Casco Bay Legacy Charters 

 14 Ocean Street, South Portland, ME 04106, United States

Casco Bay Legacy Charters 

South Portland, ME, United States
36 feet
6

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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 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 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

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Trip availability and prices

Trip Date:
Days:
Group Size:
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July 2026
SuMoTuWeThFrSa
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Number of days
1
Group Size
2 adults • 0 children
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2 Hour Inner Harbor Highlight
FREE Cancellation 3 days notice
2 hour trip multiple starting times (8:00 AM, 9:00 AM, 10:00 AM, 11:00 AM, 12:00 PM, 1:00 PM, 2:00 PM, 3:00 PM, 4:00 PM, 5:00 PM, 6:00 PM)
+3
US $600
Private tour: up to 6 people
4-Hour Private Charter
FREE Cancellation 3 days notice
4 hour trip multiple starting times (8:00 AM, 9:00 AM, 10:00 AM, 11:00 AM, 12:00 PM, 1:00 PM, 2:00 PM, 3:00 PM, 4:00 PM)
+3
US $1,100
Private tour: up to 6 people
There are 3 people looking at this charter.

Customer reviews

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FAQs about Casco Bay Legacy Charters

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What the boat is like

Boat category
Cabin cruisers
Boat type
Downeast
Boat manufacturer
Sabre
Boat Model
36 Express
Year built
1998
Boat length
36 ft
Capacity
6 persons
Engine model
Caterpillar
Max crusing speed
20 knots
Powered by
2 x 300HP
Engine Type
Inboard
Fuel Type
Diesel
Number of cabins
2 cabins
Number of berths
1 berth
Number of heads
1 head
Number of toilets
1 toilet
Boat category
Cabin cruisers
Boat type
Downeast
Boat manufacturer
Sabre
Boat Model
36 Express
Year built
1998
Boat length
36 ft
Capacity
6 persons
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