The Best Sailboat Rentals Near Portland

Sailing Lesson on a 19' Pearson Resolute Sloop in Olga, Washington

We had the pleasure of sailing with Nat over the 4th of July weekend, and it was a fantastic experience from start to finish. He was punctual, courteous, and instantly put us at ease with his friendly demeanor. What stood out most was how attentive he was to our individual experience levels on the water — he adjusted his approach throughout the day so that everyone, regardless of sailing background, felt comfortable and included. Nat is clearly a highly accomplished sailor, but he wears that expertise lightly. The day felt relaxed as we navigated the waters of the San Juan Islands. — great conversation, great skill, and a great time on the water.

Sailing Trips out of La Conner, Washington

TK was communicative, flexible with our needs, incredibly knowledgeable, and took us out for an amazing time! We did this with my 3yo daughter and he was attentive, safe, and responsible every step of the way. I highly recommend him.

Puget Sound Sailing Adventure on 32' Hunter Sailboat

We had a great time on our sailing adventure! The boat was very nice and outfitted to protect us from the wind. We saw some wildlife and it was just a picturesque experience. The Captain was knowledgeable and engaging. Overall, we enjoyed our time on the water.

35ft Classy Allmand Sailboat for Extended Charters in Vancouver and Gulf Islands

We had a great trip with James, he was very knowledgeable about the area and suggested several trip options depending on what we were looking to do and how long we wanted to be out. He was great to talk to while sailing and was completely flexible while on the trip. Our son loved getting to sail the boat. If we come back, would definitely look to setup another (maybe longer) trip. Thanks!

42 Sailing Monohull Tours in Sausalito

We had the perfect day with Rick! We loved his boat and were very confident in his seamanship. He’s also a fun guy to hang out with with!

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

Amazing experience with Jan & Allen, they are amazing hosts and had great gift ready for us and our pet 🐶 she loved the trip as well. One of the best trips, will be returning back for sure 😊