The Best Boat Rentals in Boston

Expect most small motorboats with a captain to start around $200 per hour, classic sailboats to run about $150–$250 per hour, mid-size cruisers and day yachts to average $300–$600 per hour, and larger luxury yachts to range from roughly $700 to $1,200+ per hour. Many hosts set 2–4 hour minimums, with popular 2–3 hour sunset cruises priced as a package. Rates usually include the boat and basic safety gear; captain’s fee and fuel may be included or charged separately, and taxes, marina/landing fees, and cleaning may be extra. Gratuity for the crew, often 15–20% for great service, is customary but typically not included. Booking early for weekends and holidays helps secure the best time and price.

You’ll find a wide mix suited to different outings: comfortable motorboats for harbor cruising, classic monohull sailboats for a hands-on sailing experience, spacious cabin cruisers and motor yachts for celebrations, center consoles and RIBs for fast harbor hops, and a handful of catamarans for stable group lounging. If you’re planning a special occasion, look for boats with ample deck space, shaded seating, a Bluetooth sound system, and a head (bathroom) to keep everyone comfortable.

Both options exist. Many guests choose a captained charter for a stress-free day while a licensed local captain handles navigation, docking, and harbor traffic. Experienced boaters may be able to book a bareboat (self-operated) rental, subject to owner approval and insurance requirements. Massachusetts does not require a general boating license for adults to operate a motorboat, but operators must be qualified, and hosts often ask for a boating résumé. For safety, children under 12 cannot operate a motorboat, and minors have specific supervision rules; if in doubt, choose a captained trip to keep planning simple.

Common pickup points include Fan Pier Marina in the Seaport, Rowes Wharf near the Boston Harbor Hotel, Boston Yacht Haven on Commercial Wharf, and Constitution Marina in Charlestown. Some trips also start from Charlestown Marina, Long Wharf, or nearby Marina Bay in Quincy and Hingham Shipyard on the South Shore. Your exact meeting spot will be confirmed by the host after booking and may vary based on tides, events, or dock availability.

Typical routes showcase the skyline and Seaport, the historic Charlestown Navy Yard with the USS Constitution, Fort Independence at Castle Island, bustling ship channels with ferries and tugboats, and planes on approach to Logan. Many captains also cruise past the Boston Harbor Islands—Spectacle, Georges, and Peddocks are favorites—and, on longer trips, out toward Boston Light, the oldest continually lit lighthouse site in the United States. Sunset trips add golden light on the city and often spectacular photo angles.

For captained charters, no license is needed—just bring a government-issued ID and your booking confirmation. For self-operated rentals, adults generally do not need a state boating license in Massachusetts, but owners may require proof of competency (such as prior experience or a boater safety course card). Age rules apply for minors, and personal watercraft have stricter requirements. If you’re unsure, opt for a captained charter to streamline the process.

Yes—families are welcome on most listings. Every legal charter provides U.S. Coast Guard–approved life jackets sized for the guest list, and Massachusetts requires children under 12 to wear a life jacket while on deck when the boat is underway. Let the host know the ages and approximate weights of children so they can load the right gear. Strollers are usually stowed dockside, so plan a carrier for infants, bring layers for sea breezes, and pack sunscreen and snacks.

In most cases, yes. Many boats are BYO for snacks and beverages and have a cooler or small fridge; some allow catering or will recommend local options. Glass may be restricted on deck, and red wine or heavily dyed drinks are sometimes discouraged to prevent stains. Alcohol is for guests 21+ only, and the captain always has the final say on onboard safety. Ask your host whether ice, cups, plates, or a grill are available so you can pack accordingly.

Pet policies are set by each owner. Many captains welcome well-behaved dogs, especially on private charters, while others restrict pets due to deck materials or allergies. If your pup is joining, bring a non-slip mat, leash, waste bags, and a pet life jacket if you have one. Always include your pet in the guest count and confirm any cleaning fees before you book.

New England weather changes quickly, and captains watch marine forecasts closely. Light rain or passing clouds often won’t cancel a trip, but unsafe conditions—such as thunderstorms, high winds, dense fog, or rough seas—can prompt the captain to reschedule or cancel. If the captain cancels for safety, you’ll typically be offered a new time or a refund per the listing’s policy. To maximize calm water and clearer skies, morning departures are often best.

Absolutely. Private charters are popular for celebrations and team events. Most non-inspected “six-pack” boats carry up to six guests plus crew; for larger parties, look for inspected vessels rated for bigger groups. Share your headcount, preferred vibe (relaxed cruise, photo-friendly, or lively), and any décor requests. Many hosts allow balloons and banners but prohibit confetti or anything that could blow overboard. For smoother planning, confirm music setup, pick-up location, and any catering or beverage details in the booking chat.

Peak boating season runs June through September, with pleasant shoulder days in May and October. Memorial Day weekend, the Fourth of July, Boston Harborfest events around early July, and Labor Day weekend are the busiest times on the water and book up far in advance. Weekdays usually offer more availability and sometimes better pricing; mornings are calmer, while late afternoons deliver great light and sunsets. If you want the most relaxed harbor, consider a weekday morning outside holiday weekends.

Yes—many captains offer trips to the Boston Harbor Islands for sightseeing, swimming on calm days, or picnicking at anchor near Spectacle, Georges, or Peddocks. Docking or going ashore depends on island facilities, seasonal schedules, and your boat’s size. Longer private outings may reach Boston Light or, with the right vessel and conditions, head offshore for wildlife viewing; these require extra time and favorable weather. Ask your captain about route options, timing, and fuel considerations when you book.