• Old Port - Begin your private charter from Portland’s Old Port, the historic core of Maine’s largest city. This lively waterfront area combines 19th-century brick warehouses, cobblestone streets, and active fishing piers with boutique shops, renowned restaurants, and vibrant pubs. Just a short walk from our dock, it’s where contemporary Portland meets its maritime heritage.

For large private groups—corporate events, weddings, reunions, or any celebration—the Old Port offers an ideal mix of charm and convenience. It’s more than just a meeting spot; it’s a prelude to your Casco Bay adventure. As you board one of our classic wooden vessels, the city’s hustle fades, and the bay’s beauty unfolds—starting your private cruise with both excitement and elegance.

• Bug Light Park - Officially known as Portland Breakwater Light, Bug Light is a delightful, cast-iron lighthouse marking the entrance to Portland Harbor. Though modest in size, its elegant Greek Revival design and striking white tower make it one of Maine’s most photographed beacons. As the first of four iconic lighthouses typically seen on our cruises, Bug Light offers a postcard-perfect moment at the start of your journey.

For large private groups—whether for a celebration, corporate outing, or 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 the open bay ahead, it’s a breathtaking introduction to Casco Bay’s maritime charm.

• Spring Point Ledge Lighthouse - Extending 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. Initially, 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.

• Portland Head Light - 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.

• Ram Island Ledge Light - 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.

• Fort Gorges - 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.

• Peaks Island - 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.

• Fort Scammel - 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.

• Bottled water
• MARIE L is equipped with an environmentally friendly composting toilet
• All Fees and Taxes
• Cooler and ice
• Licensed Captain & Local Guide
• Beer and wine available for purchase on board
• This is a private charter for groups of up to 15 guests (including children)

• No food or drinks included, but beer/wine available for purchase on board.
• Parking in the Old Port is not included

100% Private Charter for Groups up to 15 — Flat Rate Pricing

This unique 2-hour boat tour is crafted for private groups desiring a genuine, intimate experience on Casco Bay. Unlike busy public cruises, your group of up to 15 guests will relish the full comfort and charm of one of our classic wooden vessels—all to yourselves.

Sail past iconic lighthouses, historic granite forts, and breathtaking stretches of Maine’s coastline, with chances to see harbor seals, seabirds, and other local wildlife along the way. Whether celebrating a special occasion or simply gathering with friends, this charter provides a personalized, relaxed way to enjoy the best of coastal Maine.

Feel free to bring your own food—we supply all the glassware, plates, and utensils you’ll need. Local craft beer, wine, and other beverages are also available for purchase onboard, making it easy to sip, savor, and soak in the scenery.

For a full refund, cancel at least 24 hours before the scheduled departure time.