Ultimate Florida Keys Road Trip Itinerary

Looking for an outstanding road trip itinerary for the Florida Keys? I have you covered. Recently I embarked on a near week road trip throughout the Keys to see delicious food, luxe digs and adventures I could find waiting for me. 

This itinerary is packed with crystal clear blue waters, stunning resorts, incredible food, and activities that will keep your trip fun at every turn. 

When I was working on this itinerary, I decided to start in Miami and drive down the Keys with stops along the way and end in Key West and fly home from there. Of course you can go in either direction, but Miami International Airport is much bigger and has more flight options in and car rental options. 

Full disclosure, I did partner with The Florida Keys to bring you this itinerary – but as always, opinions are entirely my own. 

Florida Keys Road Trip Itinerary 

Day 1 and 2 

I started in Miami and drove down to Key Largo. Before I arrived at my destination, I stopped for my very first slice of key lime pie! I went to Mrs Macs in Key Largo and this slice had whipped cream, it was thick and the lime flavor was outstanding. Before I got my pie, I also had breakfast, and highly recommend! The food was delicious. 

This part of my trip I added on to the itinerary myself because so many of you ask about this resort constantly, and I wanted to cover it. I checked into The Bungalows! This is one of the only true all-inclusive resorts in the entire USA and the only luxury all-inclusive adults only resort in Florida. Which means, you do not need to leave the country for an all-inclusive experience!

I checked into a Garden King Bungalow during my stay for two nights. If you prefer an Oceanfront King Bungalow, you have to stay three or more nights. I did not have three nights to stay, so I just paid for the two. But honestly, both room categories are great. 

The property is beautiful and because it is all-inclusive, there is no real reason to leave and eat off property. You have already paid for your meals and drinks – take advantage of that! However, there is a lot of adventure waiting off property for you. 

Dining:

One thing I was pleasantly surprised by was the food. All-inclusive resorts can be hit or miss and The Bungalows was a hit! Every single meal was good.

The resort offers three restaurants:

Fish Tales – serves breakfast, lunch and dinner. Fish Tales was my favorite place to dine for all three meals. Robust menus, creative dishes and the staff was amazing. 

Sea Senor – serves lunch and dinner. I only had dinner here, but the chicken chimichanga and caramel flan were to die for. I would have eaten 10 of those flans, but resisted! But you can if you want – it is all-inclusive. 

Bogie and Becall’s – serves dinner 

Activities:

On site, the resort offers two pools, one that is waterfront and the other, a Zen pool, which is surrounded by greenery. One thing to note – the chairs and cabanas are included but also, first come. So plan to get there early if you want one.  

There is a beautiful spa on site (this is extra). I would recommend booking in advance or when you arrive to ensure you get the treatment(s) you want. 

As for water activities, there are activities like kayaking, paddleboards, water trikes, snorkel gear, and you can swim – but please note, this is not a walk in beach. It is rocky and you will use stairs to enter. 

Yoga is also included with your stay, you just need to sign up. 

For a fee – the resort offers some excellent boat tours. You can get a private boat or join a group from the resort and see the Everglades, do a sunset sail or even head out to crystal clear waters and sandbanks. 

The resort also gives you a complimentary bike to use during the duration of your stay. You bike all over the property. 

A few things to take note of:

• Room service is not included but you can pay extra for it 
• Bogie and Becall’s, the steakhouse on site, is not included unless you stay four or more nights, and even then, you can only dine here for dinner once complimentary. Otherwise, the add on fee is $300 for two people to dine here. 
• Check in time is 4:00pm. If you would like to check in early at 12:00pm, there is a $300 fee per two people. 

Day 3

When I left The Bungalows to head further down The Keys, I stopped into The Blonde Giraffe for Key Lime Pie! This is the first time I have had it with meringue and it was so good. Highly recommend and it was only about 10 minutes drive from The Bungalows.

After eating pie, I stopped into Robbie’s Marina for lunch and to feed the tarpon. I was not sure what to expect when I showed up here, but I was lucky to get a table close to the tarpon feeding and my eyes were glued to it the entire time. The tarpon are huge and a lot of people came through to feed them. Highly recommend feeding them. 

For lunch, I went with the grouper, as recommended by my server and it was cooked to perfection and golden. 

After about a 30 minute drive, I arrived at Isla Bella Beach resort! Located in Marathon and right before the Seven Mile Bridge, this lush getaway was perfect. 

During my stay I checked into an Oceanfront Balcony King with sweeping views of the water and the property below. I loved that the room was spacious, beautifully decorated and light and airy. 

For me, I found that this property was amazing because it sits on a mile of waterfront views and has five pools. You could enjoy the pool and see the water or there is beach access, whatever you decide. 

I spent the day enjoying the property, going for a swim and at night, walking the Seven Mile Bridge during sunset – which is a must!! You can get complimentary bikes from the resort as well if you wish to ride. 

Isla Bella has a fantastic restaurant on site called Mahina that I got to enjoy dinner at. I started with the Mahina Salad, for my entrée enjoyed Kurabota Pork Chop and to finish, Pineapple Upside Down Cake. I cannot stress enough – the food was fantastic, starting with the hot loaf of bread and whipped butter they bring to the table. 

Day 4:

Day four was exciting – I was thrilled to get to do something I had been waiting to do for a long time, but first, breakfast. There is a restaurant right outside the resort called Sunset Grille and I popped in for the beautiful views and stayed for the Acai bowls!

My first adventure of the day was taking a boat cruise with Islander Girl Tours to the Islamorada sandbar. You may have already seen my video on Instagram or TikTok of this magical place – but the water is so blue and clear. It comes out of nowhere and is so beautiful. 

I promise you that you will LOVE this boat tour. When you arrive to the sandbar, you get off the boat and wander around freely. It is truly a fun experience and the ladies at the tour company are so friendly and knowledgeable. 

After this tour I was so excited that I skipped lunch and went back to Isla Bella to continue swimming. Isla Bella is really beautiful, so it will be hard to tear yourself away from there. 

For the evening, I went back to Islamorada and started at the Florida Keys Brewing Co. If you love beer, this is a must visit. There are a lot of beers on tap, a beer garden to enjoy and a tasting room if you prefer to stay indoors. 

I love dark beers, so I was very fortunate that my five choices for my tasting were all dark except one. I also wanted to try the Iguana Bait, the best beer in house – and it sure was. Very crisp and refreshing. 

My favorite beer is called “Big Dick” and it was named after a guy who used to play at the brewery, as they have live music outside. The beer is the Snipes Imperial Stout and aged in a Jack Daniel’s Barrel. The perfect combo to be honest. Definitely try it if it is available. 

After my brewery experience, I went a few doors down to Chef Michael’s for dinner. Highly recommend getting a reservation in advance as they were pretty booked when I went. I ended up eating at the bar as I think this is a great way to meet locals and talk to the bartender. Everyone overwhelmingly said there was “no bad dish on the menu!”

Even though everyone recommended the fish, I went with my gut instinct and got the roast duck, and I am so glad I did. Unbelievable. It was crispy, juicy and the accompaniments were even better!

Day 5:

I started day five eating breakfast at Sunset Grille again because it was close and I loved it so much! On this day I got biscuits and gravy with eggs. Another solid winner in my book. 

When I left Sunset Grille, it was finally time to drive over Seven Mile Bridge and the weather was perfect, so it was stunning to see. It took a little over an hour to get to Key West, but once I arrived I checked into Parrot Key Hotel and Villas. 

I just want to note, I have stayed in Key West before, downtown, and this was a new experience for me – that I LOVED. Parrot Key is located less than three miles from downtown and feels like a private oasis. You feel like you are in a lush tropical destination and that a city is not outside the walls of the property. That good. 

During my stay I checked into a Waterfront Two Bedroom Suite with Livingroom. The space was massive and over two floors. The room had two master bedrooms, one on each floor, a living room, two balconies – and one overlooked the water in the direction of the sunset, and was decorated minimally to reflect the area. 

Arguably the best part of the hotel is the center, which contains four pools, all individual and surrounded by lush greenery. This is a great property to pair with a Key West Itinerary because you can do everything in Key West and also relax. 

In the evening I went and walked around Mallory Square – there is always something going on here. Singers, people doing tricks, shopping, etc. This is also a great place to watch the sunset but I didn’t get to this time because my dinner reservation was at the same time. But if you have a free evening – definitely check it out. 

For dinner, I took a quick ferry over to Sunset Cottages to dine at Latitudes. Can I just say, not only is the food fantastic, but the restaurant also offers the BEST sunset views while dining. 

You will need a reservation to dine here and I recommend booking as soon as you can. I would request a table outside as well to get the best views. 

I went with the seared scallops for an appetizer, Caribbean Lobster for dinner and of course, key lime pie for dessert. Everything was so, so good and I can’t give enough raving reviews about this restaurant. 

Day 6:

Today was my busiest day, but I would not have had it any other way! I started the day with a coffee on my balcony at my hotel and got ready for an adventure on the water. I booked a dolphin watch and snorkel excursion with Honest Eco Tours. The tour was about four hours long and they take you to find dolphins and then for a snorkel. 

The staff was so nice, extremely knowledgeable about dolphins and the Keys in general. This tour was a bit long, but the boat has plenty of covered seating to escape the sun and plenty of uncovered standing room to explore. 

We did get to see a couple dolphins and some fish under the sea!

After this, I walked down the pier to Half Shell Raw Bar for lunch, and I was super hungry! I went with conch fritters and pink shrimp, because you cannot leave Key West without trying either!!

During the afternoon, I wanted to see as much as I could so I rode the Conch Tour Train, visited the Ernest Hemingway Home and Museum, the Butterfly Conservatory, Key West Lighthouse and Keepers’ Quarters, Mel Fisher Maritime Museum, Key West Museum of Art and History at the Custom House, walked Duvall Street, and saw the Southernmost Point Buoy. 

My two favorite places that I love to visit when I am in town is the Hemingway Home and the Butterfly Conservatory. The cats at the Hemingway Home have six toes and they are the cutest and friendliest. 

For my last dinner, I dined at Matt’s Stock Island Kitchen and Bar. I tried completely different items from my entire trip here and got the black bean empanadas and the kobe tri tip, with a side of brussels sprouts. 

Everything was great at dinner – I could not have put a better pairing together. Highly recommend if you are in Key West and looking to eat somewhere amazing not in the downtown area. 

Optional but also, unmissable: Walk down Duval Street, stop into a bar or two for drinks and live music. I did not get the chance to on this trip because I was super busy, but I have been to the city many times before. Sloppy Joe’s is my hands down favorite!

Day 7:

I thought about trying to go to the beach super early in the morning since my hotel had a shuttle to Smather’s Beach, but I just couldn’t make it work. 

I checked out, filled up my car rental and headed to the Key West Airport. The airport is very small and easy to navigate. Returning the car was a breeze, check-in and security went fast, and I had a direct flight home to Washington, D.C. It was truly easier than driving back to Miami. 

Overall:

I really enjoyed this trip. I had never been able to stop and experience The Keys before, only passing through to get to Key West or Miami. I think the Keys have so much to offer and would recommend splitting your time with any of them and Key West, if that is your final destination. I can see myself visiting any of these destinations just by themselves.