Long Island, with its extensive shoreline, sparkling harbors, and scenic bays, makes for a perfect destination for cruises and boat tours. Unlike many places, Long Island offers a diverse range of water experiences—from luxurious private yacht charters in the Hamptons to relaxed public schooner sails on the North Fork. Whether you’re after a private celebration, a scenic sailing, or a family outing, the options here promise memorable moments on the water. Each tour type highlights different aspects of the area’s charm—some focus on celebrity homes, others on peaceful sailing, and a few provide customized adventures that suit your group’s interests.
What sets Long Island apart is its mix of high-end yachts, easygoing sailing tours, and accessible public sails. It caters to those wanting to luxuriate aboard a private yacht, explore the coast on a casual schooner, or learn sailing from an experienced captain. This guide explores the best options available, helping you decide which water trip aligns with your budget, schedule, and style.
Quick Overview of the Best Cruises and Boat Tours in Long Island
Below, you’ll find a carefully curated list of six outstanding tours, each offering a different flavor of Long Island’s waterscapes. From private yacht experiences (Private Yacht Charter in The Hamptons, Montauk or Sag Harbor) to scenic sailing with Captain Steve (Captain Steve’s Sailing Experience on Long Island), you’ll find options suited for groups, families, or those seeking a relaxed day on the water. Other options include customizable boat rentals, large-party fun boats, private Long Island Sound sailing, and affordable public schooner sails in Greenport.
Now, let’s take a closer look at each one.
1. Private Yacht Charter in The Hamptons, Montauk or Sag Harbor
At number one, this private yacht charter offers the chance to splurge on a personalized, luxurious experience along the Hamptons shoreline. For around $2,390 per group (up to 10 people), you get 2 to 4 hours of cruising on a fleet that boasts over 30 boats ranging from 22′ to 100′ yachts. The tour includes stops at Sag Harbor, Montauk, or other Hamptons hotspots, giving you the chance to see celebrity homes, hidden coves, and scenic beaches.
This tour is perfect for celebrations like bachelorette parties, birthdays, or family gatherings. The company specializes in water sports and offers complimentary water toys like Sea Bobs and paddleboards, making it easy to add some fun to your day. The itinerary includes a scenic tour of Sag Harbor and nearby areas, and you can customize your experience to include swimming, sightseeing, or just relaxing on deck.
Bottom line: If you want a flexible, high-end experience with plenty of options for water toys and privacy, this yacht charter delivers. It’s best suited for groups wanting exclusivity and a splashy celebration on the water.
2. Captain Steve’s Sailing Experience on Long Island
Number two on our list is the Captain Steve’s Sailing Experience, offering an intimate, 2-hour sailing trip for up to 6 people at $475. Captain Steve, with his 25 years of sailing experience, guides you through the waters with a focus on relaxation and learning.
This tour is unique because you’re not just a passenger—you’re encouraged to participate in sailing the boat, making it an engaging and hands-on experience. The route includes spots like Kings Point, City Island, and even views of the NYC skyline, providing a perfect blend of peaceful sea air and cityscape views. Many travelers appreciate Captain Steve’s friendly demeanor and detailed commentary about the sights and local history.
The tour is ideal for those seeking a quiet, personalized outing or a chance to learn sailing basics in a relaxed setting. It’s a great choice for couples or small groups wanting a calming escape with an expert at the helm.
Bottom line: With its focus on hands-on sailing and scenic views, this tour appeals to those looking to learn and relax at a reasonable price point.
3. Boat or Yacht Rental in Sag Harbor, The Hamptons, or Montauk
Number three features a customizable boat or yacht rental perfect for groups wanting a tailored experience. For around $1,990 for up to 8 people over approximately 4 hours, this option allows you to craft your own water adventure.
The company emphasizes personalized itineraries—whether you’re planning a romantic sunset cruise, a lively family day, or a bachelorette party. The staff provides insider recommendations and helps craft your perfect route, whether it’s exploring coves, anchoring for a swim, or cruising past the celebrity homes in the Hamptons. It’s especially attractive for those who want flexibility and expert guidance without the formality of a set itinerary.
Guests appreciate the attentive staff and the chance to design a trip that matches their interests, making this a top pick for groups with specific ideas or those wanting a more private, bespoke experience.
Bottom line: This option balances customization with professional support, ideal for anyone seeking a personalized day on the water.
4. 4 Hours of Spacious 50 Foot Private Fun Boat in Hampton
At number four, the 50-foot private Fun Boat offers a spacious, party-ready vessel called Jubilance for $5,000 (up to 15 people). With a U-shaped bar, DJ booth, and a full sound system, this boat is built for celebration.
The vessel features plush sun beds, a fully-equipped bathroom, and panoramic views of the Hamptons’ coastline. It’s perfect for groups wanting a lively, social experience with plenty of space to move, dance, and enjoy the scenery. The boat’s design emphasizes comfort and entertainment, making it suitable for larger groups or those celebrating special occasions.
Although no reviews are available yet, the features suggest a fun, high-energy day on the water. It’s best suited for groups willing to invest in a more luxurious, party-focused outing.
Bottom line: For groups seeking a spacious, entertainment-oriented water experience that combines comfort and fun, this vessel fits the bill.
5. Private Long Island Sound Sailing Experience
Number five offers a 3-hour private sailing tour of Long Island Sound for $650, accommodating up to 6 people. The route covers Manhasset Bay, with sights of Manhattan’s skyline, Throgs Neck Bridge, and the iconic lighthouses like Steppingstone and Execution Rocks.
What makes this trip special is the opportunity for passengers to participate actively in sailing if they wish, under Captain guidance. It’s well-suited for those who want an intimate, educational experience with a mix of sightseeing and hands-on sailing. The route is flexible—whether you want to anchor for a swim or just enjoy the scenery, the captain can tailor the day.
This tour is ideal for lovers of the water who want a balanced experience of instruction, relaxation, and sightseeing. It’s a versatile choice for birthdays, anniversaries, or a peaceful escape.
Bottom line: If you want to learn some sailing basics while soaking in spectacular views of both Long Island and New York City, this tour offers a personalized, flexible experience.
6. Public Schooner Sail in Greenport
Rounding out the list is an affordable public schooner sail in Greenport for just $130 per person. This 2-hour ticketed sail offers an authentic experience aboard a classic schooner, perfect for those who want to see the North Fork from the water without private charter costs.
Sailing on a schooner provides a hands-on experience where you can help hoist sails and learn about traditional sailing methods. It’s a great way to enjoy the East End’s scenery at a reasonable price, especially for visitors who want a taste of maritime history and ocean air.
Since it’s a public tour, it’s best for travelers open to sharing the experience with strangers, and those who appreciate a more immersive, historic vibe. It’s ideal for first-time sailors or those curious about traditional sailing craft.
Bottom line: This public schooner sail hits the mark for affordability and authenticity, making it a memorable introduction to Long Island’s maritime side.
How to Choose the Right Cruise or Boat Tour in Long Island
When selecting a boat tour, consider your budget, the size of your group, and what kind of experience you’re after. Want a private, luxury celebration? The Private Yacht Charter or the Fun Boat might suit you best. Looking for a relaxed, educational sail? The Captain Steve’s Sailing or Long Island Sound options focus on participation and scenery.
Budget constraints can also guide you—public sails like the Greenport schooner deliver authentic sailing at a lower cost. For groups planning a special celebration or seeking privacy and luxury, private charters provide maximum customization.
Booking early is advised, especially during peak summer months, to secure your preferred date and boat type.
Final Thoughts
Long Island’s waters offer a broad spectrum of experiences—from high-end private yacht cruises to casual public sails and sailing lessons. For a lavish celebration, the private yacht (Private Yacht Charter in The Hamptons) is tough to beat. If you’re after a peaceful, participatory sailing trip, Captain Steve’s experience (Captain Steve’s Sailing Experience) provides a memorable, hands-on outing.
For those seeking affordability combined with fun and tradition, the public schooner sail in Greenport offers authentic maritime charm. No matter your preference, booking early ensures you’ll get the best experience on Long Island’s gorgeous waters.