Fall sailing adventures on Long Island and Manhattan

A group of people enjoy The Circle Line fall cruise. Credit: Chela Crinnion
Summer may have come and gone, but those seeking time at sea can still set sail this fall. Passengers can pick their own adventures on Long Island and in Manhattan, with sailing and boat tours offering itineraries for everyone.
"It's my favorite time of year to go sailing," says Steven Faber, owner and manager of Captain Steve's Sailing Experience in Port Washington.
"Sailing in the fall is nice because there is less boat traffic, sunsets are earlier in the day and colors are usually better," he says.
It's also the perfect time to have a serene experience at sea. "Many guests just relax, take in the sights and sounds of sailing," Faber says.
Wind and cool temps are literally the driving force behind his excursions.
"One thing that you can usually count on is unfurling the sails and turning off the engine," Faber adds. "There is nothing like the feeling, when the wind powers the boat."
From fishing charters to party boats, here's where you can sightsee, party, marvel at fall foliage and try to hook the catch of the day:
Sail away with Captain Steve's Sailing Experience
Behind 410 Main St., Port Washington
Customers take in the sunset during a trip wtih Captain Steve's Sailing Experience. Credit: Captain Steve's Sailing Experience
Ride with Captain Steve around Long Island Sound on a sailing excursion. Offering trips daily, there are Community Sails, where each seat is sold individually ($120 per person for three hours) and typically held at sunset.
Check out the Senior Community Sails for passengers 55 and older, which run during weekdays ($75 per person for two to two-and-a-half hours). Additionally, you can charter private trips for three to four hours, which are daytime ($450 for two hours on weekdays, $550 on weekends; sunset trips have a three-hour minimum, $700 on weekdays, $800 on weekends). The captain will take you to waterfront restaurants on Manhasset Bay or City Island in the Bronx during longer outings, if desired.
- WHAT YOU'LL SEE Passengers will get a look around Manhasset Bay, the western Sound, the New York City skyline, and bridge views, plus Hart Island and City Island in the Bronx. Trips can also pass by the Stepping Stones, Execution Rocks and Sands Point lighthouses, but must be at least three hours in duration to include that option.
- GOOD TO KNOW All trips are six-guest maximum; guests can bring food and beverages.
- MORE INFO 516-902-9099, captainstevesailing.com
Capture calamari with Viking Fleet
462 W. Lake Dr., Montauk
A customer on the squid fishing trip with Viking Fleet. Credit: Viking Fleet
Head out on the fleet's Starlite vessel most nights in October and November (7 p.m. to 1 a.m.) in nearby Fort Pond Bay and put a twist on a typical angling trip by trying squid fishing ($75).
- WHAT YOU'LL SEE If you manage to snag a squid, you will get a chance to see and possibly hold one or more of the cephalopods during the journey.
- GOOD TO KNOW Equipment and tackle is included.
- MORE INFO 631-668-5700, vikingfleet.com
Capture fall foliage on Circle Line
Pier 83, W. 42nd St. and Second Ave., Manhattan

The Circle Line offers an Oktoberfest cruise this fall. Credit: Chela Crinnion
Take in four hours of autumn colors while aboard the sightseeing company's "Hudson River Fall Foliage Cruise," which travels up the river toward Hook Mountain State Park in Rockland County.
- WHAT YOU'LL SEE The views include cliffs along the river, wildlife, and the George Washington and Mario Cuomo bridges.
- GOOD TO KNOW The vessel has both outdoor decks and indoor, heated seating with large windows and concessions. Music plays along the way, and the trip is narrated. There's standard boarding ($64), which includes indoor and outdoor seating, plus access to the concessions-and priority seating ($104), which features advance boarding, exclusive top-level seating, a private bar, an "Oktoberfest"-inspired German-style food platter, and unlimited water, coffee, tea and soda.
- MORE INFO 212-563-3200, circleline.com
Dance as the sun sets on Nautical Mile Cruises
31 Woodcleft Ave., Freeport
Join a two-hour jaunt that launches from the Nautical Mile, through the Captain Lou Fleet, aboard the Atlantic Pearl with Captain Anthony Gillespie at the helm.
- WHAT YOU'LL SEE Each trip ($32 per person) travels as the sun sets while passing along the South Shore through Baldwin Harbor, Mansion Harbor, Randall Bay, and Parsonage Cove-and provides a view of any seabirds or other wildlife passing by.
- GOOD TO KNOW Guests don't need to spend the entire time sightseeing; there's a cash bar and a DJ spinning danceable beats throughout the trip. Dates are available most Saturdays in September through Oct.11. Group bookings of 10 or more receive a discount of $3 off per person.
- MORE INFO 516-544-6698, nauticalmilecruises.com
Marvel at the city skyline with Manhattan by Sail
Pier 17 at South Street Seaport, 89 South St., Manhattan
Take a 90-minute river voyage aboard the Clipper City, a passenger 19th century-inspired tall ship sailboat that lays claim to being the largest such vessel based in New York’s harbor ($78 ages 13 and older, $35 ages 5‑12).
- WHAT YOU'LL SEE The Clipper City glides by the Manhattan skyline as the Big Apple's buildings, bridges and landmarks are lit up for the evening.
- GOOD TO KNOW There’s a full bar and snacks available for purchase; passengers should arrive at least 30 minutes early to check in and get settled (it’s about a five block walk from Fulton Street subway station). Trips start at 8:30 p.m. Sept. 18-Oct. 4, 8 p.m. Oct. 9-18, 7:30 p.m. Oct. 23-30.
- MORE INFO 212-619-6900, manhattanbysail.com