The Best Sailboat Rentals Near Portland

Add a SPARK to Your Special Event with a 65 ft Sailboat Cruise on the Bay

Great experience - everything exactly as described. we had 28 people on the boat, had a great trip with communication from the admin staff and boat crew on the day 😊

Safe & solid sailing catamaran - Green power! Stunning beauty & great location!

Captain Jan Passion is very welcoming, accommodating, and super communicative. His vessel is clean and just as advertised. I can’t wait to book a next trip with him.

Catalina 30 sailboat in Portland, Oregon

Captain Shane warmly welcomed us into his boat. He was really accommodating throughout the course of sailing. I love the conversations and trivia he tells us about the views. The boat was superb and amazing! I love it with or without the mainsail. Overall, our experience was really great! We will definitely want to do this again with him as our Captain.

Sailing on the Columbia River aboard 27' Cape Dory Sailing Vessel

I highly recommend sailing with Sean! He is not only a professional captain with years of experience but he has a great personality to make your sailing trip enjoyable. He made sure everyone onboard was safe and having a great time throughout our trip. I will definitely book his boat in the future.

50' Pirate Ship Adventure Aboard Queen Anne's Revenge in Seattle

Pirate bachelorette/bachelor party is not only doable but amazing with Peter. Everyone had a wonderful time and the crew were all so accommodating of all requests! Great communication and easy loading and unloading. Will pillage with them again anytime!

36' Catalina Sailing Yacht in Lake Union, Seattle

Andrew is a very polite professional captain! We sailed in the middle of the snowmagedon in Seattle area and Andrew was ok with that! The views of snowy Lake Union, skyline of Seattle downtown were pretty on a frosty day! Thank you for the trip! My family enjoyed it!