A Different Adventure Each Day
Many local boaters plan a “big adventure” to Block Island or Newport each summer. But how about changing things up and 
taking an engaging and entertaining boat vacation in your own backyard?
If you’re thinking that a voyage around Long Island would be an undertaking that’s too far or too time-consuming, think again. The trip is about 250 nautical miles and can be completed in less than two weeks, including fun harborside stopovers.
The beauty of this trip is its flexibility — you can skip a harbor that just doesn’t appeal and linger at one that does. You can head in one direction or the other, tweaking the tempo to take advantage of what’s happening in a particular village. While your individual pauses may vary, the idea behind this is to visit as many of Long Island’s appealing harbors and enjoy as many local attractions as possible.
Port Washington
Picture yourself aboard a gilded age yacht as you as you navigate through Manhasset Bay, gliding by mansion after mansion on the way to Jay Gatsby’s dock. The boater-friendly village of Port Washington has engaging shops, entertainment, and eateries galore both along the water and a stroll away. Need provisions? The village has mini markets, delis, and a supermarket.
Manhasset Bay Marina (516-883-8411) offers transient docks and moorings — reservations are required. Alternatively, there are free mooring balls offered by the Town of Hempstead’s town dock on a first-come, first-served basis (you can stay for 48 hours). For transport to land, hail the Port Washington Water Taxi on VHF channel 9 or call 516-767-1691.
In addition to the municipal marina and moorings, Manhasset Bay Marina (516-883-8411), Capri Marina (516-883-7800), Toms Point Marina (516-883-6630), and Colony Marina (516-883-8008) may have transient space. Always call for availability.
If you’re leaving Port Washington early on Sunday in July or early August, 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 by 1:00 pm to enjoy live music from the band shell facing the water (schedule at http://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.
Website: https://www.pwcoc.org/port-washington
Town Dock: Main Street, Port Washington 516-767-4622
Bay Constable: Monitors marine channels 9
Walk-in medical care: City MD 516-829-2273
Pumpout: Town Dock, or hail the pumpout boat on VHF channel 9
Cold Spring Harbor & Oyster Bay
Your next destination is Oyster Bay Harbor. It is 20 nautical miles from Manhasset Bay (15 from Hempstead Harbor); both Cold Spring Harbor and Oyster Bay are accessible. Cold Spring Harbor, known for its vibrant whaling history, is a quaint village with specialty shops and a few tasty restaurants (there’s also a deli for picnics in the park or for replenishing the pantry). 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.
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, where Teddy Roosevelt strolled, know that the main shopping and dining area is a few blocks from the water. Be sure to make a stop at Nobman’s Hardware (circa 1910). 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.
Websites: http://oysterbaytown.com/ and http://www.coldspringharborvillage.org/
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
Northport
The next stop on your journey around Long Island is Northport Village, 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, 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, where early 1900s trolley tracks are still visible along Main Street, is a great destination. Spend a day strolling in and out of Main Street and Woodbine Avenue’s quaint and appealing shops, restaurants (some with outdoor dining), and ice cream parlors. You can also pick up picnic treats from the Copenhagen Bakery or Organically Yours, a great choice for vegans and vegetarians. There are two kid-friendly and dog-welcoming waterfront parks. The whole family will enjoy entertainment at the John Engeman Theater.
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). Lloyd Harbor is very close to Huntington Harbor, where you will find fuel and restaurants (the main village is not along or nearby the water). As you cruise by, wave to the beautiful Huntington Lighthouse, built in 1912.
Website: https://northportny.gov/
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
Your next destination is a village 23 nautical miles from Northport. 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, pet food and supplies, clothing, souvenirs and more, and then cool off with ice cream or bubble tea. Delicious eateries abound, and your dog is welcome to dine along with you at some spots 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 Long Island Explorium in the historic Shipyard Building and playing in the park. Theatre Three features concerts, plays, and children’s entertainment. There are also free movies and concerts presented by the village all summer.
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.
Websites: https://portjeff.com/ and www.portjeffchamber.com
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 VHF channel 73
Trip note: Watch your approach to the harbor from the Long Island Sound — large ferries head between Port Jefferson and Bridgeport, Connecticut all day.
Mattituck
The last harbor on the north shore before you make the cut through Plum Gut towards the Peconic is Mattituck. Strong’s Water Club and 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, and/or spend the night.
Greenport
Mattituck to Greenport is three nautical miles as you travel south between Orient Point and Plum Island to Gardiners Bay. Greenport is a popular destination for boaters, with ample docking at 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.
Greenport’s streets are lined with shops, restaurants, art galleries, and other interesting places such as the Railroad Museum, East End seaport Museum, and the Firefighter fireboat. Mitchell Park, featuring an antique carousel with a beautiful water view, has plenty of space for kids to romp, and frequent performances on the lawn. The view of boats and water provide a nice backdrop for dining or a post-meal walk. After touring Greenport, take the ferry across to beautiful Shelter Island and rent bicycles to explore.
Websites: https://www.southoldtownny.gov/246/Mattituck, http://villageofgreenport.org/, and https://www.shelterislandtown.us/
Greenport Harbormaster: 631-477-2200, option 1
Walk-in medical care: HRH Care Health Center at Greenport 631-477-2678
Laundry: Greenport Laundromat 631-477-1994
Pumpout: Greenport Yacht Yard or hail the pumpout boat VHF channel 9
Sag Harbor
This leg of your journey runs about 13 nautical miles around Shelter Island to Sag Harbor — a village that’s over 300 years old that packs a lot into two square miles. There’s plenty to do in this posh place, with multiple art galleries, shops, the Bay Street Theater featuring both live theater and events, the Sag Harbor Whaling Museum, 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.
Website: https://www.sagharborny.gov/
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.
Riverhead
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 tasty restaurant choices (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.
Website: https://www.townofriverheadny.gov/
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
Ocean Beach
Your next leg takes you through the Shinnecock Canal towards Ocean Beach. As the waters can be challenging here, please learn about the area and boating through locks before undertaking this portion of the 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 more than 64 nautical miles.
On your way to Ocean Beach, plan to stop and explore the Fire Island Lighthouse and the National Seashore’s Watch Hill and Sailors Haven. Transient slips are available at Watch Hill Marina as well as Sailors Haven Marina.
Ocean Beach on Fire Island is a place with little red wagons, bicycles, bare feet, and no cars. Enjoy the beautiful ocean and bay beaches, restaurant, nightlife, and art shows. Ocean Beach Marina has transient slips, as does Flynn’s and The Inn Between.
There’s even more to Fire Island. Every community is fun and different, and the restaurant scene is always enjoyable.
Website: https://www.nps.gov/fiis/index.htm
Watch Hill/Sailors Haven Dock Master: 631-583-5153
Ocean Beach 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 notes: 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. Be sure to bring flying bug repellent!
Tobay Beach
After all that fun on Fire Island, you’ll enjoy the quiet of your next destination, Tobay Beach. The trip from Ocean Beach is approximately five nautical miles. You can swim or simply hang out on the bay or ocean beach, then dine by the bay. There’s a large kiddie park and a wildlife sanctuary (the sanctuary is a 550-acre stretch of protected wetlands, open year-round, but visitation hours are limited during June, July and August and a permit is needed).
Website: http://oysterbaytown.com/departments/parks/beaches/
Pumpout: Tobay Beach Boat Basin 516 -679-3900
Trip notes: 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
Zachs Bay at Jones Beach State Park is almost halfway between Tobay and Freeport, the next leg of your Long Island escapade. There are no facilities here, but it is a favorite anchorage for many western south shore boaters to drop anchor and relax. At the western part of Jones Beach State Park is the Theodore Roosevelt Nature Center — kids love the 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.
Website: https://parks.ny.gov/environment/nature-centers/4/details.aspx
Pumpout: West End Boat Basin
Freeport
This boater and family friendly village is famous for its Nautical Mile, which boasts fresh-off-the-boat seafood eateries, kiddie amusements, and relaxing waterfront dining (for a change of pace, have a barbeque at John J. Randall Park).
The Village of Freeport has transient floating dock slips on Woodcleft Canal.
Website: https://www.freeportny.gov/
Bay Constable: 516-897-4100
Walk-in medical care: Advantage Care Health Centers 516-686-4400
Pumpout: Freeport Bay Marina, Guy Lombardo Marina
Home… or NYC
To complete the trip back, 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 then back into the Long Island Sound. Or perhaps you’ll extend this glorious trip one more night by staying in New York City.
Does time in the Big Apple sound good? Head up the Hudson River — there are several marinas that offer transients slips. Liberty Landing Marina in New Jersey offers free water taxi rides into Manhattan; on the New York side is Chelsea Piers.
Trip notes: Freeport to Port Washington will run 50 nautical miles. If you plan on going directly to the Long Island Sound, the quickest way is via the East River. From the Hudson River you can continue north to the Harlem River to head to the Long Island Sound or reverse the route south to the lower Hudson and then up the East River.
