Explore our Private Charter Experiences
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. Every experience is fully private, fully flexible, and departing from the Portland, Maine waterfront.
Watch the sky turn gold over Portland Harbor on a fully private evening charter. Perfect for couples, anniversaries, and anyone who wants to experience a Maine sunset from the water.
Cruise past Portland Head Light, Bug Light, Spring Point Ledge Light, and more on a private guided tour of Casco Bay’s most iconic landmarks.
Explore hidden coves, remote ledges, and the islands of Casco Bay at your own pace with a captain who knows every corner of the bay.
Proposals, anniversaries, birthdays, bachelorette parties, and celebrations of all kinds. Tell us what you are planning and we will help make it unforgettable.
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.
Every charter we offer is 100% private. Your group will never be combined with other guests. The boat is yours from the moment you step aboard to the moment you return to the dock.
All of our captains hold USCG licenses and, combined, have decades of experience on the water. Your safety and comfort are always the top priority, from departure planning to weather monitoring to everything in between.
Tell us what you want to see and we will make it happen. Sunset over the harbor, historic lighthouses, hidden island coves, or a special celebration on the water. Every trip is built around your group and what you want to experience.
We are not a big tour company. We are a small family business and we take every charter personally. When you come aboard you are our guests, and we will do everything we can to make sure your time on the water exceeds every expectation.
Set Your Own Schedule
Every private charter in 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 charter includes:
- Licensed USCG captain and first mate
- Light snacks, soft drinks, and cooler included
- Fully private - your group only, never shared
- Flexible itinerary built around what you want to see
- Portland waterfront pickup and drop off
- Available May through October
A perfect escape on the water — sunset cruises, scenic bay views, and intimate celebrations for up to 6 guests.
The full Casco Bay experience — lighthouses, islands, hidden coves, and open water for up to 6 guests.
How to Book a charter
01
Choose Your Portland, Maine Charter
Select either our 2-hour or 4-hour private charter. Whether you are planning a sunset cruise, a lighthouse tour, island exploring, or a special celebration, every booking is fully private — just your group, the bay, and your captain.
02
Reserve Your Date
Click Book Your Charter below or contact us directly to check availability. We will work with you to find the perfect departure time — morning, afternoon, or sunset.
03
Secure Your Booking
Secure your private charter with a 50% deposit through our secure payment gateway. We accept all major credit cards. The remaining balance is due 7 days before your departure.
04
Get Ready for Departure
After booking you will receive a confirmation email with your departure time, dock location, and everything you need to know before you arrive. We look forward to welcoming you aboard.
Meet Your Captains
Your guides on the bay:
Captain and Co-Founder
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.
Captain and Co-Founder
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.
Guest Captain
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.
Still have questions?
FAQ
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.
No — every charter we offer is completely private. When you book with us, the boat is yours and yours alone.
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.
Feel free to bring your own cooler stocked with your favorites, or use ours — we provide complimentary light snacks, bottled water and soft drinks on every charter. We also recommend a light jacket, sunglasses and a camera. The views are worth capturing!
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.
Your safety is our top priority. Our Maine-built Sabre 36 features a covered cockpit and is designed for Casco Bay’s variable conditions. The licensed captain retains sole authority over all departure and safety decisions. If conditions are unsafe we will reschedule your charter or issue a full refund — your choice.
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.
Absolutely — we love hosting anniversaries, birthdays, proposals and celebrations. Contact us to discuss how we can make your trip extra special. Optional add-ons include premium charcuterie boards, celebration packages and custom itineraries.
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Casco Bay Legacy Charters, LLC
Portland, Maine.
Operating May through October.