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Wedding Charters in Portland, Maine

Learn More & Reserve Your Date

Embark on the journey of a lifetime with Portland Discovery. Elevate your wedding festivities with our signature trolley transport and exclusive boat cruises, designed to make your special moments unforgettable. From picturesque rides between venues to unique rehearsal dinners and welcome drinks as you sail around Portland, Maine’s beautiful Casco Bay, we offer a seamless blend of romance and ease to make your special day memorable.

Trolley Services for Your Special Day:

Leave the diving and the details to us!

Connect your wedding venues with timeless elegance. Our trolleys offer a charming and convenient way for you and your guests to navigate between venues and even back to their lodging once the night is over!

Boat Cruises & Charters:

Rehearsal Dinners & Welcome Drinks!

Start things off by sailing style in Casoy Bay Our boats provide a serene backdrop for rehearsal dinners and welcome drinks. With the sea breeze and sunset views, your pre-wedding events will be as memorable and magical as the day itself.

Charter Inquiry

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