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.
More ways to explore the area's outdoor wonders
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.
Difficulty
easy
Duration
2 hours
Fitness Level
Suitable for most fitness levels; requires ability to climb a small boarding ladder and stand on deck for periods
Wildlife
History
The schooner When And If traces back to a 1939 commission by General George Patton and preserves classic wooden-schooner lines popular in early 20th-century coastal America.
Conservation
Sailing in the Florida Keys National Marine Sanctuary means obeying reef protection rules—avoid anchoring on coral, keep a respectful distance from wildlife, and pack out all trash.
Reserve your spot on the Key West Historic Schooner When And If Sunset Cruise today and enjoy a trusted, highly rated experience designed to help you make the most of your adventure.
Arrive Early
Plan to arrive 15–30 minutes before departure for check-in at slip H16 (look for Bad Boys Taqueria) to avoid rushing boarding procedures.
Dress for Breeze
Even in summer the sunset brings a cool wind—bring a light windbreaker and closed-toe, non-slip shoes for stable footing on deck.
Bring Motion-Sickness Remedies
If you get seasick, take preventative medication or use acupressure bands; the Two-hour sail can include chop depending on conditions.
Respect Wildlife Viewing Etiquette
Observe dolphins and sea turtles from a distance—do not feed wildlife and follow crew instructions during sightings.
Non-slip deck shoes
Provides stable footing on wet or rolling decks.
Light wind jacket
Blocks the evening breeze and keeps you comfortable after sunset.
spring
Sunscreen & sunglasses
Protects from strong tropical sun during the pre-sunset portion of the cruise.
summer
Binoculars
Useful for spotting distant dolphins, birds, and reef features from the deck.