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Page 16 of 39 • 930 listings
898
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Chesapeake Bay
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LA
LisaMarie
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.
NA
Nicole
Charter this Ultra-Luxury Beneteau 37 Sailboat downtown San Francisco
Everyone I worked with while planning a sailing excursion for my team was amazing. I called lots of times to get answers to questions regarding the itinerary and the team was very helpful and responsive. The team went above and beyond in all aspects and the trip was fantastic. I would highly recommend this company!

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.
FG
Frank
42' Wanderlust - The Best Sailing Cat in the Market - Sarasota
Thank you for such an amazing and memorable time. Our family had a blast. It was exactly what we were looking for! Boat was gorgeous and the staff was attentive, friendly and knowledgeable ! Anyone looking to charter, you guys will be our go to recommendation for sure!
DK
Dmitri
Charter 36ft Sloop In Westbrook, Connecticut
We had a fantastic 2-hour sail out of Westbrook! The boat was in great shape, and Captain Joy was a Joy to sail with: she was professional, friendly, and very experienced. She made us feel safe and relaxed the entire time, and even shared some interesting local facts and recommendations along the way. The views were beautiful and the whole trip was smooth and enjoyable. Highly recommend booking with this captain – we’ll definitely be back!
DC
Donte
New Yacht Charter Bali 5.4 Sailing Catamaran in Annapolis Maryland
From start to finish, the entire experience was seamless and professional. There was zero chaos—everything ran like clockwork. The crew was exceptional: friendly, attentive, and incredibly knowledgeable about the Chesapeake Bay and Annapolis. The yacht itself was spotless and in pristine condition. From the moment we arrived, the crew went above and beyond—helping us load in, beautifully setting up our catering, keeping our group refreshed with drinks and snacks, and later packing up leftovers and loading them into our car. Every detail was handled with care. If you’re considering a yacht rental, don’t hesitate—this experience was truly top-notch. We’re already looking forward to booking again!