Long Island offers a fantastic mix of coastal scenery, lively harbors, and historic waterways, making it an ideal destination for boat tours and cruises. Whether you’re craving a relaxing sail with spectacular views of Manhattan’s skyline, a lively private charter to celebrate a special occasion, or an affordable public schooner trip along the North Fork, Long Island’s waters won’t disappoint. We especially love the Captain Steve’s Sailing Experience for its combination of personalized guidance and stunning scenery, and the Oyster Bay Two Hour Sailing Experience for its tranquil setting and modern amenities. Those looking for a more intimate or budget-friendly outing will find plenty of options.
If you’re planning your trip, our list below highlights the very best boat tours in Long Island, including private and public cruises, with details on what makes each one special. Dive into the options to find your ideal maritime adventure.
Quick Overview
This guide covers four top boat experiences in Long Island. First, we have the Captain Steve’s Sailing Experience, a private 2-hour sail with professional guidance. Next is the Oyster Bay Two Hour Sailing Experience, a private sunset sail designed for relaxed wildlife sightings and excellent amenities. For those seeking a more affordable, shared experience, the Public Schooner Sail in Greenport offers a classic North Fork sailing trip. Finally, the Private Long Island Sound Sailing Experience delivers a customized multi-hour private charter showcasing mansions and city skyline views. Read on to see which fits your trip best.
1. Captain Steve’s Sailing Experience on Long Island
Touring with Captain Steve is a standout for its personalized approach and spectacular views. This 2-hour private sailing trip is perfect for groups of up to six and costs $475, making it a manageable splurge for a memorable outing. The experience includes a beautifully maintained boat and the chance to learn the basics of sailing from an experienced captain. Captain Steve’s local knowledge shines as he points out landmarks like Kings Point, City Island, and city skylines, all while you relax and take in the scenery.
What makes this tour truly special is the combination of professional guidance and relaxed atmosphere. Many reviews highlight how Captain Steve’s friendly demeanor enhances the trip—one caller mentioned their surprise 30th birthday was made extra special with this experience. Even with some cloud cover, they enjoyed the views of NYC and the surrounding area. It’s an ideal choice for travelers who want a personalized, scenic, and educational outing.
Bottom Line: If you’re looking for a private, guided sail with excellent scenery and a friendly captain, this experience offers value and a personal touch that’s hard to beat. Booking ahead is recommended, especially for sunset cruises.
2. Oyster Bay Two Hour Sailing Experience
The Oyster Bay Two Hour Sailing Experience is a fantastic way to enjoy Oyster Bay Harbor’s natural beauty. At $595 for up to six people, this private sail offers a great balance of comfort, scenery, and exclusivity. The boat, WINDSWEPT, boasts modern amenities like a fully shaded cockpit, Bluetooth stereo, and a swim platform—perfect for relaxing or jumping in for a quick dip.
This tour stands out for its spectacular sunsets and wildlife sightings. Captain Jonathan, known for his attentiveness, ensures everyone has a good time, whether it’s pointing out local landmarks or helping guests with sailing basics. Many reviewers praise the easy booking process and the incredible views of the local coastline, making it an ideal choice for celebrating special occasions or simply escaping the hustle.
The experience is particularly suited for those wanting a luxurious, laid-back sailing experience with plenty of opportunities for swimming and relaxing. Unlike larger commercial tours, this charter offers a more intimate vibe, perfect for families or small groups.
Bottom Line: For a relaxed, well-equipped private sail with sunset views and wildlife, this trip hits all the right notes. It’s a bit pricier, but the amenities and personalized service make it worthwhile.
3. Public Schooner Sail in Greenport
If you’re after an affordable way to experience traditional sailing on Long Island’s North Fork, the Public Schooner Sail in Greenport is an excellent choice at $130 per person. This 2-hour ticketed sail on a historic schooner offers a classic maritime experience without the need for a private booking. It’s great for those who want a taste of sailing, without the added cost of a private charter.
The schooner’s historic design offers a different vibe compared to modern boats. The trip provides views of the East End, including local landmarks and the surrounding waters. While it doesn’t include a personalized guide, the shared experience creates a friendly environment for meeting fellow travelers and enjoying the sea breeze.
This tour is best suited for budget travelers, casual cruise lovers, or visitors who want a quick, authentic sailing experience. The shorter duration and lower price point make it accessible for families, couples, or solo travelers. Keep in mind that the lack of reviews suggests it’s a newer or less-reviewed option, but the price and concept are compelling.
Bottom Line: For a budget-friendly, traditional sailing experience that captures the essence of Long Island’s coast, this schooner trip is a solid pick.
$130.00 per person
4. Private Long Island Sound Sailing Experience
This 3-hour private charter offers a customizable sailing adventure on Long Island Sound. Costing $650 for up to six people, it’s ideal for special occasions like birthdays, anniversaries, or bachelorette parties. The boat explores Manhasset Bay, known for its multi-million-dollar mansions, and offers spectacular city skyline views as you cruise past the Throgs Neck Bridge, Hart Island, and the lighthouses of Steppingstone and Execution Rocks.
What makes this tour stand out is the participatory element—passengers can help sail the boat if they wish—and the option to anchor for lunch and swimming. This flexibility makes it ideal for travelers wanting a personalized, multi-hour experience that combines sightseeing with relaxation and active sailing.
Though there are no reviews available, the itinerary suggests it’s perfect for those looking for a private, luxurious, and customizable sailing trip. The opportunity to see NYC skyline views from the water combined with mansions and historic lighthouses provides plenty of photo opportunities.
Bottom Line: For a private, flexible, and scenic sailing adventure tailored to your group, this experience offers excellent value for a memorable long afternoon on Long Island Sound.
$650.00 per group (up to 6)
How to Choose the Right Boat Tour in Long Island
When selecting your ideal boat experience, consider your budget, the level of privacy desired, and the types of sights you want to see. If you want a personalized and guided experience, Captain Steve’s Sailing Experience offers the best combination of scenic views and expert guidance. For a relaxing private sunset sail with modern amenities, the Oyster Bay two-hour trip is a top pick.
If you’re on a budget or prefer a more social atmosphere, the Public Schooner Sail provides a traditional sailing experience at a reasonable price. For those celebrating a special occasion or seeking a more exclusive, customizable experience, the Private Long Island Sound Sailing offers the most flexibility.
Booking early is advisable, especially during peak summer months, and consider weather conditions—many tours are weather-dependent. Think about your priorities: scenic views, active sailing, affordability, or privacy—and match your choice accordingly.
Final Thoughts
Long Island’s diverse waterways offer a range of memorable sailing options. If you’re after a guided, scenic, and educational experience, Captain Steve’s private sail is hard to beat. For a relaxing sunset cruise with modern comforts, the Oyster Bay private experience shines. Budget travelers and those seeking a classic schooner adventure will find the Greenport sail appealing, while those celebrating something special will love the flexibility of the private Long Island Sound cruise.
No matter which you choose, booking early will help ensure you secure your preferred date. So, set your sights on the water—Long Island’s boat tours promise plenty of beautiful views and good times.