Best ways to see Key West sunset

By Lucy Komisar

The sky has to be just right for a Key West sunset. Some clouds to capture and spread the rays, but not so many that the sunset is blocked. The wind has to be good, too, enough to push sailboats through the waves, but not so wild as to rock passengers too roughly and disturb people on land. If the stars are in alignment, ie the weather is right, a Key West sunset is a gorgeous thing to watch.

Key West sunset from the When and If.

Here are three ways to do it.

  • Sunset sail on the Sebago Schooner Appledore
  • Sunset sail on the When and If
  • Drinks at the sunset deck, Margaritaville Key West Resort & Marina Bistro

Or just hang out at the pier.

The Sebago Schooner Appledore

The Schooner Appledore.

I like a bit of history with my sunset cruises, and the two I took both had them. The Sebago Appledore II is a prime example of a historical traditional wooden schooner and is the largest of the five Appledore Schooners.

Schooners originated in Europe in the 17th century with a typical tall ship like this one carrying 2-masts. In the 18th century, schooners became popular in America for their speed, ease of handling and shallow draft.

Putting up the sails.

There were as many as 2,000 schooners on the Great Lakes during the 19th century. Alas, engines meant sailing ships for commerce was not practical.

This one is not original but a very good copy.

The wine and good food were plentiful on the Appledore.

In the summer, you will find her in Camden, Maine, sailing 2,000 miles twice a year between the two ports.

But in winter, you can enjoy some excellent food and wine with the sunset.

The “When and If”

The When and If boarding passengers.

The “When and If” appeals to sailors, those who like some speed even when the water is choppy. It‘s got a history, which you can see below decks.

The two-masted schooner was built for General George Patton in 1939. Patton commanded the U.S. Seventh Army in the Mediterranean and European theaters of World War II. “When” the war was over and “If” he got out of it alive, he and his wife would sail around the world.

Patton’s berth.

Below deck you can see Patton‘s berth and the galley with standing room and hatches that let in the daylight.

It‘s the galley where our snacks were prepared. And your berth if you charter the boat.

Captain Dylan.

The crew is quite serious, including Captain Dylan, who takes the boat north in the summer.

And notice Zoe, who signed on for the winter to help crew. In the very intimate setting, you are close to the work, to putting up the sails and steering the boat.

Zoe pulls the halyard to raise a sail.

We lounged on the deck, drank wine and nibbled cheese. I noticed that when it got quite windy, the Appledore dropped sails and people could move about calmly. On the When and If,” the sails stayed up, the boat lurched from side to side, and we stayed put and grabbed onto whatever we could. This is a cruise for real sailors!

Margaritaville Key West Resort & Marina Bistro

At the Margaritaville Key West Resort & Marina Bistro sunset deck.

Drinks at the Margaritaville Key West Resort & Marina Bistro sunset deck is for land-lubbers. Seated at the bar or on deck chairs facing the sea, patrons enjoyed a superb view. The imbibing was pretty good, too.

And the sunset was gorgeous!

From the Margaritaville’s aptly named sunset deck.

The Sebago Schooner Appledore, 205 Elizabeth Street, reservations 305 294-5687.

Sunset Sail on When and If, Sunset Sail Key West, reservations 305 587-4488. Departure from 7009 Shrimp Road, Stock Island, next to Key West. If you call in advance, a van will pick you up.

Margaritaville Key West Resort & Marina Bistro, 245 Front Street, reservations not required.

Photos by Lucy Komisar.

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