Itinerary from Miami to Key West: One Week

We drove from Homestead to Key West, with Key West being our destination and really just enjoying the drive. We honestly had no idea that there was so much to do along the way!! Now that we did that and spent about 24 hours in Key West, we have advice for anyone who is thinking about doing this same drive: “It’s the Journey … not the Destination”

We spent a lot of time researching on the drive and later in Key West and had NO idea the history of the Overseas Highway and the area. We also, like I mentioned above, had no idea there was SO much to do along the way: Restaurants, TONS of state parks, attractions, beaches, history….If we could do it all over again THIS would be what we would do (and a sample agenda) when driving from Miami area to Key West:


Pay $5.00 and download the: GyPSY Guide THIS IS A MUST and I am SUPER bummed we didn’t find this until after we drove to Key West. It is an audio tour of the trip from Miami to Key West and it is like your own personal tour guide. You hit START and the app uses GPS to tell where you are and narrates the entire way!! It only works on the way there (but we tried a little bit on our way back by turning around and it was REALLY cool!!)


Take AT LEAST 2 days to get to Key West (and keep in mind that Key West is not for everyone) For us, we found the places we did stop on the way were more our style and after hearing about some other places along the way that we had no idea about, we believe we would have preferred to stay there vs Key West. Do your research; Key West is VERY party heavy (in some places) and there are a lot of adult-only hotels. If you are not into the party scene or have kids, I would suggest spending just the day in Key West. There are a lot of excursions from Key West, that are family friendly BUT they are MUCH more expensive than some of the other very similar excursions along the way.


Since the audio tour I suggested plays as you drive, it can be hard to decide what to go to as you don’t know what else is coming up. Do your research and plan extra days, it takes much longer than we thought to just drive there, let along stop at all the amazing places along the way…it will also be a challenge if you have limited time to pick the places as there are so many options from Miami to Key West. You can research places along the way via Google, travel blogs and also there are a couple suggestions in the description of the app or read on to see my suggestions 😉


Read the history – it will bring so much more appreciation. As I mentioned in my earlier blog, I had no idea the history of the Overseas Highway and once I did I could not get enough. I want to read books and see if there are any interviews with people who had family who worked on the highway/railroad, etc. From when we drove by (and I had zero knowledge) to when we were on our way back, it changed everything about my perspective and appreciation for this highway.


If you are OK with sticking to a tighter schedule, plan far enough in advance so you can make reservations at the busier places along the way. Mainly the Turtle Hospital, State Parks (for camping), and The Dolphin Experience.

If we could do it all over again, Our Dream Itinerary from Miami to Key West

Day 1: Start EARLY from Miami –> Travel to John Pennekamp State Park

Ideally, you will start your drive in Miami, as that is where the app starts and before the Overseas Highway starts, you will get additional history and information about Miami, Florida and foreshadowing the drive ahead. If we do this again, since Miami is not as accessible as Fort Lauderdale, we would probably fly into Fort Lauderdale but then go through Miami on the way so we could hear the first 10-15 pieces of the audio tour.

What the GyPSY Guide says about John Pennekamp State Park: “This state park was the first underwater park in the USA, having opened in 1963. The park’s borders include the shorefront and three miles out to sea. Enjoy a swim in the clear and tranquil waters, or go snorkeling or scuba diving (you can rent gear) and check out the nooks and crannies of a Spanish shipwreck. If you want to peer into the underwater world without getting wet, you can take a glass bottom boat tour.”John Pennekamp Coral Reef State Park (Photo Credit:

Spend most of the day at John Pennekamp State Park and then stay over in Key Largo to visit some additional tour attractions later in the afternoon and/or the next day. Here were some that sounded fun (the last two are pop culture related): Dolphins Encounters, Spiegel Grove, Uscg Duane, African Queen and Caribbean Club

Day 2: Travel from Key Largo –> Islamorada. If timing works, grab lunch at Mrs. Mac’s Kitchen (99336 Overseas Hwy, Key Largo) which was mentioned in many of the articles on where to stop to eat and featured on Food Network. Try to leave Key Largo early enough to get to Islamorada by 4:30-5:00 (only about a 30 minute drive) so you can catch the sunset at the Tiki Bar.

What the GyPSY Guide says about The Tiki Bar: “This laid-back bar is a famous stop along the journey to Key West, so it’s worth taking a break here to stretch your legs. Rebuilt after damage sustained with Hurricane Irma and open as at Dec 2018. The bar is famous for the Rumrunner Cocktail. It was invented right here at the bar and it is delicious – potent and refreshing. The story of the RumRunner cocktail is a simple one that arose out of necessity – the local bartender had an excess of rum and came up with a creative and delicious way for customers to drink it.”

After your World Famous Rumrunner Cocktail I HIGHLY recommend staying at the Postcard Inn (in full disclosure I have not stayed here, just had breakfast and saw the property…check out my earlier post for more pictures) but this place appears to have it all!

Day 3: Enjoy a day on the beach at Postcard Inn. As you can see from my prior post, this hotel is breach front and has everything! You can kayak in the morning, read a book on the beach in the afternoon and then take a paddle board out for sunset. They also have a swimming area (very rare in the Keys we learned) where you can actually enjoy a dip in the water.

Enough sun? Head to Theater of the Sea which is right next store. Another option (you can either take a short drive there or go on your way the day before, as it is a small back track) is to go to The Rain Barrel Village

Day 4: Travel from Islamorada –> Bahia Honda State Park. Get up early and take your time traveling from Islamorada to Bahia Honda State Park. There are A TON of places to stop along the way and given what you enjoy, you might want to spend a couple hours at some. Here are some of the places that we would have made a stop: The Hurricane Monument At Islamorada, Turtle Hospital, Dolphin Research Center, Pigeon Key, Annie’s Beach, Florida Keys Aquarium Encounters, 7 Mile Bridge, Veterans Memorial Park, Crane Point Museums & Nature Center, Marathon, bird-rescue center and natural history museum, drive through fancy houses of the rich and famous, and understand and appreciate the history when passing through Lower Matecumbe Key at about MM 73.1

Veterans Memorial Park

What the GyPSY Guide says about Bahia Honda State Park: “Home to one of the best beaches in the USA (according to numerous travel studies), this postcard-perfect park is a lovely place to stop for a swim.You can paddle in the warm water, stroll the sandy beach, take a nap in the shade of a palm tree or even go snorkeling in Looe Key. The park charges a small entrance fee and it opens from around 8am to sunset.”Enjoy the day road tripping to the state park and stay over at (or close by) Bahia Honda State Park. (photo credit: Trip Advisor)

Day 5: Travel from Bahia Honda State Park –> Key West About a 45 minute drive, without stops. There are some places to stop a long the way, given again with what you are interested in, but note that I found there are much fewer stops than above and a lot of shorter stops, my top ones would be the National Key Deer Refuge Visitor Center, No Name Key (to look for Key Deer), and No Name Pub.

NOTE: If you stop to see the Key Deer on No Name Key please be careful and drive slow and remember “speed kills” !

Spend the rest of Day 5 in Key West hitting the places I suggested in my Key West post and maybe (if you get in early enough) taking an excursion. Here are some pictures and suggestions from our last day in Key West and what was not in my first day in Key West Post (the app also has a lot of suggestions of what to do once you get to Key West): Truman Little White House, Hop-On-Hop-Off Trolley, The Key West Butterfly and Nature Conservatory, Eat Key Lime Pie, Ernest Hemingway Home, Southernmost Point of the Southernmost Spot in the Continental US, and Smathers Beach.

Day 6: Spend the most of the day in Key West and head back to Miami for a late night flight. Try to space your trip back so you are at Lorelei Cabana Bar (96 Madeira Rd, Islamorada, FL 33036) for the sunset (and it is around the half way mark)

If you can stay one more day in Key West, I highly recommend making:

Day 7 a day trip to Dry Tortugas State Park “The Dry Tortugas National Park is made up of seven small islands, it is one of the world’s most unique eco-attractions. Its crown jewel, the historic Fort Jefferson, was once used as a prison during the Civil War. Explore and learn of its history with one of our guides and enjoy an array of activities.” Dry Tortugas National Park

Dry Tortugas National Park

Hopefully this helps give you the information we wish we had! Have fun and please leave comments with your thoughts and/or suggestions of your favorite things to do on the Overseas Highway and surrounding area!


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