Where the Road Ends and Island Time Begins: Key West

The weather forecast in Jacksonville, showed lows in the 30s and highs in the 50s with clouds. That did not fit our definition of warmth and sunshine! So we decided to head south, as far as we could go. And that meant Key West, Florida! While I had been here once before on a cruise stop, Eric has never been south of Orlando. We weren’t sure what to expect but were ready to embrace the adventure and feel the vibe!

Driving from Jacksonville to Key West

The trip to seek warmth almost never happened. You see, when we were in Kansas over Thanksgiving we renewed our driver’s licenses. In Kansas, when you renew they give you a paper print out license and then ship you your permanent license by mail. That was going to be fine, as we’re seeing my sister in Jamaica at the beginning of January and she could bring it to us. We booked a bed and breakfast in Key West, made an online booking for a car rental, and were ready to hit the road on Monday morning. There was an Avis car rental shop just a few blocks from our Airbnb in Jacksonville, so we set off bright eyed and bushy tailed ready to get on the road. Except Avis wouldn’t take our paper license. No amount of discussion helped. We’d prepaid the car and the bed and breakfast. This was about to be a very expensive non-adventure. Determined not to let them stop us, we turned to our friend ChatGPT who told us we may have better luck with Enterprise or Hertz. Back to the airbnb we go to make some phone calls. Eric tackled Avis corporate. After 10 minutes of trying to reason with them that the paper was valid, they agreed us to refund the prepaid amount. I called Enterprise. She assured me that the paper license was fine. So into an Uber we went to head to the airport (30 minutes north of our Airbnb) to get an Enterprise rental car. We went in to the desk and low and behold, they too would not accept our paper licenses. We were really starting to feel depressed but thought we’d stop by Hertz to plead our case one final time. Success! It cost us $200 more but it saved our week! And we were off!

Unfortunately, we were now 2 hours behind schedule with an 8 hour drive if there was no traffic. But because we were running behind, we hit Miami right at 5pm. That added a full hour onto our day. This was our first time driving through Florida. And I’ll say we don’t need to do it again! When we finally got on Hwy 1 and left the mainland it was dark. It was a long slow drive the 120 miles to Key West, but in good news, we watched the temperature steadily increase as we went!

Sightseeing in Key West

We stayed in Old Town, which is on the far west side of the island. We stayed in a bed and breakfast called The Mermaid and the Alligator. It was super cute! We were in one of the smaller rooms, which was a cottage with a front porch. There is a small pool on the property. Breakfast is served every morning on their patio and there is a happy hour every afternoon.

We found Key West to be extremely walkable. We parked our car at the hotel on Monday night and didn’t move it again until Friday! For that reason (and to not have to drive the horror that is I-95), if we come back we’ll fly directly into Key West. There are tons of golf cart rentals, which would be great if you had a group or someone who has mobility issues. There are also a ton of bike rentals which I’d do if we went back! We walked 8-10 miles every day!

There quite a few things to do on the island. Of note are the Ernest Hemingway House, The Little White House (used by several presidents including Truman and Clinton), the Key West Lighthouse, and the Key West Shipwreck museum. These all cost $20-$30 a piece for tickets. You can also take the Conch Train or Old Town Trolley tours to see the whole island by vehicle.

We prefer to wander and see what we’ll find. And we loved it! Key West really feels unique for an American city. There are hints of New Orleans, hints of Nashville, hints of Hawaii. It is incredibly tropical and we loved the lush flowers and palm trees everywhere. And the chickens and roosters add a very unique touch. There are thousands of roosters and chickens wandering the streets and hanging out at restaurants looking for handouts. I can’t tell you how many times I wondered “why did that chicken cross the road”?

Key West Beauty

The houses in Old Town are absolutely charming. Its a relatively old city by American standards, with a lot of the houses dating back to the mid 1800s. It was especially fun to be here in mid December as they really go all out with holiday decorations!

Sunsets in Key West

Being the southernmost point of the United States, and with the Old Town on the west side of the island, Key West is a fantastic place to watch the sunsets. Every evening crowds gather in Mallory Square to watch Mother Nature put on a show.

Sunset Cruise

We were told by a restaurant server that the best way to enjoy Key West is from the water and we can’t disagree! On our last night we took a sunset cruise. There are numerous companies that you can book through and we chose Sebago. It was a 2 hour cruise for $69 per person and included light appetizers and unlimited beer, wine, champagne, and cocktails. While it was a cloudy day and we couldn’t see the sunset, the temperature was perfect and we loved getting out on the water. It was also fun to see the Christmas lights in the marina!

Fort Zachary State Park in Key West

We spent two 1/2 days at Fort Zachary Taylor and the beach there. The Fort dates back to the Civil War era where it was occupied by the Union during the war. It also was active during the Spanish American war in the late 1800s. Walking around the fort is interesting and there are guided tours by the park staff. From there you can walk over to the only beach on Key West. Its small but nice and there were quite a few people there and in the water both days we went. We walked to the park both days and it was $2.50 per person. It is slightly higher priced for cars but still very reasonable.

Bars and Restaurants in Key West

Of course no trip to Key West is complete without enjoying the bar scene. Duval Street is the main street through Old Town for nightlife. Restaurants and bars are all open air, with live music pouring out all day and night. We saw live music in three bars: The Bull, Sloppy Joes (yes, home of the original sandwich in the 1930s!) and Willie T’s. The music fits the clientele, which we found to be mostly adults in their 50s and 60s. Just our kind of music. Lots of yacht rock and southern rock.

Seafood and Key Lime Pie are must haves while in Key West. We enjoyed the marina area for some great seafood. We found that the restaurants off of Duval Street were better, so its worth wandering around the neighborhoods for meals.

Key West is a vibe. We would definitely consider returning for a week or two long stay! The weather in December was perfect and it wasn’t crowded. We would highly recommend it to anyone wanting a low key tropical escape within the US. As Jimmy Buffet says, It’s Five O’Clock Somewhere!