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Sunset Sails in Key West

Sailing every day out of Stock Island Marina Village, with a complimentary shuttle service from your accommodation right back to your door...or dinner reservation! Free ice, bottled water and La Croix on board and a delightful gourmet cheese platter - all our sails are BYOB. Book now to enjoy the most elegant, sailorly sunset sail in Key West!

Daysailing on When and If

Fridays, Saturdays and Sundays are your chance to soak up the sun on a gorgeous 2 hour afternoon sail on When And If. Book here to blow away the weekend cobwebs and come sailing with us!

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Private Charter

When and If is a great family boat, or perfect for a weekend with friends! With prices from just $1,800 for a two-hour daysail or $2,000/night for a three-night charter, we're bound to have a package that's perfect for you!