Your private charter sets sail from Portland’s Old Port, the historic heart of Maine’s largest city. This vibrant waterfront district blends 19th-century brick warehouses, cobblestone streets, and working fishing piers with boutique shops, acclaimed restaurants, and lively pubs. Just steps from our dock, it’s where modern Portland meets its salty roots. For large private groups—corporate gatherings, weddings, reunions, or celebrations of any kind—the Old Port offers the perfect blend of charm and convenience. It’s not just a meeting location; it’s a built-in prelude to your Casco Bay experience. As you board one of our classic wooden vessels, the buzz of the city fades and the beauty of the bay unfolds—starting your private cruise with both energy and elegance.

Officially named Portland Breakwater Light, Bug Light is a charming, cast-iron lighthouse that marks the entrance to Portland Harbor. Though small in stature, its elegant Greek Revival design and striking white tower make it one of the most photographed beacons in Maine. As the first of four iconic lighthouses typically seen on our cruises, Bug Light offers a postcard-perfect moment right at the start of your journey. For large private groups—whether you’re here for a celebration, corporate outing, or just a memorable day on the water—this scenic highlight sets the tone for the rest of your experience aboard our beautifully restored wooden vessels. With the Portland skyline behind you and open bay ahead, it’s a breathtaking introduction to Casco Bay’s maritime charm.

Jutting proudly from a granite breakwater in South Portland, Spring Point Ledge Lighthouse is one of the few sparkplug-style lighthouses in the U.S. that visitors can see up close by boat. Built in 1897 to warn mariners of the dangerous ledge that claimed countless ships entering the harbor, this working lighthouse still stands guard over Casco Bay. In its early days, the light stood isolated in open water, and vessels that passed on the wrong side often ran aground—until the breakwater was added decades later. Beside the lighthouse sits Fort Preble, a historic coastal defense fortification dating back to 1808. Originally built to protect Portland during the War of 1812, Fort Preble later served in the Civil War and both World Wars. For private groups aboard our classic vessels, this stop offers a dramatic juxtaposition of elegant maritime engineering and raw military history—perfect for photos, storytelling, and a deeper appreciation of Portland’s role in coastal defense.

No trip through Casco Bay is complete without a view of Portland Head Light, the most photographed lighthouse in the country and a true symbol of Maine’s rugged beauty. Perched on a rocky cliff in Fort Williams Park, this historic beacon has guided mariners since 1791 and remains an active aid to navigation today. From the water, you’ll enjoy the absolute best vantage point—especially for photos. When weather and sea conditions allow, we slow down and spend extra time in front of the lighthouse, giving your group the chance to take in its grandeur and hear stories of shipwrecks, wartime watchmen, and its connection to early American history. While we don’t go ashore or tour the lighthouse itself, the experience of seeing it from the deck of a classic wooden vessel is unforgettable. For large private groups, this is a moment to pause and take it all in—an iconic highlight of your time on Casco Bay and a perfect opportunity for a group photo against a timeless Maine backdrop.

Standing sentinel on the opposite side of the harbor channel from Portland Head Light, Ram Island Ledge Light offers a striking contrast. Perched atop a rocky outcrop and surrounded by swirling tides, it often appears to float—completely detached from land. Unlike the stately charm of Portland Head Light, Ram Island is raw and weathered: no keeper’s house, no easy access, just a skeletal pier and a rusty ladder leading 30 feet up the tower’s face. It’s a powerful visual reminder of the unforgiving nature of Maine’s coastline and the bravery of the keepers who once served here. For large groups aboard our private cruises, this lighthouse always sparks conversation—its haunting beauty and remote presence add depth and drama to the Casco Bay experience.

Rising from a small rocky island between Peaks and Little Diamond, Fort Gorges is Casco Bay’s most striking stone fortress. Built in the 1850s to defend Portland Harbor, its walls were designed to unleash more than a dozen cannons on approaching enemies from any direction. During World War II, however, the fort found new purpose as a U.S. Army storage site, supporting an expanded coastal defense network that included underwater mines, magnetic sensing cables, and more. With Portland serving as a major shipbuilding hub and the start of a crucial oil pipeline to Montreal, the city—and Fort Gorges—remained a point of strategic importance well into the 20th century. For large private groups, this stop is a favorite for history buffs and photographers alike. From ghost stories to granite engineering, Fort Gorges adds a dramatic and mysterious layer to your Casco Bay cruise.

Often called the “Coney Island of Maine” in its heyday, Peaks Island is the largest and most populated island in Casco Bay. Just a short ferry ride from downtown Portland, it blends quiet residential charm with a rich history of summer resorts, amusement parks, and even a World War II military outpost. From the water, you’ll see the island’s blend of cottages, wooded trails, and beaches, along with hints of its more colorful past. During World War II, Peaks served as a critical coastal defense site, complete with large gun batteries and lookout towers aimed at protecting Portland Harbor. Today, it’s home to a lively year-round community, local artists, and the world’s only Umbrella Cover Museum. For large groups, Peaks Island adds a sense of liveliness and layered history to your cruise—an island that feels both timeless and alive, offering a glimpse into Casco Bay living from past to present.

Tucked into the western edge of House Island, Fort Scammel was built in 1808 as Portland Harbor’s first—and only—fortification ever to fire in defense of the city. Updated and expanded through the Civil War, Spanish-American War, and both World Wars, it served as a critical link in Portland’s evolving coastal defense network. Its thick granite walls, hidden gun placements, and commanding harbor views were designed to stop enemy ships from reaching Portland’s busy waterfront. Though no longer active, Fort Scammel remains privately owned and rarely visited, making it one of Casco Bay’s most intriguing and exclusive sights from the water. For private groups aboard our classic vessels, Fort Scammel is a favorite hidden gem—combining military history, natural beauty, and a touch of mystery as we cruise past this storied island stronghold.