The Best Boat Rentals in Sag Harbor

Expect smaller captained powerboats and bowriders to start around $300–$700 per hour, classic sailboats to run about $250–$800 per hour, and day yachts to range from roughly $1,000–$2,500+ per hour depending on size, season, and crew. Ultra‑luxury yachts can exceed $3,000 per hour. Most captained charters include the boat, captain, basic fuel for local cruising, and standard safety gear; many also provide water and ice, with gratuity and add‑ons like water toys or special routes priced separately. These ranges reflect current Sag Harbor listings and category pricing on Getmyboat.

In Sag Harbor you’ll find crewed motor yachts for celebrations, sailboats and catamarans for relaxed cruising, and versatile powerboats or center consoles for quick hops and swim stops. Choose a larger motor yacht for bachelorettes or birthdays, a sailboat for sunset sails, or a nimble powerboat for beach and cove time around Noyac Bay and Shelter Island. Getmyboat’s Sag Harbor marketplace shows strong availability across yachts, sailboats, and private tours throughout the season.

Most visitors book captained charters because it’s the simplest option for groups: the captain handles docking, routing, and safety so you can focus on your event. If you plan to operate a motorized rental yourself, New York now requires a boating safety certificate for all operators; captained trips do not require guests to hold this certificate.

As of January 1, 2025, Brianna’s Law is fully in effect statewide, meaning every motorboat operator—regardless of age—must carry a New York State–approved safe boating certificate. This applies on the waters around Sag Harbor and Shelter Island. If you’re booking a captained charter, the licensed captain operates the vessel and guests do not need certification.

Common meeting points include the Sag Harbor Village Marina at Long Wharf, right in the heart of town, and the Sag Harbor Yacht Club on Bay Street. The Village also manages transient docks and a mooring field near Marine Park and Marine Park Basin, which some trips may use for pickup by arrangement. Always confirm your exact dock gate and time with your captain before arrival. (dockwa.com, sagharboryc.com, sagharborny.gov)

Typical routes circle Sag Harbor Bay and Noyac Bay with views of the Long Wharf windmill, the Lance Cpl. Jordan Haerter Veterans Memorial Bridge to North Haven, and the cedar‑lined shores of Shelter Island’s Mashomack Preserve, a Nature Conservancy gem known for ospreys and quiet coves. Many cruises also point toward Cedar Island Lighthouse off Cedar Point, a photogenic landmark overlooking Gardiners Bay. (aaqeastend.com, easthamptonstar.com, nature.org, en.wikipedia.org)

Yes, most captains welcome families and provide U.S. Coast Guard–approved life jackets in a range of sizes. New York law requires children under 12 to wear a life jacket on boats under 65 feet while underway unless inside an enclosed cabin, so plan for little ones to be in PFDs whenever cruising. If you have an infant or specific fit needs, tell your captain in advance so the right sizes are ready.

Bringing your own snacks and beverages is common, and many boats supply a cooler, ice, and bottled water. Captains may limit glass or red wine to protect decks and upholstery, and some allow light decorations or catered setups with prior approval. If alcohol is on board, remember that boating under the influence is illegal for operators; your captain will make the final call on weather, route, and safety. (getmyboat.zendesk.com, parks.ny.gov)

Many boats allow well‑behaved dogs with advance notice, while others prefer no pets due to space and upholstery considerations. Always message the owner before booking to confirm pet policies, bring a leash and water bowl, and be prepared for a modest cleaning fee if applicable.

Captains watch wind, tide, and local marine forecasts closely. Summer afternoons on Long Island often bring a sea‑breeze pickup, so morning departures can be calmer; if conditions are unsafe, your captain will recommend rescheduling or canceling. On Getmyboat, weather‑related refunds or reschedules follow the cancellation policy on your specific listing, with many owners offering flexible options when the water isn’t safe. (arxiv.org, getmyboat.zendesk.com)

The boating season in Sag Harbor runs roughly April 1 through October 31, with peak demand from late June through early September. Memorial Day weekend, July 4th, and Labor Day are the busiest holiday periods, and Sag Harbor Yacht Club’s Independence Day fireworks and other summer shows draw extra boat traffic. Weekdays and morning or sunset departures are great for smoother water and easier parking around the docks. (sagharborny.gov, sagharboryachtclub.com, patch.com)

Absolutely. Many Sag Harbor charters specialize in private events, from low‑key family birthdays to bachelorette cruises with a swim stop and sunset photos. Share your headcount early so the captain can match you with a vessel that fits your group within Coast Guard capacity, and ask about add‑ons like catering, playlist hookups, or a photographer.

Plan ahead for HarborFest in September, when the village hosts waterfront activities and the historic whaleboat races off Windmill Beach, and for midsummer fireworks that light up the harbor. For easy half‑day outings, many groups cruise to Foster Memorial Beach (Long Beach) on Noyac Bay for a swim, circle Shelter Island’s Mashomack shoreline, or head toward Cedar Island Lighthouse for photos before returning to the village docks. (patch.com, southforker.com, southamptontownny.gov, nature.org, en.wikipedia.org)