Long Island is home to some of the most beautiful coastlines in the Northeast, and there’s no better way to experience its charm than from the water. Whether you’re cruising through calm bays, winding canals, or hugging the shoreline of quaint waterfront towns, a boat ride offers a unique vantage point of Long Island’s most iconic and scenic landmarks.
From historic lighthouses to celebrity hideaways, these seven local landmarks are best appreciated with the breeze in your hair and a drink in your hand. Whether you’re a first-time visitor or a local rediscovering your home turf, let this list—and your friendly tiki boat guide—help shape an unforgettable day on the water.
1. Fire Island Lighthouse
Rising tall on the western end of Fire Island, this iconic black-and-white-striped lighthouse is visible from miles away and stands as a symbol of Long Island’s maritime heritage. Built in 1858, the Fire Island Lighthouse once guided ships safely into New York Harbor and is now a favorite backdrop for boaters, photographers, and history buffs alike.
From the water, you’ll get a sweeping view of the tower against the pristine dunes and Atlantic Ocean backdrop—a stunning photo opportunity, especially around sunset.
Bonus: You may even spot deer or seabirds along the shoreline as you pass by.
2. Jones Beach Amphitheater (Northwell Health at Jones Beach Theater)
Located right on the bay, this iconic outdoor concert venue is visible from the water and often alive with the sounds of live music during the summer months. As you cruise past, you may catch a soundcheck or even the distant beats of a headlining act echoing across the bay.
It’s a cool, unexpected thrill for music lovers and a reminder of how closely entertainment and the water are intertwined on Long Island.
Pro Tip: Ask your tiki boat guide to time your cruise near show hours for an added musical bonus.
3. Freeport’s Nautical Mile
The Nautical Mile in Freeport is a lively stretch of waterfront that’s packed with restaurants, bars, shops, and marinas. From the boat, you’ll get a front-row seat to the buzz of this famous boardwalk scene—complete with string lights, waterfront dining, and live music echoing from patios.
It’s a festive sight during the day and truly comes alive at night, making it a favorite route for evening and sunset cruises.
Best Seen During: Friday or Saturday evenings when the area is buzzing with weekend energy.
4. Long Beach Boardwalk
Stretching over two miles along the Atlantic, the Long Beach Boardwalk is one of the most scenic and well-loved spots on the South Shore. From the water, you’ll get a panoramic view of the sandy beach, bikers and joggers cruising the boardwalk, and the dramatic skyline of apartment buildings and hotels just beyond.
This is one of the best places to catch a classic Long Island sunrise or sunset with uninterrupted views of the horizon.
Local Tip: Sunrise boat rides with a view of the Long Beach shoreline are unforgettable and perfect for early risers.
5. Zachs Bay and the Jones Beach Tower
Zachs Bay is a calm, protected inlet near Jones Beach, often used by boaters for swimming, floating, and relaxing. Overlooking the bay is the Jones Beach Water Tower—often nicknamed the “Pencil” due to its tall, narrow structure. The tower has become a recognizable symbol of summer on Long Island.
It’s an ideal location to anchor, relax, and enjoy a peaceful break while surrounded by classic Long Island scenery.
Photographer’s Note: The tower reflecting on the still waters of the bay makes for a perfect postcard-worthy shot.
6. Oyster Bay Harbor
Oyster Bay is a picturesque North Shore harbor town known for its colonial history, vibrant marine activity, and connection to President Theodore Roosevelt. From the boat, you’ll cruise past yachts, fishing boats, and the tree-lined shoreline of Sagamore Hill—Roosevelt’s former summer home, which now operates as a National Historic Site.
The harbor’s calm waters and charming landscape make it a favorite among boaters seeking a more serene, historical experience.
Fun Fact: You may also spot working oyster farms in the bay—a nod to the town’s namesake and its legacy in shellfish cultivation.
7. Captree State Park and Bridge
Sailing beneath the Captree Bridge is a dramatic and scenic experience. As you glide through the Great South Bay, you’ll see the arched structure stretching across the water, connecting Jones Beach Island and Fire Island. To your sides, you’ll spot Captree State Park’s marina, packed with fishing boats and day cruisers.
The park itself is a hotspot for anglers and birdwatchers, but from the water, it’s all about the view—open bay on one side, endless sky on the other.
Best Time to Visit: Midday for bright skies and calm water or late evening for golden hour reflections.
Long Island’s coastline is packed with charm, history, and natural beauty—and exploring it by boat unlocks a new perspective that’s impossible to experience from land. These seven landmarks showcase the diversity of Long Island’s waterfront, from cultural icons to peaceful retreats.
Whether you’re taking it all in with a camera or just enjoying the moment with good company, let your tiki boat guide point the way and share local insights along the journey. Because out here, every cruise is more than just a ride—it’s a floating adventure through the best of Long Island.