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All listings in Oregon

Incredible sailboat rentals in Oregon, United States.

5.0(Average of 14 reviews in this area)
5 listings
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
$99-199hour
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

5.0
$100hour
Catalina 30 sailboat  in Portland, Oregon
Sailing in Portland · 12 guests

Catalina 30 sailboat in Portland, Oregon

5.0
$199hour
Sailing the Columbia in Longview!
Sailing in Washington · 6 guests

Sailing the Columbia in Longview!

New
$250hour
Catalina 30 Sailboat on the Columbia River in Portland
Sailing in Portland · 7 guests

Catalina 30 Sailboat on the Columbia River in Portland

New
$125hour

Top Destinations Nearby

Sailing Reviews in Oregon

  1. 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.

  2. GO
    Gunther
    Catalina 30 sailboat in Portland, Oregon

    Capt Shane made sure we had a great time and shared lots of great stories about Oregon and Portland.

  3. 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.

  4. 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.

  5. AN
    Alex
    Sailing on the Columbia River aboard 27' Cape Dory Sailing Vessel

    What a wonderful experience!!! Sean was so kind, warm and knowledgeable, and his boat is beautiful, adorable, and was just the perfect vessel for our sailing excursion. I highly recommend. Thank you, Sean!

  6. RP
    Rena
    Sailing on the Columbia River aboard 27' Cape Dory Sailing Vessel

    Captain Sean was awesome! The trip was fun and relaxing. Got to be involved as much as we wanted. Can’t wait to go again. Sean was very flexible with the weather and our schedules!!