Our promise to you !

At Jack sailing we want to exceed your expectations of an enjoyable sailing experience. One that goes beyond just satisfaction and cater to your personal  interest. We know that you can not put a price on memories, nor time.

We would consider it an honor and pleasure to serve you and be in your memories for many years.

Captain Jack

Weekly Yacht Charters

Complete Service

Can be hired as your personal captain for barefoot charters or boat deliveries, including crew.  

Gratuities are appreciative, but not expected

Sail the beautiful Caribbean sea and enjoy the privacy of your own sail boat. Have a opportunity to take the helm or sit back and catch some rays. I am always here to be your captain.


Jack Sailing Charters

‚Äčand Boat deliveries

51 Main St. Dunedin Florida 34698 


50 % deposit is required to secure your reservations.

Just purchase a new boat and not comfortable in handling her, give us a call for hands on help

Jacks Sailing Charters

Pick your island and we will

arrange to meet you there

: Bahamas, Turks and Caicos,

Virgin Islands, BVI, St. Kit, Nevis

, Anguilla, St. Martin, Antigua,

Montserrat, Guadeloupe, Dominica

Martinique, St. Lucia, Barbados,

St. Vincent, Grenada, Grenadines

Martinique, St. Luc etc. 

For reservations call 727 678 0435

0r email Jack@jacksailing.com 

Come sail with us on the beautiful west coast of Florida. Choose from a half day, full day or a spectacular sunset sail.

We also specialize in weekly charters including captain and crew in the eastern and southern Caribbean.

6 Passengers Maximum

Call or email for quotes