Key West Historic Schooner When And If Sunset Cruise — Champagne Toast & Hands-On Sailing

THE ADVENTURE COLLECTIVE® · Independent discovery and booking for outdoor travel

Read the full experience

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.

Trip highlights

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

Frequently asked questions

Where do I check in and is there parking?

Check in at Slip H16 at Perry Marina in front of Bad Boys Taqueria; there is ample free parking at the marina.

Can I take the wheel or help raise the sails?

Yes—under crew supervision guests are invited to steer and assist with lines for a hands-on experience.

Are children allowed and are there age restrictions?

Children are welcome at a discounted fare; infants must sit on an adult’s lap and all minors must be accompanied by an adult.

What is the cancellation policy if weather is bad?

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.

Local insights

Wildlife

Bottlenose dolphins
Green sea turtles

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.

About Sunset Sail Key West

Sunset Sail Key West operates guided outdoor trips and adventures with an emphasis on safety, stewardship, and memorable experiences.

Base locationKey West, Florida

Tours offered4+

Specialtyboat-charters

StewardshipLeave No Trace

Adventure tips

Arrive EarlyPlan 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 BreezeEven 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 RemediesIf you get seasick, take preventative medication or use acupressure bands; the Two-hour sail can include chop depending on conditions.

Respect Wildlife Viewing EtiquetteObserve dolphins and sea turtles from a distance—do not feed wildlife and follow crew instructions during sightings.

Recommended gear

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.
Sunscreen & sunglasses: Protects from strong tropical sun during the pre-sunset portion of the cruise.
Binoculars: Useful for spotting distant dolphins, birds, and reef features from the deck.