The Best Boat Rentals Near Greenwich

Expect most captained powerboats and sailboats to start around $200–$350 per hour, with mid-size yachts commonly $400–$800 per hour and luxury yachts from about $1,000+ per hour. Half-day outings typically range from roughly $800–$1,800, and full days from about $1,800–$4,000+, depending on the boat, date, duration, and group size. Listings usually include the vessel, required safety gear, and, on captained charters, the captain’s time and expertise. Fuel, docking, gratuity, and taxes may be additional, and some hosts provide ice and bottled water—always check the specifics in your Getmyboat offer.

You’ll find an easy mix for every outing: comfortable pontoons for relaxed cruising, center consoles and fishing boats for active days, classic sailboats for a scenic tack on Long Island Sound, and express cruisers or motor yachts for celebrations. Many options are captained so you can just show up and enjoy, while some listings allow qualified guests to operate the boat themselves.

If you plan to operate the boat yourself, Connecticut requires the appropriate state boating certificate (a Safe Boating Certificate for most motorboats, or a Certificate of Personal Watercraft Operation for PWCs). Qualified U.S. Coast Guard–licensed operators also meet the requirement, and many out-of-state certifications are recognized through reciprocity. If you book a captained charter, you don’t need a boating license—the captain handles the operation.

For celebrations, first-time visitors, or groups that want a smooth, hands-off day, a captained charter is the easiest option—your skipper manages the route, docking, navigation, and safety so you can focus on the fun. Confident boaters with the proper Connecticut certification sometimes choose a self-operated rental, but keep in mind that Long Island Sound can have afternoon chop, busy weekend traffic around Greenwich Harbor and the Mianus River, and strong currents. If in doubt, go captained.

Common meeting points include Greenwich Harbor by Roger Sherman Baldwin Park and the Arch Street ferry dock downtown, Grass Island Marina just across the harbor, Cos Cob Marina on the Mianus River, and Byram Marina near Byram Park. Depending on the listing, some captains can also arrange pickups at nearby harbors if it fits the itinerary and tide.

A typical cruise takes you past Greenwich Harbor and the waterfront homes of Belle Haven and Indian Harbor, out toward Great Captain Island with its historic lighthouse, and by Island Beach and the protected shores around Calf Island. Heading west or east, you might also glimpse sparkplug-style lighthouses and, on clear days, distant views toward the New York City skyline. In summer, look for ospreys and egrets; occasional dolphin or whale sightings do happen in Long Island Sound.

Yes—most captains welcome families. Every legal charter carries U.S. Coast Guard–approved life jackets for all passengers, and children must wear them while the boat is underway. Let your captain know the ages and approximate weights of any kids so properly sized jackets are ready. Many boats also have shaded seating; bring sun protection and soft-soled shoes for little ones.

On many charters you can bring your own snacks, picnic spreads, and beverages. Some captains can stock the cooler or coordinate catering if you ask in advance. For safety and cleanup, many boats limit glass and discourage red wine; cans and reusable bottles are preferred. If you plan to celebrate, mention it when booking so the crew can advise on space for cakes, decorations, or a champagne toast.

Pet policies vary by boat. Small, well-behaved dogs are sometimes allowed with prior approval and may require a refundable deposit or cleaning fee. For your pet’s comfort, bring a non-slip mat, water bowl, and consider a pet flotation device. If any guest has allergies or concerns, tell the captain during booking so they can recommend a suitable vessel.

Your captain monitors marine forecasts for Long Island Sound and will adjust the route or reschedule if conditions are unsafe due to high winds, thunderstorms, or advisories. If the weather is marginal but safe, the trip can usually still run with a calmer itinerary. Cancellations and refunds follow the specific cancellation policy in your Getmyboat booking; many owners offer a reschedule or refund for truly unsafe conditions.

Peak boating season runs from late May through early September, with the warmest water in July and August. Big holiday weekends—Memorial Day, July 4th, and Labor Day—book up quickly and bring more traffic on the water. Greenwich’s own Memorial Day weekend festivities at Roger Sherman Baldwin Park can make the harbor lively, and the Norwalk Boat Show in mid-to-late September adds regional marina activity. For calmer water and easier parking, choose weekdays or morning departures; sunset cruises are popular but can be breezier in the afternoon.

Absolutely. Many boats are set up for special occasions with great sound systems, comfortable seating, and easy photo stops near the islands or harbor. Share your headcount, vibe, and preferred date and the captain can suggest the right boat and itinerary. Keep in mind that most uninspected vessels carry up to six passengers; larger groups require inspected passenger vessels that are designed for events—booking early helps secure the best fit.

Yes—private charters commonly cruise by Great Captain Island and Island Beach for lighthouse views and swimming stops when conditions allow. Calf Island, part of a national wildlife refuge, has no public docks; boats can anchor off designated beaches and guests must follow any posted landing restrictions to protect birds and habitat. Your captain will advise on the best route that day based on tides, wind, and wildlife guidelines.