Key West or Stock Island — Which Departure is Best for You?

Both departures offer the same elevated sail, full service, and unforgettable sunset — the only difference is where you begin your adventure.

If you're staying in Key West, the downtown departure is the most convenient and places you right in the heart of the island’s iconic marina scene.

Staying at The Perry Hotel, Ocean’s Edge, or elsewhere on Stock Island? Or simply looking to explore a quieter, more local side of the Keys? The Stock Island departure is a wonderful choice, offering a serene waterfront atmosphere and a beautiful alternative perspective of the islands.

No matter which you choose, you’ll enjoy the same style of sailboat, the same attentive crew, and the same breathtaking Key West sunset — just two equally lovely ways to begin the journey.