The 6 Best Cruises And Boat Tours in Long Island
Long Island’s coastline is a treasure trove of scenic beauty, celebrity mansions, and historic lighthouses. Whether you want a private yacht experience through the Hamptons, a relaxing sail with Captain Steve, or an affordable schooner trip in Greenport, the options are varied and exciting. The water here isn’t just a backdrop—it’s a way to see iconic sights like Montauk’s rugged cliffs, Long Island Sound’s mansions, and even New York City’s skyline from a fresh perspective.
In this guide, we’ll help you navigate through six of the best boat experiences available. From high-end private charters to intimate sailing adventures, each offers a unique way to enjoy Long Island’s waters. We’ll detail what each tour includes, who it’s best suited for, and what you should consider before booking—so you can pick the perfect way to make your water-bound memories.
Quick Overview
This list covers a range of experiences, including luxury private yacht charters in the Hamptons, sailing trips with professional guides, customized boat rentals for special occasions, spacious fun boats with lively features, private Long Island Sound sails, and affordable public schooner rides. Whether you’re after a quick 2-hour sail, a full afternoon of luxury, or a budget-friendly adventure, there’s something here to match your style and budget.
1. Private Yacht Charter in The Hamptons, Montauk or Sag Harbor
The Private Yacht Charter in The Hamptons is a top-tier way to indulge in Long Island’s luxe side. Priced at $2,390 per group (up to 10 people), this 2 to 4-hour cruise offers a tailored experience. You’ll glide past celebrity homes, explore hidden coves, and enjoy panoramic views of the picturesque shoreline.
This fleet boasts over 30 boats and yachts, from 22’ vessels perfect for intimate groups to 100’ yachts for larger celebrations. The tour includes stops at Sag Harbor, Montauk, or other Hamptons hotspots, with a focus on showcasing the area’s most glamorous sights. Water toys like Sea Bobs and paddleboards are included, making it ideal for families or groups wanting fun on the water.
What makes this experience stand out is its focus on personalization—you can customize your itinerary, whether it’s celebrating a birthday, bachelorette, or just enjoying a day with friends. The crew’s professionalism and attention to detail earn high praise, and the boat options are consistently rated 5.0/5.
Bottom Line: If you want a private, luxurious, and customizable water day with your own crew, this yacht charter is hard to beat for value and style.
2. Captain Steve’s Sailing Experience on Long Island
For those seeking a more relaxed, hands-on adventure, Captain Steve’s Sailing Experience offers a 2-hour sailing trip suitable for groups of up to 6 for $475. The highlight? You get to learn the ropes from an experienced captain while enjoying breathtaking views of the area.
This tour stands out for its professional guidance and the chance to participate in sailing. Captain Steve shares his expertise, making it perfect if you’re curious about sailing or want a more authentic experience. The scenery includes sights such as Kings Point, City Island, Hart Island, and even NYC’s skyline in the distance. Many guests comment on how peaceful and beautiful the experience is, with one reviewer saying, “This was a five-star experience all around.”
The tour is best suited for those who want a relaxed, educational, and scenic outing without the hassle of boat ownership. It’s a great choice for couples, small groups, or anyone looking to try sailing with a friendly guide.
Bottom Line: A small-group, personalized sailing experience that’s ideal for those wanting to learn and enjoy Long Island’s waters at a gentle pace.
3. Boat or Yacht Rental in Sag Harbor, The Hamptons, or Montauk
If you prefer the freedom to craft your own adventure, this custom boat or yacht rental is perfect. For $1,990 per group (up to 8), you get about 4 hours to explore at your own pace, with expert guidance available to help tailor your trip.
This rental service emphasizes personalized experiences. Whether you want a romantic sunset cruise, a lively family outing, or a celebratory bachelorette party, the staff works with you to create your ideal day on the water. The focus is on insider tips and making sure your itinerary matches your preferences, from scenic stops to watersports.
While the cost might seem high, it’s justified by the flexibility and tailored service. It’s well-suited for those who want a bespoke experience without the formality of a guided tour, or for groups with specific plans.
Bottom Line: A premium, flexible option for those who know what they want out of their day on Long Island’s waters.
4. 4 Hours of Spacious 50 Foot Private Fun Boat in Hampton
For a lively, party-ready experience, the Spacious 50-foot Fun Boat is a standout. Priced at $5,000 for up to 15 people, this vessel is designed to entertain. It features a U-shaped bar, a DJ booth, and a top-notch sound system, perfect for celebrating with friends.
This boat offers 360-degree views and plush sun beds for lounging. Its modern amenities make it suitable for bachelor/bachelorette parties, birthdays, or just a fun day out with a larger group. The fully equipped bathroom and ample space mean comfort isn’t sacrificed for fun.
Note that this experience is more about entertainment and socializing than sightseeing, but the scenic surroundings of the Hamptons add to the overall appeal. The vessel’s size and features make it a good choice for groups wanting a lively, music-filled day.
Bottom Line: A high-capacity, party-oriented boat perfect for celebrations and those looking to enjoy the Hamptons in style and comfort.
5. Private Long Island Sound Sailing Experience
This private sailing trip offers a 3-hour journey for up to 6 people at $650. It’s a fantastic way to enjoy the Long Island Sound, with a chance to participate in sailing or simply relax and take in the views.
The tour explores Manhasset Bay, with sights of mansions lining the coast, plus the opportunity to sail in open water. As you cross into Long Island Sound, you’ll encounter iconic sights like Hart Island, Throgs Neck Bridge, and the lighthouse at Steppingstone. The experience is flexible—captain or guests can help with sailing, or just enjoy the ride.
It’s perfect for those seeking a slightly more private, immersive sailing adventure or celebrating a special day like a birthday or anniversary. The main appeal lies in the personalized experience and stunning scenery.
Bottom Line: A balanced choice for sailing enthusiasts or those wanting a private, scenic route through Long Island’s waters.
6. Public Schooner Sail in Greenport
The Public Schooner Sail is a budget-friendly way to enjoy the North Fork’s maritime charm. At $130 per person, this 2-hour evening sail offers a classic schooner experience on a historic vessel.
This trip is all about the experience of being on a traditional schooner, with the wind in your hair and the chance to see Long Island’s coastline from a different angle. Unlike private charters, this is a more accessible option, making it ideal for solo travelers, couples, or small groups wanting a taste of sailing history.
The setting sun and gentle breezes make for a memorable and romantic outing, especially for those new to sailing. The boat’s classic design and the scenic surroundings embody the maritime spirit of the North Fork.
Bottom Line: An authentic, affordable way to enjoy Long Island’s waters and see the North Fork from a historic schooner.
How to Choose Your Perfect Water Experience
When selecting your boat tour, start with your budget and what kind of experience you want—whether that’s private luxury, a guided sailing adventure, a party boat, or a quick scenic trip. Consider the group size and your activity preferences: do you want to learn how to sail, party on a high-capacity boat, or just relax and enjoy the scenery?
Booking early is wise, especially for private yachts and popular sailing times in summer. Check the weather forecast and plan around calmer days for sailing or relaxing trips.
Final Thoughts
Long Island offers a fantastic variety of boat experiences, from lavish private yachts to affordable schooner sails. If your priority is a tailored, luxury day out with celebrity home views, the private yacht in the Hamptons is hard to beat. For a more hands-on, educational experience, Captain Steve’s sailing trips provide both scenery and learning. Families or groups wanting a flexible, personalized outing will find the boat rental ideal, while party animals and groups celebrating a special occasion will love the spacious fun boat.
Ultimately, these options let you enjoy Long Island’s waters in ways that suit your style and budget. Whether you want to cruise past mansions, learn to sail, or dance on a lively boat, you’re bound to find a water adventure that will make your trip memorable. Book early, pack your sunscreen, and get ready for a day on the water that you’ll talk about for years.