Top Portland Water Tours - page 2

100% Private Charter for Groups up to 15 — Flat Rate Pricing This exclusive 2-hour boat tour is designed for private groups seeking an authentic, intimate experience on Casco Bay. Unlike crowded public cruises, your group of up to 15 guests will enjoy the full comfort and charm of one of our classic wooden vessels—all to yourselves. Cruise past iconic lighthouses, historic granite forts, and stunning stretches of Maine’s coastline, with opportunities to spot harbor seals, seabirds, and other local wildlife along the way. Whether you’re celebrating a special occasion or simply gathering with friends, this charter offers a personalized, relaxed way to experience the best of coastal Maine. Feel free to bring your own food—we provide all the glassware, plates, and utensils you’ll need. Local craft beer, wine, and other beverages are also available for purchase onboard. Due to our liquor license, we do NOT permit outside alcoholic beverages on board.

Experience the stunning beauty of Casco Bay on a personalized intimate (up to 6 guests per trip), public 2-hour powerboat cruise. Whether you're looking for a scenic sightseeing tour, an up-close encounter with Maine’s wildlife or a journey through the region’s rich maritime history, this exclusive charter is designed to provide an unforgettable adventure. Departing from the working waterfront, you’ll glide past busy wharves lined with lobster boats, ferries, and historic brick buildings that reflect Portland’s seafaring heritage. From the start, the mix of city energy and natural beauty sets the tone for an unforgettable journey on Casco Bay. Seals often bask on rocky ledges, ospreys and bald eagles soar overhead, and in the summer months, porpoises sometimes surface alongside the boat. Whether it’s spotting seabirds, breathing in the salty ocean air, or simply enjoying the thrill of the ride, a powerboat cruise from Portland offers both adventure and relaxation in equal measure.

This two-hour sunset private sail is the perfect way to experience Maine's sunset on the coast - complete with lighthouses, seals, and seabirds. Sail aboard Heart's Desire, a 101 year old schooner, designed by famed yacht designer, John Alden. Heart's Desire measures 53' feet and features some of John Alden's trademark design elements including a long bowsprit and dramatic, raked transom. Built in 1925 by T.S. Soule in South Freeport, Maine, Heart's Desire has been used mainly for chartering along the Eastern seaboard in New York, New Jersey, Massachusetts, and Maine.

Visitors to Portland can easily miss some of Maine's most stunning sights, since you really need a car to explore the scenic coastline. Avoid the headache of arranging your own transportation, or renting a car, on this guided tour of Portland's must-see sights. Stop in downtown Portland, and visit three lighthouses, including Portland Head Light—an historic lighthouse perched on the rocky coast.

Discover the lighthouses and coastal landmarks of Portland on a small-group biking tour. Hop on a provided bicycle and follow your guide to the Bug Light, Spring Point Ledge, and Portland Head lighthouses. Along the way, learn about their storied histories. Other highlights include the Liberty Ship Memorial, Cape Elizabeth, and Willard Beach. Set at a leisurely pace, the adventure also includes a complimentary lobster roll lunch at an award-winning food truck.

Learn about Portland's history with this walking tour, which will take you through the Old Port, downtown, and waterfront areas. You'll see all sorts of historic attractions, including the home of Hendry Wadsworth-Longfellow, the Eastern Cemetery, and the Abyssinian Church, all with a professional guide on hand to share stories about the city's past.

Spend three hours kayaking through Casco Bay with this small-group tour led by a professional guide. You'll launch from Mere Point in Brunswick and paddle over to a couple of different islands, with the opportunity to see all sorts of marine birds, and maybe even a seal or two, along the way.

Private Casco Bay Cruise – Up to 5 Guests Experience the beauty of Maine’s coast on a private 2-hour tour through the scenic Casco Bay islands. This intimate charter is perfect for small groups looking to explore hidden coves, spot local wildlife, and soak in the iconic charm of the Maine coastline. Departures daily at 10 AM, 4 PM, and our most popular sunset cruise at 6:30 PM.

Explore the stunning scenery and rich maritime history of Casco Bay on a private 2hr, 4hr or 6hr powerboat cruise. Ideal for families, friends, or small groups, this exclusive charter offers a personal adventure, allowing you to encounter marine wildlife, view iconic lighthouses, and discover unique islands at your own pace. With flexible scheduling and customizable experiences, this cruise promises an unforgettable day on the water, complete with opportunities for swimming and exploring Maine’s rugged coastline. - Private cruise for up to 6 passengers, ensuring an exclusive experience - Encounter marine wildlife like seals, porpoises, and seabirds - View famous lighthouses including Portland Head Light and Bug Light - Flexible departure times and customizable itineraries available – Alternative pickup available in Portland for added cost, saves 30 min of driving, contact us for availability

Spend two hours kayaking on Sebago Lake with this guided tour led by a professional guide, suitable for experienced kayakers and complete beginners. As you paddle along the gentle waters, your guide will tell you all about the local area. Expect to see all sorts of birds, fish, and turtles as you paddle against the backdrop of the setting sun.

Explore the Portland Peninsula by bike with this small-group guided tour. Start at the Eastern Promenade, making your way along the waterfront bike path until you reach the Back Cove Trail. Your guide takes you to the Old Port to see some of the City of Portland's prettiest old brick buildings, and you learn the significance of local food, history, and culture of this area.

Witness the stunning transformation of Portland Harbor and Casco Bay during a private sunset powerboat cruise. Aboard the classic Avelinda, enjoy a two-hour journey as the sun sets, painting the sky with vibrant hues. Marvel at iconic lighthouses like Portland Head Light and glide past charming islands, keeping an eye out for local wildlife such as seals and seabirds. This intimate experience is perfect for all ages, whether celebrating a special occasion or simply relishing the natural beauty of Maine's coastline. - Exclusive private cruise for up to 6 guests - Comfortable Maine-built powerboat with marine restroom - Experienced captains share local history and ecology - Flexible scheduling with multiple evening departures available - Alternative pickup available in Portland for added cost, saves 30 min of driving, contact us for availability

Take in the famous autumn foliage of New England during a private 2.5-hour sightseeing cruise from Portland. With room for six people, it's an ideal intimate experience for couples, friends, or families. It’s also a great opportunity to photograph the leaves and wildlife from a unique perspective. Learn about the area from your private guide as you cruise at a gentle pace.

Kayak through the natural Maine wilderness and vast lake views for an on the water adventure. This two hour guided tour will begin with a safety briefing and lesson covering the fundamentals of recreational kayaking. Using the EZ launching system at Sebago Trails Paddling, the tour will explore the water-carved bends and twists of a meandering stream unveiling local wildlife in a rustic backdrop. Then continue onto Jordan Bay of Sebago Lake as the guides share stories dating back to the settlements of the region.

This two-hour afternoon private cruise is the perfect way to experience Maine's coast, your special event, or a family get-together that will never be forgotten. Ride aboard Heart's Desire: designed by famed yacht designer - John Alden, measures 53' feet and features some of his trademark design elements including a long bowsprit and dramatic, raked transom. Built in 1925 by T.S. Soule in South Freeport, Maine, Heart's Desire has been used mainly for chartering along the Eastern seaboard in New York, New Jersey, and most recently Massachusetts.