Step aboard Gypsy Rose Yacht, a beautifully restored 1981 Cruisers Yachts VillaVee 288 Cruiser (fully renovated in 2025), and experience the thrill on The Hudson River.
Viking Fly Charters is a classic 2008 SeaCraft center console based in Norwalk, offering private, customizable trips for up to 3 guests.
Step aboard Coastal Castaways, a beautifully maintained 2001 Sea Ray 400 Sedan Bridge yacht and experience the Hudson River from an entirely new perspective.
"My Family of six adults and two children enjoyed a terrific day on Utopia, We sailed with Capt." — Jack,
Sail Long Island's Gold Coast aboard a beautifully maintained 2012 Jeanneau Sun Odyssey 36i.
"From the start, Jonathan was both a gracious host and a skilled, knowledgeable captain." — Todd,
Step aboard Nirvana, a timeless 38’ Pearson 386 sailing yacht, and experience the beauty of Long Island Sound without the crowds, just you, your guests, and the open water.
Gypsy Soul Tours offers private, custom sailing charters from Stamford, Connecticut, delivering unforgettable experiences on the scenic Long Island Sound.
"We had such a wonderful afternoon on the water with Captain Jon!" — Samantha,
Step aboard the 2025 Galeon 560 Fly and experience New York Harbor like never before.
Sailaway NY is a 2006 Hatteras 60 Motor Yacht, restored in 2020 and based in New York City. With space for up to 35 guests, this spacious yacht is an excellent choice for sightseeing cruises, celebrations, and special events on the waters of NYC.
Experience unforgettable adventures aboard Sea Dog Cruising, a beautifully maintained 2006 Atlantic Boat Company Duffy 35 Downeast, proudly based in Northport.
Peekskill sits on a scenic bend of the Hudson River, perfectly placed for relaxed cruising and quick adventures into the Hudson Highlands. Calm stretches of water in Peekskill Bay make it a welcoming spot for first-time captains and seasoned boaters alike, with sweeping views that take in nearby forested ridges and the iconic Bear Mountain Bridge.
Launch for a laid-back afternoon on the river, or chart a longer route past dramatic cliffs and historic river towns. Tidal currents add a touch of excitement while still offering plenty of gentle windows for sightseeing, photography, and family outings. Wildlife sightings—especially soaring raptors—are common along the tree-lined shores, and fall foliage cruises here are a local favorite.
On shore, the waterfront parks and piers provide easy access to the docks and a comfortable place to gather before or after your time on the water. Protected inlets and nearby creeks offer quieter pockets for picnicking at anchor or dropping a line, while open channels invite you to stretch out and enjoy a steady cruise.
Choose Peekskill boating charters to explore this classic stretch of the Hudson at your own pace. Whether you’re planning a short sunset spin, a half-day of sightseeing under the bridge and highlands, or a full-day river run between charming riverfront communities, Peekskill delivers the right blend of scenery, accessibility, and small-town waterfront vibe.
