Key West Travel Guide

June 28, 2021

I can’t believe I finally went on a trip! Last week, I went on a plane for the first time in over a year. For someone that traveled at least once a month pre-pandemic, I can’t even put into words how great it felt to travel again. I truly felt like myself for the first time since January 2020. Of course I have to address that it is important to get covid tested before you travel anywhere, and make sure to be extremely cautious. I’m at the point now where it seems like we’re going to have to live with this for a while, and when the proper precautions are taken, safe travel is possible. So let’s get to the Key West Travel Guide!

What to Know

Covid Precautions & Safety
Unlike the rest of Florida, Key West actually acknowledges that we are in the middle of a global pandemic. Masks are required everywhere and restaurants are seated with distancing in mind. In fact, you can actually get a ticket for not wearing a mask in public. Since almost everything is done outside, that helps too. But I will say that it is extremely important to make smart decisions. We saw lots of crowded bars and booze cruises; we did not put ourselves in those situations. For the most part, we stuck to getting food to go and when we did dine-in, we made sure we were seated 6+ feet away from anyone else, even though we were outside.

Getting There
Although the Keys are comprised of many islands (/”keys”), you can actually drive there via a very long bridge. It does take a long time (about 4 hours from Miami), but luckily there are quicker options. Obviously, you can fly into EYW via commercial or private (flying private is very popular here!), which takes under an hour from Miami. Another option is to take a ferry. There are many options from different Florida cities. This doesn’t seem like the most covid-friendly option in my opinion since most of the ferries are more like booze cruise style, but travel time is MUCH shorter than driving, so it’s possible to just go for the day and then take the ferry back home in the evening.

Getting Around
The main area in Key West is Duval Street. It’s 1.25 miles, so definitely fully walkable. We walked almost everywhere except once when we had to go from the bottom of Duval (where we stayed), to the top of Duval for a boat ride. For this, we took a Lyft and it was about $10. Another very popular things to do is rent bicycles or scooters. There’s not much car traffic there, so this would definitely be a great option. Unfortunately, we didn’t have time to do that, but I will definitely make the time for our next visit. We also saw lots of golf carts. This is probably something the locals use or an added benefit to getting a vacation rental home, but you can also rent them.

What to Pack

Key West is definitely nice and warm! We went in the beginning of February and it was in the 70s during the day and in the 60s at night. This is the coldest it gets down there and we just happened to go during a cold front. It was still nice enough to lay by the pool and sip on a tropical drink.

As far as style goes, Key West is very casual. There’s no need for heels. Think Jimmy Buffet Margaritaville vibes. Loose, flowy, comfortable clothes will make your visit that much more relaxing. My dear friend Erica made me this chic summer bag and it was so perfect for my trip. Obsessed!

Where to Stay

For Couples: H2O Suites
H2O Suites is pure luxury and absolutely heaven on earth. The boutique hotel has just 22 rooms–all with their very own private pools. This place is the perfect honeymoon getaway for so many reasons. First of all, the location is absolutely perfect. It’s about a block from Duval street near the southernmost point. So it’s not in the middle of the action, but peacefully tucked away within walking distance to everything. It’s couples only, so very romantic and quiet.

Another great perk is that in addition to the private pools in each room, there’s also a rooftop pool–with free drinks all day! In the morning it’s mimosas and bloody marys, and in the afternoon to evening, it’s wine. Have you ever heard of such a thing?! Plus there are free snacks as well like chips + guac and pita + hummus. H2O Suites is the ultimate luxury option for couples!

Use code MEGA for 10% off your stay at H2O Suites! I was given a comped room in exchange for organic coverage.

For Groups: Santa Maria Suites
If you’re traveling with a group of friends or as a family, then Santa Maria Suites is your best bet. All the suites at this gorgeous luxury hotel are two bedrooms, complete with a full kitchen and laundry. Both of the rooms are nice and spacious and there are of course two bathrooms as well. Our room opened right to the pool for a VIP resort feel. Santa Maria Suites is actually the sister hotel of H2O so of course the service is just as phenomenal. As far as the location goes, it is only two blocks away from H2O, so it’s also nice and quiet, but close enough to walk home after a night on the town.

The pool area at Santa Maria Suites is much more lively than H2O since there are more groups and families. The atmosphere is still pretty relaxed…until happy hour! There’s a bar open all day long, but from 4-6 they offer free wine for guests. During the day, you can also get tasty non-alcoholic frozen drinks at no charge.

Use code MEGA for 10% off your stay at Santa Maria Suites! I was given a comped room in exchange for organic coverage.

On a Budget: Southwinds Motel
Southwinds Motel is another sister hotel to H2O and Santa Maria, so even if you’re on a budget, you can experience great service and a quintessential Key West experience. They have a pool, which is harder to find in a hotel than you’d think. And a major plus is the Tipsy Rooster: an awesome bar and liquor store that is actually connected to the motel! They even have live music on some evenings. So fun!

Where to Eat & Drink

Of course, I have to mention the great local beer we had before anything else: Key West Sunset Ale by Florida Beer Co.

Ana’s Cafe Cubano
We ate breakfast at Ana’s Cafe Cubano almost every day. Ana’s is a Cuban cafe featuring Cuban coffee, Cuban sandwiches, and delicious fries. We got ours to go and it was super quick convenient, though they do offer dine-in as well, all outdoor seating which is great right now!

Seaside Cafe
Omg, just thinking about this place makes me drool. They have the best pizzas ever. Seaside Cafe is known for their popular lobster pizza, which we did get and were blown away by, but we also got their truffle pizza with mushrooms and caramelized onions. I have never loved a pizza so much and yall, I LOVE pizza. We sat outside right on the beach and felt so incredibly happy and relaxed. Ryan actually met the owner in the bathroom and he was the sweetest guy ever. He came by our table to make sure we were enjoying ourselves and the food. It’s funny because he told us that his son is the chef, and the lobster pizza was his idea. The owner was 100% against it, but it has now become their most popular dish!

Blue Heaven
I’m so sad to say that we didn’t have the chance to go here! It was by far the number one recommendation so I couldn’t skip mentioning it.

Tipsy Rooster
Ohhh the Tipsy Rooster! So much fun! If you’re looking for a casual, laid-back place to grab cocktails before or after dinner, this is your place. They actually have housemade infused liquors they can use for their drinks. I got the pineapple jalapeño tequila and Ryan got the strawberry mango rum. The Tipsy Rooster is actually part of the Southwinds Motel and right in between H2O and Santa Maria, so we stopped by quite often. In fact, the team at H2O was kind enough to give us a few drink vouchers. Score!

Sloppy Joe’s & Irish Kevins
The Iconic Sloppy Joe’s is known for being Ernest Hemingway’s favorite hangout when he lived in Key West. Due to covid, we skipped both that and the highly recommended Irish Kevin’s, which is right next door. If you go when it’s safe, definitely stop by these two famous bars!

What to Do

There are so many things to do in Key West, but at the same time it’s so nice to just relax when you’re there. Key West is not a big beach destnation. It is Florida, but if you’re looking to have relaxing beach days, Key West is not ideal. But there’s still plenty to do! We stayed for almost four full days and there’s still so much we didn’t get to do (as you can see in my recommendations above, ha!). I wish we could have stayed longer, but now that I’ve been and I know what it’s like, I think one more visit will be enough to do everything I had on my list. Here’s what we actually did get a chance to do during our stay:

Sunset Sail
This was probably my top favorite thing we did the entire trip. If you’re in Key West, do not skip a sunset sail!!! It was my first time on a sailboat and I cannot believe how peaceful it was. I can totally see why people get addicted to the lifestyle and sail on the seas for days on end. Since there’s no engine, you’re just kind of rocking on the water and can fully take in the sounds of the ocean. It was absolutely beautiful and so calming. I cannot recommend Sunset Sail Key West enough. The experience really made our trip so special!

The Hemingway House
This was the top thing on my list when I went to Key West. I’m an avid reader and of course love Ernest Hemingway’s books. It’s well known that he spent a lot of his life in Key West and I’ve read many fictional history books about his time there. To see his home in person was incredible. The beautiful architectural details and art deco touches was very inspiring. I loved seeing the famous “Hemingway tile” in person.

I learned that the pool is the largest residential pool in Key West. There’s even an adorable pool house with bathrooms and a gift shop in the floor level and then the top level is what I can only imagine to be Hemingway’s writing room. What I would do to have that writing room! I’d get a lot more done, that’s for sure!

The Hemingway House offers guided tours, or you can walk around yourself. Tickets are $16 each and the guided tour lasts about 30 minutes. We spent 30-45 minutes there and that was plenty of time, though there are some peaceful places to sit and relax so you could spend more time there if you wanted to.

Another thing to note is that there are tons of cats everywhere! Hemingway was known for his love of cats (and booze, ha!) so the grounds have become home to about 50 cats: 50 six-toed cats to be precise! Back in the day, a ship captain gifted Hemingway with a white six-toed cat named Snow White. So today the descendants of that original cat wander the grounds of The Hemingway House–and all across Key West!

Mallory Square
If you’re looking for the party, then go to Mallory Square. This is where all the boats can be found, as well as a ton of restaurants and breweries. We did eat at a couple places here, but none that blew my socks off. But regardless, it’s where the action is, so post-covid, it’s definitely a must! And I highly recommend watching the sunset here if you’re not out on the water!

Drag Show
No trip to Key West is complete without a drag show! These are an absolute must and so much fun. I’ve been to many drag shows in my life–all over the world–and I have never seen one like the one we saw at 801 Cabaret. At only $15 a ticket, it’s a total steal and the best way to spend your night! After the show, all the queens come mingle with the guests and it is an absolute treat. Ryan and I both had the time of our lives! Another popular option is Aqua. Since our trip was only 3 nights, we didn’t make it to both, but that is the plan for next time!

Clearly it was an amazing trip. I’m actually really glad I chose it as my first travel destination in over a year. The weather was beautiful, the hotels were incredibly luxurious, and the covid precautions made me feel safe. I do think I got the travel bug again though…

Have you ever been to Key West?

Pin for Later:

Photos by Ryan Carpenter.