The Best Boat Rentals Near Portland

Most private, captained harbor cruises for up to six guests run about $150–$250 per hour for simple sightseeing boats, $225–$275 per hour for private sailboats (often shown as $450–$550 for a typical 2‑hour sail), and $300–$400+ per hour for newer or larger premium powerboats. If you’re planning a big celebration, large vessels that host 50–250+ guests are typically priced as flat packages of roughly $2,000–$2,600 for a three‑hour private charter. Rates usually include a licensed captain, USCG‑required safety gear, and basic fuel for standard routes. Extras can include catering, all‑inclusive beverage packages, extended cruising time, or special docking stops; many hosts also allow BYO food and drinks.

You’ll find classic sailboats for relaxed harbor sails, comfortable Downeast and trawler‑style cruisers for lighthouse and history tours, center consoles for quicker runs around Casco Bay, rigid‑inflatable (RIB) adventure boats for small‑group wildlife and lighthouse loops, and larger motor yachts or small passenger vessels for weddings, corporate outings, and parties. Fishing‑forward boats and working lobster boats also run private scenic or “lobster demonstration” charters.

Most Portland harbor trips are captained, which keeps logistics easy in a working port with tides, shipping traffic, and occasional fog. Experienced boaters can find limited self‑operate options on smaller powerboats; if you plan to drive, Maine requires anyone born on or after January 1, 1999 to complete an approved boater safety course to operate motorboats of 25 hp or more, and personal watercraft operators must be at least 16 with boater education. Maine doesn’t issue a “boating license,” but a boater education card serves as proof. Many planners choose captained trips so the whole group can relax.

Common downtown pickup points include DiMillo’s Old Port Marina on Long Wharf and Fore Points Marina by the Ocean Gateway. You’ll also see departures from Portland Yacht Services along West Commercial Street and, across the bridge in South Portland, Spring Point Marina and South Port Marine. For public ramps, the Cutter Street/Eastern Promenade Boat Launch is the city’s main trailer launch. Group cruises and ferries use the Maine State Pier/Ocean Gateway area on the east waterfront.

Expect postcard views of the working waterfront and a string of lighthouses, including Portland Head Light in Cape Elizabeth, Spring Point Ledge Light, and Portland Breakwater Light (“Bug Light”), with Ram Island Ledge Light offshore. You’ll pass granite forts like Fort Gorges and the “Calendar Islands” of Casco Bay such as Peaks Island and Great Diamond Island. Wildlife sightings often include harbor seals, porpoises, ospreys, eiders, and seasonal seabirds.

Maine’s law is simple for most visitors: there’s no traditional “license,” but if you operate a motorboat of 25 hp or more and were born on or after January 1, 1999, you need to complete a NASBLA‑approved boater safety course and carry proof. For personal watercraft, you must be at least 16 and have boater education. These rules don’t affect you when you book a captained charter, which is the norm in Portland.

Yes—family groups are common, and all legitimate charters carry USCG‑approved life jackets for every passenger. Maine law requires children 10 and under to wear a life jacket while underway, and your captain will provide properly sized vests. If you’re bringing infants or toddlers, ask about sizes ahead of time. For the smoothest family ride, many planners choose morning departures when winds and chop are typically lighter in summer.

Most private charters happily allow BYO snacks and beverages and will suggest no‑glass containers or no red wine to avoid stains. Several boats can provide coolers and ice, and some offer all‑inclusive bar or catered menus if you’d rather not pack anything. If a vessel has its own liquor license, BYO alcohol may be restricted. As always, the captain cannot operate under the influence, so designate the pros and enjoy the ride.

Policies vary by boat, but many private captains welcome well‑behaved dogs with prior notice. If you’re using local ferries to island‑hop, leashed dogs are allowed with a small pet fare. For pre‑ and post‑cruise walks, Bug Light Park in South Portland is a popular, dog‑friendly shoreline spot with harbor views.

Your captain monitors the marine forecast closely. Light rain often isn’t an issue thanks to covered cabins and flexible routes, but trips may be delayed or rescheduled for strong winds, heavy fog with low visibility, or thunderstorms. If the operator cancels for safety, you’ll typically be offered a free reschedule or a refund. Portland’s coast can see morning calm and breezier afternoons in summer, so plan timing with your group’s comfort in mind.

Absolutely. The Old Port’s walkable waterfront makes it easy to gather your crew, and boats range from intimate six‑person charters to large private vessels for big celebrations. Many operators let you bring decorations, playlists, and desserts, or they’ll arrange catering and bar service. Popular themed cruises include lighthouse loops, sunset toasts, and island drop‑offs for dinner.

Peak boating season runs from late June through early September, when highs are usually in the 70s and evenings are cool. Memorial Day weekend, July 4, and Labor Day book up fast, and the city’s July 4 fireworks over Casco Bay are a prime on‑water viewing night. A uniquely local date is Maine Open Lighthouse Day, typically the second Saturday in September, which draws extra traffic. May and October can be gorgeous shoulder months with lighter crowds and lower prices—just dress warmer. Weekdays are calmer than weekends, and morning trips are usually smoother than late‑day outings.

For Saturdays in July and August—and any holiday weekend—secure your boat four to six weeks ahead if you want a specific time, vessel style, or onboard food and beverage setup. For weekday sails or small groups, one to two weeks is often fine. If you’re planning a large private boat for 50–250 guests, reserve several months in advance to lock in your preferred date and departure window.

Yes. Private charters and local ferries make it easy to build a relaxed loop to Peaks Island, Great Diamond Island/Diamond Cove, Chebeague, or Long and Cliff islands. Many planners do a late‑morning lighthouse and Fort Gorges cruise, stop ashore for lunch or ice cream, then finish with a sunset pass by Bug Light and Portland Head Light before returning to the Old Port.