Sail the Florida Keys aboard Leona — private sunrise, afternoon, or sunset charters.
Private Sailing Cruise aboard Leona, a classic Key West sailboat.
boat-charters · Key West
A three-hour private sail from Stock Island aboard Leona offers an intimate way to experience the Florida Keys—choose morning, afternoon, or sunset for wildlife, reef views, and easy cruising. Perfect for small groups who want a relaxed, captain-led boat experience.
Island Sailing and Excursions operates in Key West, Florida, offering private sailing experiences on Leona, a classic sailboat. The company provides Private Sailing Cruise charters that allow guests to sail the Florida Keys in privacy aboard Leona.
Trips are suitable for sunrise, afternoon, or sunset escapes and are booked for a group's exclusive use. Guests on the Private Sailing Cruise experience water views, gentle breezes, and a relaxed vibe while aboard Leona. Island Sailing and Excursions focuses on private charters that keep each sailing intimate and tailor departure times to sunrise, afternoon, or sunset when available.
Bookings are made for a single group per cruise to preserve privacy and a personalized atmosphere. The Private Sailing Cruise departs from Key West and sails within the Florida Keys, offering visual access to surrounding waterways and coastal scenery. Island Sailing and Excursions provides information about vessel Leona and the trip options to help guests plan sunrise, afternoon, or sunset outings.
The listing describes the sailboat as classic and emphasizes calm sailing conditions, water views, and a relaxed experience. Island Sailing and Excursions presents clear, trip-specific summaries for potential guests and maintains factual descriptions of the vessel and schedule options. Prospective guests are encouraged to review the Private Sailing Cruise details for availability, departure windows, and group arrangements to select the most appropriate sunrise, afternoon, or sunset sailing for their needs. Booking and specific logistical information are provided through the trip listing to ensure guests can make informed choices before confirming a private cruise.
“Every outing is organized with local river knowledge, basic safety instruction, and equipment checks before departure.”
Departing from Key West, Florida
Classic sailboat used for charters
Flexible departure windows available
One group per cruise for privacy
Open the individual experience guide to confirm current availability, pricing, policies, conditions, and inclusions before booking.
The operator provides clear meeting points, departure times, and destination coordinates for all outings.
Personal flotation devices, emergency protocols, equipment checks, and paddling orientations are provided before departure.
Recommended layering, water shoes, sunscreen, and dry bags are detailed in each experience guide.
Guides share rich knowledge of regional flora, fauna, scenic landmarks, and river navigation.
A glimpse into the experiences, natural landscapes, and adventures waiting on your next trip.
Images supplied on the current Island Sailing and Excursions listing.
Island Sailing and Excursions offers a variety of guided outdoor excursions, scenic routes, rentals, and custom itineraries tailored for families, couples, and adventure enthusiasts.
Yes. Most trips feature comprehensive safety orientations, equipment fittings, and calm routes suited for first-time adventurers. Check the details on individual experience guides for specific age and skill requirements.
Standard safety equipment (such as certified life vests and essential gear) is supplied for each booking. Detailed checklists regarding weather-appropriate attire and personal items are provided prior to departure.
Reserve Leona for a sunrise, afternoon, or sunset escape — check availability on the trip listing.
Click into any experience card above to view current dates, live availability, transparent pricing, cancellation policies, and booking details.