Long Island offers some of the best water-based experiences along the East Coast. With its sprawling bays, scenic waterways, and historic harbors, it’s a natural choice for boat tours and cruises. Whether you’re after a peaceful sailing, a lively private charter, or an affordable way to see the coastline, Long Island has options that suit a range of interests.
We especially like the Captain Steve’s Sailing Experience for its personalized approach and stunning views, and the Public Schooner Sail in Greenport for its accessible, traditional sailing vibe.
If you’re considering a trip on the water, this guide highlights four of the best boat tours in Long Island. From private charters that let you participate actively to public sails with historic charm, there’s something here for everyone. Read on to find your perfect match.
1. Captain Steve’s Sailing Experience on Long Island
At number one, Captain Steve’s Sailing Experience combines scenic beauty with expert guidance. Priced at $475 per group (up to 6 people), this 2-hour sailing tour is perfect for anyone wanting a relaxed, personalized water adventure. Captain Steve is a seasoned sailor who shares his knowledge of the area while taking you past notable sights like Kings Point, NYC skyline, and Hart Island.
What makes this experience stand out is its intimate setting and the chance to learn some sailing skills if you’re interested. Many reviews highlight the friendly, professional nature of Captain Steve, who makes you feel at home on the water.
The most common praise is for the beautiful scenery from the water and the expert commentary that makes the trip both relaxing and informative. The sunset cruise is a particular favorite for romantic outings, offering spectacular views and a peaceful atmosphere.
This is best suited for small groups wanting a private, hands-on experience with top-notch guidance. The only potential downside is that the price might be higher than other options, but the quality and intimacy justify the cost.
Bottom Line: For a personal, scenic sailing with knowledgeable captain, Captain Steve delivers excellent value and memorable views.
2. Oyster Bay Two Hour Sailing Experience
Second on our list is the Oyster Bay Two Hour Sailing Experience, costing $595 per group (up to 6). This tour takes you through Oyster Bay Harbor, known for its spectacular sunsets, diverse wildlife, and large estates dotting the shoreline.
The boat, WINDSWEPT, is well-maintained and equipped with modern amenities like Bluetooth stereo, refrigeration, and a shaded cockpit. It’s designed for comfort and relaxation.
Most guests appreciate the smooth sailing and the opportunity to unwind on the water, especially during sunset hours. The owner, Captain Jonathan, is praised for his attentive service and making sure everyone has a great time. The boat’s features, like the fully shaded cockpit and swim platform, add to the appeal, making it easy to relax or take a refreshing dip during the cruise.
This experience is excellent for small groups celebrating a special event or simply wanting a peaceful escape. The value is high, considering the amenities and the quiet beauty of Oyster Bay. The only possible drawback is the slightly higher price, but many find it worth every cent for the atmosphere and scenery.
Bottom Line: For a luxurious, modern sailing experience in a quiet harbor setting, this tour offers comfort and beauty in equal measure.
3. Public Schooner Sail in Greenport
Third, the Public Schooner Sail in Greenport provides an authentic sailing experience at an accessible $130 per person. This 2-hour ticketed sail on a traditional schooner offers an affordable way to enjoy Long Island’s North Fork from the water. The focus here is on the experience of sailing aboard a historic vessel, feeling the wind in your hair and the salt in your face.
What makes this tour unique is its public nature—it’s one of the few opportunities to join a classic schooner without booking a private charter. It’s ideal for travelers wanting to experience the region’s maritime heritage in a relaxed setting. The sailing itself is straightforward, with the crew sharing insights about the boat and the area.
While it doesn’t include personalized amenities, the charm of sailing on a traditional schooner makes up for it. It’s perfect for budget-minded travelers or those eager to try sailing without committing to a private charter. The main limitation is that it isn’t a private experience, so it may be less tailored to individual preferences.
Bottom Line: An affordable, authentic schooner sail that captures the spirit of Long Island’s maritime culture—great for first-time sailors or budget travelers.
4. Private Long Island Sound Sailing Experience
Finally, the Private Long Island Sound Sailing Experience offers a 3-hour tailored cruise for $650 per group (up to 6). This private charter explores Manhasset Bay and Long Island Sound, with options to participate actively in sailing or simply relax and enjoy the scenery.
As you pass by the waterfront mansions of Sands Point and see the New York City skyline, you’ll get a sense of the region’s grandeur.
This tour is highly customizable, with the opportunity to anchor for lunch or swimming. It’s ideal for special occasions like birthdays, anniversaries, or bachelorette parties, thanks to its flexibility and privacy.
Many reviews highlight the chance to get involved in sailing, which appeals to those wanting a hands-on experience. If you prefer a more passive outing, the captain is happy to handle the sailing while you soak up the views.
The main appeal is its exclusivity and ability to craft a personalized day on the water. The downside is the higher price and longer duration, which might not suit travelers on a tight schedule. Still, it offers great value for a private, in-depth experience with stunning scenery.
Bottom Line: Perfect for groups seeking a customizable, private adventure that combines sailing, sightseeing, and leisure.
How to Choose Your Perfect Long Island Boat Tour
When selecting the right boat experience, consider your budget, group size, and what you want from the trip. Want an intimate, guided sail with stunning views? Captain Steve’s sailing experience is hard to beat. For a leisurely, modern cruise in Oyster Bay, the two-hour experience offers comfort and scenic beauty.
If you’re after a low-cost, traditional sailing adventure, the public schooner is an excellent choice. For a fully private, customizable outing, the Long Island Sound experience delivers exclusivity and flexibility.
Think about the type of scenery that interests you most—harbors, city skylines, or estate-lined coasts—and match that with the tour’s focus. Also, consider your group’s activity level: some tours involve active sailing, while others are more about relaxing and enjoying the views.
Final Thoughts
Long Island’s boat tours cover a broad spectrum—from private sails with expert guidance to affordable public schooners that let you experience traditional sailing in a relaxed setting.
For a personalized adventure with stunning sights, Captain Steve’s sailing experience is a highlight, especially for romantic or special occasions. If you prefer a luxurious, modern boat with amenities, Oyster Bay’s experience offers a peaceful escape.
Budget travelers or history enthusiasts will appreciate the charm of the public schooner, while those wanting a bespoke, private day should consider the Long Island Sound charter.
Booking early is recommended, especially in the busy summer months, to secure your spot on these memorable water adventures. No matter which you choose, a day on Long Island’s waters promises a refreshing perspective on this beautiful region.