Moving 2700/3300 miles (“as the crow flies/Google maps driving distance) away from Portland would maybe give the impression that I don’t love Portland and wanted to get far far away, which couldn’t be farther from the truth, but I figured why not make it even farther anyways! So I headed to the southernmost place in the continental United States — the one immortalized in all the Jimmy Buffet songs I would listen to with my dad- Key West!
Key West is about 160 miles from Miami and a lot of people describe the drive as longer than expected and that’s partially because most of the drive is one lane in either direction and your speed is determined by the cars in front of you (reminds me a lot of the 101 on the Oregon Coast). The other thing is that once you reach Key Largo you start to feel like you’ve arrived with the scenery, but you’re still about 100 miles from Key West at that point. We left quite early in the morning on a weekday and we had good traffic so it only took about 3 hours. On our way back the opposing traffic heading to Key West mid-day was more backed up, but it also was Spring Break season. Later on in the day, especially on weekends and busy times of year, it can take 4 hours or longer to make the drive. The slow pace of the drive can be frustrating for some, but it’s a beautiful drive and I think part of the experience. The quickest way from Miami is to take the Florida Turnpike down to Homestead (with a shortcut on the Don Shula Expressway to the Turnpike) and connect with US-1 instead of taking US-1 all the way from Miami. The Turnpike doesn’t do cash any more so you should make sure you have a Sunpass on your car or do Toll-By-Plate. For info on buying a Sunpass (it’s super cheap and easy, even if you’ll never have another need for it) or Toll-By-Plate check out the Turnpike website- http://floridasturnpike.com/all-electronictolling/index.cfm. If you are getting a rental car check with your car companies because they usually have various programs set up for you to add-on.
The drive to the Keys is part of the experience with various towns to stop in and places to stop off and take in the views/take pictures. If you want to check out the Keys, but don’t want to commit to such a long drive Key Largo is a nice place to go for a day trip from Miami and start to get the scenery. Islamorada is a bit farther and I think it’s one of the more beautiful parts of the drive- incredible blue water of many different shades. Marathon is the major city you’ll hit before Key West and is one of the top places to go for sportsfishing.
Once we got to Key West we got a late breakfast on Duval St, the main street with a lot of restaurants and bars. The island is really not that big and most of Old Town and the stuff to see isn’t too far from each other if you want to walk a good amount. Another great alternative is to rent a bike, scooter, or electric cart, which are all over Key West. Parking around Old Town wasn’t bad at all, even during Spring Break, so I’d ditch the car somewhere in Old Town, if you’re not staying in the area anyways. We parked our car off Duval St and walked down to the Truman Annex area and saw the “Little White House”, where numerous presidents have come to visit Key West. The neighborhood around the Little White House is cool to explore- quiet streets with very “Key West” architecture. We checked out the outside of the Little White House and grounds, but were fine not exploring the small exhibits inside. It then was a reasonable walk to Fort Zachary Taylor (there is a fee for entrance even when walking/biking). Along the way we stopped at the Florida Keys Eco-center, which has some smaller exhibits on the sea and land flora and fauna around the Keys and was free to visit. The fort was cool to see. There isn’t much besides the shell of the building, but there are some cool views from the top. Our friends who live in Key West also told us that the beach there next to the fort is nice and where locals usually go.
Afterwards we explored Duval St a bit more and stopped for drinks. If you’re into architecture like I am you can really enjoy just walking around Old Town and the streets off of Duval. A lot of the businesses on Duval are in converted houses. After drinks we drove over to “New Town” on the eastside of the island. If you’re staying on that side of the island or head over to the grocery and chain stores there you’ll definitely want to drive. After picking up some groceries we met our friend who lives in Key West and went to Dante’s on the north side of the island near where the ferry from Fort Myers comes in. Dante’s is a water-side bar with a decent sized pool. During Spring Break it definitely attracts a younger crowd, but I could see people of different ages enjoying it if they want a great bar to get drinks and bar food. Dante’s, especially their happy hour, is a great deal! Between our group we got 9 drinks (the more elaborate cocktail kind) and a huge plate of nachos (which were really good) and it came in around $50 plus tip. From my time in Miami I was expecting it to be 2-3 times more than that. Similar to times in Vegas I had a great time hanging out in the pool and hanging out with drinks and food.
After Dante’s we headed over to Mallory Square to check out the street performers and the stands. The Sunset Celebration is a big gathering of street performers. They seem to have a official/unofficial arrangement where each of the major street performers put on a performance one at a time. We only stayed for a few performances, many involving fire and balance, but it was cool to see and I really like the pier area. There are a lot of small stands if you’re looking for some street art like jewelry, paintings, or mementos.
After Mallory Square we headed back to Duval Street and went on one of the ghost tours. We went on the “original” ghost tour, which takes you walking around various haunted points around Old Town. There also are some other companies who do trolley tours, including ones that take you out to the Martello Museum to see the most famous doll in Key West- Robert. The tour was cool to go on and you learn a lot of history about Key West, which I enjoyed. I’d recomend doing it on your first day in Key West, especially if you drive down late, because you visit or hear about a number of different sights in Miami that you can then go check out the next day (like the Little White House and the Audubon House). It’s less going into and experiencing “haunted” places and more hearing stories of ghosts around Key West. The ghost tour store for the one we went on is on Fleming St just off Duval and leaves from the La Concha Hotel in the same building.
After the ghost tour we went back to our friends’ hotel room in one of the larger bed and breakfasts. Key West has some awesome bed and breakfasts, many which are quite updated and nice in cool old Key West homes. There’s was a number of blocks of Duval St (about half a mile), but it still was a pretty easy walk there and back. Afterwards we went out on Duval St, which has a lot of great bars and nightlife. Many of the biggest most popular bars are congregated on the same block with a few others (like Fat Tuesdays) only a few blocks away. We spent a lot of time at Rick’s and Durty Harry’s. They are part of a larger complex that also includes a few smaller clubs that once you’re in (it was a $5 cover for us on a Tuesday during Spring Break season) you can walk around to each of them as much as you’d like. We also checked out a cool “dive” bar (still pretty nice but it had the peanuts on the floor and was more laidback and quieter) called the Tattoo and Scars Saloon and played some beer pong with Strongbow and then went to the Lucky Gecko across from Rick’s before returning to Rick’s to finish the night. I had a really great time and Duval St all had everything you’d be looking for (hanging out and getting drinks, dancing, louder, more laidback, etc).
My friend was only able to get one day off work so we headed back early this morning and really only spent about 24 hours in Key West, but I still think it was worth the trip and we squeezed a lot in and it felt like we were there for much longer. I especially liked exploring Old Town, seeing all the cool architecture, and then going out on Duval St. Being on the water and having so many options in terms of restaurants and sights to see on the piers was also one of my favorite parts. Key West has a great atmosphere and a lot of charm. I definitely encourage people who move to South Florida to check it out and for visitors to think about adding it to your Miami trip if you have the time or making it your primary destination.