Casco Bay Legacy Charters
Casco Bay Legacy Charters
Experience Casco Bay Your Way!
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 conveniently from the Portland, Maine waterfront.
As a family-owned business welcoming guests aboard to share the iconic highlights of 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 famous lighthouses, our fully 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.
Casco Bay Legacy Charters features a Maine-crafted 1998 Sabre 36' Express Downeast motor yacht. We can take up to six guests. Our vessel is powered by twin 300 HP, turbodiesel inboard Caterpillar engines, offering a maximum cruising speed of 28 knots. The vessel comes equipped with an audio system, fishfinder, grill, ice box, and refrigerator, full galley and head. We also provide all necessary safety equipment.
Every private charter is built around your group and your timeline. We suggest our 2-hour or 4-hour tours, 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
Experience Casco Bay Your Way!
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 conveniently from the Portland, Maine waterfront.
As a family-owned business welcoming guests aboard to share the iconic highlights of 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 famous lighthouses, our fully 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.
Casco Bay Legacy Charters features a Maine-crafted 1998 Sabre 36' Express Downeast motor yacht. We can take up to six guests. Our vessel is powered by twin 300 HP, turbodiesel inboard Caterpillar engines, offering a maximum cruising speed of 28 knots. The vessel comes equipped with an audio system, fishfinder, grill, ice box, and refrigerator, full galley and head. We also provide all necessary safety equipment.
Every private charter is built around your group and your timeline. We suggest our 2-hour or 4-hour tours, 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
Trip availability and prices
| Su | Mo | Tu | We | Th | Fr | Sa | |
|---|---|---|---|---|---|---|---|
Customer reviews
Rating
All reviews (1)
We were searching for a fun, romantic experience to celebrate our anniversary. Casco Bay Legacy Cruise made it fantastic. Tim, the owner reached out and kept me fully apprised of all the details. He served as First Mate, tour guide and host. Ben, our Captain steered a great tour. Both of them were so friendly, knowledgeable of the area, and accommodating. Tim prepared us a beautiful and delicious charcuterie tray. My wife Laurie and I thank them both for making our trip to Maine so special. We would love to cruise with them again.
It was a pleasure meeting you both & we are honored you chose to join us for part of your anniversary celebration. Thank you so much fir being such great guests & if you decide to come back to Maine, we’d love to bring you out again! Safe travels!
FAQs about Casco Bay Legacy Charters
What are the trip rates for Casco Bay Legacy Charters?
- US $600 per group - 2 Hour – Inner Harbor Highlights (2 hours)
- US $600 per group - 2 Hour – Inner Harbor Highlights - 1:00 PM (2 hours)
- US $600 per group - 2 Hour – Inner Harbor Highlights - 10:00 AM (2 hours)
- US $600 per group - 2 Hour – Inner Harbor Highlights - 11:00 AM (2 hours)
- US $600 per group - 2 Hour – Inner Harbor Highlights - 12:00 PM (2 hours)
- US $600 per group - 2 Hour – Inner Harbor Highlights - 2:00 PM (2 hours)
- US $600 per group - 2 Hour – Inner Harbor Highlights - 3:00 PM (2 hours)
- US $600 per group - 2 Hour – Inner Harbor Highlights - 4:00 PM (2 hours)
- US $600 per group - 2 Hour – Inner Harbor Highlights - 5:00 PM (2 hours)
- US $600 per group - 2 Hour – Inner Harbor Highlights - 6:00 PM (2 hours)
- US $600 per group - 2 Hour – Inner Harbor Highlights - 8:00 AM (2 hours)
- US $1,100 per group - 4 Hour – Private Charter (4 hours)
- US $1,100 per group - 4 Hour – Private Charter - 1:00 PM (4 hours)
- US $1,100 per group - 4 Hour – Private Charter - 10:00 AM (4 hours)
- US $1,100 per group - 4 Hour – Private Charter - 11:00 AM (4 hours)
- US $1,100 per group - 4 Hour – Private Charter - 12:00 PM (4 hours)
- US $1,100 per group - 4 Hour – Private Charter - 2:00 PM (4 hours)
- US $1,100 per group - 4 Hour – Private Charter - 3:00 PM (4 hours)
- US $1,100 per group - 4 Hour – Private Charter - 4:00 PM (4 hours)
- US $1,100 per group - 4 Hour – Private Charter - 9:00 AM (4 hours)
Which amenities are available onboard with Casco Bay Legacy Charters?
- GPS
- VHF Radio
- Radar
- Chart Plotter
- Depth Finder
- Sonar
- Autopilot
- Anchor
- Dinghy
- Wheel Steering
- Life Jackets
- Bimini
- Kitchen
- Shower
- Aft Sundeck
- Bathing Platform
- Audio System
- Inside Speakers
- Outside Speakers
- Refrigerator
- Ice Box
- Grill
- Galley Stove and Oven
- Fishfinder
What add-ons can be available with Casco Bay Legacy Charters?
- Snacks
- Drinks
- Lunch
Which kinds of activities does Casco Bay Legacy Charters offer?
- Boat & Yacht Tours
- Sunset Dinner Cruises
- Island Hopping
- Booze Cruises
- Eco-Tours
- Birthday Celebrations
- Bachelorette & Bachelor Parties
- Proposal & Engagement Trips
- Corporate & Group Events
Your operator
Casco Bay Legacy Charters offers unforgettable cruising experiences aboard a beautifully crafted 1998 Sabre 36' Express Downeast motor yacht, showcasing the charm and beauty of South Portland's coastal waters. Specializing in boat tours, sunset cruises, eco adventures, and relaxing booze cruises, they provide guests with a unique way to explore Maine's stunning coastline in comfort and style.
Casco Bay Legacy Charters offers unforgettable cruising experiences aboard a beautifully crafted 1998 Sabre 36' Express Downeast motor yacht, showcasing the charm and beauty of South Portland's coastal waters. Specializing in boat tours, sunset cruises, eco adventures, and relaxing booze cruises, they provide guests with a unique way to explore Maine's stunning coastline in comfort and style.
What the boat is like
Which kind of activities are offered
Which amenities are available onboard
What's included in the trip price
What’s allowed on the boat
What additional terms you should be aware of
Security deposit is not required
A refundable deposit is not required by the charter operator.
Fuel is included
Fuel is included in the price of the rental.
How cancellations work
Free cancellation up to 3 days prior to trip
You can cancel or modify your booking up to 3 days before the trip date, free of charge. If you cancel or modify your booking later, or fail to show up, you'll forfeit 100% of what you've paid.
How you can pay
Pay online in full
Pay online in full through BoatBooker and save on credit card fees at the dock.
No additional fees.
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