Explore Our Private Boat Tours in
Portland, Maine
Whether you’re chasing a golden sunset, cruising past iconic lighthouses, or celebrating something special on the water, we have casco bay charters built around exactly what you’re looking for. Every experience is fully private, fully flexible, and departing from the Portland, Maine waterfront.
Why Choose Legacy Charters
What started as a love for Maine’s coastline and time spent on the water has grown into something we are truly proud to share. As a family-owned business welcoming guests aboard during our very first charter season on Casco Bay, every trip we take out on the water matters deeply to us. From glowing sunsets and historic island visits to close-up views of iconic lighthouses, our private 2 and 4 hour charters offer a memorable way to explore the coast.
When you book with Legacy Charters you get the entire boat to yourselves. No strangers, no set schedule, and no rushing past the moments that matter. Just your group, a licensed captain who genuinely cares about your experience, and the beautiful waters of Portland, Maine all to yourselves.
Set Your Own Schedule
Our boat tours portland maine is built around your group and your timeline. We suggest our 2-hour and 4-hour windows as a starting point, as they give you enough time to truly experience the best of Casco Bay without feeling rushed. That said, we are happy to work with you on something that fits your day perfectly. Reach out and let us know what you have in mind.
Every Legacy Charter Includes:
How to Book Private Boat Tours in Portland Maine
Meet Your Captains
Your guides on the bay:
Tim holds his USCG OUPV “6-Pack” license and brings 35 years of hands-on experience across New England’s most demanding coastal and inland waters. From Long Island Sound to the Maine coast, he has spent a lifetime on the water and knows these bays, harbors, and tides the way most people know their own backyard. Tim oversees guest experience, partnerships, and daily charter operations.
Jack holds his USCG OUPV “6-Pack” license alongside a BS in Mechanical Engineering, a combination that means every charter is operated with the highest standards of both seamanship and vessel safety. He grew up on Sebago Lake, spent his formative years working at marinas on both the lake and the ocean, and has been reading these waters his entire life. Jack manages mechanical oversight, maintenance, and daily operations aboard the Sabre 36.
A veteran marine journalist with 40 years of experience, Eric served as Editor-in-Chief at Powerboat magazine for 10 years and Senior Technical Editor at Boating magazine for a decade, testing thousands of boats and winning numerous awards along the way. A former offshore powerboat racer, Eric unofficially holds the title of the world’s fastest marine journalist — having piloted the 36-foot Skater catamaran Flight Club at 172 mph.
FAQ
No — every charter we offer is completely private. When you book with us, the boat is yours and yours alone.
We offer 2-hour ($600) and 4-hour ($1,100) fully private charters on Casco Bay aboard our Maine-built 1998 Sabre 36 Express. Your group has the entire boat to yourselves — perfect for sunset cruises, island and lighthouse tours, romantic outings or private celebrations.
Have something else in mind? We’re always open to hearing your ideas. Whether you’re dreaming of a longer day on the water, a custom route, a sunrise departure or something unique — reach out and let’s talk. Contact us at info@cascobaylegacycharters.com or call (207) 228-5600.
We can accommodate up to 6 guests per charter in accordance with U.S. Coast Guard regulations. This makes our private charters perfect for couples, small families, or a close group of friends looking for an intimate experience on the water.
None at all! Just show up and enjoy. Your captain takes care of everything while you relax and soak in the scenery.
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Absolutely. Let us know if you have specific islands, lighthouses, or areas of the bay you’d love to see and we’ll do our best to work them into your trip.
A 50% deposit is required at booking. The remaining balance is due 7 days prior to departure. Cancellations made at least 48 hours in advance receive a full refund. Cancellations within 48 hours are reviewed on a case by case basis. Weather-related cancellations are fully refunded or rescheduled at the captain’s discretion. If a charter is ended early due to weather or safety conditions, a pro-rated refund will be issued for unused time.
We offer convenient pickup at multiple public locations along the Portland waterfront including the State Pier public dock, the dinghy dock near Fore Points/Ocean Gateway, Bell Buoy Park Landing and Mavadones Landing. Your confirmation email will include your specific departure point. Feel free to contact us beforehand if you have a preferred pickup location.
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