide a nice backdrop at Scrimshaw or Claudio’s, or walk down the street to the Greenport Tea Company for lunch or dinner. After you finish touring Greenport, take the ferry across to Shelter Island and rent bicycles to explore this beautiful area.
There is ample docking in Greenport, including the town docks adjacent to Claudio’s, Mitchell Park Marina, and Preston’s Marina. Coecles Harbor and Nassau Point on the southern side of Shelter Island are great spots to drop anchor and stay the night.
This leg runs 54 nautical miles, and takes you into the open waters of the Long Island Sound. Heading east from Port Jefferson you will pass Mt. Sinai Harbor, Shoreham, Wading River, Wildwood State Park, and Mattituck before turning south between Orient Point and Plum Island to enter Gardiners Bay.
Our next destination is Sag Harbor, a place that packs a lot into two square miles. The 300-year-old village has multiple art galleries, the Bay Street Theater (featuring both live performances and classic films), the Sag Harbor Whaling Museum, and shops and restaurants for every taste.
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.
Trip Note: Getting to Sag Harbor by boat requires concentration to avoid hazards. From Gardner’s 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.
On the way to the Shinnecock canal, stop off in Riverhead and visit the Long Island Aquarium, a family entertainment favorite. Attractions there include a 20,000-gallon coral reef display tank, an aviary of Amazon parrots and an Amazon Rainforest, sea lions, sharks, and seals. 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 Larry’s Lighthouse Marina.
Riverhead is 17 nautical miles from Sag Harbor.
Next, you’ll go through the Shinnecock Canal to travel to Watch Hill. This is an experience that every boater should have, and you’ll find tips and techniques on our website.
Watch Hill is part of the Fire Island National Seashore, where you can explore the barrier island habitats, salt marsh, and the dark and mysterious maritime forest at Sunken Forest. Arrange ahead of time for a Forest Ranger Tour, or pick up a guide to spot the flowering plants and animals that inhabit the area, including the white-tailed deer and red fox.
Boaters may berth at the Watch Hill Marina.
Riverhead to Watch Hill is 40 nautical miles using the Great South Bay route or 73 nautical miles using the Atlantic Ocean route.
There are two ways to navigate to Watch Hill once you exit the canal — through the bay, or heading out the Shinnecock Inlet into the Atlantic Ocean. The bay route is not without its challenges. Many sections are narrow channels; follow the route closely or you’ll run aground. The ocean route has plenty of water, but it will add on approximately 30 nautical miles to the trip.
The next destination is Ocean Beach on Fire Island, with its little red wagons, bicycles, and lack of cars. Enjoy the beautiful ocean and bay beaches, restaurants, hotels, bed and breakfasts, nightlife, movies, concerts, and art shows.
Ocean Beach Marina has transient slips, as does Flynn’s and The Inn Between.
The distance from Watch Hill to Ocean beach is just less than 14 nautical miles.
Next, head to TOBAY Beach, which is generally a quieter place than Fire Island. You can swim or simply hang out at 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 at TOBAY is a refuge for migratory waterfowl and shore birds including creeks, dunes, salt marshes, and both fresh and salt-water ponds.
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 only use the facility Mondays through Thursdays on a first-come, first-served basis, so plan your trip accordingly). If you decide to anchor offshore, you will need to pay a beach use fee to come ashore.
Zach’s Bay at Jones Beach State Park is almost halfway between TOBAY and Freeport. 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, which has both indoor and outside interactive marine habitat exhibits and a butterfly garden. There are transient slips available at the west end of the basin by the Coast Guard station.
Zach’s Bay to Freeport is 7.0 nautical miles.
Last, but never least, is Freeport, famous for its Nautical Mile. This boat-friendly, family-friendly village attracts many visitors. Dine at restaurants such as Otto’s, Nautilus Café, Rachel’s, Pier 95, and Waterside Café, or barbeque at John J. Randall Park.
The Village of Freeport provides transient floating dock slips.
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 Governor’s Island into the East River through Hells Gate and back into the Long Island Sound. Or maybe you’ll extend this glorious trip one last night by staying in New York City!
Freeport to Port Washington will run 50 nautical miles.
More resources, details, routes, and links online!
Port Washington: There are six free mooring balls offered by the Town of North Hempstead, and good grounding for anchoring in the bay. For pick up and transport to the Town Dock, hail the Port Washington Water Taxi on VHF Channel 9 (or call 516-767-1691). Transient space may be available at Manhasset Bay Marina (516-883-8411), Brewer Capri Marina (516-883-7800), and Toms Point Marina (516-883-6630).
Cold Spring Harbor: H & M Powles Marina, monitoring VHF frequency channel 10, has limited transient moorings and launch service (call 631-367-7670 for availability)
Oyster Bay: Boaters with yacht club privileges may contact the Sagamore Yacht Club (516-922-0555) to make reciprocal arrangements. Others looking for transient space should contact the Oyster Bay Marine Center (516-624-2400, VHF Channel 71)
Northport: The Village Dock offers transient space on a first-come, first-served basis at no charge until 8:00 pm. Seymour’s Boatyard (631-261-6574) has transient moorings and Britannia Yacht Club (631-261-6500) offers transient docks (check ahead for availability).
Port Jefferson: There are three marinas offering transient space: Danfords Marina, 631-928-5200, monitoring channel 9; Port Jefferson Marina, 631-331-3567, monitoring channels 9 & 67; and Silver Bay Marina, 631-689-8262, monitoring channel 68. All are on a first-come, first-served basis. For further information about the event visit: www.atasteofportjefferson.com
Greenport: Transient docking can be found at the Mitchell Park Marina (it’s worth a try to call 631-477-2200, ext. 400). Claudio’s Restaurant and Marina (631-477-0355) offers transient space for day trippers, and Preston’s Marina may have available transient space (631-477-1990).
Sag Harbor: Transient space may be available at the Sag Harbor Village Marina (631-725-2368), the Waterfront Marina (631-725-3886), Malloys Sag Harbor Cove Marina (631-725-3939), Sag Harbor Yacht Club (631-725-0567), and the Mill Creek Marina (631-725-1351). Always confirm availability before setting out! You can also contact Robert Bori, Harbormaster for Sag Harbor at 631-725-2368 for transient slips and mooring reservations.
Riverhead: Transient space is available at Larry’s Lighthouse (631-722-3400), Treasure Cove Resort Marina (631-727-8386), or the Riverhead Town waterfront (no overnight stays without permit), but always check for availability before heading out.
The Watch Hill marina, open through mid-October, has about 180 slips that can accommodate boats with beams up to 13’ and drafts up to 5’. Most slips have water and 50-amp electricity, and there is a pump out station. There is a maximum stay of two weeks; limited reservations are accepted by phone (631-597-3109), while other slips are available on a first-come, first-served basis. Docking fees run $2.00 per foot, plus an additional fee for electricity (check the website for specials). The Dockmaster monitors channel 9.
Ocean Beach: Ocean Beach marina offers 17 slips so empty ones can be scarce. Ocean Beach Marina dock master: 631-583-5153
TOBAY: Non-residents can access the marina weekdays for up to three days between Mondays and Thursdays. Transient rates will vary by size of your boat. At the time of printing, fees range from $75 for the first day ($40 thereafter) for boats up to 25 feet, $85 ($45) for those 26-31 feet, and $95.00 ($50) for vessels over 31 feet.
Oyster Bay residents need to obtain a watercraft sticker at a cost of $30-$55, depending on the size, and then pay $10-$18 per day to use the marina on weekdays, and $20-$30 on weekends. Those anchoring off the beach to come ashore will need to pay a beach use fee of$10 for boats up to 25 feet and $14.00 for larger boats.
The Theodore Roosevelt Nature Center (516-679-7254) is across from the marina. Transient boat slips are available on the West End of Jones Beach State Park by the Coast Guard Station. There are 71 daytime transient slips available on a first come, first served basis from the end of June through Labor Day. Slips run $8 per day at press time. For further information call 516-785-1600.
Freeport: The Village of Freeport provides nine free, first come, first served transient floating dock slips along The Mile, as well as 23 floating dock slips for a fee (with available water and electric) at the end for day trippers as well as overnighters.
Leeds Pond: http://boatingtimesli.com/NY/?p=6123
Sand Hole: http://boatingtimesli.com/NY/?p=520
West Harbor, Oyster Bay: http://boatingtimesli.com/NY/?p=978
Cold Spring Harbor Whaling Museum: http://boatingtimesli.com/NY/?p=9752
Lloyd Harbor: http://boatingtimesli.com/NY/?p=173
Pirates Cove: http://boatingtimesli.com/NY/?p=2821
Long Island Aquarium: http://boatingtimesli.com/NY/?p=3030
Navigating the Shinnecock Canal: http://boatingtimesli.com/NY/?p=5068
Shinnecock Inlet: http://boatingtimesli.com/NY/?p=602
Freeport for Kids: http://boatingtimesli.com/NY/?p=6771
Pet Friendly Destinations: http://boatingtimesli.com/NY/?p=5542
East End Locations Kids Love: http://boatingtimesli.com/NY/?p=3775
Mets Ballpark, U.S. Open Tennis, & Flushing Meadows Park: http://boatingtimesli.com/NY/?p=19