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This is an entirely custom experience. Please send us a few detail details about what you’re looking for and we will send you a quote. Step aboard a sailing experience where luxury isn’t defined—it’s curated entirely around you. This is not a preset itinerary or a standard charter; it’s a fully bespoke escape designed to match your every desire, down to the smallest detail. From the moment you inquire, our team begins crafting a journey tailored to your vision. Private chef? Hand-selected wines? Sunset dinners on secluded sandbars? Spa treatments on deck? Last-minute requests? Consider it handled. Whether you’re seeking serene relaxation, elevated celebration, or a bit of both, we make the impossible feel effortless. Our vessels are impeccably appointed, blending refined comfort with understated elegance, while our crew delivers a level of service that is intuitive, discreet, and anticipatory. You won’t need to ask twice often, you won’t need to ask at all. This is luxury without limits. No compromises, no constraints—just a seamless, indulgent experience shaped entirely around you. Wherever you want to go, however you want to feel… we make it happen.

NH
I’m so glad I decided to book this vessel! Booking was simple. The communication was accurate, timely, always professional, and with forethought, before the trip. My group was in town for a bachelorette weekend and enjoyed our day sailing with Captain Dan. We departed and returned right on time, which we appreciated as we had a schedule we were trying to adhere to. We also appreciated the blankets as it got windy at some points and we didn’t want to go inside. Overall 10/10 experience. I’d definitely book again!
AU
Just book it! Had the best time. The vessel was great and Captain Dave and First Mate Joe were even better. Exactly as advertised and couldn’t have been more fun
LS
Excellent service, fantastic boat, beautiful sunset.

Captain David: I have always enjoyed being on the water, and when an opportunity came up to start doing boat charters with my daughter it was an easy decision. In 2020 at the start of the pandemic I sold my company and purchased our first sailboat. After buying the boat I figured we better learn how to sail, so Emma and I went to Captains school and received our captains license. Please join me and Captain Emma aboard Second Wind, and experience the fun of sailing.
You’ll get helpful information for your departure after your booking is confirmed.
Street Address For Arrival
Departure Location
95% refund of offer amount up to 30 days prior.
Full refund if captain deems weather conditions unsafe to sail through. No refund for trips canceled within 30 days of departure.