The Best Sailboat Rentals Near Portland

Captained Sail on San Francisco Bay on 51' Morgan Out Island Ketch

We had the best day sailing with Captain Ed and Joan - part of Captain Pam’s crew! They kept us safe and worry free. We celebrated on Glory Days with a surprise engagement party, could not have been better experience! Captain Ed helped us maintain the surprise in the dock.

42 Sailing Monohull Tours in Sausalito

Our afternoon with Rick was simply spectacular. We were able to experience all of San Francisco's microclimates, and special spots... fog and fog horns from the Golden Gate, heeling over in the bay with great wind, stunning views of the city, other fun sailboat regattas, calm and warmth of the back side of Angel Island...all while having lovely lite apps, fun conversation and James Taylor tunes. :) Rick is a great captain; we all certainly felt safe and confident in his knowledge, skills and ability. And he keeps beautiful Gentle Storm in tip top shape. We will be back for more adventures, Rick!

MAXUM 46' YACHT FOR RENT IN VANCOUVER

We had an incredible experience on the yacht! The conductor was professional, skilled, and made sure everything went smoothly, even with the weather. The trip was safe, fun, and unforgettable. Highly recommend this service for a great time on the water!

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.

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.

Luxury Italian Sailing Yacht on the Puget Sound — Seattle

Highly recommend this bespoke experience on the Serafina with Matt. The boat is beautiful and easily accommodated 5 adults and one child for a very leisurely sail around Shilshole and Elliot Bay. When we decide to charter again we will definitely look to Matt and the Serafina.