beer Florida Food Key West Florida trip reports

End of the road in Key West

a sunset over a body of water

After buying a Frontier $58 round trip ticket for Las Vegas to Miami last November during a 99% off flash sale, I had the brilliant idea to ask my octogenarian parents if they wanted to join me for a 5 day trip to Florida.

What was I thinking?

Florida seemed like an opportunity to make up for missing a family gathering in Hawaii in December. In retrospect, I think this was the first time I traveled on a road trip alone with my parents since the 1970s without my sisters or my wife accompanying us.

We logged many thousands of road miles as a family across the USA and Europe when I was young. Every single year I was in grade school from kindergarten to 10th grade we moved from state to state including California, Alabama, Oklahoma, New Mexico, and Virginia. We spent three years in Germany on two different military bases near Stuttgart and Mainz with lots of road tripping around Europe too. My parents settled down on the Monterey Peninsula after my father retired from the U.S. Army, where I attended my final 1.5 years of high school.

My parents had been to Key West once before about 10 years ago. Apparently I booked them a room at the Sheraton Suites Key West for their trip. All I really knew about Key West is my mom said it was a city where a lot of people hang out in bars drinking and Sheraton Suites was too far to walk to Duval Street for the bar scene.

If you have been to Key West, then I have little insight to offer. But if you have never been to Key West, then here are some of my impressions and a few tips for the first time visitor.

End of the Road in Key West – U.S. Route 1, Mile Marker 0

Key West-End US1
U.S. 1 Mile 0 marker at Whitehead and Fleming St.

Key West impressed me as the most enjoyable place I have been in Florida. The town has many of the attributes I like in European cities with frequent and even free public transportation service, a concentrated series of bars and restaurants along Duval Street with lots of live music and people/animal watching opportunities. And plenty of interesting characters.

Key West Angel
South Pier butterfly at sunset.

Three days in Key West barely allowed me to scratch the surface of entertainment, dining and drinking in this city at the end of the road – the southern terminus of U.S. Route 1.

Key West Duval St
Duval Street bar scene.

Tips from a first-time visitor in Key West

Tip 1: Ditch the Car. Walk, bike and Duval Loop free bus.

Key West Duval Loop
Duval Loop free bus

Duval Loop is a free bus shuttle around the west end of Key West.

Parking is $4 per hour in the entertainment area of Duval Street. We stayed at Best Western Hibiscus (link to my hotel review) at the south end of Simonton Street. Mallory Square, the 100 to 200 block of Duval and surrounding streets are the main tourist entertainment center of the city with dozens of bars and restaurants around the north end of Duval Street.

The advantage of having my parents with me was my dad’s disabled parking sticker allowed us to find free parking around Mallory Square and other streets in Key West, however, even with the advantage of free parking, finding an available parking space was challenging at times. 

Duval Street is about 1.25 miles long from the north end of the street with the largest concentration of bars in Key West and ending at South Beach pier.

South Beach pier
South Beach Pier at end of Duval Street

There are bars all along Duval Street for most of the 1.25 miles, along with retail stores, art galleries and dining.

Key West Tree bar 202 Duval
“Hemingway Pissed Here†– Rick’s Tree Bar, 202 Duval St.


Tip 2: Happy Hour drinks and food 3-6pm.

Key West Drinking

Key West has some cheap drink opportunities. There are many places with 3-6pm happy hour drinks and other drink specials. We passed one Irish bar somewhere in the center of the city a few blocks from Waldorf Astoria Casa Marina with 12-2am happy hour.

Key West Flying Monkey
Flying Monkey Bar, Duval Street

Tip 3: Open containers on Key West streets is tolerated, but actually not permitted by law

In the party area of Key West around the 100-200 block with a high concentration of bars there is plenty of open container drinking on the streets. All along Duval Street I saw people walking the street with beer and drinks. From what I read, police generally do not bother people about public drinking on Duval Street and around bars as long as you are not creating a public nuisance.

a group of people crossing a street
Duval Street drinking while walking

Tip 4: Book a hotel on the west end of Key West if you want  the party scene.

Hyatt Centric Key West, Waldorf-Astoria The Reach, Crowne Plaza La Concha and Best Western Hibiscus are some of the chain hotels available for points on the west end of Key West. These hotels are all within walking distance of Duval Street bars and the Duval Loop bus. Duval is a north-south street about 1.25 miles in length.

Hotels on the east end of Key West are more than two miles from Duval Street.

Key West Hotels

Loyalty Traveler Key West 15 Chain Hotels Google Maps

Many of the chain hotels are on the east end of Key West a few miles from Duval Street. Fairfield Inn and Hilton Garden Inn Key West are near the bridge on the east end of the island and about 2.3 miles from Duval 100-200 block, which is the center of the bar scene. Check your hotel to see if they offer shuttle service.

Tip 5: Watch out for Key West ‘gypsy chickens’ on the streets

Gypsy chickens-1

One of the quirkier aspects of Key West are hundreds, perhaps thousands of ‘gypsy chickens’ roaming freely along the streets.

gypsy chickens-2

Bicyclists and chickens are road hazards to watch out for when driving.

Key West cyclist

Tip 6: Winter Sunset seen from Key West South Pier

We went to Mallory Square to watch sunset our first night with crowds of people gathered around the docks.

Mallory Square sunset
Mallory Square crowd at sunset

Turned out the sunset view was better from South Pier near our hotel.

Key West sunset-3
South Beach Pier sunset
Key West sunset-2
South Beach Pier Sunset

Have you been to Key West with other tips to share?


  • JC January 29, 2018

    Blue Heaven is a must-do at 729 Thomas St (but only if the weather is nice so you can sit outside). My preference is breakfast with blueberry pancakes.

  • Ric Garrido February 1, 2018

    Clarification on my “What was I thinking?” comment about traveling with my parents since I left that dangling with no explanation. This trip was a wonderful time hanging out with my parents.

    My thoughts were more about how Key West is a great place to go hang out in bars drinking and talking with people, which is something I enjoy on trips, but not really my parents style. The bars of Key West were not part of this Key West adventure as the designated driver for this trip. 

    One of the interesting aspects of this trip for me was visiting the Vietnam Memorial in Key West with my dad. He pointed out the places in Vietnam where he was stationed during his three tours from 1963-1971. Vietnam was a significant event in our family during the several years my Dad was away and my mom raised me and my sisters in a single mom household. Fortunately everything worked out and we are all still around to share life and travel together so many years later.

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