A scenic view of a coastal bay at sunset, showing boats anchored in the water, surrounding green hills, and a partly cloudy sky.

Sway

Sailing Charters

Private crewed sailing charters designed for small groups and individuals seeking unforgettable experiences at sea

Details

Beach scene with a few tall palm trees leaning towards the ocean, clear turquoise water, white sandy shore, partly cloudy sky, calm water, distant land on horizon.

Destinations

View from a sailboat showing a coastal city with historic buildings, a fortress on a hill, blue water, and partly cloudy sky.

Experiences

A sailboat with white sails on the ocean, with a person on board, under a partly cloudy sky.

Catamarans

Overhead view of a white yacht sailing through dark green water, creating a wake behind it.

Open Bookings

Our Crew

Captain Dan is a USCG Captain and certified ASA Sailing Instructor who has spent a lifetime on the water. With over 30 years of global sailing experience, he brings a depth of seamanship that is hard to match. Friendly, knowledgeable, and genuinely at home on the sea, Dan is exactly the kind of captain you want at the helm — calm, capable, and completely focused on making your experience one to remember

First Mate J.Ro will be your host for the week and manages most of the communications for Sway. She is well versed in sailing, prudent seamanship, safety, and is currently accruing sea time for her captain's certificate.

J.Ro has an extensive background in travel, customer service and runs another successful small business based in Minneapolis,

Captain Steve is a USCG Captain, a certified ASA Sailing Instructor, and airline pilot. Steve is passionate about providing an experience where every guest feels safe, at ease, and genuinely having the time of their life. His exceptional seamanship and natural ability to make people feel welcome on the water make him as much a host as he is a captain.

What People Are Saying

  • Captain Dan was the perfect host - genuinely fun to be around. Can't recommend him enough

    Michael T., sailed the British Virgin Islands

  • An absolutely unforgettable week. We're already looking at dates for next year

    Sarah & James K., sailed the Greek Islands

  • Best vacation we've ever taken. Full stop

    The Donnelly Family, sailed the Dalmatian Coast