Key West Road 4-day Road Trip
The Florida Keys consist of over 1,000 tropical islands, each known as a “Key.” If you don’t mind a bit of driving, I highly recommend a road trip from the southernmost Key, Key West, up to the mainland of Florida. The Keys are connected by US Highway 1, a scenic overseas highway offering breathtaking views of clear teal water. This destination is perfect for those looking to escape everyday life and enjoy tropical weather.
So, you’re probably here for the itinerary! This plan includes stays in Key West, Duck Key, and Key Largo, before heading to Miami Beach and Boca Raton. I hope this helps inspire or guide anyone planning their own tropical escape!
Itinerary Hacks:
ChatGPT: Before diving into the details of your trip, use ChatGPT to create an itinerary based on the places you’d like to visit. This will help you gather popular activities for each island so you can pick and choose what interests you most.
Groupon: Surprisingly, Groupon was the only site that listed a hotel in Key West for under $250. Given that prices are generally very high on this island, it’s worth checking out Groupon to help keep costs down.
Car Rental: For car rentals, I highly recommend using a Costco membership. I got my annual membership for about $30 through a coupon site a friend recommended, but a standard membership is around $60 a year. Costco’s car rental website is user-friendly and offers discounted rates through several major rental companies. I found I could save between $100 and $250 compared to other sites. I chose not to go with the cheapest option available and instead rented through Enterprise, as I’ve had problematic experiences with budget rentals that came with hidden fees and issues. For our 6-day trip, the total cost for renting a car was around $350 (excluding tolls), which I found reasonable and worth the experience.
KEY WEST ROAD TRIP ITINERARY:
- 3 nights, 3.5 days on Key West
- 2 nights 2.5 days visiting family and friends.
Day 1: Key West
5:00 AM Depart from home to the airport, arriving 2 hours prior to the departure for a domestic flight.
7:30 AM Flight departs.
11:15 AM Flight arrives at Key West Airport.
11:30 AM We picked up the car at the airport. The car rental kiosk was conveniently located right as you stepped inside the terminal.
11:45 AM We drove out of Key West Airport and found parking near the Ernest Hemingway Home. Parking was quite easy for my father and me because he is handicapped and able to use a disabled parking placard for up to 4 hours. The museum was worth the approximately $30, and I recommend taking a guided tour to explore the historic house and gardens filled with six-toed cats.
12:45 PM We enjoyed a leisurely stroll along Duval Street, known for its vibrant atmosphere, shops, and restaurants.
2:00 PM We had a late brunch at Blue Heaven, which reminded me of the Los Feliz area in Los Angeles, CA. The setting was like a little jungle, with art and a grungy yet relaxed atmosphere. We both got the steak eggs Benedict and enjoyed trying a local beer.
3:30 PM We drove to Hilton Garden Inn Key West, The Keys Collection. Recommendation: This hotel was serviceable but not exceptional. We had a nice view of the pool and two double beds, although someone unexpectedly entered our room with a duplicate key, which was awkward, and the fire alarm kept going off. The decor was somewhat dated and not very exciting in my opinion.
4:00 PM We hung out at the pool and had a drink. It felt great to be in the sun and a bathing suit after a long, cold winter up north.
7:00 PM While many people watch the sunset at Mallory Square, where street performers and vendors gather every evening, we opted to venture south on the west side of the island to John D. MacArthur Beach State Park. I met a really nice park ranger during sunset, and there was a beautiful beach and nature surrounding us.
8:15 PM We stopped by the Southernmost Point landmark! It was surprisingly empty when we drove by, so we decided to park and snap a picture together.
8:45 PM We grabbed Sonic fries and an ice cream sundae on the way back to the hotel.
9:00 PM We settled in for the night and prepared for the next day back at the hotel.
Day 2: Key West to Marathon
10:00 AM: Drove to Marathon, which is approximately halfway between Key West and Miami. We checked out earlier than necessary because the hotel wasn’t particularly noteworthy. I was excited to reach the next destination because it was a resort! I put on my bathing suit under my clothes and we hit the road. We stopped at Cudjoe Key for coffee, and my dad enjoyed a cinnamon roll pastry. I picked up a giant $20 submarine sandwich from a convenience store that I nibbled on sporadically throughout the remainder of the trip.
12:30 PM: We arrived in Marathon, which is approximately halfway between Key West and Miami. In my humble opinion, Marathon Key is the most beautiful key, with its clear-water beaches. We drove straight through this key to Duck Key, where our next hotel, Hawks Cay Resort, was located. We got there early, as the email confirmation mentioned that we could enjoy the resort’s amenities until our check-in at 4 pm.
We absolutely loved Hawks Cay! When we arrived, the entire place looked newly renovated with adorable decor and thoughtful art on the walls. When you walked through to the back, there was a man-made mangrove! We immediately changed into our bathing suits and got into the water. I paddle-boarded around the area while my dad swam. He’s a great swimmer and thrives in the water, even though he’s disabled on land—a true merman!
I noticed that there was even a dolphin sanctuary located right next to the mangrove in a fenced-off area. It was truly spectacular to peek over and see possibly a half dozen dolphins swimming around and coming up for oxygen.
2:00 PM Because I booked through my Capital One credit card, I received a call from the hotel saying they had upgraded our room to one overlooking the pool and resort and that we could check in early. This was such a nice call to get! My dad and I took our time because we were busy playing ‘Name that TV Intro Theme Song’ by the pool. We had so much fun!
3:30 PM We explored the resort and found a putting golf area, a completely empty pool, a children’s water park that my dad enjoyed frolicking through, and a children’s center where parents can drop their kids off for the day. This place is great!
4:30 PM We went back to the main resort area and stopped by the Tiki Hut for the most delicious coconut piña coladas. Just what I needed! Afterward, we got dressed for our dinner reservation.
6:00 PM While I thought I had booked a dinner reservation at the Angler & Ale restaurant, it seems that I didn’t properly do that in advance, but that wasn’t an issue. We were able to get a $50 credit to the restaurant with our Capital One reservation when charging the meal to the room. We sat on the back porch patio and overlooked the ocean. We both had the burger and a beer, and it was delicious! We got the key lime pie for dessert, a must-have on Key West, and our day was complete!
7:45 PM We were back in time to enjoy sunset at the mangrove! We sat by the dolphins until dark in Adirondack chairs. We said good night to the dolphins and headed back to our hotel room. What a glorious day at Hawks Cay Resort!!
Day 3: Explore Marathon and Drive to Key Largo
10:00 AM In the morning, I had a bit of a late start due to having to write a few emails for upcoming interviews. I headed to the pool for a half-hour swim, which was glorious. I also dipped my head in the mangrove and swam around because I was YOLO-ing and needed to soak up all the fun I could have before checkout time. I happened to have a random key on my keychain, so I threw this in the ocean to mark the end of a chapter in my life and the beginning of something new!
10:15 AM I have to note that I caught the tail end of the dolphin morning dance! This was beautiful as the dolphins had a choreographed number where they jumped out of the water and flipped their tails in synchrony. I loved this so much I can’t even express it in writing.
12:00 PM We were able to get a late checkout by one hour. I showered, and then we sadly left!
12:30 PM We headed to Sombrero Beach on Marathon Key! We backtracked slightly to visit this stunning must-see beach with some of the clearest waters. People were fishing, and a sign mentioned that there is a lot of wildlife in these waters. I want to compare the hues of this beach to Elafonisi Beach in Crete, Greece. The difference here was that the dead coral at Sombrero Beach causes the ocean floor to appear white, which likely contributes to the water’s striking teal color. Elafonisi Beach, on the other hand, had pinkish hues. My dad shared that live coral can be very colorful and full of marine life. He used to scuba dive when he was younger and told me great stories about diving in Cozumel, Mexico.
2:00 PM A tropical rainstorm cut our beach day short, so we drove through Islamorada to Key Largo, our previous hotel destination along the Keys. We stopped at a sandal store and each bought a cheeky tourist shirt for $4. We also visited the cutest coffee café in Islamorada called Moka, where the woman at the counter was incredibly sweet. Outside the café was an adorable outdoor artist area that reminded me of the semi-grungy, artist-inspired gardens in East LA, like Los Feliz.
4:00 PM We continued to the hotel where we stayed for one night on Key Largo at the Waterfront Suites and Marina. Honestly, it was a nice and clean apartment-style stay. There were two floors and it overlooked a marina where boats were docked. It had two bathrooms, a full kitchen, two TVs, and a waterfront porch—it was nicer than many apartments I’ve rented! There was a restaurant across the way with music and people, which made me feel safe, like humanity was around. That said, Key Largo was no Duck’s Key… If I were to do this experience again, I would only stay at Hawks Cay on Duck’s Key because that was truly magical and nothing can top the morning dolphin dance routine.
5:00 pm We decided to get Dairy Joy ice cream we saw on the way and then went to John Pennekamp Coral Reef State Park, which was closing for the day, for $9. The kind park ranger was super friendly and told us we could come back the next day because we had just missed all the activities.
6:00 PM We explored various areas to grab a bite to eat. To be completely honest, there was a weird vibe everywhere we went on this Key. There was an interesting resort/restaurant that I explored while my dad sat in a swinging seat and texted my family. I decided the resort was creepy, even though it had very cute waterfront views. It might have been due to the overcast weather, but the vibe was just a little eerie, and there were not many people around.
6:30 PM We ended up going to Snook’s Bayside Restaurant for wine at the bar. We walked out to the waterfront patio and could see the rain clouds in the distance. Within a matter of minutes, it started raining, so we finished our wines at the indoor bar and then left. The sunset was not visible this day, but this restaurant has a great western view of the island’s horizon.
8:00 PM We got back to the hotel and wound down for the night. There was a pull-out couch downstairs for my dad, and I had a king-size bed upstairs. I took a picture from the kitchen patio showing people sleeping in their boats at the marina.
Day 4: Miami & Boca Raton
11:00 AM We checked out of the hotel and were on our way again! We drove to Starbucks, where I got a coffee frappuccino and my dad had a standard hot coffee—a 10/10 way to start the morning.
11:20 AM We arrived back at John Pennekamp Coral Reef State Park and checked out the aquarium. My dad went swimming while I dipped my toes in the water and observed the white pieces of coral on the shore.
12:00 PM We were on our way to Miami Beach to meet a friend.
2:00 PM We took many wrong turns and found ourself on Miami Beach area after major highway stress. We picked up two Pizzas around 17th street and then parked in a clutch handicap parking spot around 29th street. We met my friend on the beach at the 29th street entrance and the three of us mow-ed on barbecue chicken & sausage mushroom pizzas. My friend had to get back to work providing tele-therapy so I went swimming in the beautiful teal water. I kind of let the water wipe me out and wash me up onto the shore. I loved swimming at this beach due to the strong tides.
3:45 PM My dad and I were rolling again to Boca Raton to meet my Uncle/my Dad’s brother.
5:45 PM We jammed out to Roy Orbison and arrived in Boca Raton where we dumped our bags, made up the two guest beds, and were off to dinner.
7:00 PM Dinner was great! My uncle’s bestie in Boca was there and the two of them have a great light sense of humor.
9:00 PM We walked down to live music and danced a little bit. We headed back to my Uncle’s place and went bed
Day 5: Boca Raton
10:00 AM We were all up and showered. We had pizza for breakfast and enjoyed some great coffee. We spent the morning hanging out, chatting, and listening to music loudly, which was a lot of fun.
1:15 PM T-Time! We met up with Richie and played a round of golf. As it was our first game of the season, our skills were a bit rusty. My uncle and Richie weren’t too impressed with our early-May performance, so we skipped a few holes but decided to complete all 18. I usually play on the executive course, which has only 9 holes, so it felt great to be back on the full course.
4:00 PM I went with my uncle to Walgreens to get some hair paste while we waited for the pharmacy to reopen. We tried to use a coupon for a second hair paste, but the cashier didn’t apply it correctly. My uncle was a bit disappointed, but I enjoyed seeing him try to be savvy. Meanwhile, my dad explored the Costcos in Boca Raton and came back with dog treats for our dog back home.
5:00 PM I accidentally locked myself out while taking out the trash. To make matters worse, I also locked myself into the pool area by shutting a gate that was propped open. I managed to scale a fence to get out, and a kind young man with a golden retriever helped me back into the building.
6:00 PM We had more pizza and leftovers from the night before and relaxed. I assisted my uncle with fraudulent charges on his Costco credit card and tried to investigate who was buying shoes online and T-Mobile cell phone minutes. The mystery remains unsolved since we couldn’t trace the shipping addresses.
8:00 PM We lounged around and then went to bed.
Note on Soundtrack for the Keys Adventure: Taylor Swift’s new album was released just in time for our trip, and it was perfect for the Florida vibes! Her songs like “Florida!!!” and “Fortnight” reflect the healing nature of Florida, especially for those who’ve been through hardships. The album played on repeat through the car’s MyChevrolet Bluetooth app, setting the mood for our journey. If you listen to the Amazon Music version of the album, you can hear narrated tracks where Taylor explains the meanings behind some of her songs. The release of her new album was a fortunate coincidence and made the soundtrack for our trip unforgettable. I also played some of Roy Orbison’s greatest hits so my dad could enjoy the music as well.
It was such a fun adventure, and I feel incredibly lucky to have shared it with my father and to have met up with friends and family along the way! ❤️ I hope this itinerary helps someone else plan a fulfilling road trip through the Florida Keys.
