THE ADVENTURE COLLECTIVE® · Independent discovery and booking for outdoor travel
Step aboard the historic When And If at Perry Marina for a two-hour Key West sunset sail — champagne toast included and opportunities to take the wheel. Perfect for history buffs, families, and anyone who wants a small-group, hands-on evening on the water.
Step aboard the historic When And If at Perry Marina for a two-hour Key West sunset sail — champagne toast included and opportunities to take the wheel. Perfect for history buffs, families, and anyone who wants a small-group, hands-on evening on the water.
The varnished wooden masts catch the last light as the schooner slips away from Slip H16 at Perry Marina. Saltwind tugs at jackets and the horizon deepens from gold to bruise; dolphins arc through turquoise water as the crew prepares chilled flutes for a sunset champagne toast.
Verified experiences and guided adventures in the surrounding area.
Operated by Sunset Sail Key West · Key West, Florida
The varnished wooden masts catch the last light as the schooner slips away from Slip H16 at Perry Marina. Saltwind tugs at jackets and the horizon deepens from gold to bruise; dolphins arc through turquoise water as the crew prepares chilled flutes for a sunset champagne toast.
This is a brief history you can feel beneath your feet: the When And If was commissioned in 1939 by General George Patton and rebuilt and maintained to retain its classic schooner lines. The vessel threads the shallow limestone shelf and coral heads that form the Florida Keys — geology that creates the clear basins and mangrove flats you’ll pass through. Culture here is maritime and practical: Stock Island’s working docks and Key West’s seafaring traditions frame a cruise that blends heritage with hands-on sailing.
Expect two hours of easy, small-group sailing with room for 28 guests, onboard restrooms, bottled water, and select beer and wine; a champagne toast is included. Under crew supervision guests can take the wheel or help handle lines, making it part lesson, part celebration.
Practical notes: arrive 15–30 minutes early for check-in at Perry Marina (look for Bad Boys Taqueria), wear non-slip shoes, and bring a light layer for the evening breeze. Seas here can be glassy or chop-prone depending on wind — bring motion-sickness remedies if you’re sensitive. Wildlife encounters are common but brief; please observe, don’t feed. For a compact, maritime evening that mixes history, instruction, and island sunset, this schooner sail delivers a polished, accessible Key West experience.
Check in at Slip H16 at Perry Marina in front of Bad Boys Taqueria; there is ample free parking at the marina.
Yes—under crew supervision guests are invited to steer and assist with lines for a hands-on experience.
Children are welcome at a discounted fare; infants must sit on an adult’s lap and all minors must be accompanied by an adult.
Cancel at least 24 hours prior for a full refund; the operator may cancel for bad weather and will provide a refund in those cases.
Sunset Sail Key West operates guided outdoor trips and adventures with an emphasis on safety, stewardship, and memorable experiences.
The varnished wooden masts catch the last light as the schooner slips away from Slip H16 at Perry Marina. Saltwind tugs at jackets and the horizon deepens from gold to bruise; dolphins arc through turquoise water as the crew prepares chilled flutes for a sunset champagne toast.
The varnished wooden masts catch the last light as the schooner slips away from Slip H16 at Perry Marina. Saltwind tugs at jackets and the horizon deepens from gold to bruise; dolphins arc through turquoise water as the crew prepares chilled flutes for a sunset champagne toast.
This is a brief history you can feel beneath your feet: the When And If was commissioned in 1939 by General George Patton and rebuilt and maintained to retain its classic schooner lines. The vessel threads the shallow limestone shelf and coral heads that form the Florida Keys — geology that creates the clear basins and mangrove flats you’ll pass through. Culture here is maritime and practical: Stock Island’s working docks and Key West’s seafaring traditions frame a cruise that blends heritage with hands-on sailing.
Expect two hours of easy, small-group sailing with room for 28 guests, onboard restrooms, bottled water, and select beer and wine; a champagne toast is included. Under crew supervision guests can take the wheel or help handle lines, making it part lesson, part celebration.
Practical notes: arrive 15–30 minutes early for check-in at Perry Marina (look for Bad Boys Taqueria), wear non-slip shoes, and bring a light layer for the evening breeze. Seas here can be glassy or chop-prone depending on wind — bring motion-sickness remedies if you’re sensitive. Wildlife encounters are common but brief; please observe, don’t feed. For a compact, maritime evening that mixes history, instruction, and island sunset, this schooner sail delivers a polished, accessible Key West experience.