If you are looking for the best tropical escape that the continental United States has to offer, then this Key West itinerary is exactly what you are looking for! I recently got back from an incredible trip to this Florida paradise for the first time. Here are my tips and tricks and the best things to do while in the Florida Keys.

If you love watersports, fresh AF seafood, key lime pie, gorgeous beaches, this island paradise is definitely for you!

Key West offers something for everyone. It felt like the perfect mix of slowing down and relaxing by the water, drink in hand, with plenty of history, culture, and adventure. Just the way I love to travel!

Hey, if you prefer to watch a video, I’ve got this entire trip in vlog form here:

Getting to Key West

To get to Key West, Florida, you’ve got two options. The easiest is to fly into the Key West Airport and go from there. That being said, because it is a smaller airport, the fares to fly there can be a little pricer. You can also fly into the Miami airport, rent a car, and drive down to Key West. The drive from Miami takes about three hours, FYI. Its a gorgeous drive and you can check out the views along the seven mile bridge as you go!

We decided to do the latter, and make a stop for a couple nights in Duck Key. Make sure to check out that post here for more Florida Keys travel ideas!

Where to Stay in Key West

On my trip to Key West with my girls in Babes that Wander, we stayed at the Southernmost Beach Resort, and loved every bit of our stay! This hotel is located in Old Town Key West. It’s a super easy walking distance to Duval Street as well as the beach.

Southernmost Beach Resort is a newly renovated beach resort in Key West and boasts 3 pools, multiple bars, a private beach as well as a sandbar, private beach, tanning pier, fitness center, and a spa. They also have tons of scheduled activities on property, such as morning yoga, wine tastings, live music, and, something that looked so interesting to me….”Salsa and Shots.” Check out their current events here!

Key West Itinerary: How to Spend 2 Days in the Keys!

Day 1: Key West Itinerary

The first thing we did when we arrived was check into our hotel at Southernmost Beach Resort. After dropping our bags in our room, we headed down to the resort’s Pineapple Pool where they had some live music. After a quick dip, we walked down to the resort’s Beachside Cafe for lunch. This is also where the resort’s private beach is located. You will find that the Keys doesn’t have a ton of beaches, so it was nice to have access to the lounge chairs on this white sand beach!

The Beach Cafe is pretty delish! Even if you’re not staying at Southernmost, it is definitely one to check out and it has a great beach view. Definitely try the Key Lime Colada, it is to die for!

There are so many great Key West landmarks around the Southernmost Resort, so we took the afternoon to explore…

Not to be confused with our hotel, the Southernmost Guest House is a very quaint and historical option for accomodations in Key West. Check it out if you prefer a boutique hotel that is adults only. They also have a bar that (according to them) is the closest you can get to Cuba. This is the southernmost home in the continental US, and was built in 1897. It definitely is rich in charm! Definitely grab a mojito from their oceanside bar.

The Key West Butterfly Conservatory

Right across the street from our hotel was the Key West Butterfly Conservatory. This is definitely a spot to check out, and it will probably take you 30-45 minutes tops to see it. This small topical oasis is home to 50-60 different butterfly species as well as 20 different exotic bird species from around the world. Be advised though, this is climate controlled, ie, they keep it super humid in here. Make sure to stay hydrated here, especially in summer!

I highly recommend checking out the Key West Vacation pass. Its a booklet that can help you potentially save hundreds of dollars on your Key West vacay, and it contains savings for the Key West Butterfly Conservatory and most of the other activities I’ll be sharing, plus more! Get yours here.

Ernest Hemingway Home

After our visit, we took a short drive to visit the home of Ernest Hemingway in the Key West historic district. Hemingway and his wife lived in this beautiful French Colonial style home during the 1930’s. It was in this home that Hemingway wrote some of his most acclaimed works, including the non-fiction work Green Hills of Africa (1935), the 1936 short stories “The Snows of Kilimanjaro” and “The Short Happy Life of Francis Macomber”, and the novels To Have And Have Not (1937) and Islands in the Stream (1970).

I loved walking around the home and learning about its history, but my favorite part had to be the cats! There are approximately 60 polydactyl (six-toed) cats who live here and are the descendants of Hemingway’s cat, Snow White. The custodians of the home have continued the tradition of naming the cats after famous people. I made friends with this cutie, Etta James.

The Hemingway House is open daily 365 days a year from 9am-5pm for walk-in visits and admission is payable in cash only. This is definitely one of the must-stop places in Key West!

Next, we headed out toward the water. If you’re looking for a fun photo opp, make sure to check out the Southernmost Point, located on the south side of Key West. This is the southernmost point of the continental US…there are only 90 miles to Cuba from this point. Be warned though, there’s always a long line of tourists waiting for their turn to snag a photo next to this landmark.

Sunset Cruise with Fury Watersports

Of course, no Key West itinerary is complete without some water activities. One of my favorite things we did on this Key West itinerary was the Sunset Party Cruise by Catamaran. This is basically a “booze cruise,” but it was a great time! Definitely hang out on the open air deck for the best views and vibes.

We had such a blast enjoying the live band and we definitely danced the evening away as we cruised along into the sunset. This cruise includes an open bar and snacks. The open bar essentially consisted of wine, beer, and pre-batched margaritas. The bubbly was definitely flowing and my glass was never empty; the whole staff made sure we had a blast! Make sure to bring cash to tip, as these folks do make their living similarly to restaurant workers.

Another great sunset option if you’d rather stay on dry land is the world-famous Key West Sunset Celebration in Mallory Square. This is a nightly arts festival that happens at Mallory Square Dock in Key West, Florida. Each night around two hours before sunset both locals and tourists alike flock to the docks to experience a multicultural happening and to watch the sun sink into the Gulf of Mexico. This is definitely a great, free way to enjoy Key West at sunset!

Dinner at Half Shell Raw Bar

After all that dancing and bubbly, we needed some dinner! Half Shell Raw Bar is an iconic restaurant that any seafood lover must visit while visiting Key West. This spot is casual and the staff is super friendly, plus you can’t beat the oceanfront views as you feast on their daily fresh catches.

This spot has been a local’s favorite for years, and its clear to see why! We had some incredible oysters, lobster, crab, and shrimp that night and this seafood lover was in heaven.

Day 2: Key West Itinerary

Breakfast + Cuban Coffee at Ana’s Cafe

You know I couldn’t create a Key West itinerary is complete without partaking in some Cuban coffee. One thing I loved about our location at Southernmost Resort was the fact that Ana’s Cafe was right across the street. When you’re traveling with your girls, you can have some late nights, which means a strong cup of coffee is in order! I will admit, I’d never tried Cuban coffee before this trip. My need to try it dates back to 2013 when I saw this one episode of Kourtney and Khloe Take Miami….if you know, then you know 😉

Ana’s Cafe was my spot every morning of this trip and I thoroughly enjoyed their Cuban coffee and breakfast. If you love coffee, its definitely worth trying out at least one of these Cuban coffee stands. The coffee ordering experience is totally different, but this article helped me understand the different coffees and how to order.

There’s also the iconic Cuban Coffee Queen, which is another famous coffee stand in Key West.

Morning Yoga with Salute to the Sol Yoga at Truman Waterfront Park

After the craziness of the previous night’s festivities, the Babes definitely needed to find our center again. Salute to the Sol Yoga was just what we needed to start day two off on the right foot.

If you’re headed to the Keys, you can book a customized waterfront yoga session with one of their certified instructors. You can also join them every Sunday, Wednesday, and Saturday at 8:45am at The Perry Hotel & Marina Key West for an all-levels vinyasa class on their event lawn!

Lunch at Blue Heaven

One of the highest rated spots for breakfast, lunch, or dinner on the island is Blue Heaven. This restaurant is known for their American/Caribbean cuisine. This place has tons of charm and character as well and really has a true island vibe. Breakfast + lunch is served on a first come, first served basis and dinner has limited reservations available. Come for the amazing food, stay for the fun live music!

Fun on the Water

There are so many great options for water excursions when you’re in Key West. Between snorkeling, kayaking, wind surfing, parasailing, jet skiing and more, there is so much to choose from. On our second afternoon, we booked both a snorkeling and jet skiing excursion back to back. This amount of watersports is a lot for one day. If you want to have a more leisurely day, maybe just pick one to keep yourself from getting too worn out.

Double Dip Snorkeling Tour with Fury Water Adventures

For our first water adventure, we headed back to the Fury docks to get on board one of their high-powered catamarans for the Double Dip snorkel tour. This excursion lasts 3 hours and includes snorkeling gear, sunscreen, and beverages. After you are done snorkeling, they give you the option to enjoy some beer and wine as well.

On this excursion you stop and snorkel at two different spots along the only living coral reef in North America. The Fury staff is also so knowledgeable and instructs you on best practices to enjoy your time snorkeling while doing no harm to the reef.

I will say, if you are prone to sea-sickness, bring some sea bands with you on this trip. Usually, I don’t have issues, but I felt a tad nauseous when the boat wasn’t moving as the water was a little choppy that day.

I also highly recommend this underwater smartphone case if you’re like me and want to document your underwater adventure! If you’re skeptical about it being fully waterproof, so was I, but not one drop of water got inside while I snorkeled. Plus, it has a handy wrist-strap to make sure you can’t accidentally lose your phone.

Jet Skiing with Barefoot Billy’s

Probably my favorite activity in this Key West itinerary was jet skiing with Barefoot Billy’s. I had never jet skiied before, so I was a little nervous! Their instructors walk you through everything you need to know to have a fun and safe time out on the water.

However, if you’re under the age of 35, be prepared to take a test. Per Florida law, you are required to take a short test to obtain a temporary boating license in order to jet ski. The test is open book and multiple choice, but it did take us about 30-40 minutes to complete. No surprise, we all passed with flying colors because the Babes that Wander are not only beauty but also brains!

On this 90 minute tour, you will circle the island as your guide takes you to all the best stops along the way. Ask for David, he was awesome and made the entire experience so fun…he even spent about 20 minutes directing us so we could get this fun group shot. Of course, as with all these activities, make sure to tip your guides! In this case David had venmo, which made it super easy to take care of him since he took care of us.

By the end of the tour, I felt like a jet-ski pro, much like I did after we tried snowmobiling in Bend last January. What can I say…I’ve got a need for speed!

Dry Tortugas National Park

If you’re looking for an afternoon activity that doesn’t involve being on the water, check out Dry Tortugas National Park. This national park lies 70 miles from Key West, making it one of the most remote US national parks, so this may be suited to more of a day trip. The national park service details all their recommended forms of transportation to Garden Key on their site.

I wish we would’ve had time to trek out and check out Fort Jefferson. This fort is the largest all-masonry fort in the United States and was built in 1846 to protect the US’ gateway to the Gulf of Mexico. You can also camp in this national park, but be advised, you must bring ALL supplies you will need with you, as there is nowhere to purchase water, food, beverages, or any other supplies on the island.

Key West Shipwreck Museum

Another great afternoon outing option is the Key West Shipwreck Museum. This museum takes you back in time to explore the maritime history of Key West and how Key West became the richest city in the United States. The reefs around Key West made sailing treacherous, so the museum utilizes actors, films, and artifacts from the 1985 rediscovery of the wrecked vessel Isaac Allerton, which sank in 1856 to explore this piece of Key West history.

Dinner at the Docks Stock Island

For dinner that night we went to a new restaurant, the Docks Stock Island. Every local person we told that we had reservations here gushed either about how good it was or that they had heard it was amazing, so I knew we were in for a treat. This restaurant serves up freshly caught seafood in a modern and sleek space, right in the marina. Currently, they only take walk-ins and they are open 7 days a week from 12pm to 9:30pm.

We ordered up a bunch of their share plates to start, including the Tuna Carpaccio Pizza, Figs in a Blanket, and, of course, oysters. I ordered the Cauliflower Seafood Bake which was so delicious and heary, which is exactly what I needed after such an action-packed day. Their cocktail menu was also bomb, make sure to check out the Key Lime Catel, it was so good!

Drinks + Drag Show at 801 Bourbon Bar

You can’t come to Key West and not enjoy the nightlife, especially the gay bars. After a delish dinner and a quick outfit change into something more fabulous, we walked from our hotel down toward the stretch of Duval Street between Angela and Petronia Streets. We knew we were headed in the right direction when a man on bike exclaimed, “Yas queens, werk!” as he passed.

Yes, that happened. I mean, we are pretty fabulous!

Key West is definitely known for being very LGBTQ+ friendly and thus has fabulous drag shows. We decided to try out the show at 801 Bourbon Bar on Duval St. and it is not to be missed. They host two shows nightly, at 9 and 11pm. You can make reservations online here, and I highly suggest springing for the VIP section so you can be front row and center. The queens who performed that night were incredible and we had such a blast. Make sure to come with plenty of bills to throw!

That is my complete 2 day Key West Itinerary! I hope this gave you some great ideas of what to do on your trip. If you’ve ever been to Key West, make sure to comment below your favorite spots and activities so that I can try them next time, because I’ll definitely be back someday.

Special thanks to the Florida Keys Tourism Board for giving myself and the Babes that Wander such an epic opportunity to see the best that the Keys has to offer! Definitely check out their site for even more info for planning your trip to Key West or anywhere else in the Keys.

Check out this short Web Story for quick points on this post here!

Key West, Florida FAQ’s

florida keys itinerary florida keys travel guide key west key west florida key west itinerary key west travel guide key west travel tips things to do in key west florida