The Best Boat Rentals in Long Island

Most private charters on Long Island start around $150–$250 per hour for smaller powerboats and sailing yachts, $250–$450 per hour for mid‑size cruisers, and $600–$1,200+ per hour for larger luxury yachts. A short 2–3 hour cruise commonly totals $400–$1,200 depending on size, captain, and day of week; half days often run $700–$1,500, and full‑day outings $1,800–$4,000+. Rates usually include the boat, standard safety gear, and either a licensed captain or the option to self‑operate where allowed. Fuel for local cruising, dockage, cleaning, gratuity, or special add‑ons like floats may be extra and vary by listing.

You’ll find a wide mix suited to bays and open water: comfortable bowriders and center consoles for sandbar stops and sightseeing, classic sailboats for Long Island Sound or Peconic Bay breezes, sportfishing boats for inshore or offshore runs, and mid‑to‑large motor yachts for celebrations, sunset cruises, and Hamptons or Fire Island days.

Yes, if you plan to operate the boat yourself. New York’s Brianna’s Law requires all operators of motorized vessels to hold a boating safety certificate beginning January 1, 2025. If you book a captained charter, you do not need a certificate—your licensed captain handles the vessel while you relax.

For most trip planners, a captained charter is the easiest path: the captain manages navigation, anchoring, and local rules so your group can focus on fun. Self‑operated rentals suit confident boaters who meet New York’s safety‑certificate requirement and are comfortable with tides, channels, and traffic on the Great South Bay, Peconic Bay, or Long Island Sound. If you’re celebrating or visiting new waters, go captained; if you’re experienced and want flexibility, consider self‑operate.

Popular departure points include Port Washington’s Town Dock on Manhasset Bay for North Shore cruises, Captree State Park’s boat basin by the Robert Moses Causeway for Great South Bay trips, Freeport’s Nautical Mile and Sea Breeze Park docks, Bay Shore Marina for access to Fire Island, the Patchogue River for runs to Watch Hill and Davis Park, Sag Harbor’s Long Wharf and village docks, Greenport’s Mitchell Park Marina on the North Fork, and Montauk Harbor (Lake Montauk) for East End adventures.

On the South Shore you can cruise past the Fire Island Lighthouse, sandy barrier islands, and the bridges to Jones Beach and Robert Moses. On the North Shore and Long Island Sound, expect views of Gold Coast estates, the Stepping Stones Lighthouse, and on clear days distant glimpses of the New York City skyline. Out East, sailors and yachts pass Shelter Island, the Peconic Bay, Greenport’s waterfront, Sag Harbor’s Long Wharf, and the iconic Montauk Point Lighthouse.

Yes—family outings are common. Boats carry U.S. Coast Guard–approved life jackets for every passenger; ask in advance for infant and youth sizes to ensure a perfect fit. New York law requires children under 12 to wear a life jacket while underway on vessels under 65 feet, and during the cold‑weather season (November 1 to May 1) everyone on boats under 21 feet must wear one while underway. Captains will brief you on safety before departure.

Most charters are BYO and happy to have you bring snacks, picnic spreads, and beverages. Many allow beer, seltzers, and wine in moderation; hard liquor and red wine are sometimes restricted, and glass is often discouraged for safety. Ask about cooler space, ice, and catering options—some captains can arrange dock‑and‑dine stops in places like Freeport’s Nautical Mile, Patchogue, Port Jefferson, Sag Harbor, or Greenport.

Pet policies vary by boat. Small, well‑behaved dogs are frequently welcomed with advance notice, and some owners charge a modest cleaning fee. Bring a non‑slip mat, water bowl, and leash for docks. If your day includes swimming or sandbar time, consider a canine life jacket and check that your captain is comfortable with pets onboard.

Safety comes first. If conditions are genuinely unsafe—strong winds, electrical storms, dense fog, or small‑craft advisories—most captains will offer a free reschedule or a refund according to the listing’s policy. Summer afternoons can see a healthy sea breeze and choppier water; mornings are often calmer. Keep your phone handy on trip day so you can coordinate any weather calls quickly.

Peak boating season runs from late May through early September, with prime holidays on Memorial Day weekend, July 4th, and Labor Day. June through August offers the warmest water and longest days; September is a favorite for sunny, less‑crowded cruises. Weekday mornings are typically the quietest and smoothest; weekend afternoons are the busiest. On the South Shore and off Montauk, wildlife sightings like dolphins and, in season, whales are possible in summer and early fall.

Absolutely. Many boats are set up for celebrations and can help you plan playlists, décor touches, swim stops, or photo‑worthy routes—think sunset sails on Long Island Sound, sandbar days near Fire Island, or harbor cruises in Sag Harbor and Greenport. To keep planning simple, share your headcount, date window, budget, and must‑haves (catering, champagne flutes, floats, or a specific pickup) when you inquire.

Yes—those are classic local outings. Many groups anchor at Fire Island’s sandbars for swimming and beach time, and Zachs Bay is a popular spot to relax on concert nights at the Jones Beach theater. Always follow your captain’s guidance on depth, tides, and designated zones; during special events like the Memorial Day weekend air show off Jones Beach, the Coast Guard enforces temporary no‑entry areas offshore, and boats must remain outside those safety zones. Your captain will handle the details so your crew can enjoy the day.