The Best Boat Rentals in Southampton

In peak season, expect smaller powerboats to start around $300 to $600 per hour, classic sailboats from about $250 to $750 per hour, and mid-size motor yachts in the $800 to $1,500+ per hour range. Larger luxury yachts can run $1,500 to $3,000+ per hour. Many trips have a 3–4 hour minimum. Rates typically include the boat, safety gear, and a licensed captain if it’s a captained charter; fuel for easy bay cruising may be included, while longer runs and gratuity (often 15–20%) are usually extra. Prices rise on weekends and holidays, so booking early helps you lock in the best options.

You’ll find a wide mix suited to different groups and budgets, including comfortable sailboats for leisurely cruising, center consoles and fishing boats for anglers, sporty wake or jet-style boats for towing fun, and sleek motor yachts for celebrations. If you’re planning a bigger group outing, look for inspected yachts that can host larger parties with lounge space, sun pads, and shaded decks.

Most visitors opt for a captained trip because it removes all the stress—navigation, anchoring, and docking are handled by a local pro who knows the bays, tides, and best swim spots. If you prefer to operate the boat yourself, verify listing requirements and your experience level. New York requires a boating safety certificate to operate a motorboat as of January 1, 2025, and local waterways like the Shinnecock Canal and the inlets can have strong currents, so many planners find a captain well worth it.

Common pickup points include Shinnecock Canal Marina in Hampton Bays for quick access to both Shinnecock and the Peconics, Sag Harbor Village Marina by Long Wharf for trips toward Shelter Island and Gardiners Bay, Strong’s Southampton Peconic Bay Marina on North Sea Road for Peconic Bay cruising, and Ponquogue Marine Basin near the Ponquogue Bridge for Shinnecock Bay runs. Your captain will confirm the exact dock and parking details after you book.

From Shinnecock Bay you’ll cruise past the Ponquogue Bridge, the sand dunes and ocean beaches along Dune Road, and the dramatic Shinnecock Inlet. North through the canal, the Peconic Bays open up to Robins Island, Jessup’s Neck and the shoreline of the Elizabeth A. Morton Wildlife Refuge, with ospreys and other seabirds overhead. Around Sag Harbor you’ll pass historic Long Wharf and its windmill replica, and farther east you may spot Cedar Island Light near Cedar Point. Sunset and golden-hour views across the Peconics are a highlight.

For motorized boats, New York State requires all operators to have a boating safety certificate starting January 1, 2025. This doesn’t apply if you’re booking a captained charter; in that case, you’re a passenger. Some rental liveries can provide limited instruction for short-term rentals, but many owners still require proof of safe-boating completion, so check the listing details before you book.

Yes—families are welcome. Coast Guard–approved life jackets are carried on all charters, and New York law requires children under 12 to wear a life jacket while underway on most boats. Let the owner know your child’s ages and sizes so the right gear is on board, and consider bringing your own infant PFD for the best fit. Captains can recommend calm swim coves and shorter itineraries for younger crews.

Most listings are BYO for snacks and beverages, and many provide coolers, ice, and bottled water. Hard liquor policies vary by boat; beer, seltzers, and canned wine are commonly allowed. For easy cleanup and safety, plan cans over glass and avoid staining drinks like red wine. If you’d like catering, ask your captain—many can arrange platters or suggest dock-and-dine stops.

Some boats welcome small, well-behaved dogs with advance approval. Policies vary by captain and vessel type, and there may be a cleaning fee. Bring a leash, a non-slip mat, fresh water, and a canine life jacket if your pup is joining the cruise.

Your captain monitors marine forecasts and will make the final safety call. If conditions are unsafe—think high winds, storms, or rough seas—you’ll usually be offered a reschedule or a refund according to the listing’s policy. Summer afternoons can be breezier on the bays, so morning starts are often the calmest; on hot days, sunset cruises are popular for cooler temps and great light.

Absolutely. Many charters are set up for celebrations with Bluetooth sound, spacious decks, and swim ladders. Smaller boats typically carry up to six passengers, while inspected yachts accommodate larger groups—be sure to enter your true headcount when you inquire so you’re matched with the right vessel. Captains can help with décor, ice, and timing, and some will coordinate photo-friendly anchorages and sunset routes.

Peak boating season runs June through early September, with the busiest days on weekends and around Memorial Day, July 4th, and Labor Day. Two late-summer events can also impact travel and availability: the Hampton Classic Horse Show in Bridgehampton (August 24–31, 2025) and the Shinnecock Indian Powwow over Labor Day weekend. For the smoothest experience, choose weekdays if you can, aim for morning or sunset departures, and reserve several weeks in advance for weekend or holiday dates.

If your itinerary includes Shelter Island or Gardiners Bay, departures from Sag Harbor Village Marina near Long Wharf are the most direct. For Peconic Bay cruising with quick access from Southampton Village, Strong’s Southampton Peconic Bay Marina on North Sea Road is convenient. Heading for Shinnecock Bay and the ocean beaches along Dune Road, captains commonly use Shinnecock Canal Marina or Ponquogue Marine Basin in Hampton Bays. Your captain will advise the best dock based on wind, tides, and your route.

Fireworks cruises around the first week of July are a local favorite, especially in Sag Harbor’s harbor. Dates and start times vary year to year, but shows typically begin after 9:15 p.m., and harbors get busy, so book early and allow extra time for pickup and drop-off. Captains will keep you outside any safety zones and anchor among the fleet for great views of the show.