Fall Cruises with Island Style Charters | Pirates & Pumpkins, Sights & Ciders, City Nights & Tiki Lights

From our sponsors:
Fall Cruises with Island Style Charters
Purchase Tickets + Full Schedules: islandstylecharters.com

City Nights & Tiki Lights
Our NEW late-night cruise is made for grown-ups who want to soak in Portland’s sparkling skyline after dark. Sip tropical cocktails, glide under glowing bridges, and vibe to smooth tunes on this one-hour 21+ river adventure. The tiki lights turn up, the city shines, and the night is yours.
Dates: October 3rd, 4th, 10th, 11th, 17th, 18th, 24th, 25th, 31st, November 1st
Price: $34.95

Sights & Ciders
Portland’s only tiki boat meets the colors of fall! This seasonal cruise blends city views, autumn leaves, and a tropical twist. Glide beneath Portland’s bridges, past the waterfront, and through iconic landmarks while sipping seasonal cider (available for purchase). Relax, unwind, and soak in Portland from a whole new perspective.
Dates: October 12th, 25th, 26th, 31st, November 1st, 2nd
Price: $29.95 – $59.95

Sunset Cruise
Take in the breathtaking beauty of Portland’s fall evenings on this 2-hour river cruise. Watch as the skyline and surrounding trees transform into a canvas of warm autumn colors, reflected across the water. As the sun dips below the horizon, you’ll have a front-row seat to the vibrant skies and the city lights beginning to glow. Peaceful, scenic, and unforgettable, this cruise is the perfect way to enjoy the natural beauty of the season.
Dates: October 4th, 8th, 10th, 11th, 16th, 17th, 18th, 24th, 25th, 30th, 31st, November 1st
Price: $34.95 – $59.95

Pirates & Pumpkins
Celebrate fall with pirates, pumpkins, and Halloween fun on a family-friendly river cruise! This one-hour adventure is designed for families and kids of all ages, with costumes, games, contests, and pirate shenanigans. Adults can sip on fall beverages while little ones enjoy the fun and festivities. With music, dancing, and skyline views, it’s the perfect way to celebrate October together.
Dates: October 19th, 26th, and 29th
Price: $29.95 per guest