Last year for my birthday, Tom and I took a road trip from Miami to Key West, and it was one for the books. I had every intention of sharing this Florida Keys road trip on the blog sooner, but two weeks after we came back home, COVID-19 was declared a pandemic, and stay-at-home orders were issued.
It felt really tacky to post about travel last March, so I shelved this post. However, after polling you all on Instagram Stories, hundreds of folks wanted to read this post for future trip planning. Happy to share this trip, but please keep in mind that all of my experiences were pre-COVID, and traveling will look a little different for a while.
I’d also recommend Jenn’s COVID-19 Key West Travel Guide if you’re interested in exploring that area in the next few months. Truth be told, Jenn gave us most of our Key West suggestions last year: she’s a local who knows what’s up, and you can trust all her recommendations! However, here are a few tips and tricks on how to plan the perfect road trip from Miami to Key West.
Miami to Key West Road Trip: Why It Should Be On Your Bucket List
I’m so glad that we opted for the road trip throughout the Florida Keys rather than flying directly to Key West. Don’t get me wrong: I could easily see myself staying put in one town for several days. However, it was awesome to experience multiple towns in one trip! Each stop was so different. Plus, it’s one of the most beautiful road trips we’ve ever done, and there are some views on this trip that will take your breath away.
If you can, I’d highly recommend renting a convertible for your Florida Keys road trip. The weather is incredible, and the Keys are best viewed with as minimal obstructions as possible.
Technically, you could drive from Miami to Key West in one day, but where’s the fun in that? Our entire trip was five days, and we split up the driving over the course of three days, but honestly, I wish we spent more time in Marathon and gave ourselves time to stay in Islamorada. I hope we could do this trip again one day and explore those two towns a bit more in-depth!
Florida Keys Road Trip: Day 1 Itinerary
Quick Summary:
- Picked up rental car at Fort Lauderdale Airport
- Lunch and mural hopping in Wynwood Miami
- Pit stop in Key Largo
- Overnight stay at Isla Bella Beach Resort
Ok, so we flew into Fort Lauderdale in the evening, so that was technically our first day in town, but for our first full day out and about, we headed to the airport, picked up our rental car, and started our journey down Route 1.
We made a pit stop in Wynnwood, our favorite, eclectic neighborhood in Miami, and had a casual, low-key lunch at The Taco Stand and browsed some murals and art. If you’re an early riser, it is also a great place to grab a coffee if you need caffeine. I could spend hours roaming Wynwood, to be honest, so I’d budget a couple of hours here. If you need more Wynwood and Miami recommendations, make sure to check out my Miami guide here!
Getting out of Miami proper and into the Florida Keys takes a bit longer than you’d think. If we were to plan this trip differently, we’d opt to stay in either Key Largo or Islamorada the first night rather than driving all the way down to Marathon. We really wanted to get to our resort in Marathon before sunset, so we didn’t get to visit all of the places on our list.
However, once we got to Key Largo, we made a pit stop at Gilbert’s Tiki Bar, which felt like a dream. It’s a laid-back outdoor bar with live music, waterfront dining, and all of the tropical drinks you could think of. This space was huge, and we had the place pretty much all to ourselves since we came on a weekday. If we had more time, we would have stopped by Islamorada Brewery and Distillery after visiting Gilbert’s, but we rushed to get to our hotel before sunset!
We booked the Isla Bella Beach Resort in Marathon for one night, and you guys…I really wish we booked it for longer. This is one of the most beautiful resorts I ever stayed at, and I did not want to leave. We ended up requesting a late checkout because we did not want to go. The service was top-notch, the food was incredible, the amenities were insane, and every room had a water view. This was a lot quieter than Key West, and it was honestly the perfect place for a romantic getaway.
There is a 100% chance that we will be visiting again, and next time, we’ll book at least a 3-night stay (if not longer!) We had sunset drinks at The Beach Bar and dinner at Il Postino on the property, and it was the perfect evening.
Florida Keys Road Trip: Day 2 Itinerary
Quick Summary:
- Check out of Isla Bella Beach Resort
- Cross the Seven Mile Bridge
- Check in to The Perry Hotel Key West
- Take a Wine Sunset Cruise
- Dinner at A&B Lobster House
Fun fact: our second full day in Key West was my 30th birthday! I really couldn’t have asked for a better birthday. Tom planned most of this day out for us, and I’m very thankful he took the reins.
We opted for a late check out at Isla Bella Beach Resort and had brunch and lounged at the pool. Again, let me reiterate that we should have spent longer at Isla Bella! We left the hotel in the afternoon and drove into Key West. One of the highlights of the trip was crossing the Seven Mile Bridge — it’s where the Gulf and the Atlantic Ocean meet, and it’s one of the most beautiful places I’ve ever been. There is a scenic overlook here that you can pull off on, and you can also walk the bridge as well. We pulled off and walked a bit of the bridge, and we were in awe!
Afterward, we checked into The Perry Hotel Key West. The Perry is located on Stock Island, right outside of Key West. They had a free shuttle to get you to and from Key West, and I loved how modern and chic it was. It was nice being further away from Key West’s nightlife so that we could get a good night of rest!
Another highlight of our trip was our Sunset Wine Cruise with Danger Charters. I was actually really impressed with the wine selection they had: if you’re a wino, you’ll definitely be satisfied! This was pre-COVID, so I’m not sure how they’re running the tours now, but we loved the vibe, the views, and the drinks!
We wrapped up the evening with a candlelit dinner at A&B Lobster House. I loved that this restaurant was right on the marina, and it was a great way to enjoy some surf and turf.
Florida Keys Road Trip: Day 3 Itinerary
Quick Summary:
- Lunch at Moondog Cafe
- Explore the Ernest Hemingway Home & Museum
- Drinks and Snacks on Duval Street
I’m not going to lie: I was kind of tired after my birthday and got a late start. If I knew this was my last trip ever before COVID shut down everything, I would have packed my day a little more!
I skipped breakfast and had lunch with Jenn at Moondog Cafe, one of her wonderful suggestions. I loved this spot: it had a ton of healthy, fresh menu options, and it was a much-needed detox the day after my birthday.
Afterward, we walked over to the Ernest Hemingway Home & Museum. This beautiful home was built in the 1930s and was the residence of the acclaimed American writer. If you’re a cat lover, you’re in luck: this spot is packed with adorable six-toed cats. It’s a quick stop: we only spent about 45 minutes browsing here!
Afterward, we walked down Duval Street for some people watching and some snacks and drinks. We loved Wicked Lick Ice Cream for liquid nitrogen ice cream and First Flight Island Restaurant and Brewery for drinks and snacks (so much so that we went to First Flight twice during our stay!)
For some reason, this newly-minted 30-year-old was so tired that she ended up not eating dinner that night, but I’d recommend reading Jenn’s Key West guide for more dining ideas!
Florida Keys Road Trip: Day 4 Itinerary
Quick Summary:
- Brunch at The Perry Hotel Key West
- Drinks at Dante’s and The Green Parrot
- Lunch at Off the Hook Bar and Grill
- Tasting at Key West Distilling
For the most part, we just ate and drank on our last day — we had a 7 PM flight home, which gave us plenty of time to explore before heading to the airport.
We had a slow breakfast at Matt’s Stock Island at The Perry Hotel before checking out and exploring. We left our bags at the hotel and explored Old Town Key West one last time. We visited The Green Parrot a few times on our trip, a fun dive bar with cheap drinks. Dante’s had a lively party atmosphere and a massive pool at the bar — I wish I brought my swimsuit here! We wrapped up our time in Old Town with a delicious seafood lunch at Off the Hook Bar and Grill — I’d highly recommend this spot for lunch or dinner!
We headed back to Stock Island and did a quick tasting at Key West Distilling, which is steps away from The Perry Hotel. They have a small selection of carefully crafted spirits, and we were pretty impressed with the selection! Afterward, we picked up our bags and headed to the airport!
Have you ever done a Florida Keys road trip before? Let me know in a comment below!
Photos by Tom McGovern
