Real.Fun.Sailing: Key West Schooner Sail

Sail away aboard the stunning classic schooner When And If, built for General George Patton in 1939. Daysail, Sunset Cruise, Private Charter.

Sunset Sails

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, and keep a lookout for dolphins and other marine wildlife.

Whether you kick back, or grab a line and help raise sail, you’ll forever be a part of this schooner’s history.
Available From Thanksgiving to Memorial Day
Two-hour Sunset Sail
Share the boat with up to 28 guests
Complimentary boutique wine and select beers on board.

Schooner Day Sails

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 historic schooner is a treat.
Available From Thanksgiving to Memorial Day
Two-hour Day Sail
Share the boat with up to 28 guests
Complimentary boutique wine and select beers on board.

Weekend Day Sails

Description:

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 historic schooner is a treat.

Included:

Coolers on board are stocked with ice, bottled water, and seltzer. Complimentary boutique wine and select beers on board.

What to bring:

Please bring appropriate weatherwear and sun protection for the day. The sun is more intense out on the water and the temperature is often about 10 degrees cooler. We request that you wear flat shoes or remove high heels before embarking.

Departure Details:

When and If sails from the gorgeous new Perry Marina at Stock Island, where free parking and amenities abound including bars, restaurants and pool access.

Sunset Sails

Description:

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, Look out for dolphins and other marine wildlife. Whether you kick back, or grab a line and help raise sail, you’ll forever be a part of this schooner’s history.

Included:

Coolers on board are stocked with ice, bottled water, and seltzer. Complimentary boutique wine and select beers on board.

What to bring:

Please bring appropriate weatherwear and sun protection for the day. The sun is more intense out on the water and the temperature is often about 10 degrees cooler and can be chilly after sunset. We request that you wear flat shoes or remove high heels before embarking.

Departure Details:

When and If sails from the gorgeous new Perry Marina at Stock Island, where free parking and amenities abound including bars, restaurants and pool access.
Ready to Sail?

Experience the sunset like never before

Key West Day Sails

Sun-soaked Florida Keys Sailing.

Book Day

Sunset Sails

The best sunset in Key West

Book Sunset
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