Lucy B Charters invites you aboard a beautifully restored 1986 Phoenix 29 Sportfishing vessel, lovingly upgraded in 2022 and based in scenic South Portland.
"The boat was beautiful and fit our party of 5 perfectly. Capt Chris was a great host and gave us a delightful tour of the bay and lighthouses, with a great mix of stops, where he shared interesting history, and cruising along the water." — Alex,
Bird’s Eye Maine is a 2021 Sea Hunt 234 Ultra Center Console based in Portland, offering an unforgettable way to explore Casco Bay in comfort and style.
"We had a perfect day on the water. Captain Matt was very responsive when setting the trip up and helping us navigate getting on board." — Shannon,
Experience Casco Bay Your Way! Whether you’re chasing a golden sunset, cruising past iconic lighthouses, or celebrating something special on the water, we have a charter built around exactly what you’re looking for.
"We were searching for a fun, romantic experience to celebrate our anniversary." — Mike,
Step aboard the beautifully restored Portland Harbor Cruise, a classic 1980 Bruno Stillman 35’ Downeast Sportfish, fully refurbished in 2022 for modern comfort and timeless charm.
Miss Madison Charter Service LLC offers unforgettable boating experiences aboard a beautifully maintained 1977 Pacemaker 36/SF Sportfishing vessel, based out of scenic Saco.
"had a great experience on this large boat. Captain brought out a loveseat for my wife and I to sit on and saw beautiful sites and a gorgeous waterfall." — Scott,
Experience the beauty of Casco Bay aboard Boomerang Yacht Charters, a classic Maine-built Young Brothers 38' lobster boat designed for comfort, stability, and unforgettable coastal adventures.
Coleman’s Guide Service is a 1992 Grady White Weekender Sportfishing boat based in Freeport, Maine, offering comfortable and versatile cruising for up to four guests.
Valenti Charters invites you to explore the beautiful waters around Wells aboard a comfortable 2016 Parker 2120SC Pilothouse.
"Unfortunately, the weather didn't cooperate for an Ocean tour, but Captain Tristan suggested a tour up the Piscataqua instead." — Kenneth,
Discover the beauty of Casco Bay aboard Seawalker Excursions’ sleek and versatile 2019 Seapro 219 CC Center Console! Based in Freeport, Maine, this 22-foot vessel is perfect for small groups of up to 4 adult guests, 6 with children, offering an inti
Discover why South Portland is a favorite New England launch point for coastal exploration. South Portland boating charters give you easy access to sheltered waterways, open ocean vistas, and island-dotted horizons, making it an ideal base for half-day cruises, full-day adventures, and relaxed sunset outings. With convenient marinas, calm inshore routes, and quick access to deeper waters, captained and bareboat trips here suit both first-time cruisers and seasoned skippers.
Out on the water, you can trace rugged shorelines, pass classic New England beacons, and watch working boats ply their daily routes. Seabirds ride the breeze, seals occasionally surface, and on clear days the panoramic coastline stretches for miles. The varied conditions—protected channels, tidal rivers, and open swells—create a natural playground for powerboats, sailboats, and modern RIBs.
Spring through fall brings crisp mornings, long golden afternoons, and photogenic evenings, while the height of summer often delivers gentle seas ideal for family-friendly outings. Many charters highlight local history and maritime traditions, weaving stories of the coast into each itinerary. Anglers can target inshore species along structure-rich edges, and leisure cruisers can drop anchor in quiet coves for a picnic or swim.
Whether you're planning a private sightseeing cruise, a hands-on sailing lesson, or a custom itinerary with a local skipper, South Portland offers reliable access, knowledgeable crews, and diverse vessels. Choose South Portland boating charters to experience classic New England scenery, flexible routes tailored to the day's conditions, and a welcoming harbor that makes getting on the water refreshingly simple.
