Blue Ocean Club
5 days · 5 stops

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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  1. 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)
  2. 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
  3. 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
  4. 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
  5. 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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