5-Day New England USA Yacht Charter: Casco Bay & Southern Maine
Discover the tranquil beauty of Casco Bay and Southern Maine on this relaxed New England yacht charter. This itinerary focuses on quieter anchorages, charming islands, and the serene beauty of the region's coastline, perfect for those seeking a peaceful escape. Feel the gentle sway of the ocean, enjoy fresh seafood straight from the source, and immerse yourself in the unhurried pace of island life. A New England yacht charter here promises a rejuvenating experience amidst classic American charm.
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Plan this charter
- First planned stop
- South Portland, Maine
- Final planned stop
- Kennebunkport, Maine
Shore plans to discuss with your crew
- Day 1Walk the Eastern Promenade Trail
- Day 1Visit Bug Light Park
- Day 1Explore Fort Preble
- Day 1Dine with views of Portland Harbor
- Day 2Rent a golf cart to explore the island
- Day 2Visit the Peaks Island Museum
Confirm joining and departure ports, yacht availability and the daily passage plan before paying a deposit. The captain decides anchorages and any route changes for weather, sea conditions and local restrictions. Shore venues, marine-park permissions and activity bookings require separate confirmation.
Map connections are schematic, not a navigable passage plan. Distances, safe approaches and passage times must be checked by the captain.
Ask for an itemised quotation covering the charter fee, taxes, APA or package expenses, berth charges and any delivery or redelivery costs.
- DAY 01
South Portland, Maine
Begin your journey in South Portland, offering excellent marina facilities and easy access to the vibrant city of Portland across the harbor. Enjoy views of the city skyline and the historic Fort Preble.
- Walk the Eastern Promenade Trail
- Visit Bug Light Park
- Explore Fort Preble
- Dine with views of Portland Harbor
- Anchorage
- Spring Point Marina
- Dining
- Fore Street Restaurant (in Portland, short transfer)
- DAY 02
Peaks Island, Maine
A short cruise brings you to Peaks Island, one of Casco Bay's most accessible and charming islands. Rent a golf cart to explore its quiet roads, rocky shores, and scenic viewpoints, offering a taste of island life.
- Rent a golf cart to explore the island
- Visit the Peaks Island Museum
- Relax at Sandy Beach
- Enjoy views of Whitehead Passage
- Anchorage
- Peaks Island Harbor
- Dining
- Inn on Peaks Island Restaurant
- DAY 03
Chebeague Island, Maine
Sail deeper into Casco Bay to Chebeague Island, known for its historic summer cottages, quiet roads, and the iconic Chebeague Island Inn. It offers a peaceful escape with opportunities for biking and beachcombing.
- Bike along the island's scenic roads
- Visit the Chebeague Island Historical Society
- Relax on Hamilton Beach
- Play a round at the Great Chebeague Golf Club
- Anchorage
- Stone Pier Harbor
- Dining
- The Chebeague Island Inn Restaurant
- DAY 04
Orr's Island & Harpswell, Maine
Explore the connected islands of Orr's and Bailey, part of the scenic Harpswell peninsula. Discover charming fishing villages, the unique Cribstone Bridge, and picturesque coves perfect for kayaking.
- Walk across the Cribstone Bridge
- Visit the Orr's Island Library
- Explore the Harpswell Heritage Land Trust trails
- Enjoy fresh seafood at a dockside eatery
- Anchorage
- Potts Harbor
- Dining
- Cook's Lobster & Ale House
- DAY 05
Kennebunkport, Maine
Your New England yacht charter concludes in the charming and upscale town of Kennebunkport. Famous for its beautiful beaches, art galleries, and historic architecture, it offers a sophisticated end to your coastal journey.
- Stroll through Dock Square
- Visit Walker's Point (Bush Compound)
- Relax on Gooch's Beach
- Explore the Seashore Trolley Museum
- Anchorage
- Kennebunk River (moorings)
- Dining
- The White Barn Inn Restaurant
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