Private Sailing Charters in Portland, Maine
Your Boat. Your Day.Maine Harbor Tours offers private sailing charters on Casco Bay for guests who want the boat to themselves and the freedom to shape the experience.
Whether you’re celebrating something special or simply looking for time on the water without a set agenda, our private charters are designed to feel relaxed, personal, and unhurried.
No crowds. No scripts.
The Best Way to Experience Casco Bay
Private charters begin in Portland Harbor and explore Casco Bay at a pace that fits your group.
Some guests want a quiet sail with room to talk and look around. Others are interested in island views, local history, wildlife, or the working waterfront. We let the conditions—and your interests—guide the day.
Our captains are there to handle the boat, answer questions, and share local insight when it adds to the experience.
What to Expect on a Private Charter
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Approximately 2 hours on the water
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Flexible departure times, when available
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Experienced, USCG-certified local captain
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Comfortable sailing aboard a well-maintained vessel
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BYOB welcome
Charters are kept intentionally small to maintain space, comfort, and a relaxed atmosphere.
Sailing Aboard Enchanted, Sea Chase, or Good to be Bad
Private charters are offered aboard our sailing vessels, Enchanted and Sea Chase, depending on availability and conditions.
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Enchanted offers a more refined, comfortable setting with a warm interior and spacious cockpit.
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Sea Chase provides a classic sailing experience with traditional lines and plenty of character.
- Good to be Bad offers unmatched flexibility. As a powerboat, tides and winds don’t dictate our trips.
All boats are well-suited for private sailing charters on Casco Bay and maintained with care.
Built Around Your Group
A private charter gives you flexibility you don’t get on a shared tour. Private sailing charters are well-suited for:
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Special occasions and celebrations
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Proposals and anniversaries
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Family outings and small groups
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Visitors looking for a quieter experience
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Locals spending a day on the water
No sailing experience is required.
Fun, Local Experience
We don’t rush the day or try to fit everything in at once.
A private charter with Maine Harbor Tours is about spending time on the water, seeing Portland and Casco Bay from a different perspective, and enjoying the experience as it unfolds.
It’s simple, personal, and it’s one of the best ways to experience the harbor.
Book a Private Sailing Charter
If you’re looking for a private sailing charter in Portland, Maine, we’d be happy to help you plan the right trip.
If you have questions about timing, vessel availability, or what to expect, just reach out—we’re always glad to talk it through.