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Headed on a Miami to Key West road trip for your next vacay? If the idea of driving to an island blows your mind, then you are in for some excitement. It’s a known fact that making the drive from the U.S. mainland over the various bridges connecting the Florida Keys is a truly unforgettable and unique experience.
Even writing about this trip puts me in such a good mood. It’s a combination of many things I love: tropical vibes, road trips, and even historical sights. The moment I learned it was possible to drive the 159 miles between Miami and Key West, I knew this road trip was in my future. Especially since both Miami and Key West are both such awesome places to explore!
I found that spending a little bit of time in both Miami and Key West gives you the best of two different worlds. Miami is the faster paced, more energetic portion, while Key West slows things back down for a calm finish. And of course, the road trip is the scenic buffer in between!
If you are in desperate need of a getaway, a road trip from Miami to Key West is just what you need. This is a vacation that will bring you both adventure and relaxation, with the occasional dose of key lime pie and rum punch. With that, let’s get into how to plan an unforgettable Miami to Key West road trip with this dreamy one week itinerary.
Ultimate Miami to Key West Road Trip Itinerary
Up front, I want to say that this is not really a party itinerary for either Key West or Miami. Don’t get me wrong – my husband and I are all for a little bar hopping, but we rarely make it out past midnight. In fact, I’ve more so come to love being a morning person, and having the quiet streets to myself before the rest of the world rises.
As this is a seven day Miami & Key West itinerary, it’s a good idea to pace yourself anyhow. You can still find some great people watching, without actually partaking in Miami’s crazy (and expensive) club scene.
Table of Contents:
- Best Time of Year for a Miami to Key West Road Trip
- Getting Around Miami Beach & Key West
- Where to Stay in Miami Beach & Key West
- Part I: 3 Days in Miami Beach
- Part II: Road Trip from Miami to Key West
- Part III: 4 Days in Key West
Best Time of Year for a Miami to Key West Road Trip
Miami and Key West tend to have sunshine and warmth all year round. However, summer weather can get scorchingly hot and humid, and early fall brings hurricanes. Therefore, December through May is the ideal timeframe for planning a Miami to Key West road trip.
Getting Around Miami Beach & Key West
It is very easy to get around both Miami Beach and Key West by walking, biking, or ordering an Uber. The only time you will need a car on this entire trip is for the round trip drive from Miami to Key West.
Where to Stay in Miami Beach & Key West
Miami
Stay in a classy Art Deco hotel on the water. When you aren’t out strolling the streets of Miami, you could lounge at your hotel’s pool, or grab a couple of your hotel’s chairs along the beach.
The Savoy Boutique Hotel is a great option, and we personally loved our stay here. We found great room prices for our late May trip when we booked it with our flight on Expedia. We were also excited to have our room upgraded upon arrival to an ocean view suite. It could be a coincidence, but we have always been upgraded whenever we’ve booked on Expedia without even asking!
Key West
Key West is the perfect place to grab an Airbnb or vacation rental on VRBO. If that’s not quite your style, there are plenty of hotel and bed and breakfast options. However, lodging in Key West can get rather expensive.
My husband and I stayed in the Old Town Garden Villas, and had our own condo, which was nice and spacious for the two of us. It was tucked back on a quiet side street, but also very well located, being just a block from Duval, a five minute walk from the Ernest Hemingway House, and an eight minute walk from the Southernmost Point.
It also had a kitchen, which is great for saving money and preparing your own meals, as well as a small dipping pool to cool off from the hot sun. Most of all, we loved the convenience of being able to easily walk or bike to everything.
Travel Savvy Tip
Want to know how we never check bags for vacations, including this one? Take a look at my beach trip packing list, which includes all the essentials that you’ll need in your carry-on.
Part I: 3 Days in Miami Beach
Day 1: Arrival in Miami Beach
On the day you arrive into Miami, you’ll mostly be getting settled in. Therefore, I wouldn’t plan on squeezing in too much sightseeing. Just treat anything you do manage to see as a bonus.
-Dinner in Miami-
What you may have time for is some good food. Since my husband and I arrived into Miami around 3:14 p.m, and only had a twenty minute taxi to The Savoy Hotel, we made a dinner reservation at Joe’s Stone Crab, which is known to be a Miami Beach institution.
If you are visiting from October to May, you too will be able to check this place out. However, be ready to spend some dough. My husband and I were on a tight budget, and I don’t think our limited spending allowed us to fully enjoy this place. If you are on a budget like we were, your money will likely go further elsewhere.
-Evening People Watching on Ocean Drive-
If you have any steam left, find a perch on Ocean Drive for some people watching. One of my favorite moments during our trip was chilling at a Miami Beach sports bar on Ocean Drive, when the flashy club-goers were just getting primed for the evening. We watched as luxury car after luxury car slowly rolled by, music bumping, and we could definitely feel the energy of the evening beginning to unfold.
Travel Savvy Tip
Ocean Drive can be a nightmare to drive down at certain times of the day. While Ubers are highly accessible in Miami, often times walking is a more time efficient option. For distances that are too far to walk, still order an Uber or taxi, but just have them drop you off once you get within walking distance, as traffic truly is that slow.
Day 2: Miami Beach
-Take a Morning Walk-
Mornings in Miami are quiet and peaceful, in contrast to the rowdy night scene where the bars stay open until 5:00 a.m.. This is the perfect time to take a walk in Miami Beach, and you won’t be alone. Many residents of South Beach are dedicated to maintaining their physiques, and you’ll see plenty of people out doing their workouts.
Full transparency – Miami is not all glamour. Like any other big city, Miami has its share of poverty, and you will sadly see some people sleeping in small parks along Ocean Drive.
Travel Savvy Tip
Miami Beach is famous for its Art Deco style buildings along Ocean Drive. My favorite thing we did in Miami Beach was simply walking along this famous area, and taking in the scenery and vibe. Being that it was May during my visit, the sun was shining and the weather was perfect for being outside.
-Breakfast Followed By Beach Time-
Hands down, one of my favorite places we checked out in Miami was Under the Mango Tree. If you love green juice and smoothie bowls like me, then this will absolutely be the place for you. We liked it so much, we came here every morning during our stay in Miami Beach.
After this delightful start to your day, spend the afternoon relaxing either poolside at your hotel, or check out the expansive beach. If you are staying on Ocean Drive, chances are that your hotel will set you up with some beach chairs and an umbrella. The beach in Miami is large in both width and length, and is perfect for long walks or tossing a football.
-Head Out for Dinner-
If you are traveling as a couple and seeking something formal for a romantic date night, consider making reservations for Pied a Terre. This high-end French restaurant is located in the ambient Cadet boutique hotel, and is sure to please the most refined of palates.
If you’d like a more unique, cultural experience, then head to Miami Beach’s vibrant Little Havana neighborhood. It’s full of charm, great food, and hip bars that will keep you entertained into the wee hours of the night. If you’re going to pick one place, then head to Sanguich de Miami for Cuban sandwiches with batidos, or Cuban milkshakes.
Day 3: Miami Beach
It’s your last day in Miami Beach before heading down to Key West. Hopefully you wake up well-rested and hang-over free!
I recommend either taking it easy again today with another beach/pool day, or heading out for a little shopping. I personally recommend taking full advantage of the beach while you can, as Key West’s rocky and largely man-made beaches simply will not measure up.
-Do Some Shopping-
If you’d like to do a little shopping during your time in Miami, just a couple streets over from Ocean Drive is Collins Avenue. This street is lined with popular retail shops, such as Club Monaco and Sephora.
An even better place to check out is the Lincoln Road Mall, which was only about 1.5 miles from our hotel. This beautiful outdoor mall contains a wide selection of shops and restaurants, including our favorite: Doraku Sushi.
-Sushi For Dinner-
After an afternoon at the beach or perusing the shops at Lincoln Road Mall, you’ll surely work up an appetite. End up at Doraku (at Lincoln Road Mall) in time for dinner, and enjoy some mouth-wateringly good sushi rolls.
For your last evening, check out the vibe on Ocean Drive, and maybe pop into a souvenir shop or two. My husband and I found ourselves at a sports bar called Finnegan’s Way, where we watched the Cavs lose a playoff game to Toronto before drowning our sorrows with a quick stop at Gelato-Go on the way home. There may or may not have been a subsequent delivery order placed for Insomnia Cookies. I can neither confirm nor deny.
Part II: Miami to Key West Road Trip
Now for the adventurous part of the trip: driving south over 40 bridges through the Florida Keys on Highway 1 (aka the Overseas Highway). The trip ends when there is no more highway left to drive.
The road trip between Miami and Key West is the only time during the trip that you’ll need a rental car. We found it easiest to pick up a rental car from the airport before leaving Miami. That way, we could simply drive straight back to the airport from Key West at the end of our trip, and head to security before our flight.
The road trip from Key West to Miami is a three and a half hour drive as a straight shot. However, this will also depend on traffic and how often you stop. I have listed some places to check out along the way to Key West that are totally worth your while.
Miami to Key West Road Trip Stops:
I have listed the below stops in the order that you’ll see them on the drive down to Key West, as well as the required drive time between each one. The journey down Highway 1 is one of the most relaxing and scenic drives you will ever do, so keep your camera ready and enjoy the ride.
- John Pennekamp Coral Reef State Park (Drive 1 hour and 8 minutes to Key Largo): Kayak through mangrove trails or take a glass bottom boat tour over coral reef habitats. We loved paddling in these incredibly gentle waters, and even got to see a couple dolphins. Single kayak rentals are $20 per hour, or $40 for four hours.
- Island Grill (Drive 27 minutes to Islamorada): Stop here for a drink with a view in order to instantly enter vacation mode. Also, an order of the tuna nachos is a must!
- Bahia Honda State Park (Drive 1 hour and 3 minutes to Bahia Honda Key): Stretch your legs in gorgeous scenery, including white sand beaches and the remnants of an old bridge. This is an awesome place to simply walk around, or do a little swimming and snorkeling. Entry is $8 per vehicle; be mindful that the eastern facing beaches do see sargassum seaweed in the spring/summer months.
- Hogfish Bar & Grill (Drive 40 minutes to Stock Island): This laid-back eatery is located next to a marina. Listen to live music while devouring their specialty: fried hogfish, which is caught locally. They also make really good cocktails, like my excellent skinny margarita.
From there, it’s just another fifteen minutes or so to the action in Key West.
Road Tunes:
You’ll of course want to have a fun playlist for a road trip as epic as this one. Here is the perfect tropical playlist, which you can feel free to use or pull from for inspo.
Part III: 4 Days in Key West
The Key West portion is when I felt like our trip began to turn into a vacation. Miami was fast-paced, with lots of partying and emphasis on looking good, shopping, and fancy cars.
That all began to fall away when we started our drive down through the Keys. The shops and strip malls began to give way to bridges and irresistibly calm turquoise water. The tropical vacation vibes were growing stronger with each mile.
Arriving into Key West, aka The Conch Republic, was a relief. I felt myself stop obsessing about what I looked like, and welcomed the laid back atmostphere. Nachos were consumed, and I downed the likes of rum punch and pina colada left and right. Key West simply won’t allow you to do anything but have a good time!
Day 4: Arrival in Key West
-Settle in and Rent Bikes-
Your arrival day in Key West is all about adjusting to your new surroundings and getting a lay of the land. Before all else, check into your new lodging and get your bearings.
The next step is to rent bikes as your primary mode of transportation for the duration of your stay. While you have your rental car available, you won’t need it on this small island. Plus, traffic is congested and parking can be tricky (though not impossible). My husband and I rented bikes from A&M Scooters for about $97 total to use over four days.
-Find Some Dinner-
Once you’re settled, it’s time to find food. Make your way to DJ’s Clam Shack, which is right in the heart of Duval Street, or Key West’s main drag.
DJ’s Clam Shack is a tiny outdoor restaurant that has been featured on Diners Drive-In’s & Dives. Sometimes these places end up being overrated, but not this one.
First of all, the restaurant was still quite low key, and not overrun by tourists at all. Second, their food was mouthwateringly good. It is mandatory to try their super-stuffed lobster roll and conch fritters – you won’t be disappointed!
-Drinks on Duval-
Afterwards, why not stroll down Duval Street and see what there is to see? There are a ton of bars lining this street, so here are two suggestions to help you decide where to start:
- Rum Bar: This small bar serves awesome rum cocktails, including my St. John favorite: the painkiller. Any place that gives a nod to the Virgin Islands is alright in my book. On our latest trip, we came here every day to sit on the porch with our drinks and people watch.
- Sloppy Joe’s: This old Key West standby is known for its famous regular: Ernest Hemingway, as well as piña coladas and live music. It’s also very loud in there, so don’t go if you were hoping for hours of catching up with an old friend.
Fun Fact
Key West feels very Caribbean, but is not technically in the Caribbean Sea. There is the Atlantic Ocean to the east and the Gulf of Mexico to the west. South of Key West are the straights of Florida, which connect the Atlantic Ocean to the Gulf of Mexico.
Day 5: Key West
For your first full day in Key West, it’s time to get into the good stuff. We’re talking landmarks, history, and majorly ambient restaurants. Find yourself some breakfast and coffee, and let’s get to it.
-Visit the Southernmost Point-
Get to the “Southernmost Point of the continental United States” landmark early to enter the quick-moving line for your photo. This is simply one of those things that are a “must-do” on any trip to Key West. Even though waiting in line for a simple photo is annoying, I must say people were very courteous about taking their turn and snapping group photos for one another.
-Tour the Ernest Hemingway House-
To get in your slice of history for this trip, visit the ever-so-charming Ernest Hemingway House, where he lived with his second wife, Pauline, for almost ten years. You’ll get to see the studio Hemingway kept above the carriage house, where he’d spend his mornings writing.
The Ernest Hemingway House is also famous for being home to generations of six-toed cats. Keep a lookout for these little fellas and pay your respects to those who went before at the cat cemetery.
-Visit the Key West Lighthouse-
Continue your morning sightseeing by making your way over to the Key West Lighthouse – just one minute from the Hemingway House. This lighthouse has been in service since 1848, and had the highly unusual circumstance of a female lighthouse keeper. Today, you can tour the grounds, and even climb the 88 steps to the top.
-Dinner at Latitudes-
Making reservations for Latitudes on Sunset Key is an absolute MUST for any Key West trip. This open air restaurant by the water is loaded with ambience and has an amazing menu. Our dinner here was definitely one of the best experiences we had on our trip.
To get to Latitudes, simply take the quick shuttle from Slip #29, behind the Opal Key Resort & Marina. This short ride gives you the extra bonus of being on the water for a second.
-Grab a Couple Drinks-
Our first trip to Key West had a bit of a sports theme, with the Cavs being in the Eastern Conference Finals against Toronto. Therefore, we had to find a bar with a good game-watching atmosphere.
If that’s something you’re after during your trip, I highly recommend Sandbar Sports Grill or Jack Flats. They both have the perfect setup, with plenty of TV’s so that you don’t miss the big game while on vacation.
Day 6: Key West
-Watch the Sunrise-
Sunrises and sunsets in Key West are legendary, and you need to experience both during your trip. For the optimal sunrise viewing, rise early enough to head to Higgs Beach Park for its pier with a perfect, unobstructed view of the horizon.
-Indulge in Some Donuts-
Glazed Donuts is the place to hit up for your donut fix in Key West. Just be sure to get there early, or they may sell out.
We ordered the Cuban coffee, blueberry cheesecake, and key lime donuts, and they were ridiculously good, with a nice chew. We actually liked the key lime donut better than many of the key lime pies we tried!
-Have Some Beach Time-
Although Key West is not widely touted for its beaches, they do exist there. Our favorite was at Fort Zachary Taylor State Park.
The beach there has fluffy white sand, and is large enough to fit plenty of visitors. It is also in a more natural environment, being removed from the action and traffic of Key West, and has lots of trees for shade.
There are chairs and umbrellas available for rent at Fort Zachary Taylor State Park, as well as a concession stand for snacks and refreshments. Also, this park is an excellent location for watching the sunset. Entry is $6 per vehicle.
-Sunset Sail-
This day will lead up to a sunset sail with Danger Charters at 6:30 p.m. where you will see a sunset like no other. This is one of the most fun things you could do in Key West.
During our trip, the water was so still that we couldn’t even sail, and the boat had to use its motor. In these relaxed conditions, the wine was flowing and we ate so many snacks.
After this, we had a good time at Schooner Wharf. I simply love this divey seaside spot for its harborside location, stiff drinks, and fried conch fritters. You could just picture the saltiest of sailors enjoying this type of place after being relieved of their duties for the day.
-Dessert at Better Than Sex-
End your evening with the ultimate indulgent experience at Better Than Sex. This dessert restaurant makes decadent, downright sinful desserts, such as Man Flowers (dense chocolate stout cake) and Blueberry Birthday Suit (dessert French Toast).
Day 7: Key West
Although the sun is starting to set on this Key West trip, we’re not quite finished yet. There are still some great places to see before your time in the tropics is done.
-Brunch at Blue Heaven-
You cannot go to Key West without stopping at Blue Heaven for brunch and key lime pie. This colorful place perfectly encompasses Key West with its vibrance, laid back vibes, chickens freely clucking about, and excellent food. I can confirm that both the pineapple pancakes and key lime pie with its tall meringue were winners!
Can’t make it for brunch? Blue Heaven is also great for dinner, and accepts limited reservations. They even have live music most nights of the week.
-Harry S. Truman Little White House-
It’s time for one more little peak into history before leaving Key West. Although visited by other presidents, this site was most heavily used by President Harry S. Truman as his winter White House throughout his presidency. Truman ultimately spent 172 days here, where he would contemplate the issues of the time following World War II.
Today the Little White House is open every single day of the year for touring. Admission ain’t cheap at $22.20 a person, but it’s worth it to see Key West beyond just the bars and festivities.
-Watch the Sunset at Mallory Square-
Don’t leave Key West without partaking in this nightly tradition that dates back to the late 1960’s. Every night, about two hours before sunset, Mallory Square hosts a “Sunset Celebration”.
Not only is this an amazing spot to watch the gorgeous orange glow of the sunset over the horizon, but there are also festivities to partake in before the main event. This includes the likes of street performers and local vendors, who add to the energy building up to sunset.
-Grab Dinner-
On your last night in Key West, head to Hank’s Hair of the Dog Saloon. This fun outdoor spot features live music, a full bar, and the Garbo’s Grill food truck in the back of the property.
Garbo’s Grill serves delicious tacos, poke bowls, and their signature lobster roll. If you visit during happy hour (4 pm to 7 pm or 10 pm to midnight) you can sample three of their tacos for just $11.
Departure Day
It’s time to finally free up the parking spot you’ve been hoarding, and make your journey back through the Florida Keys to Miami. Depending on how early you need to leave, you may have a little time to sit and eat breakfast before you depart.
If you feel in need of a cleanse after all you’ve consumed during this trip, the Green Pineapple Cafe is the perfect stop. Their green smoothies and salads will have you feeling good as new!
Have More Time?
If you have another day available to spend in Key West, then I highly recommend a visit to Dry Tortugas National Park. It is uniquely situated seventy miles west of Key West, in the middle of the Gulf of Mexico. The island is a cool place to spend the day at a gorgeous isolated beach and explore historic Fort Jefferson.
You can arrive either by ferry or seaplane. We made our visit via seaplane, and the views couldn’t have been more incredible.
• • •
So was that an epic Florida adventure or what? With seeing two such different places as Miami and Key West, this trip is bound to feel like more than a week.
The road trip from Miami to Key West is a unique opportunity to make a driving journey over islands and bridges, with the calmest waters of the Gulf and Atlantic that you’ll ever see. It’s definitely a trip that is worthy of any bucket list!
Will you be making the memorable drive between Miami and Key West soon?
Loving this post!! Your writing is so clever and funny too. We just got to key west after following your Miami tips. Thank you!!
Love to hear it! Hope you have the best time!
Love your post and pictures! Driving from Miami to the Keys in January. I have one question: Do you keep your rental car the whole time you are on the Keys? I think we will be walking most of the time.
Thanks in advance 🙂
Thank you! I definitely see your point here. We kept our car for the whole four days we were there, but you’re right – we didn’t use it at all. I suppose you could see about dropping it off upon arrival and picking up a new rental car when you are ready to drive back. It does seem like most rental car agencies are on the outskirts of the city though, so you’d have to weigh the cost of Ubering vs. paying for your car on those days. Plus, the extra time those extra steps would take. Hope that helps!
We are heading out on our first drive to Key West. Land inMiami and want to stay one night on the way down. What hotel would be your suggestion? Just two adults on the first get away in a year!
So excited for you! While I have never personally stayed in any Florida Keys besides Key West, I suggest deciding based on how you’d like to split the drive. If you’d like to do the full Overseas Highway in one day, I suggest staying in Key Largo, which has a lot of hotel options, before making the rest of your way down. If you’d like to break up the drive though the Keys, Islamorada is another good stop several hotel options, and just under two hours from Key West. Hope that helps!
Thank you for sharing! I was wondering about how much did you end up paying for this whole 1 week itinerary – what would be a good estimate of the budget? 🙂
This Miami to Key West Road Trip guide is incredibly helpful. You’ve really thought through everything you need to know before planning a trip. Thank you for this helpful resource. Saving this guide for later!
Thank you for such a detailed itinerary! My fiancé and I are getting married next year and we are thinking about making this our honeymoon trip 😄 Your post will definitely be our guide.
Thank you so much! 🙂
Love all of this! We are thinking this for our honeymoon and this itinerary really helped! What was the total cost for this trip not including airfare since that depends on where you are flying from.
Thanks Jessica! It’s an awesome destination for a honeymoon. I will need to do a little math and get back to you. I’m on the road, and can’t get the numbers right away, but will circle back in a few days. 🙂