Key West: A Great Weekend Getaway!

Sunset sail on General Patton’s 1939 schooner

This was probably our favorite activity of the weekend. We boarded the vintage, double-masted schooner the When and If and set off for open water. The crew asked for volunteers to help raise the sails, so we all jumped in. With the sails aloft, we promptly caught the wind and sailed up and down the coast while sipping wine and beer. The sailing was glorious and was the perfect way to experience the gorgeous sunset.

Hanging out by the pool

We stayed at the Havana Cabana, and the pool was amazing! There was a pool concierge with suntan lotion available as well as pool towels. At noon, they served smoothies, at 2 p.m. they served Jell-O shots, and at 4 p.m. they had warm churros. The bar had great drinks, including the welcome drink we were given when we arrived. There were floats available and cabanas you could reserve. One of the palapas had games like ping-pong and giant Jenga. It was a perfect place to hang out, especially in the afternoon when the heat could be oppressive.

Bar hopping & shopping in the Old Town District

One of the people in our group said there were over 200 bars in a one-mile strip. I don’t know if that was true, but you did not have to go too far to find the next bar. This was an activity that required us to pace ourselves. In between the bars was a plethora of shops selling anything from antiques to clothing to souvenirs. We spent two days just walking up and down the streets enjoying all the offerings.

Visit to the Hemingway Distillery

The philosophy here is simple: “A life well-lived is the only life worth living. Here’s to never being a spectator.” This distillery and their Papa's Pilar rum were inspired by the author, Ernest Hemingway, and his beloved boat, the Pilar. They have a lovely gift shop with rum and alcohol-related gifts as well as T-shirts, caps, and more. There is a large picture window into the distillery, and they give tours as well as tastings. Veterans and military were offered a free cocktail.

Truman’s Little White House

Key West also has something for the history buffs. This is Florida’s only presidential museum. You can view presidential documents and Truman’s 1950 Cosmopolitan Lincoln Limousine. The building was built in 1890 as the headquarters of the naval station during the Spanish-American War. In 1946, it became the winter residence of Harry S. Truman. Not too far from the main street, the Little White House is a treasure trove of history and a nice respite from the craziness of the strip.

Santiago’s Bodega

Brunch here was a real treat. The restaurant serves tapas-style plates, including seafood and local flavors. The Saganaki was a favorite, especially since it came with a show. They poured brandy over the cheese and lit it on fire. The spicy shrimp bisque was delicious. On Saturday and Sunday mornings, they have bottomless mimosas or sangria, and I do believe we drank our $20 worth!

Lolita’s

This restaurant had an amazing view of the water and the boats going in and out. It was the perfect place to eat dinner while watching the sunset. It specializes in Mexican cuisine. The food and drinks were wonderful, which made up for the less-than-desirable service. The Oaxacan old fashioned was phenomenal!

Olive’s Mediterranean Grill

Olive’s was a little hole-in-the-wall café located across the street from Santiago’s. There are only a couple of tables inside, but the owner was so friendly and loved to tell us about his home in Ephesus, Türkiye. His family owns a large restaurant there, so when he moved here, he wanted something a little less stressful and he opened Olive’s, which embodies the chill vibe of Key West. The baklava was made with pistachios and was delicious. The Turkish tea was served very hot, as is the custom, and surprisingly made us feel cooler, not warmer!

Tropicado

Some claim they have the best mojitos in Key West. We were only there for a few days, so we didn’t get a chance to try every place in town, but Tropicado’s Island Mojito was definitely a winner!

Schooner Wharf Bar

Schooner Wharf Bar is what I would call a dive bar, except that it is quite large. Located right on the water, you can pay to watch people feed the tarpon or, for a little extra, you can feed them yourself. Drinks were good and breakfast was fantastic!

Sloppy Joe’s

Another large dive bar with live music. The rum punch in Sloppy Joe’s was the best we had on the island. Service was quick and friendly and the vibe was perfect.

Waterfront Brewery

A great place to land after a sunset sail. My husband saw Fish Dip on the menu and insisted we go in. It was a good choice! The Fish Dip was wonderful, as were the peel-and-eat shrimp, the pulled pork nachos, and the seared scallops.