The Top-Rated Sunset Sail.
This Is Why You Came To Key West.

Nothing but the soothing sounds of the ocean lapping against the hull.

Owned and operated by local Key West characters full of stories and recommendations.

Experience the romance of the sea in Key West. It's unmatched.

Instagram worthy? Witness the most spectacular sunsets on the island.

Say you sailed aboard General Patton's personal private yacht. Because you did.

This is the perfect family bonding activity in the Keys.

Not a fan of large crowds of drunken college kids? Neither are we.

An experience so refined, it deserves it's own wine. Crafted especially for this ship.

But don't take our word for it.
Here's what people are saying.

"EPIC Sunset Sail aboard the Schooner When & If!! The crew was fantastic and seemed to enjoy it as much as we did. They even let me have the helm for a few minutes! The schooner is historic and absolutely the most beautiful vessel in the Key West fleet. Can’t wait to do it again!"

Kim S
Dec 2022

"The crew were all amazing. My husband and I really enjoyed the experience of sailing on a historic wooden schooner. We were able to help raise the sails and steer the ship. Our photos did not disappoint. We would do it again and we recommend you do it soon!"

jsfun
Dec 2025

"The boat is a classic schooner from 100 years ago perfectly maintained. The crew very capable and friendly And a perfect sunset!"

Jerry N
Dec 2025

"Amazing sunset cruise on this beautiful schooner. Seth and his crew were outstanding. The highlight of our trip!!! Would highly recommend!"

Cathy O
Nov 2025

"Pretty boat high end services, even an opera singer. This boat has it all. Small and intimate. Had a birthday sail, which didn’t disappoint. Loads of rain , a waterspout, and an amazing sunset."

Nemolly
Nov 2025

"Everything was great, from the crew, to the boat. They were very punctual from start to finish. They both made us feel very comfortable the entire sail. I would highly recommend this company. Thanks again for a memorable evening."

design1kmaz
July 2025

"We had a wonderful sunset cruise through the harbor. Got to see some dolphins and learned some interesting facts about Key West. The captain and crew were entertaining and very helpful. Would definitely go back."

pauldelaney
May 2025

Read all of our reviews:

Got questions? Let's dive into the details.

Is this really General Patton's personal yacht?

Yes, it was!

Built in 1939 for General George S. Patton, "When And If" was commissioned by Patton himself from naval architect John Alden, and built by FF Pendleton in Wiscasset, ME to sail around the world “When the war is over, and If I live through it.”

Unfortunately, he never got the chance to sail aboard her.

Fortunately, you do.

What is included on a sunset sail?

Each sunset sail is 2 hours in duration, and includes unlimited boutique wine, unlimited select beers and unlimited water (including La Croix!).

Depending on the temperature, blankets can be provided. And the crew will happily take your photo during sunset!

Should I make reservations now or when I get to Key West?

We might be biased, but we would make them now. Waiting until the last minute can leave you out of luck, considering we sell out quickly.

You can book easily online here.

Is parking available?

Yes! There is a pay to park lot at the corner of Margarett and Caroline St.

You can find directions to the parking lot here.

What kinds of wine do you serve onboard?

2 distinct wines have been created to celebrate sailing on the When and If.

Both of which you can enjoy during your sunset sail.

Red: A cabernet blend akin to the reds from Provence, France. Not too heavy, not too light. Just right to enjoy on the water.

White: Similar to a balanced chardonnay that is light, crisp, and not too buttery or heavy on the oak.

Where do I need to be? And at what time?

The ship is located on the floating dock in front of the Schooner Wharf Bar at 202 William St. We board 15 minutes before departure time. So you're best to arrive 30 minutes before departure time so you won't be rushed for parking.

You can find directions to the Schooner Wharf Bar here

Can I buy "When and If" merch?

You can! We have a ship's store with everything from shirts to mugs and hats.

Click here to visit the ship's store

Before booze boats. Before cruise ships.

This is true Key West.

Before booze boats.

‍Before cruise ships.

This is true Key West.

We're not your typical booze cruise. This is the real deal.