Incredible sailboat rentals in Oregon, United States.

Average of 4 reviews in this area.
4 listings
Cascade 29 daysailor  in Portland, Oregon
hour$199
PortlandCruising Monohull
6 guests

Cascade 29 daysailor in Portland, Oregon

Charter 22' Chrysler Sailboat in Oakridge
day$99
OakridgeCruising Monohull
6 guests

Charter 22' Chrysler Sailboat in Oakridge

Sailing the Columbia in Longview!
hour$250
WashingtonCruising Monohull
6 guests

Sailing the Columbia in Longview!

Centurion Surf Boat
day$495
JosephBowrider
10 guests

Centurion Surf Boat

Rent or charter a sailboat for a memorable experience in Oregon.

Are you ready for a fun adventure out on the open water onboard a sailboat in Oregon? Rent or charter a sailboat with or without a captain and experience the joy of exploring the water by wind power. From hourly, half-day, full-day or multi-day sailing excursions, you are sure to create memories that will last a lifetime. Oregon is a wonderful sailboat rental destination.

Using GetMyBoat to book your next sailing experience.

Experiencing the water has never been easier thanks to GetMyBoat. GetMyBoat allows you to quickly search, compare prices, submit rental inquiries, and pay for your rental or charter from the convenience of your phone or computer. We offer a secure platform for renters to facilitate a seamless rental transaction. For boat owners, we connect millions of renters to their boat and provide the security and safe checks on each rental transaction.

Search for the perfect experience now and book your dream day out on the water.

GetMyBoat customer reviews for Sailing in Oregon.

  1. AL
    Ana
    Cascade 29 daysailor 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.

  2. AM
    Allison
    Cascade 29 daysailor in Portland, Oregon

    Wonderful experience. Great boat and experience and knowledgeable Cpt. Shane. Thank you and looking forward to another glorious day on the river.

  3. AP
    Alecia
    Cascade 29 daysailor in Portland, Oregon

    Captain Shane was great! He was personable and shared many interesting factors along the way. We will definitely be back to do a 3 hour sail!

  4. DT
    Daniel
    Cascade 29 daysailor in Portland, Oregon

    Captain Shane is great to communicate with. Boat is in good shape and very easy to operate. Looking forward to chartering again!