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All listings in Oregon

Incredible sailboat rentals in Oregon, United States.

Page 1 of 15 listings

Catalina 30 sailboat  in Portland, Oregon
Sailing in Portland · 12 guests

Catalina 30 sailboat in Portland, Oregon

5.0
Best of 2025
$199/hour
Open 29' daysailor for up to 12 friends in Portland, Oregon
Sailing in Portland · 12 guests

Open 29' daysailor for up to 12 friends in Portland, Oregon

5.0
Best of 2025
$129+/hour
Celebrate Boldly. Sail Beyond Ordinary on our 86 foot Schooner
Events in Portland · 49 guests

Celebrate Boldly. Sail Beyond Ordinary on our 86 foot Schooner

New
Best of 2025
$999/hour
Sail in style on the Willamette River
Sailing in Portland · 4 guests

Sail in style on the Willamette River

New
$120/hour
Instant Book
Sailing on the Columbia River aboard 27' Cape Dory Sailing Vessel
Sailing in Portland · 4 guests

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

4.9
Snoozed - Active 03 Sep 2025

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Sailing Reviews in Oregon

  1. AL

    Alison

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

    Sean and his boat are top notch. Our family, including one senior and one toddler all enjoyed ourselves on our trip. Sean was friendly, patient and kind, and easy to chat with but not too pushy with the chat either. Loved it!

  2. AD

    Andrea

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

    Sean did such an amazing job being our captain. Our group of four had the best time getting to know Sean and learn things about sailing while having the most gorgeous view of the Columbia. It’s such a wonderful experience and highly recommend!

  3. JT

    Jordan

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

    Capt Sean took great care of us for my wife’s BDAY. Wonderful conversations, expert sailor, felt safe the whole time, amazing experience.

  4. Ana

    Ana

    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.

  5. MP

    Mindy

    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.

  6. EJ

    Edward

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

    We really enjoyed captain Sean. He clearly has tons of experience on the boat and is very hospitable. He was great with our 1 and 3 year old kid and made the boat ride a relaxing one. Would 10 out of 10 recommend.