EASTERN NEW YORK AREA BOAT TOURS

Priscilla sails from the Snapper Inn Restaurant on the Connetquot River. Step aboard and travel back in time as we sail the very waters she worked harvesting oysters when first launched in 1888.

We will motor down the Connetquot River and into the Great South Bay where we will raise sail, shut down the engine, and go sailing! If so inclined, you can join the crew in raising the sails, or just sit back and take in the sights.

From the decks of the venerable Rip Van Winkle cruise boat, you will relax and enjoy a clear view of historic Hudson River lighthouses, waterfront mansions, and other notable locations on this 2-hour Sightseeing Cruise.

Highlights of your cruise include the Kingston-Rhinecliff Bridge that connects East Kingston with Rhinebeck, the Esopus Meadows, and the impressive Mt. St. Alphonsus seminary, a castle-like seminary.

Our music cruises feature a variety of live bands for your listening and dancing pleasure. Our evening cruises offer a unique locale for all types of different events!

At night, it’s another world! Warm summer evenings bring together music, romance and fun as our vessel glides under a canopy of stars.

From the decks of the venerable Rip Van Winkle cruise boat, you will relax and enjoy a clear view of historic Hudson River lighthouses, waterfront mansions, and other notable locations on this cruise.

Join us aboard the Pride of the Hudson for a Murder Mystery Cruise performed by Murder Cafe.

Cruise through the majestic Hudson Highlands aboard the luxurious Pride of the Hudson! Your captain will narrate the sights along the way.

July 21, 2024

Enjoy a nice meal and beautiful views while sailing to the historic, old-fashioned Fire Island Lighthouse from the 1850s on this wonderful four-hour cruise.

Sail around Bay Shore while enjoying a delicious lunch on this three-hour cruise. A cash bar is included on all cruises!

Sail around Bay Shore while enjoying a nice luncheon buffet on this three-hour cruise. A cash bar is included on all cruises, so get ready to relax and enjoy some beverages.

Soak up the views from the decks of our classic yacht, sit back and enjoy a magical city lights cruise, and take part in a climactic fireworks display while cruising the local waterways.

Experience New York City lights like you never have on this sail along the bright and beautiful borough of Manhattan. End your sail with a fireworks display in NY Harbor!

Come join us on this special full circumnavigation of Manhattan to celebrate Earth Day and experience a comfortable tour through the Hudson, East, and Harlem Rivers.

On this festive cruise, enjoy a four-course, Irish-themed brunch menu and listen to the cheerful stylings of a live Irish fiddler playing throughout your journey with us!

Celebrate this Valentine’s Day and drink champagne with your special someone or your close and dear friends while taking in all the beauty the New York City skyline has to offer.

Spend your evening with friends or a loved one by enjoying our live Holiday Jazz Trio on this special warm and cozy cruise to see the New York City lights!

Experience New York like you never have before and leave the noise of city street life behind. Cozy up in our enclosed glass observatory with our signature holiday beverage!

Step inside this toasty solarium in full holiday decor and join us for this special warm and cozy 1.5-hour cruise to see the New York City lights.

Sip on wines hand-picked by our adored wine expert Wendy Crispell! On this two-hour cruise, she teaches you which wines go perfectly with everything on your holiday table.

Come sail on one of our yachts with a holiday weekend brunch. The warm, cozy, and spectacularly decorated main cabin is sure to bring you and your guests into the spirit of the season!

Step aboard the yacht Full Moon, our cozy, elegant, fully restored 1950 Grebe, as we travel north to explore the grand foliage of the Palisades Park on the Hudson River.

Join us on this autumn sail out of the busy city to the elegant, foliage-adorned cliffs of the Palisades aboard the 80-foot Schooner Adirondack, an 1890s-inspired pilot schooner!

Admire the last leaves of fall in all their splendor aboard the Kingston, one of our cozy, elegant, 1920s-style yachts. Observe New York’s most dramatic natural wonders and colorful foliage!

Colorful fireworks soar in the sky in celebration of PRIDE! Exhale your “oohs and ahs” as you glide through the sparkling reflections of fireworks on the water on the Schooner Adirondack.

Take in the sites while listening to live Irish music by the well-traveled band, Sláinte. Hear classic old Irish tunes, Dropkick Murphy covers, and anything in between!

Step aboard the teak decks of one of our yachts for a full-day cruise up the Hudson River to Bear Mountain and explore, hike, or just relax in this fantastic State Park!

See the key NYC harbor sights in just one hour aboard the smaller, more intimate wooden yachts of the Classic Harbor Line fleet and depart from North Cove Marina.

Start your Sunday off with a Mimosa Sail aboard the stunning Schooner Adirondack. Sit with friends and family and enjoy an early afternoon out on the water in NY Harbor!

Help support Hetrick-Martin Institute’s mission by setting sail this June with Classic Harbor Line! We will be flying a nearly 400-square-foot Pride Flag for a significant portion of the sail!

See the city and the statue lit up at night! On this sail aboard the Schooner America 2.0, experience the splendor of the New York City skyline by moonlight.

Enjoy the lights as you sip on champagne in the peaceful night breezes of the harbor. The city lights sail is exquisite for an after-dinner event or to finish any day in the city.

Join us for a magical, moonlit view of Manhattan aboard the Schooner Adirondack. Sail aboard this elegant vessel under the vast sky and luminous full moon!

Cruise on the vibrant waterways of the Kill Van Kull and the Arthur Kill and into the heart of Freshkills Park in Staten Island on one of our luxury yachts.

Step aboard one of the smaller, more intimate wooden yachts of the Classic Harbor Line fleet and depart from North Cove Marina for a cruise in New York Harbor at sunset.

This light dinner sail features renowned NYC sushi from Iron Chef Morimoto and cool, refreshing assorted sake, served on the decks of New York’s newest and most elegant schooner!

Cover all the major sites of Lower Manhattan (below 59th Street) and pass beneath the Brooklyn, Manhattan, and Williamsburg Bridges while taking in monuments, architecture, parks, and infrastructure.

Climb aboard our 80-foot wooden pilot schooner and forget the mayhem and noise of Manhattan street life. Take in the famous Manhattan skyline from the water!

Enjoy Happy Hour aboard a classic yacht in NY Harbor right after your work day is over. Kick back and relax with friends and coworkers on this 60-minute cruise.

This tour will explore the military history of New York Harbor. We will visit historic military sites, monuments, fortifications, and see historic and modern fighting ships up close!

With a focus on historic buildings, enjoy NYC’s architecture and landmarks from the water on this comfortable and unique tour.

See the key lower Manhattan sites on the Hudson River from our gorgeous, 1920s-style yacht on our shortest tour. A great option for families or travelers with little time.

Step aboard a luxurious yacht for a full round-Manhattan cruise that takes an in-depth look at the engineering marvels of New York City’s bridges, tunnels, infrastructure, and mass transit feats!

This Mother’s Day, honor your mom by taking her aboard the elegant yacht she deserves! The Manhattan or Manhattan II is the perfect setting for a spectacular family brunch.

This tour includes interactive tastings that will focus on a different region exploring the grapes, styles, soils, viticulture, and tasting techniques that will help you enjoy your wine!

Cruise New York City’s famous harbor aboard the 1920s-style yacht Manhattan or Manhattan II while listening to live jazz music by the Classic Harbor Line’s live jazz trio – “The Sound Waves!”

Join us for a leisurely weekend brunch on a luxury yacht. Our menu is packed with delicious New York State foods and fresh bakery goods from NYC purveyors. Eat up!

Glide peacefully through the waters of the New York Harbor and take in the majestic colors of the sunset on the most relaxing, beautiful, and romantic boat excursion in the city.

Climb aboard our beautiful 80-foot schooner, Adirondack, for this peaceful, picturesque sail away from the concrete and noise of the city and experience a New York City sunset from the water.

This tour offers a premium sailing experience with spectacular views of Ellis Island, the Statue of Liberty, and the Brooklyn Bridge on the newest, largest, most elegant ship in our fleet.

Experience New York like you never have before on this two-hour sail aboard the Adirondack, an 80-foot wooden pilot schooner. See the famous Manhattan skyline from the water!

Experience a beautiful New York City sunset and the illuminated cityscape during a comfortable and unique NYC Harbor sunset cruise through the Hudson and East Rivers.

Sit back and experience New York from the water in our enclosed glass observatory and leave the noise of city street life behind on this 1.5-hour cruise that shows off all the best sights.

Step aboard the teak decks of our elegant 1920s-style yachts! Circumnavigate the island of Manhattan while taking in monuments, architecture, parks, and infrastructure.