Key West Historic Schooner When And If Sunset Cruise

Historic Schooner. Champagne Sunset Toast. Elegant and Exclusive. Step aboard the historic schooner When And If, commissioned by General George Patton in the late 1930s, and sail into a breathtaking

Historic Schooner. Champagne Sunset Toast. Elegant and Exclusive. Step aboard the historic schooner When And If, commissioned by General George Patton in the late 1930s, and sail into a breathtaking Key West sunset. Raise a champagne glass as the sun dips below the horizon, while your experienced crew handles the sails — or try your hand at steering this classic wooden schooner yourself. Glide along turquoise waters, spot playful dolphins and local wildlife, and enjoy an unforgettable evening that blends history, luxury, and adventure. Highlights: Historic schooner experience aboard the When And If, commissioned by General George Patton in 1939. Champagne sunset toast included Elegant and exclusive cruise - Avoid the crowds Hands-on sailing opportunity: take the wheel under guidance from your experienced crew. Spot dolphins, sea birds, and local marine wildlife. Perfect for romantic evenings, family adventures, or history enthusiasts — children sail at a discounted fare.

From: $0.00

Location: Key West

What's Included

Soda/Pop
Bottled water
Select Beer and Wine Included. Sunset Champagne Toast and Bottle Service Upgrade Available
Experienced Captain and Crew
Restroom on board
Opportunity to Take the Wheel and Help Raise Sail

Community Discussion

Q&A

Q: Is there an age limit for kids on this sunset cruise?

A: No specific age limit, but children can sail at a discounted fare. The crew is great with kids and makes sure everyone is safe and having fun. Just remember to bring life jackets if you have little ones—though they have some on board, it's always good to check! Overall, it’s a very family-friendly experience.

Q: What happens if the weather is bad? Do they cancel?

A: If the weather is too rough, they will likely cancel the cruise for safety reasons. You'll be notified ahead of time, and they usually offer an option to reschedule or refund. Just keep an eye on the forecast, and it’s always a good idea to call them if you're unsure!

Q: What should we wear for the sunset cruise?

A: Casual beachy attire is perfect! I wore a sundress, and my partner had on shorts and a nice shirt. The breeze can pick up a bit, so maybe bring a light sweater for after sunset. Flip flops or boat shoes are great, just be careful with anything too slippery on the deck.

Discussions

Just booked the When And If Sunset Cruise! Any tips?

I'm so excited! Just booked the sunset cruise on the When And If for our 5th anniversary. I heard the champagne toast is amazing, and the views are supposed to be out of this world! Any tips on what to expect or things to bring? We really want to soak in the history of the schooner as well.

Had a fantastic time on the When And If!

I went on the When And If sunset cruise last weekend, and wow, what an experience! The history behind the boat is so cool, and the sunset views were breathtaking. The crew was friendly and even let me steer for a bit! Totally worth it—highly recommend this for anyone looking for a romantic night out or just a cool adventure.