The Best Sailboat Rentals Near Friday Harbor

35' Sailing Yacht Charter in Sausalito

We had an absolutely beautiful time with Captain Kirk’s San Francisco Sailing!! My parents came to visit and I took them out on the bay for the afternoon. Our captain, Rowan, was a master boatman—friendly, helpful, encouraging, and hilarious. He truly took the time to ensure that we enjoyed ourselves. Captain Kirk runs a great operation; we had everything we could’ve needed on the boat and they made it very easy to find the boat and ensured we were well-prepared with all the info. It was also extremely well-priced. Overall, very happy with our experience and we will remember it forever!! Couldn’t recommend it enough. Thank you to Rowan and Captain Kirk!

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

Terje - TK - is a great captain with such varied and useful experience on the water - fisherman, captain, and tour guide for the San Juans. We had a great 5 days on the water!

Stunning Dufour 38 Sailboat for Charter. Learn to Sail. Fireworks. Team Building

We had a great trip with Paul! He was super communicative and easy to plan with

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

We really enjoyed our sailing on 9/12 with Jan’s crew. The boat was beautiful and everyone on board was extremely friendly and attentive!

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.