A two-hour day sail on the pristine waters of Key West is always a delight, but from the deck of the When and If it will become a cherished memory. Elegant, stately, and the fastest schooner in the Keys, sailing on this celebrated charter is a treat. Make your reservations early– they book up quickly.

Coolers on board are stocked with ice, bottled water, and seltzer. Alcoholic drinks are aloud on board, but it is BYOB.

We welcome you to bring food and drinks of your choice. We’ve got plenty of room in our coolers for mixers and “adult drinks.” We suggest you bring a hat, towels, and sunscreen. Check ahead of time with us to see what the sailing conditions look like–If you are prone to motion sickness, you may want to take something in advance or try wearing anti-motion sickness wrist bands.

When and If sails from the well-appointed marina at Stock Island, where free parking and amenities abound.

A two-hour sunset sail on the gorgeous schooner When and If offers an unforgettable memory– a sunset view from the fastest, most historic schooner in Key West. Experience real sailing away from the noise of party boats, at times in the company of dolphins. Whether you kick back or grab a line and help raise sail, you’ll forever be a part of this schooner’s history. Make your reservations early– they book up quickly.

Coolers on board are stocked with ice, bottled water, and seltzer. Alcoholic drinks are aloud on board, but it is BYOB.

You will be sharing the boat with up to 28 lovely guests, so bring a friendly attitude! As the sun sets and we sail away from the shore, it can get a little chilly. We provide blankets, but you may want to bring a jacket. Check ahead of time with us to see what the sailing conditions look like–If you are prone to motion sickness, you may want to take something in advance or try wearing anti-motion sickness wrist bands.

When and If sails from the well-appointed marina at Stock Island, where free parking and amenities abound.