Four Days in the Florida Keys

By Kate Riley February 25, 2021

In late February of 2020, I took a trip to the Florida Keys. It was two weeks before shelter-in-place orders went into effect in California in March, and I remember when I arrived home and landed in San Francisco airport feeling like oh wow, this is getting serious. The next week we were all mandated to stay home. Talk about a pendulum swing, from feeling the total freedom of exploring magical islands to the restrictions of a hometown lockdown.

It’s been a full year since my trip to the Florida Keys. I’ve been to a lot of special places on this earth, but there’s some sort of magical dust that floats through the air and makes the atmosphere in the Florida Keys extra appealing. It’s not just the location, it must be something to do with the history of the region and the cultures that mix in that part of the world.

The Florida Keys are a series of coral archipelagos in the southernmost part of the continental United States, they get their name from the Spanish word cayo, meaning small island. I covered a lot in four days there, spending most of my time exploring Key West and one day making the long drive to Key Largo and back.

On arrival, the laid back vibe of Key West was instantly apparent. I dropped down in Key West just a few hours before sunset and headed to Mallory Square. I was greeted with the sounds of steel drums and slack key guitar and the most amazing sunset.


Key West is small and easy to navigate, most people get around on a bicycle, scooter, or on foot. The sounds of coastal breezes in the swaying palm trees paired with the whirring of air conditioners was the background music I heard as I explored. Here’s a glimpse of what I saw and few of my favorite stops.


Duval Street is famous but filled with tourists. It’s lined with shops and bars and I didn’t enjoy it very much during the day because of the crowds…



…  it’s much more fun in the evening when it’s balmy and you can enjoy live music while you sip a rum drink.

Mallory Square is a popular destination for the sunset, but equally appealing is the seaport walk along the harbor with all the boats and open air restaurants located along the meandering wharf, all playing live music.

I stopped in to see the Ernest Hemingway House and really loved the architecture, especially the second story wraparound porch. Lucky Ernest to live in such a beautiful home! Below is a picture of his personal office. He loved cats and I spied about a dozen on the property!

Taking a self guided tour of the Key West Cemetery in the Old Town is a thing, it’s there you’ll find a lot of history and a few comical gravestones.


Another worthwhile stop was the Butterfly & Nature Conservatory, walk around inside where exotic birds and butterflies are flying all over and don’t miss the cute flamingo couple in the middle.


What about the other Keys? There are so many! I’ve always wanted to drive this highway between Key West and Key Largo so I spent a full day on a road trip back and forth. It’s 100 miles from the 0 mile marker in Key West to Key Largo.

I was feeling ambitious so I drove from Key West to Key Largo in the morning and all the way back to Key West in the evening. I didn’t get to see and do everything the other Keys have to offer, but I stopped at several famous spots. Much of the appeal for me was just driving the highway, it’s something I’ve always wanted to do!

I rented a car in Key West then I drove to Key Largo enjoying the morning views over the Seven Mile Bridge and arriving two hours later in Key Largo for an early lunch at Mrs. Macs, located at the 99 mile marker. There are two locations, I chose the larger one and it’s true they have the tastiest fish (get the fresh catch!) and it’s there I developed a serious crush on the floor.



My next stop after lunch was to feed the tarpons at Robbies is Islamorada at mile marker 78. Pay a few dollars and head out to the docks to feed the tarpons, they are huge! But watch for the pelicans, they’re swarming everywhere and very greedy. Robbie’s also offers boat rentals if you feel like a water adventure and there are artisans on the property selling local goods.


I stopped in Islamorada to spend the afternoon, to see Morada Bay, and to visit the local art shops. It’s here where I photographed this art print which I named ‘Serenity Now’ because… obviously. :)


Across the highway I stopped in for a taste at the famous Florida Keys Brewing Company with its very colorful and creative interior. I loved their rainbow resin countertops and now I want a BEER sign made with bottlecaps too.



I wanted to make it to the Sunset Grille at mile marker 47 in Marathon Key for dinner and a sunset. It sits right at the edge of the Seven Mile Bridge. I arrived early because it’s a popular place with swimming, great food, live music, and a view of the bridge. I stayed for almost two hours I loved the vibe so much, and wow what a sunset!

I left after sunset and made it safely back to Key West that evening. It was a 200 mile road trip but what an incredible day!

I spent my last day biking around Key West but having to pause every minute because…. the real estate. I can’t even with the island style homes and their bright colored shutters surrounded by lush plantings and swaying palm trees. Dreamy!



Lodging is really expensive in Key West but I found a budget alternative. I stayed in a shared female bunk room at NYAH resort and just stored everything in a locker. It was perfect, they had a pool, free bicycles, and breakfast every morning and the hotel is centrally located within walking distance of everything in Key West.


So that’s my glimpse of a trip to the Florida Keys, it was such a fun place to hang out and I can tell it’s an amazing place to live! The Keys captured my heart, I look forward to a return someday.

My next trip to Florida will be a road trip along the Gulf to see Fort Myers, Marco Island, Naples, Bonita Springs, Sanibel Island, Clearwater and St. Pete, so if there’s anyplace I should stop on that road trip, let me know!


  1. I loved this trip re-cap, thank you for sharing your beautiful photos! We had a stop in Key West on a cruise with my grandparents in the early 90’s, my sister and I were 15 & 14 and they let us explore the island on our own but we got turned around/lost and barely made it back to the cruise ship on time! My grandma re-calls the agony we put them through as they waited and waited, what they were going to tell our parents had something happened to us, etc. We didn’t even get in trouble, they were thrilled to see us. :)

  2. Maybe skip fort myers… there’s honestly nothing worth seeing here lol! Clearwater/st Pete are nice and so is sanibel island (but very sleepy). Everything else would be perfect to skip right over!

    • Downtown Ft. Myers is beautiful! First Street is the historic district with great restaurants and shops. A fun place to people watch and have happy hour at Izzy’s where there’s “Buck a Shuck”. One dollar fresh oysters!!!!

  3. Next time you go, you must visit the Marathon Community Theater on Overseas Hwy.! It’s quirky and fun. They have beautiful artwork all over the walls and a raffle at intermission. Also live music by a lovely lady whose name I don’t recall but we called bouncing Betty. Actors were perfect! Oh, and the Turtle Hospital also on Overseas Hwy. You see the effect pollution and climate change has on these huge creatures.
    I am anxious to return after everything settles down. That Key West vibe…sigh

    • You should have seen the keys in the 70s,less tourist, more laid back and the original over seas highway that were just 2 lanes and not much more.

      • The first time I was in KW was in 1960. I was 4 years old and was bitten by the keys. Been going there ever since. KW and Stock Island were a lot of dirt roads. Nothing but laundry mats and Liquior stores

  4. Definitely stop in Sarasota and Siesta Key. Siesta Key beach has been named the most beautiful beach in the US several times..

  5. Check out Boca Grande on Gaspiralla Island. Also Fort Myers has the Thomas Edison and Henry Ford museums and estate tours…really fascinating and educational.

  6. I would visit The Chesapeake in Islamorada!! Theatre of the Sea is hands down the best place to swim with dolphins amongst many more!! Mangrove Mikes is a legendary place to eat there as well as Bentley’s. Hawks’s Cay is a momentous place with dolphin encounters as well near Marathon.

  7. The photos and sounds are just as I imagined. Never been to Key West but I really want to now.
    Thank you

  8. We really liked Marathon key. We kayaked through the mangroves, also went fishing.

  9. Looks like a wonderful vacation, Kate! Beautiful pictures, too. For your next Florida trip, I would recommend stopping at the Mucky Duck restaurant on Captiva (which is the northern tip of Sanibel Island) for drinks and a beautiful sunset on the beach. Also, the Ding Darling wildlife refuge on Sanibel Island is a very scenic place to kayak, canoe or standup paddleboard through the mangroves where you can view lots of wildlife. Enjoy!

    • Great recep! You definitely captured the feel of the keys and passed it on to us. I totally agree with the special atmosphere of the keys, something very close to the feeling of the aloha spirit of Hawaii. 💕

  10. I loved reading about your adventure. We went to the Keys 2 years ago and stayed in Key Largo and did a day trip to Key West! Seeing all of your gorgeous photos just brought back great memories!!!

    • Go to manasota key Beach or Venice Beach for shark teeth hunting. Sanibel for the best shelling. Also on sanibel get a ice cream at pinocchios

  11. I suggest Anna Marie Island, just north of siesta key, which is less commercial. Plus, pine Island is different more like old Florida. Naples is very expensive. If you take a budget flight could fly into Sarasota airport.

  12. I lived in Key Largo 20 years I can definitely relate!! That was some awesome reading n pics to take me down memory lane!! I worked 30 years for FLA Keys Aqueduct Authority the water company in the Keys!! The Keys have always been awesomely wonderful!! Thank you!! Susan Gannaway I miss the sunsets the beautiful sights and sounds!! Sue

  13. Ft. Myers Beach is a blast. Make sure you stop at Doc Ford’s Rum Bar And Grill. Food and drinks are sublime

  14. If you get to Clearwater, make a trip slightly north to Tarpon Springs. It is an old greek community with sponge diving history, and a tourist destination. Lots of greek food and shops. There are short boat tours down the river to the sea. We are partial to the one that takes you to Anclote Key (unspoiled, no buildings) where you can get off the boat for a bit and walk in the water and pick up shells, you will probably have dolphins swimming in the boat’s wake on the way back. If you want to keep going north I believe you can do manatee tours.

  15. Thank you. I grew up in Florida. Coastal Florida has become encroached in too much urban. I was an island girl. Basic habitat was defined w/out AC, shower outside after our beach or dock swim, gulf’s salty breezes mixed with wake’s rhythm slumbered our sunny, morning rise & sleep, TP was always damp, seasons were defined by the depth of waters on a beach and trade winds, Salty Sal radioed the morning tide times & fishing sights, and those party lines…Keys hold their mystery is true…thank you for your fresh eyes in the coastal wonder of Florida🌺

  16. We were just in the Keys for our 1st time in Jan & loved every minute of it. We stayed in Homestead & drove to the Keys each day, to reduce costs. Islamorada Brewing Company is also a great stop (right down the highway from FKBC). We’re already planning another trip to the Keys in Jan 2022. The rest of the Keys are so laid back that Key West was almost too busy for us, but that’s just us. I highly recommend this gorgeous little archipelago to anyone thinking about it. Thanks for taking the time to write about your trip there!

  17. Cannot miss the Marie Selby orchids in Sarasota, and the Ringling Estate. Elegant like the Deering Estate in Coconut Grove.

  18. I live in Ft Myers. A few restaurants at Ft Myers beach (my favorites) Doc Fords and Parrot Key. If you go to downtown Ft Myers you have to go to The Sky Bar and The Lodge for fabulous martinis and beautiful views. I love living here. A lot of gated communities with heated swimming pools under beautiful Palm Trees. I live in paradise.

  19. I disagree with the others. Fort Myers is funky and lively big Beach, Music Walk Fridays and Art Walk Friday’s. The Edison Estate and Gardens, Boat House Restaurant on the beach or Caloosahatchee River. We love it here.

  20. I highly recommend Siesta Key beach at sunset, beautiful and the locals come out with their musical instruments and play. Also Honeymoon Beach State Island in Dunedin is seriously the most beautiful beach I have ever been too!

  21. I am an active 70 year old female dreaming about a little vacation inthe keys
    I live in Miami and prefer not to drive down there by myself. Company preferred
    Your descriptions of your trip there makes me want to go ASAP
    Thanks for sharing as a solo female traveler!

  22. For those snorkeling lovers, don’t forget John Pennicamp (sp?) Park in Key Largo. Lagoon, snorkeling boat charters, and a “underwater hotel”. Great place to bicycle too.

  23. Just got back from my 5th or 6th trip to Key West. For some reason, I enjoyed it much more this time. It was busy but not insanely busy as it had been in the past because of the China virus. Might be a good idea to check out Marathon Key as well.

  24. Most definately go to Siesta Key. The sand is like flour and it’s absolutely beautiful. I spent several weeks a year there for 20+years and loved every minute.

  25. Loved Key West. I entered the Hemmingway look-a-like contest in 2005. Great time could not buy a drink, the bartenders wouldn’t let you pay. When you entered a restaurant they announced you as “another Hemmingway contestant” and people applaud. Same thing at Sloppy Joe’s Bar. Absolutely great time. Would go back in a minute, but my 83 year old body and wive say maybe next year.🙂

  26. I ‘ve always wanted to visit the Keys . Thank you so much for sharing this delightful and informative article!

  27. Omgoodness!!! These ; are amazing!!!
    I was wondering if you were there again.
    This does look like paradise !!!!;
    You are one lucky girl!!!!
    Miss you !!!!

  28. Sarasota is a must.beautiful beaches.also St. Armands circle is a fun place to visit.lots of shops and restaurants.St. Pete and Clearwater nothing much exciting

  29. We have driven from CT. to Key West for the last 6 years but not this year so your trip was a beautiful reminder of what we love about the Keys! Thanks for transporting me back to our favorite place. We will be back next year! Loved your fabulous photos too!

  30. Stop in South Tampa I for get it’s name but I can see the manatees swimming in warm water from the power plant near by..

  31. Tarpon Springs sponge docks, Siesta Key beach and village, and Venice/ Casey Key are all worth visiting. Moved to Florids in 2009 from Ohio because it’s cheaper to live here than to vacation every year. And,ahhh…. the balmy breezes and extraordinary sunsets…..

  32. Loved reading this. I went the with a couple friends on a fishing trip, and been wanting to do that all my life And go to the furthest southpoint and party on Duval Street. Done it all down there loved every minute of it plan on going back next month

  33. Need to visit Pine Island, St James City we loved it. Some parts make you think of the old florida days. Need to stop at the Ragged Ass Saloon for the best onion rings that we have had in years. The beer is cold and the people are friendly. You can drive to the Island and right before getting to the island you go over and old draw bridge or you can go by boat from Ft Myers, Sanibel Island or anywhere from the gulf. We went only one time by car and the other 99 times by water simply beautiful and what a hell of a way to spend the day.

    • Agree!!! Matlatcha is on the way. Stop at Leoma Lemongroves gallery. Awesome!!!

  34. Katie, this is a well written article with great pics. I enjoyed every word. I also wish you would have found us to make your road trip up the Keys one notch better. We are Key West Adventures. Road trips up and down US1 is our specialty. We rent Jeep Wranglers (optional top down an/or doors off), Polaris Slingshots, and Mini convertibles. Next time try it our way. The sun on your face, the breeze in your hair, and the smells of the fresh salt water as you cross our 46 bridges makes the trip unforgettable!

  35. A big yes to the Edison Ford Museum- it is fascinating and leave more than the 2 1/2 hours they suggest- we had to leave because we were driving to Islamorada and that’s a hike. We stayed at Anna Maria Island at the Beach Cottages- what a gorgeous beach and had the most incredible meal at The Waterfront Restaurant. The fried green tomatoes were to die for along with a jalopeno margarita- yum

  36. Destin and the Emerald coast. I never been and it is on my list. That pink house happens to be my neighbor. That is owner is Tony, he is the visionary behind Fantasy Fest.

  37. We enjoyed your comments and especially the pictures. We have been to Key West a number of times and still enjoy going back when ever we can. We spend part of the winter in Ft Myers 10 minutes from Sanibel. Sanibel and Captiva are definitely laid back with no where near the activity of Key West. Also visit Ft Myers Beach. It’s an old time beach town and s great beach.

  38. Next time don’t leave out Blue Heaven in KW for breakfast, drinks at the bar while listening to live music, and/or especially the best key lime pie you’ll ever eat in your lifetime!!! On the west coast I recommend the quaint Siesta Key!!

  39. Drop in to see Betty at the Carlton motel
    in St Pete’s Beach. A really nice small laid
    back motel. Clean, up to date but also a
    reasonable cost.

  40. I love Key West! Where did you stay? Thinking about going there again in May for my 25th Anniversary. I think your next trip to the Gulf is way too ambitious for one trip unless you’re gonna stay for three weeks!

  41. Do Sand Dollar Spit at Tiger tail Beach on Marco island by crossing the lagoon at low tide when it is about two feet deep and take the long way back. Great shelling.

    Naples is not too expensive! Go to 5th Avenue (our version of Rodeo Drive) for early dining or happy hour and get amazing deals. Catch sunset from Naples Beach. Everyone applauds when the sun sets. If they have a no alcohol policy it isn’t enforced because we see people sipping champagne every time we go.

    There is an amazing hole in the wall Cuban place north of the Ace Hardware at Collier and Golden Gate

    First Thursday night of the month has free live music on the lawn at Mercado. First Friday of the month has live music called Legends to support First Responders and fallen police officers. $20 on Eventbrite.

  42. Forgot to mention lunch on the sand at Turtle Club in Naples. Ybor City in Tampa.

  43. Don’t miss Captiva when you hit sister island Sanibel. Call Tween Waters Inn, ask about their weekly hermit crab races. So much unique fun (and you may win cash and other prizes).

  44. I love the Florida Keys sloppy Joe’s riding a motorcycle over there. Walking around the colorful houses the nice people. I Also like Tavineer good for scuba diving. It’s being in the Caribbean without leaving the country.

  45. So fun! I live right next to Fishville in Downtown Punta Gorda. It’s a small town right off the interstate just north of Ft. Myers. Come visit and we can take you out on the boat to Cabbage Key or Boca Grande. The water around here is clear blue…heavenly!

    Beautiful post!!!

    Kim (

  46. I have been going to Key West since the 80s. I go every 2-3 years and love it! Thank you for the pictures, you captured the keys. I always stay at The Banyan Resort. Inside the resort is quiet, surrounded by tropical trees and plants. Hidden within, 2 pools, and a Tiki Bar. Stop by the Tiki Bar and ask Amy to take you for a tour. Located on White Head street. 1 block to Duval street. Going down the first week of November (Fantasy Parade). Thanks, Peg

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