Florida Keys Road Trip 🚗

Planning a trip from Miami to Key West is an overwhelming affair. There are so many incredible places you can choose to stop at between these cities, each little key has its own unique offerings of things to do, restaurants to visit, and sights to see. While this guide is nowhere near comprehensive (we would have needed at least two weeks to do it all!) I think we had a really great introduction to this area that can be helpful for anyone starting to explore South Florida.

First things first – pick up your rental car. We rented from the Budget Car Rental office location in Miami Beach, which was a lot more convenient than going back to the airport. This also saved us money and headache. We didn’t rent a car for the two days we were exploring Miami, which saved also time and hassle of trying to find parking – which seems to be a difficult task in the city.

So it began – the adventure down the tiny islands off the coast of south Florida known as the Florida Keys!

First Stop – Key Largo

Key Largo is the first or northernmost key and it’s a natural first stop after you escape the traffic of Miami and endure a rather uneventful drive south on Highway 1 past Homestead and a lot of rural nothing. It’s the start of stunning nature, awesome restaurants, and tons of things to see and do! One thing. I would definitely do the next time I am venturing in the keys is stay in Key Largo for at least a night or two, there were many things I wish we could have enjoyed but we had to press on to reach Key West before it got dark.

Restaurants in Key Largo

Buzzard’s Roost

This was our first food stop once we left Miami, and the views and food did not disappoint! We had a light lunch here at a patio table that overlooked a calm marina with a few boats bobbing in the water. It was beautiful, the cocktails were AMAZING – I would almost never advocate ordering a rum punch, but the bartenders at Buzzard’s Roost definitely know what they are doing. The fish and vegetables and oysters were all delicious and very reasonably priced. Our server was awesome and overall this was a great kick off to our road trip.

Lazy Lobster Seafood Restaurant

This was a stop in Key Largo we made on our way back to Miami. I would not say it’s a must-visit. The ambiance is great, it’s a nice outdoor seating area under a tropical-style thatched roof, but the food is really mediocre in my opinion. We should have gone to The Fish House in Key Largo, apparently it’s a favorite amongst locals but we learned about it too late. I’d say you could definitely have a good experience just drinking at The Lazy Lobster but I’d skip eating here.

Things To Do in Key Largo

Captain Sterling’s Everglades Tour

This might have been my favorite thing we did in the Florida Keys! If you love wildlife and want to explore and learn more about the outdoors in Florida, definitely book a guided boat trip with Captain Sterling’s!

Meet at Dolphin’s Plus Bayside to start your experience. It’s a dolphin research facility; I’m not a huge fan of how they do “swim with the dolphins” experiences, but a lot of good research has actually come out of this place, and this is just the meeting point for Captain Sterling’s. The Everglades tour begins on a little pontoon and you cruise around the coastal everglades – a different experience than if you do the swamp side which is more inland and typically toured on day trips from Miami.

Our guide, Captain Tony, was amazing. He is a friendly man who was knowledgeable about everything about the Florida Keys and the wildlife here. You could tell he really loved his job and loved sharing the amazing nature and experience of seeing native animals in their natural habitats with his guests. Book a boat tour with Captain Sterling’s if outdoor wildlife experiences are your thing. Seeing a manatee right next to our boat was the highlight of my Thanksgiving vacation.

John Pennekamp Coral Reef State Park

I would come back to Key Largo just to go on a diving trip here! We didn’t have time to snorkel or scuba dive, but if there is any place in Florida worth going, John Pennekamp is likely one of the best spots. This Coral Reef State Park is the first of its kind in the United States, it’s a state park that is a marine preserve, home to dozens of fish and marine animal species. It’s great for a beach day, kayaking, boat tours, and more. We also visited on a very windy day, which would have presented issues for snorkeling visibility, so instead we enjoyed the park on land.

Make sure you check out the aquarium in the visitor’s center! It’s included in your state park admission fee. It contains a bunch of information about fish species found in the keys and it’s a beautiful spot for a quick walkthrough.

Sights On the Drive From Key Largo to Key West

Seven Mile Bridge & Horseshoe Beach

We didn’t stop much between Key Largo and Key West, another reason why I would love to come back with more time to explore the in-between keys and see what they have to offer. There are many state parks and wildlife spots to check out, but we sadly didn’t have the time. The highlights we experienced was driving over Seven Mile Bridge, a feat of engineering that is one of the longest bridges in the world. Horseshoe Beach was a quick stop near Bahia Honda State Park, where I popped outo fthe car and went on a quick walk to the beach to stretch my legs.

Key West

After about four hours of driving, we made it to Key West! I’ll admit I was a bit frustrated with the parking situation at first – you have to be really careful as many spots on the street are “Resident Permit” designated, but eventually we found a bunch of spots near our accommodation which made things much easier. Get out of the traffic, park your car, and start exploring on foot. Key West is small and concentrated with awesome things to see and do – mostly all within walking distance.

Affordable Accommodation in Key West

Galleria Guesthouse

I almost want to put “affordable” since everything in Key West is absurdly expensive. A fancy hotel here is going to cost you $500/night, easy. This ended up being $150/person per night, for a tiny room with a tiny bathroom. They did a nice job of including the little touches like a coffee maker, mini fridge, silverware, plates, cups, and other small amenities. It was not the most comfortable or luxurious stay, but it was well located and had everything we needed for two nights in Key West.

Restaurants & Bars in Key West

Thirsty Mermaid

Hands down, this was the best restaurant and meal we visited in Key West. It’s a small, chic spot that is excellent for a romantic dinner. No outdoor dining unfortunately, and despite the limited seating area, we were still seated promptly by a friendly host. They had a great beer and wine selection, great service, and just a cool atmosphere. I would 100% bring a date here, or come for a drink and an appetizer to sit at the cute, tiny bar in the restaurant. I would highly recommend checking out the Thirsty Mermaid while on vacation in Key West.

We shared the steamed clams as an appetizer and it was fantastic. I had the yellowtail snapper served with tomatoes on top of pasta, while Nayda had the gnocchi in a short rib ragu. Everything was delicious.

Conch Republic Seafood Company

What’s better than a Bloody Mary and some oysters to kick off Thanksgiving after a snorkeling tour? The Conch Republic restaurant is huge and conveniently located right in the marina where our snorkeling tour dropped us off, so to refuel, we stopped here for some mid-morning cocktails and seafood snacks. It was very cheap and the fish spread and oysters were delicious. I would visit this place for drinks and appetizers again.

Pincher’s Restaurant

Pincher’s Restaurant would be my recommendation for a happy hour stop (who doesn’t love a BOGO on drinks?) but I would say the food is just meh. My lobster mac and cheese was indulgent and tasty, but of course after eating it I immediately regretted such a heavy meal at midday. It would be an excellent spot for people watching with a drink in the evening hours – it overlooks the bustling Duval Street near a bunch of busy bars.

Key Lime Pie in Key West

While it appears you can find key lime pie on the dessert menu at any restaurant in the Florida Keys, these two places were revered online as being some of the best. We visited and ate both Kermit’s Key Lime Pie and a slice from The “Original” Key Lime Pie Bakery. While I hope saying this doesn’t get me banned from visiting the Key again, I honestly was not that impressed with either. I’ve learned how to make key lime pie with a homemade graham cracker crust, and it’s just so much better than anything mass produced. I suppose this comes with the insane demand for the treat that businesses face here. Definitely eat it – you must. Key Lime Pie in Key West is good, but just nothing exceptional. The good news is that it’s an easy dessert to learn how to make yourself.

Breakfast at Cuban Coffee Queen

Going here for breakfast is a must when in Key West. Be prepared to wait – the line seems to be long no matter what, but it’s well worth it. This place has awesome coffee drinks and Cuban-style breakfast sandwiches. This was our final stop for some food fuel before hitting the road to head back up the keys to Miami. I had an iced coffee and the Cuban Bagel, which was cream cheese on pressed Cuban bread with honey and everything bagel mix on top. It was delicious but really messy – not something I’d recommend trying to eat while driving. Cuban Coffee Queen is for takeout only at the iconic location we visited, but you could find nearby seating on benches and tables around the marina.

Things to See & Do in Key West

Snorkeling Tour with Sunset Watersports

Nothing says “untraditional Thanksgiving experience” like a snorkeling tour on a catamaran! We ventured off in the morning of Thanksgiving for a 3-hour snorkeling tour with Sunset Watersports. Leaving from the main marina, we cruised to a reef and saw tons of fish and corals. Unfortunately it was a very, very choppy day, which hurt the visibility and made swimming a struggle, but the company supplied lifejackets and it was still a fun experience. The captain was really friendly too, which isn’t always the case on boat trips. I enjoyed the day even if the snorkeling itself was not top-notch. I will say that while this company provides “breakfast” onboard – it’s a pretty meager offering of some juices, coffee, and muffins, so if you’re someone who needs to eat protein in the morning, get something before the tour.

Island Cigar Factory & Wine Bar

If you want to bring back a Cuban cigar from Key West, or stop and smoke one yourself and enjoy a glass of wine – this is a nice place to stop. It’s right near Duval Street and the Key West lighthouse, and it offers a huge variety of wines and cigars to browse, as well as a relaxing outdoor patio and smoking area.

Hemingway House Tour

Even if you’ve never read a single book or essay by Ernest Hemingway, or don’t care much about his life and legacy, I would still recommend touring the Hemingway House. It’s only $7 for a 30-minute tour, given by passionate and informative guides. It’s such a quick walkthrough it doesn’t get boring, and the house itself is so beautiful, it’s an iconic spot in Key West. See the dozens of cats sleeping and roaming the yards (count how many toes they have), and learn all about Ernest’s life and feel inspired to go out and buy his books. I’ve only read For Whom the Bell Tolls, and after this tour I wanted to add all his works to my reading list.

Southernmost Point Marker

It’s a cheesy, touristy spot, but you have to do it. Get in line and wait with all the other schmucks to take your photo at the Southernmost Point Marker, another iconic location in Key West. The line didn’t take too long to work through and we got our picture. This is also a great spot to watch the sunset, but don’t count on being able to snap the perfect golden hour photo with this landmark, as it’s likely you’ll miss the opportune moment waiting for a huge family to finish their photoshoot. At least it’s a 100% free attraction.

Florida Keys Road Trip Travel Tips

1. Book excursions, accommodations, and transport early, because things sell out quickly and options are limited. For example – If you want to visit Dry Tortugas National Park – start looking to book your ferry ticket now. Unfortunately we were unable to make this day trip possible – by the time I looked to reserve our tickets (over a month in advance) they were already sold out for Thanksgiving Day, the only day we’d be able to do it.
2. Get gas before you head into the Old Town Key West if your tank is running low.
3. Research restaurants before you go there. It was overwhelming how many dining and drinking establishments populated this tiny place, and many are a bit too touristy and tacky for my personal tastes, and some are overpriced or overrated. Do your research, read those reviews!
4. Be prepared to walk more than you think! While Key West is small, there are a lot of attractions spread out on opposite sides of the islands. One night I regretted wearing my cheap sandals that were not offering my feet any support after we had walked several miles that day.

Have you been to Key West? If there is a “must do” that I missed, please leave me a comment so I can put it on my list for my next visit!