A Sunset Sail

by Jeff · March 8, 2020

Key West and it’s legendary sunsets…

We decided to go on a sunset sail cruise and booked with Sunset Sail Key West after a lot of research. They have a fleet of four vessels and we chose the one offered on the “When and If”.

The When and If was commissioned in 1939 by General (then Colonel) George S. Patton. The name hearkens to his statement that he and his wife Bea would sail around the world “when this war is over and if I live through it”. Unfortunately they were never able to realize this dream due to his death in 1945. This Classic John Alden designed Schooner was designed along the lines of the classic racing yachts of the day with some unique forward thinking concepts for providing increased performance. The schooner turned 80 years old and still shows a fine turn of maintenance and upkeep. Her captain and crew live aboard and keep her immaculate.

We were greeted on the dock at Stock Island by crew members Anna and Anya who invited us aboard and got us situated on deck. They provide ice chests with bottled water and canned sparkling water. You are encouraged to bring your own alcoholic or non-alcoholic beverages which the crew will happily open and serve for you. They also provide a cheese plate snack for the guests. Ours included three different types of cheese, mixed nuts and berries, dried mangoes and crackers.

Captain Joe gave us a very thorough safety briefing prior to untying and he and the crew warped us away from the dock and we headed out into the channel. Once we were clear of the docks and into the channel, we raised sails, killed the iron wind and our beautiful old schooner came alive and started her dance with the Atlantic and the wind.

The sight of the sails going up the old wooden masts, our pennant in snapping in the wind and our Flag lit up on our stern by the evening sun truly inspired this photographer. E and I both are sailors of old and I have raced sailboats in the past. The feel of When and If being alive and her wood thrumming with the feel of the sails driving her through the Atlantic swell, the heel over to get her extended waterline design wet for the best point of sail and her crew and captain working to get her speed up just sends a thrill through us.

I watch our crew work the lines and sails with the ease and skill of practice, the captain handling her helm with the joy of handling a well built and balanced vessel. What a lovely dance of wood, wind, water, lines and crew!

Our little group of 11 are constantly being engaged by our crew and reminded of lines running and booms moving and being kept safe and smiling while answering our never ending questions about the vessel and their lives aboard.

We met new friends from other places and our Scottish friends Dennis and Ailene shared a beer with us. We chatted, drank and gnoshed our way through the sail, at one point passing a sailing catamaran (any 2 sailboats going the same direction is a race right?) and taking pleasure in our speed and point of sail. The crew let us handle sails and we all looked forward to our sunset as we took turns taking photos and sharing stories of our individual experiences visiting the keys.

Sunset…As you can see from the photos, there is no sunset quite like the one from the deck of a ship under sail! The last couple of minutes of sunset always seem to go so very fast. As you watch the sunset across the open ocean you can really appreciate how fast the earth is rotating.

Our sail back to the dock was rather anticlimactic. Captain Joe kept us under sail all the way to the entrance to the marina where the crew dropped sails near the commercial fishing dock and we then motored in to our dock. I, for one, truly felt disappointment as we started up our iron wind and headed for the dock. We ate the last of our cheese plate and bought a souvenir shirt from the crew and bade them farewell.

We both agree that we would definitely take a cruise on the WHEN AND IF again without a doubt. The ship is a beautiful piece of history and the captain and crew are very professional and personable. Customer service is the watchword for their client interactions and they perform very well.

You can contact them through sailkeywest.com or whenandif.com.