The Best Boat Rentals in Montauk

Expect a wide range depending on boat size and trip style. Small captained sailboats and simple sunset cruises often run about $200–$400 per hour, while mid-size cruisers and day boats are commonly $300–$700 per hour with a 3–4 hour minimum. Luxury motor yachts in the Hamptons area typically start around $700–$1,500+ per hour. Private fishing charters usually price by the trip rather than the hour: half-day inshore runs about $800–$1,100, three-quarter day around $1,000–$1,500, and full-day inshore $1,500–$2,000; offshore tuna or shark trips are generally $2,000–$3,000+. Party/head boats offer per-person rates for shared fishing, often about $70–$120 for half-day outings in peak season. Most charters include a licensed captain or crew when applicable, safety gear, and fuel for local cruising; fishing trips typically include bait, tackle, and fish cleaning. Taxes, gratuity, marina fees, or extra fuel for longer routes may be additional, and premium food and beverage service is usually an add-on.

Montauk’s fleet is built for saltwater fun and includes center consoles and sportfishing boats for the rips off the Point, classic sailboats for relaxed cruising, motor yachts for upscale group days, catamarans for stable lounging and swimming, and larger passenger vessels for big-group fishing or sunset cruises. Pontoons are less common but do appear for calm-water cruising in the harbor and bays. Choose the style that fits your group size, comfort preferences, and itinerary.

If you book a captained charter, you don’t need a boating license—your crew handles the navigation. If you plan to operate a motorboat yourself, New York’s Brianna’s Law requires a state‑approved boating safety certificate for all operators as of January 1, 2025. There is a limited livery exception in New York that allows adults to rent certain motorboats after receiving dockside instruction, but many Montauk listings are either captained or require demonstrated experience and a safety certificate. Always check the specific listing requirements before you book, and bring your original certificate if you’ll be at the helm.

Most trips leave from Montauk Harbor on Lake Montauk. Common pickup points include Sam’s Star Island Yacht Club & Marina on Star Island, Montauk Yacht Club on Star Island Road, Westlake Marina along West Lake Drive, Montauk Marine Basin on West Lake Drive, and the docks by Gosman’s at the inlet. Your captain will confirm the exact meeting spot and parking details a day or two before departure.

You’ll cruise past the historic Montauk Point Lighthouse and the rugged bluffs of Camp Hero, glide along Lake Montauk and the inlet out to Block Island Sound, and often catch views toward Gardiners Island and Fort Pond Bay. In summer, it’s common to spot dolphins and, on some trips offshore, humpback whales and sea turtles; in the colder months, seals often haul out on nearshore rocks. Sunset rides frequently frame the lighthouse or Gardiners Bay in golden light—great for photos.

Yes, families are welcome on most boats. Every charter carries U.S. Coast Guard–approved life jackets sized for adults and children, and New York law requires children under 12 to wear a life jacket while underway on boats under 65 feet unless they are inside an enclosed cabin. Let your captain know the ages and approximate weights of any children so the right sizes are ready, and plan to bring sun protection, snacks, and layers since it can feel cooler on the water.

Most private charters are BYO for snacks and beverages, and many boats provide coolers with ice or have galleys for light prep. Glass and red wine are often discouraged for safety and cleanup, and hard liquor may be restricted. If you want catering, ask your captain during booking; many can arrange platters or coordinate pickup from harbor-area restaurants so everything is waiting when you arrive. Please remember that the boat operator must remain sober at all times.

Some boats allow well-behaved dogs on a case‑by‑case basis, especially for short harbor cruises. Confirm during inquiry, share your dog’s size and temperament, and bring a leash, waste bags, a small towel, and a pet life vest. For fishing trips or open‑ocean runs, many captains do not allow pets for safety.

Your captain monitors marine forecasts and sea state and will make the final go/no‑go call for safety. Light rain often doesn’t cancel, but high wind, dense fog, rough seas, thunderstorms, or tropical systems can postpone or cancel a trip. Most Montauk charters offer a weather reschedule or refund according to their stated policy, and they’ll work with you to find the next available time. Morning departures usually have the calmest conditions, especially in summer when afternoon sea breezes pick up.

Absolutely. Captains here host celebrations all summer long and can recommend routes for swimming coves, lighthouse photo ops, or a leisurely cruise with music and toasts. Share your headcount, vibe, and any décor requests in advance so the crew can plan cooler space, boarding logistics, and a playlist connection. Weekends in July and August fill first, so try to book two to four weeks ahead for Saturdays and even earlier for holiday weekends.

Peak boating season runs roughly from late May through September, with the most reliable beach‑day weather in June, July, and August. Major boating holidays—Memorial Day Weekend, July 4th, and Labor Day—sell out quickly and carry heavier harbor traffic. Local traditions like the Blessing of the Fleet on the second Sunday in June bring extra boats to the inlet and are wonderful to view from the water. For lighter crowds and smoother seas, book weekdays and earlier morning departures; late afternoons can be breezier. September often brings warm water and gorgeous sunsets with fewer boats, while October offers crisp scenery on calm days.

Captained charters are the norm here and make the experience turnkey: you show up with your group, your captain handles navigation, anchoring, and safety, and you focus on celebrating or fishing. Self-operated options are more limited due to the open‑ocean environment and inlet currents; if available, they typically require strong boating experience, a security deposit, and compliance with New York’s boating safety certificate rules. If stress‑free planning is the goal, a captained trip is usually the easiest way to go in Montauk.

Yes. Block Island lies roughly 16–20 nautical miles from Montauk, so a well‑planned private charter can make it a comfortable day run when weather and sea conditions cooperate. Closer-to-home options include swimming and sandbar time in Fort Pond Bay, cruising past the lighthouse, and scenic laps around Lake Montauk and the inlet. Discuss timing, fuel costs, and weather windows with your captain when you reserve, and build in flexibility if seas are sporty on your date.