Key West or Bust!
 

Hi Fodors,

A friend and I are traveling to Key West for the first time. We are planning on spending 3 nights there. Is that enough time? What are some of the main sights we should see? We plan to get an airbnb - any suggestions on where?

Advice or tips are welcome!

Thank you!

We had done a day trip to Key West from Miami and did feel that a few days there would have been much more fun. Three days look quite reasonable to me, but it depends on what are the activities you are planning to pack within those 3 days.

Look at rentals in Truman Annex. Three days are ok for the first time. I say that because Airbnb is super pricey there. If you can afford another day then go for it. Moondogs is great place to eat. Fausto's market, Peace Bakery and restaurant store have good food and excellent beer and wine to buy. Plenty of outside dining options.

It all depends on how much you want to do. I've spent two weeks there and was busy the entire time. Go on line to a site like Trip Advisor to see the different activities. Also, there are some unique Inns and hotels so you might reconsider them instead of an AirBnB.

Three suggestions below that we enjoyed:

https://www.keywestbutterfly.com/

https://www.trumanlittlewhitehouse.com/

https://www.hemingwayhome.com/

Tennesee Williams's museum is free and very interesting. Some great bookstores, I miss the old stores that use to be on Duval but they could not compete with amazon. Fast Freddies always had the best NY's window. The graveyard is a good stop. Jimmy Buffet has a house across from the graveyard. My husband was stationed in KW so we always love going there. There used to be great Happy hours but not so much these days. Best thing now is no cruise ships.

I attended a music festival there in January 2019 and 2020--the 2019 visit was my first time there also. I enjoyed Hemingway House (but I love cats, so...). I also took one of the Conch train tours and learned a lot--touristy? Yes, but sometimes that works just fine. Go to Mallory Square at dusk to watch the sunset. Sloppy Joe's has a great drink--their specialty and their take on a margarita--delicious, but packs a punch. If you can, catch a charter to get out on the water...I think the company name is Fury.

All of the above pertains to KW pre-pandemic, so your experience may vary.

Where are you traveling from? As far as a 3-night trip is pretty short. I'd chose a hotel or guest house. I think it connects you better with the community for such a short stay, than in a private rental. My own experience is out of date but I did enjoy the Keys, do you have time for more than just Key West??

Hi, I used to live in Key West, and I still visit frequently. You should try to stay closer to the end of Duval St, the side where Sloppy Joe's is located. This will have you withing walking distance to most places. There are a lot of AIRBnB's there, especially on Eaton St. There area couple hotels in that area like the Crowne Plaza Conch, The Saint and the Margaritaville resort. If you like to have some drinks, this is the area to do so. You'll find lots of bars, some with great history.
For activities, try the Hemingway House, Kayaking up on Stock island from Lazy Dog Charters, snorkeling and scuba can be found near the pier with companies like The Fury catamaran. Deep sea fishing charters can be found in Garrison Bight marina. The beaches aren't the greatest in Key West, but Smathers Beach is the largest, and Fort Zachary Taylor state park has a nice one was well.
For food, you can't go wrong with Blue Heaven or Santiago's Bodega, both excellent.

You're also welcome to check out my guide to Key West on my travel blog if you'd like. Hopefully it's helpful.
https://www.thetravelinglocals.com/p...the-end-of-a1a

One of our favorite things to do is a sunset cruise. Highly recommend Danger Charters.