Key West, Florida sign on beach

If you need a latitude adjustment, this Key West, Florida travel guide and four-day itinerary highlights the top things to do – a perfect destination for emptynesters, couples, friends and the entire family.

I am perfectly content to sit on a beach with a book and a beer (or a fruity cocktail). However, this trip over Labor Day weekend was my husband’s and my first time to Key West and we wanted to explore the island. If you’re a first-timer, here are our recommended top things to do in Key West.

Of course, these are only suggestions. It’s Key West. So you really don’t have to do anything.

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Tips on the best places to stay, play and eat in Key West

Key West, Florida is the perfect destination for everyone. This four-day itinerary highlights the best places to stay, play and eat in Key West.

Day 1: Top things to do in Key West – arrival, hotel, island orientation, Duval Street

Top things to do in Key West: aerial shot

Since we were limited on time, we flew directly into Key West so didn’t get the opportunity to drive over the Seven Mile Bridge. Definitely going on a repeat visit so will fly into Miami and take the scenic route next time.

We elected not to rent a car on our visit to Key West as we thought we’d walk or grab a Lyft if needed (airport-hotel). Turns out, we pretty much covered the entire island on foot. I’d give Key West a walkability score of 10 out of 10…even when we got caught in a brief rain shower (easy solution – ducked into the nearest happy hour – it’s always 5 o’clock somewhere).

Best place to stay in Key West: The charming and historic Eden House hotel

Top things to do in Key West: Stay at a quaint resort like Eden House
Book directly with Eden House and save 15% off lowest rate (and waive the resort fee).

Normally, I prefer oceanfront properties, but could not resist Key West’s historic, charming, and intimate Eden House. How could anyone with its private front-porch swings and hammocks? Eden House origins dates back to 1924. They offer a variety of room styles from a private room to an apartment to a two-story loft and two-bedroom units.

Check out more photos from our hotel experience: The best Key West boutique hotel option: The historic and charming Eden House.

Top things to do in Key West: Eat

Update: I am so disappointed the best restaurant in Key West is closed. I’m not sure if it’s permanently closed as a result of the pandemic or if it’s a temporary seasonal closure. I will still keep my recommendation in here in the event Bien Key West reopens.

Our hotel was just a few minutes away from the Key West airport and just around the corner from Bien restaurant, which our Lyft driver recommended.

Don’t let the unassuming, casual renovated gas station look deter you. This top-ranked Caribbean-Cuban restaurant deserves all the accolades (we were repeat customers). Dining at Bien was definitely one of our top things to do in Key West.

Bien restaurant West Caribbean bowl

Bien restaurant – #14 West Caribbean Bowl

Our favorite bowl was #14 on the menu (pictured above) – West Caribbean Bowl; jasmine rice smothered in black beans, salsa, mozzarella, cheddar cheese, sour cream and jalapeños with chicken thighs. A casual and affordable dining experience with flavorful dishes – order from the counter for takeout or there is limited al fresco dining with ceiling fans and misters to keep you cool on the warm days.

And if Bien Key West is closed, I will definitely attempt to recreate this dish at home.


Top things to do in Key West: Duval Street

Now every travel guide must feature Duval Street on its top things to do in Key West. It was a short walk from our hotel and we encountered several roosters on the way (thought I was back in Kauai). A

Mac and cheese happy hour in Key West
I am always on a quest for the best mac and cheese, so was naturally drawn in for
Bagatelle’s $5 happy hour lobster mac and cheese appetizer.
Top things to do in Key West: Mallory Square

Top things to do in Key West: Mallory Square

We eventually made our way to Mallory Square. It’s the best place in Key West to watch street performers, boats, people, and, of course, the iconic Key West sunsets. We ordered daiquiris first from a cocktail truck (bartender had been slinging frozen cocktails for 30 years or so) and found a prime location with a great view.

15% off at

Day 2: Things to do in Key West – sundeck, Southernmost Point, Hemingway home and polydactyl cats, Kapok tree, key lime pie, Sloppy Joe’s

The Southernmost Point in the Continental US is in Key West buoy

Top things to do in Key West: Relax poolside

We started Day 2 in Key West relaxing and reading on Eden House’s sundeck that overlooks the courtyard pool (pretty quiet and we were the only ones there that morning).

Eden House sundeck overlooking pool in Key West, Florida
View of courtyard pool

Things to do in Key West: Southernmost Point Buoy

The Southernmost Point Buoy is a popular photo op in Key West.
So disheartening to hear that vandals nearly destroyed one of the most iconic landmarks in Key West: The Southernmost Point Buoy. I’ve learned that a similar Northernmost Point Buoy is located in Minnesota’s Northwest Angle. Planning to visit that remote location later this year. It’s an extension of my Minnesota State Parks Challenge.

The Southernmost Point Buoy marks the southernmost location in the continental U.S.; only 90 miles to Cuba. At 18 feet above sea level, it is the lowest latitude land of the contiguous U.S.

Expect a bit of a line to take a “I was there” photo. But everyone was very patient and offered to take photos since selfies couldn’t quite capture it all. As you can tell, it was a bit windy and misty this day.

Things to do in Key West: Ernest Hemingway Home and Museum

Ernest Hemingway Home in Key West is a top place to visit
Ernest Hemingway Home and Museum

Ernest Hemingway Home and Museum is near the Southernmost Point. Key West is where the Nobel Prize winner called home for 10 years. You can wander the gardens and the house yourself, but recommend getting a guided 30-minute tour to learn some cool facts.

Ernest Hemingway Home and Museum polydactyl cats
The Hemingway Home cats pretty much have free roaming rights

Ernest Hemingway’s polydactyl cats

Our tour included meeting some of the ~50 polydactyl cats (about half have five or six toes per paw). We learned that Hemingway named all his cats after famous people.

Open 365 days a year; 9 a.m. to 5 p.m.; the Hemingway Home accepts cash only ($14 adult; $11.30 ages 6-12). Check their website for the most updated hours and costs.

Free things to do in Key West – The Kapok Tree

The Kapok tree landmark is one of the free things to do in Key West.

During our walk, we came across The Kapok Tree. The sacred tree of the Mayan people can grow to 130 feet or more. They believed that souls of the dead climbed a mythical kapok with branches reaching into heaven. You can find it on the corner of Whitehead and Fleming streets in Old Town Key West in front of the courthouse.

Key lime pie is one of the best things to do and eat in Key West

Key lime pie in Key West

And, of course, we had to stop for a slice of key lime pie. Pretty sure you can find a place that serves this on nearly every corner. Not pictured: We also tried delicious conch fritters during our happy hour pub crawl.

Take in live music at the iconic Sloppy Joe’s in Key West

Live music at Sloppy Joe's in Key West, Florida is at the top of things to do

We ended our evening with some great live entertainment at the infamous Sloppy Joe’s on the corner of Duval and Green Street, where Ernest Hemingway was a frequent patron. Sloppy Joe’s serve food and cocktails, and have a retail store if you’re looking for souvenirs.

Day 3: Things to do in Key West – Fort Zachary Taylor Historic State Park Beach, sunset sail, Green Room music bar

Put a sunset sail at the top of your Key West list of things to do

Fort Zachary Taylor Historic State Park

We spent our last full day at the beach at Fort Zachary Taylor Historic State Park – known locally as Fort Zach. Need a return visit as there is so much more to do there. A small entrance fee is required for cars, bikes and pedestrians, we walked so only $2.50 per person.

Bring water shoes or sandals as the beach is a little rocky with pebbles; also good to note there is no lifeguard on duty. We rented beach chairs and an umbrella, and they also offered snorkeling gear. While you can picnic in the area, alcohol is not allowed on the beach. However, you can order drinks as well as food at the Cayo Hueso Café, where they offer outdoor seating and a small gift store in case you need an extra beach towel or sunscreen. The cafe is open 10 a.m. to 5 p.m.

Take a sunset sail in Key West – one of our favorite things to do

Sunset sail in Key West was one of our favorite things to do

Our sunset sail with Floridays was a last-minute decision because the forecast had predicted rain. And turned out to be the highlight of our trip – definitely make a sunset sail a priority on your list of things to do in Key West. While they offer a variety of adventures, we chose the sunset sail with champagne, margaritas and beer option. They also offered soft drinks and water.

Our Key West sunset sail crew included a captain and a first mate. Pictures of the stunning sunset don’t do it justice – it’s something you need to experience. It does get a bit windy so wouldn’t recommend wearing a dress, and they also require shoes with rubber soles (no heels). We even saw a dolphin (although in my pic above all I managed to take a photo of was my finger). Highly recommend taking a sunset sail in Key West – one of the best things to do.

Box of DEET-free mosquito repellent wipes
I cannot recommend Aunt Fannie’s DEET-free Mosquito Wipes highly enough. I am a mosquito magnet, but they stay away when I apply these wipes. My link does include a referral code, which means I’ll receive a small compensation – but I only recommend products and services I would use myself. And I definitely use Aunt Fannie’s – I bought a case of them and give to family and friends. And they smell good and are good for the environment – biodegradable and no harsh chemicals!

See my full review of what to pack on a day hike.

Stop in for live entertainment at the Green Room

Live music at The Green Room is a must when looking for things to do

After the tour, we stopped at the Green Room (recommended by my sister-in-law), an eco-pub on the corner of Green Street and Duval. The environmentally friendly bar offers live music, unique frozen drinks, an art gallery on their wall and merchandise. A portion of the proceeds benefit Key West environmental initiatives.

Day 4: Things to do – sundeck, brunch next door, flight home

Key West brunch always makes the top things to do list
Things to do in Key West: brunch

Things to do in Key West: Brunch

Had a mid-day departure so spent our last morning on the sundeck and enjoyed brunch next door at the fabulous Azur. Sometimes the best things to do in Key West are pretty simple. Pictured above is a spinach and feta frittata and an apricot-almond oatmeal brulee. We ate there twice – first because of the convenient location and Eden House offered a discount and then returned because the food was so amazing. As was my grapefruit mimosa, which is not pictured.

Key West bucket list – more things to do next time

We conquered quite a few adventures on our four-day vacation to Key West, and there’s so many more things to do so we made the following list for our return trip. Can’t wait to visit Key West again to check off some of these bucket list items.

Sunset sail: perfect things to do in key West

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Key West travel guide and things to do

A four-day itinerary for Key West, Florida - recommended things to do and see
Ernest Hemingway Home

Top things to do in Key West collage


Twin Cities-based blogger sharing memorable emptynester, solo, family and girlfriend-getaway adventures, as well as my day hiking adventures (including all 66 Minnesota state parks), latest book reviews, and updates on my quest for the best adult mac and cheese. Also two WIPs: historical fiction and psychological thriller


  1. Hi Karen! What a nice post 🙂 I’m a huge Hemingway fan so it would be amazing to visit his house one day! But also, who knew key west had such amazing food??? Thanks for sharing!

    1. Hey, Lannie! Thank you! I absolutely loved our Hemingway House tour and, well, everything about Key West. I’m sure you’ll love it too!

  2. Love those photos from your sailing trip. Absolutely gorgeous. Hemingway’s house looks great too. One of these days I’ll get to try a key lime pie. They look delicious. Great round up Karen.

  3. What a great post! SO many things to do and see. We have been to Key West several times and you have captured so many of our favorites. Thank you for the trip down memory lane as well!

  4. I love your choice of hotel for this trip! I really wasn’t aware of what the options were to do in Key West. You have totally opened my eyes to a new place to explore.

  5. What a wonderful post about Key West. As a Florida native, I can tell you this is an excellent guide. I loved your photos too!

  6. We’ve driven to Key West once from Orlando and crossed the 7 mile bridge. It took some time due to traffic and it’s on my 2 lanes, but gorgeous! Key West is a great spot and has something for everyone.

  7. My daughter would love Hemingway’s house because she is a huge cat lover. I’ve always wanted to go to Key West. It’s been added to the list.

  8. I’ve always wanted to go to Key West and see the Hemingway stuff. I hope to tack it on to a Disney road trip one year, but I keep thinking I should wait until my daughter is just a little bit older. The Eden House looks like the perfect place to stay. And yes, I’m having some Key Lime pie!

  9. I’m in love with the Eden House! Would love to be relaxing on one of those porch swings right now. We’re planning a trip to Key West later this year, if all goes well. Will definitely add the Ernest Hemingway Home and Museum to our itinerary.

    1. I hope you get the opportunity! We normally like to stay on the water, but I could not resist the Eden House. It was so charming and loved its history. I hope your trip to Key West works out!

  10. I would love to visit Key West. And I am so happy to see that you can walk through the entire island. My kind of viewing of a place. Oh and I would love to sit in one of those balcony rocking chair.

  11. Oh, this brings me back to my old stomping ground when I lived in S. Florida. I would go to Key West at least once a month! I miss it and want to return. Many of your photos are ones that I took over 25 years ago, meaning somethings are the same which I am happy to see! It’s time to plan a trip to Key West in our future travels.

  12. We were recently talking about heading to Key West during our winter vacation. We usually head to Florida in January or February but lately the weather has been cooler than normal so we were thinking of heading further south, to Key West. This will come in handy so thank you!! And what trip to Key West would be complete without Key Lime Pie?! It’s my husband’s favorite!

  13. I’ve always wanted to visit Key West. I’ve traveled to Florida so many times, but I haven’t been yet. You’ve suggested some great things to do including the Ernest Hemingway Museum and I’d love to stay at Eden House too.

    1. I hope you get the opportunity to visit Key West. There are so many fun things to do and see. We loved our tour of the Ernest Hemingway Museum and our stay at Eden House.

  14. We’re prioritizing travel within the US this year and Key West is my top pick for our summer vacation! Thanks for sharing this itinerary!

  15. Gosh, it’s been quite a while since I visited Key West, and I can hardly remember what we did on our trip! I’d love to go back and take your guide along with me :).

    My brother and sister-in-law just went in October for their honeymoon and stayed on a house boat, and I remember them talking about visiting the Ernest Hemingway Home and Museum – and all of that cats! I’d like to see that next time too.

    Xx Sara

  16. What a beautiful place. I haven’t been to Florida but it looks lovely. And I love key lime pie so this seems like the perfect place to start. Visiting Ernest Hemingway’s house would be amazing, and fun to see all those cats

    1. Thank you! Key West is one of our favorites – so much to do and see. Can’t wait to return. The Hemingway polydactyl cats were really cool…so many!

  17. Key West has been on my go-to list for awhile and I was hoping to go now– but rooms are super expensive– everyone else wants out of the COLD– so maybe end of May would be better price wise! Great guide!

    1. Thank you! Key West can get a little spendy. We loved our stay at the Eden House as it had a kitchenette in the apartment which helped the food budget.

  18. Fab post Karen! Key West looks like a really fun area to explore and EAT ALL THE THINGS!! Especially Key Lime Pie.

    I’ve love to meet all the kitties at Hemingway Home. I love to see when they have the run of the place.

    Also, those sunsets!

    1. Thanks, Josy! Key West is a really fun area to explore. The key lime pie and sunsets are fabulous. And the Hemingway polydactyl cats are pretty cool.

  19. This article makes me happy and sad at the same time. I almost went to Key West but then, I got called into Jury Duty and missed out on the whole trip. But these photos make me feel like I’m kind of seeing it, plus lot’s of great info for when I do finally visit.

  20. I used to come to this part of Florida as a kid but haven’t been back since then. It looks like there are some great things to do here for adults too!

  21. Your four day itinerary for things to do in Key West Florida is awesome! So many great things to do for families with kids!

  22. What a spectacular weekend trip! We were just there in September of 2020; visited Dry Tortugas, but on our return, Tropical Storm Sally arrived – so we couldn’t ride our bikes around Duvall Street – it was flooded. Great recap and ideas here!

  23. Key West looks like such an interesting place to visit! I’d love to go one day. I’d especially love to visit the Ernest Hemingway Home and meet the cats! Thanks for the great guide!

  24. Your four-day Key West Itinerary is perfect for empty-nesters. Hemingway’s house is high on my list of must-sees. I love his books. Have you read The Paris Wife?

  25. I haven’t been to Florida in a while but it’d be awesome to get to go back to visit sometime — so many fun + pretty places to visit!

    I’d be allll for private front-porch swings/hammocks? (I’d love to set one up in my backyard someday if I ever get a house!)

    I really really hope Bien Key West opens back up — that food looks and sounds absolutely amazing! (If you’re able to recreate, pleaseeee share the recipe! 😛 )

    1. I really hope Bien Key West reopens also. The food was amazing – will definitely share if I can recreate the dish. We loved the private hammocks and front-porch swings at The Eden House.

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