The name Summerwind comes from the wonderful song, "Summer Wind", which has been sung by dozens of top artists, but made legendary by Frank Sinatra.

Following are the lyrics:

"The summer wind came blowin' in from across the sea. It lingered there so warm and fair to walk with me. All summer long, we sang a song and then we strolled on golden sand, two sweethearts and the summer wind. Like painted kites those days and nights, they went flyin' by. The world was new beneath a bright blue umbrella sky. Then softer than a piper man one day, it called to you, and I lost you, I lost you to the summer wind.

The autumn wind and the winter winds they have come, and they have gone. And still the days, those lonely days they go on and on. And guess who sighs his lullabies through nights that never end?

My fickle friend, the summer wind. The summer wind, the summer wind. The summer winds."

(Summer Wind is available on Apple Music).

Summerwind Adventures are experienced by:

• Romantic Couples Weekends
• Families and Group Adventures
• Bachelor and Bachelorette Outings
• Engagements and Weddings
• Memorials
• Executive Team Meetings and Team Building Adventures
• Guest Speakers Adventures
• Women’s and Men’s Groups or Annual Trips
• Customized Adventures (please contact us to discuss)

On board, we have many activities for you and your guests to enjoy such as a circular swimming platform that is deployed in the water and is attached to the yacht. This makes ocean swimming more enjoyable. Aboard you will have the use of a tandem kayak, boogie boards, windsurfer, a stand-up paddle board, surf boards and electric bicycles available throughout St. Augustine for exploring on land at any extended adventures. We offer unique adventures that aren't available elsewhere. Our adventures offer majestic sunset views and up-close encounters with sea life, which is sure to please even the most discriminating guests.

Yes, absolutely! Whether you're celebrating a special anniversary, hosting a family reunion, or planning a unique executive team-building event, Summerwind Sailing Adventures caters to all occasions with tailored experiences. You have the freedom to personalize your journey and choose to stay for a few hours or an entire week.

Summerwind offers year-round sailing adventures in two locations.  

1. Thomas (U.S. Virgin Islands) is available from November through April.

St. Augustine (Florida) is available from May through October

Our charter includes access to a range of amenities designed to enhance your sailing experience, including a circular swimming platform for ocean swimming. We also have other options such as tandem kayaks, stand-up paddleboards, boogie boards, electric bicycles and snorkel gear, perfect for adding extra fun to your sailing tour.

Advanced 48-hour bookings are available for our charters, ensuring flexibility and convenience for our guests. We recommend booking as far in advance as possible, especially during peak seasons.

There are no strict restrictions on who can charter the Summerwind yacht. Whether you're a couple, a family, a group of friends, or hosting a corporate event, we welcome guests of all ages and group sizes to experience the luxury and adventure of sailing with us.

While our experienced captains can recommend routes and destinations based on your preferences, you have the flexibility to choose your sailing route within the designated areas of St. Thomas and St. Augustine. Whether you prefer to explore secluded coves, snorkel among vibrant coral reefs, or simply enjoy breathtaking sunset views, we'll work with you to create an unforgettable sailing experience tailored to your desires.