Flight Paths: Ten Cheep Trills from a Key West Getaway

Chirped by Cass

My husband and I just spent a long weekend with a small group in Key West, Florida. The two of us had been there before, but last time was just a day trip off a cruise boat many years ago. Here are our top ten cheep trills for what we saw and did and took with us. Maybe it will help you plan your own Key West getaway!

Casa Marina – A Waldorf Astoria Resort

The hotel we stayed at was the Waldorf Astoria Resort. It had it all – from a spa, to pools, to water sports off their pier, and a great breakfast buffet.

Duval Street

An easy walk from the hotel was Duval Street, the main shopping and restaurant hub of Key West. We spent a good part of one day walking the street, window shopping and stopping for lunch. They had all kinds of shops, from popular retail chains like Banana Republic, to little boutiques and art galleries.

Lunch Spot – Pinchers

On Duval Street we stopped and had lunch at Pinchers. Like the name suggests, they are known for their crab dishes. How could we resist a two-for-one drink special with fresh-catch-of-the-day fish and chips, while also listening to live music as we ate?

Fury Boat Island Excursions

We enjoyed this four-hour sunset Fury Boat Excursion that left around 4:30 in the afternoon. The first stop was a snorkeling spot over a coral reef accessed right off the boat. Next we visited an island location for a quiet kayak trip through the mangroves. The boat ride back was timed perfectly to take in the Key West sunset. Despite the appetizers and post-snorkeling cocktails on the boat, we rounded out the evening with more bites and drinks back at the marina at the Conch Republic Seafood Company.

Audubon House & Tropical Gardens

If you’ve already toured the Ernest Hemingway Home, the Audubon House is another worthwhile destination rich in antiques and history. We enjoyed a tour of the house and garden and then a delicious dinner in the gardens with a private chef engaged just for our group.

Sloppy Joe’s Bar

If for just one night you want to throw back a few drinks and put on your dancing shoes, then go to Sloppy Joe’s Bar on Duval Street. The music is live (and loud) and the demographic leans more towards the twenty-somethings, with a sprinkling of 30 to 60-year-olds partying like the young ‘uns. If that’s your thing (it wasn’t really ours), be sure to go check it out!

Fort Jefferson National Monument, Dry Tortugas National Park

For our second excursion, we boarded a seaplane to the Dry Tortugas Islands (about a 40 minute ride) to visit Fort Jefferson, one of the largest coastal forts ever built. The US began construction in 1846 in order to control navigation to the Gulf of Mexico, but the fort was never completed. During the Civil War it served as a military prison for captured deserters. We toured the premises, had a picnic lunch on the beach, and snorkeled around the island. If a seaplane isn’t your style and you have the time, there is also a ferry (about a two hour ride) that can get you out to the islands from Key West.


From breakfast, to boat rides, to shopping, to dinner – Key West is pretty laid back for dress attire. Men can get away with shorts, collared shirts and flip-flops at most places, and women can wear anything from shorts and tops to sundresses. The footwear I ended up wearing all the time were these flip flops by Abeo. They had great support and took me from the boat to the plane to the beach to the streets. They even went with me under my maxi dress when we went out dancing the one night.

Panama Hats

The other item I never took off was this Panama hat from Amazon. Not only did it provide great protection from the sun, it also hid my hair (which was not liking the humidity)! It has adjustable strings as well, to adjust to your head size.

Key Lime Pie and Bagatelle

Another good dinner place is the Bagatelle on Duval Street. They had a terrific menu to chose from, with a lot of fresh local fish choices. Naturally we couldn’t leave without ordering a piece of key lime pie for dessert!

Have you ever been to Key West? It was a great long weekend getaway.  What were your favorites from the island?


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5 thoughts on “Flight Paths: Ten Cheep Trills from a Key West Getaway

  1. What great recommendations! I love the flip flops and hat! I will have to try the sunset boat ride next time I’m there.

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