Is prior sailing experience necessary?

No prior experience is needed; the crew will guide you through all sailing activities.

Are food and drinks included?

You can customize your charter with catering options for food and beverages upon request.

How many people can the schooner accommodate?

The 'When And If' comfortably hosts private groups, with exact capacity available upon booking inquiry.

What safety measures are in place?

Experienced crew members provide safety briefings and life jackets are available for all guests.

Can the trip be booked for sunsets?

Yes, private charters can be scheduled including scenic sunset sails upon request.

Where is the boarding location?

Boarding occurs at 7005 Shrimp Rd, Key West, FL 33040, easily accessible from downtown Key West.

Sail the Atlantic on a Historic 1939 Schooner in Key West | Boat Tour | Marina

Set sail from Key West, Florida, on the 'When And If,' a beautifully restored 1939 wooden schooner with a rich history—it once belonged to General George S. Patton. This private day sail offers a unique two-hour journey along the sparkling Atlantic coast where guests can be active participants or simply unwind while soaking in the warmth of the sun and the endless ocean views. Key West, the southernmost city in the continental U.S., is renowned for its vibrant marine life, historic architecture, and lively waterfront culture, making it an ideal launching point for this sailing experience.

What sets the 'When And If' apart is its blend of history and hands-on sailing adventure. Guests have the opportunity to raise the sails, steer the helm, and learn the ropes under the guidance of experienced crew, creating an immersive nautical experience. Whether you’re a seasoned sailor or a first-time cruiser, the vessel’s classic charm and expert operators ensure a smooth, memorable voyage.

The Atlantic waters here are celebrated for their clarity, occasional sightings of dolphins and seabirds, and warm breezes that carry the scent of salt and tropical flowers. The schooner offers an intimate setting, perfect for private charters with flexible catering options that can tailor your trip for celebrations, romantic outings, or peaceful retreats.

This sailing excursion is more than a boat ride; it’s a step into maritime heritage combined with the breathtaking natural beauty surrounding the Florida Keys. Explore the stellar coastline from a perspective few get to experience and capture photo-worthy moments against a backdrop of swaying rigging and sunlit waves. The 'When And If' stands as a standout adventure offering a compelling slice of local culture, history, and ocean exploration in one of America's most beloved island towns.

For travelers visiting Key West, this trip is an exceptional way to discover coastal Florida through a lens of tradition, excitement, and tranquility. With easy access from the heart of town and a crew that prioritizes personalized service and safety, it’s an unforgettable addition to any island itinerary.