private special occasion charters in portland, maine
Set sail from Portland, Maine, and explore the stunning islands, historic lighthouses, and scenic waters of Casco Bay.
Celebrate on the Water in Portland, Maine
Some moments deserve more than a restaurant reservation. Whether you’re planning a marriage proposal, celebrating an anniversary, or gathering your closest friends for a birthday on the water, a private boat charter in Portland, Maine is an experience nobody in your group will ever forget. Just you, the people you love, and the open waters of Casco Bay with a dedicated captain making sure every detail is perfect.
Perfect Occasions for a Private Charter
No two celebrations are the same and no two charters are either. Whether you are down on one knee, raising a glass to another year together, or simply gathering the people who matter most, a private boat charter in Portland, Maine turns any occasion into a memory that lasts a lifetime. Here are just a few of the moments we love being a part of.
How We Make Your Occasion Special
Every special occasion charter starts with a conversation. Tell us what you are celebrating, who is joining you, and what you have in mind. We will help you choose the right charter length, plan your route, and make sure everything is in place before you step aboard. From surprise proposals to milestone birthdays, we will work with you to coordinate every detail and bring whatever vision you have to life on the water.
Optional Add-Ons for Your Celebration
Want to take your charter to the next level? We offer a range of optional add-ons to make your special occasion even more memorable.
Choose Your Charter Length
Not sure which is right for you? Contact us and we’ll help you choose based on what you want to see and do.
Why Choose Legacy Charters for Your Special Occasion
We understand that some moments only happen once. When you trust us with a proposal, an anniversary, or any celebration that truly matters, we take that seriously. From the first conversation to the moment you step back ashore, our entire focus is on making sure your experience on the water exceeds every expectation. We are a family business and we genuinely care about every group that comes aboard, not just as customers, but as guests we are honored to share these waters with.
FAQ
No — every charter we offer is completely private. When you book with us, the boat is yours and yours alone.
We offer 2-hour ($600) and 4-hour ($1,100) fully private charters on Casco Bay aboard our Maine-built 1998 Sabre 36 Express. Your group has the entire boat to yourselves — perfect for sunset cruises, island and lighthouse tours, romantic outings or private celebrations.
Have something else in mind? We’re always open to hearing your ideas. Whether you’re dreaming of a longer day on the water, a custom route, a sunrise departure or something unique — reach out and let’s talk. Contact us at info@cascobaylegacycharters.com or call (207) 228-5600.
We can accommodate up to 6 guests per charter in accordance with U.S. Coast Guard regulations. This makes our private charters perfect for couples, small families, or a close group of friends looking for an intimate experience on the water.
None at all! Just show up and enjoy. Your captain takes care of everything while you relax and soak in the scenery.
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Absolutely. Let us know if you have specific islands, lighthouses, or areas of the bay you’d love to see and we’ll do our best to work them into your trip.
A 50% deposit is required at booking. The remaining balance is due 7 days prior to departure. Cancellations made at least 48 hours in advance receive a full refund. Cancellations within 48 hours are reviewed on a case by case basis. Weather-related cancellations are fully refunded or rescheduled at the captain’s discretion. If a charter is ended early due to weather or safety conditions, a pro-rated refund will be issued for unused time.
We offer convenient pickup at multiple public locations along the Portland waterfront including the State Pier public dock, the dinghy dock near Fore Points/Ocean Gateway, Bell Buoy Park Landing and Mavadones Landing. Your confirmation email will include your specific departure point. Feel free to contact us beforehand if you have a preferred pickup location.
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