The Closest Bar to Cuba
When going to visit the Southernmost Point landmark sign, park 1-2 minutes away to walk and explore around this charming area.
I parked near the Southernmost Beach Resort to explore the landmark sign, but stumbled upon some gorgeous buildings and Key West colors.
I also stumbled upon the closest bar to Cuba, which is located the Southernmost Beach Resort.
You'll also find a small beach with an additional restaurant right on the sand.
Walk around Mallory Square
Another place where I parked in the area and explored was near Mallory Square.
The picture above is located in front of the Key West Museum of Art & History.
I didn't get a chance to go inside, but for art lovers it may be worth visiting almost 130 building!
Eat good seafood
I came to DJ's Clam Shack because of their almost perfect 5-star review on Yelp and I'm so happy I did.
This would be a place you would normally overlook, but it is located at the perfect spot in Duval Street where you can sit, people watch and each delicious food.
I ordered the clam strips and Maine lobster roll with slaw... wow. They do not skimp out on the lobster meat here.
If you're in Key West, eating a good seafood meal should be at the top of your list!
Stay at a hotel with amenities
I loved waking up at the Hampton Inn, enjoying a warm breakfast, and lounging by the pool.
It's great to have an option to lay back at your hotel when you're resting from exploring the rest of Key West.
Especially if you spent the night bar hopping on Duval Street.
My hotel offered free breakfast, free parking, a beautiful pool area, a free shuttle to the downtown area, two bottled waters per day, and a complimentary drink card (2) for each night.
Overall, I'd say I received the value for the price of the hotel. I'd recommend anyone to stay here that's open to being 15 minutes away from Duval Street.
If not, I'd recommend looking at an Airbnb or Bed and Breakfast on Duval Street.
Or, you can stay at the Southernmost House, which I talk about below.
I didn't stay here, but I couldn't stop to take a picture with the charming entryway!
This Victorian styled house has welcomed famous figures like Ernest Hemingway and the president and for good reason!
So if you're looking for a charming place to stay in a great location, it might be worth looking over.
Because at least one super touristy picture is required, right??
Watch the sunset at Mallory Square
Come here to watch the sunset, but come early!
This is a a great spot in Key West to catch the sunset, but this is also where all the tourists flock.
Make sure to come early, or find a seat at a nearby restaurant like Bistro 245.
If you are in the area before sunset, try to stop by Shops at Mallory Square for shops, coffee shops, and a gallery.
Take advantage of happy hour
After watching the sunset at Mallory Square, we decided to have dinner nearby for better food options.
Since it was nearing the end (6PM) I ordered two glasses of cabernet sauvignon and I cannot complain about $5 a glass!
Key West was colorful, charming, and surprisingly quiet.
I went in December 2020 on a weekday and Duval Street was surprisingly dead at 9PM, which I'm not sure if it's because it was a weekday or because of the pandemic.
Either way it's something to consider if you're looking to party.
The only other thing I would've liked to add to the trip is a snorkeling adventure.
When we arrived, it was "chilly" considering Florida weather at 68 degrees, so we decided not to go.
But, next time I'm adding a trip to Fort Zachary State Park or other hot spot for snorkeling.
Let me know in the comments if there's any other places you'd recommend in Key West, FL!