Summer 2026
GET AWAY
on CASCO BAY
Welcome Aboard!
Join us for an unforgettable journey across the sparkling waters of Casco Bay. Whether you’re chasing a golden sunset or spending an afternoon exploring historic islands and iconic lighthouses, our 2 and 4 hour charters offer the perfect escape. Whether you’re planning a romantic outing, a family adventure, or a private celebration, every trip promises breathtaking scenery and memories that will last a lifetime.
Sunset Charter Experience
Step aboard and let the beauty of Casco Bay unfold around you. As the sun dips toward the horizon, our experienced captains will guide you past Portland Head Light, out among the islands, and through some of the most stunning coastal scenery in New England. Sit back, relax, and take it all in — this is Maine at its finest.
01
Choose Your Charter
Select either our 2-hour or 4-hour private charter. Whether you’re planning a sunset cruise, an islands and lighthouses tour, or a special celebration on the water, every booking is fully private — just your group, the bay, your captain, and your personal tour guide.
02
Reserve Your Spot
Click “Book Your Charter” below, or contact us directly to check availability and reserve your date. We’ll work with you to find the perfect departure time — morning, afternoon, or sunset.
03
Make Payment
Secure your private charter with a simple online payment through our secure payment gateway. We accept all major credit cards. For questions about pricing or deposits, don’t hesitate to reach out.
04
Receive Confirmation
After booking you’ll receive a confirmation email with your departure time, dock location, and everything you need to know to prepare for your trip. We look forward to welcoming you aboard!
MEET YOUR CAPTAINS
YOUR GUIDES
ON THE BAY
Casco Bay Legacy Charters is owned and operated by Tim and Jack Gresh — a father and son team combining decades of maritime experience with a shared passion for the Maine coast and a commitment to delivering an exceptional on-the-water experience.
Timothy F. Gresh is a lifelong mariner with 35+ years of hands-on boating experience in both saltwater and freshwater, including Maine coastal and Long Island Sound waters. Tim holds his USCG OUPV “6-Pack” license and oversees guest experience, partnerships and daily charter operations.
Jack Gresh holds his USCG OUPV “6-Pack” license along with a BS in Mechanical Engineering — a background that ensures every charter is operated with the highest standards of vessel safety and reliability. Jack manages mechanical oversight, maintenance and daily operations aboard the Sabre 36.
Hidden Gems of
CASCO BAY
Private Charter Experience
Still have questions?
FAQ
We offer 2-hour ($600) and 4-hour ($1,200) 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@lightseagreen-dotterel-244489.hostingersite.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.
Casco Bay Legacy Charters, LLC
Portland, Maine.
Operating May through October.