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Inspired by passion…

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1,200+ Boats

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1,000+ Villas

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4,000+ Planes

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30 Private Islands

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50 Countries

The largest fleet in the travel industry!

Our team specializes in curating unforgettable luxury vacations on sailing catamarans, power-cats, yachts, villas, and private islands in the Caribbean and Mediterranean.

The Captain

Ten years ago, I took my son sailing in the Caribbean and it changed my life. I’ve gone back every year since, and there’s been one consistent challenge: planning the trip. Making selections from dozens of islands, hundreds of villas and/or boats, arranging transportation, activities, dining, and making sure that the trip meets my original vision. After ten years, twelve islands, ten sailing ventures, and six island villas, the planning has never gotten any easier.

I formed Regatta to solve this problem and make these vacations readily accessible to the growing population of affluent, high net-worth individuals who desire them. Our approach is radically different. It’s activity-based and makes the process enjoyable, simple, and highly effective. Our Waypoint system pulls from thousands of options to configure the perfect trip as you remain free to anticipate and dream about your exciting upcoming adventure. If you have never sailed a large catamaran or sat by an infinity pool overlooking the seas, then you are in for a life-changing experience. I hope to see you in the tropics!


Relax. We got you covered.

How does it work?

Use the Waypoint finder to enter the activities that interest you, in addition to your anticipated trip dates (just a rough guess for now) and number of travelers. Waypoint will return a small set of options, selected based on your interests. Accept those you want. Discard those you don’t. Keep playing! When you have a short list of accepted options, set up an appointment to talk with our concierge who will finalize all the arrangements, answer any questions, and let you relax, knowing your perfect vacation is being planned for you!