What makes a perfect road trip? One where the “destination” is actually several stops along the way! We’ve partnered with road tripper Dr. Cacinda Maloney of Points and Travel to follow along on her drive through South Florida. 

Want to take that classic American road trip? I did it back in the early 80’s and recently did it again to see what has changed. Driving down the keys from Miami to Key West is a great road trip! The four-hour drive time goes by faster than you would think along the scenic US Highway 1 crossing 42 bridges. I suggest stopping along the way for some good ole’ Florida fun! Leave from the Miami airport by 7 a.m. and follow the route outlined below or drive to Islamorada, spend the night and begin the next day by exploring the middle keys.

Day #1

Robbie’s Marine and The Hungry Tarpon, 10:15 a.m.

Growing up to 8 feet long and weighing more than 200 pounds, tarpon are huge fish that live in the tropical waters off the Florida Keys. Watching the participants dangle their arms over the water, a massive sea creature suddenly leaps out and attaches its massive self via the mouth and teeth around their wrist and hand! Yikes! And people do this stuff for fun! You can buy bait in a bucket for about $3 and catch them with your hands if you dare from the dock at Robbie’s Marina in Islamorada. The food at the restaurant is great, but the fun is standing there and watching it all go down. I didn’t do it, but I sure enjoyed watching others with fish up to their wrists! Careful, they have coarse jaws and leave marks! Gawking at its finest!


The “Old 7” Seven Mile Bridge, 12 p.m.

You will be driving and driving for miles on the freeway, one bridge after another, but there is this one that you must stop for!  Actually, you stop before you get there just north of the bridge at mile marker 47 in Marathon. I recommend to rent bicycles at Overseas Outfitters. Then, you and the crew can take off for Seven Mile Bridge on bikes. The bridge was constructed in 1912 as the centerpiece for Henry Flagler’s Over-Sea Railroad. It is literally a bridge to nowhere. It was retired in 1982 as a fishing pier and walking/bike trail. For this stop, I recommend sunscreen and tennis shoes!


Turtle Hospital in Marathon, 1:15 p.m.

I loved this stop along the way to learn how the folks in Florida care for these magnificent creatures. They teach the public ways to ensure they are doing everything they can to prevent injuring them. It is really nice to see an organization that loves turtles so much! You can see everything from turtle surgeries to turtles in various states of rehabilitation due to boating mishaps, floating debris and water pollution. Once they have recovered, they release the turtles back to the spot where they were rescued! They have rehabilitated over 1,400 turtles, including loggerheads, greens, hawksbills, leatherbacks and Kemp’s Ridley turtles. However, thirteen turtles have been unable to be released back into the wild and remain as permanent residents. This is the only state-licensed veterinary hospital dedicated solely to the treatment of sea turtles. Worth a stop.


Return for R&R at Cheeca Lodge & Spa, 3:30 p.m.

In the middle keys at Islamorada, you can stay at Cheeca Lodge & Spa, the views are amazing, the beach really nice, and the food, well – scrumptious! You can check-in for the night, order a drink and relax. At this point in the drive, I suggest getting back to homebase for a little rest and regrouping, so that you can go to dinner by 7:30 p.m.

Dinner at Marker 88, 7:30 p.m.

Since 1967, Marker 88 has been offering up beachside dining and some of the Florida Keys’ freshest seafood. They have the most relaxing setup and gorgeous sunsets around; so don’t miss this final stop before you are on the road again for Key West.


Day #2

Check-in at the Ocean Key Resort & Spa, 10 a.m.

Check-in at the Ocean Key Resort and unload your luggage for a day of exploring! They offer breathtaking views overlooking the Key West Harbor, a gorgeous penthouse swimming pool and an awesome breakfast.

Duval Street Shopping, 12 p.m. 

Make your way to Duval Street, which is literally steps from this hotel. Spend your first day wandering around the streets near Duval, peering into the picketed fenced yards of houses. You will see chickens running wild and you can shop along the colorfully painted houses that have been turned into shops. Duval Street may be known for its lively nightlife, but during the day, this main drag is the best place to shop, eat & drink and buy souvenirs.



Visit Ernest Hemingway’s Home and Museum, 1 p.m.

If you are anything like me, you love history (and cats!) And there are plenty of both here at Ernest Hemingway’s old haunt. You can visit his house from the 1920’s, but even better, visit his friends that are still around: the 5-6 toed cats that are descendants from his cats and continue to live here. Fascinating!


Key West Lighthouse, 2 p.m.

While visiting Hemingway’s home, might as well cross the street and visit the first lighthouse in Key West, which was originally built in 1825. It was destroyed by a hurricane in 1846, but a new tower was built in its place in 1848.

Go See the Southernmost Buoy Marker, 4 p.m.

If you have done this before, then skip it, as it is extremely touristy and the lines are long. Maybe just drive by and thank God that you are not in the line of people waiting in the humid sun. But if you have to, the concrete buoy marking the “Southernmost Point in the Continental USA” is at the corner of South and Whitehead streets in Key West. It is only “90 miles to Cuba” from here! I skipped it this time, but snapped a photo on my trip when I was here before!

Marvel a Key West Sunset, 6:40 p.m. (varies depending on time of year)

The sunsets in Key West are some of the best, so grab a few munchies and margaritas from El Meson de Pepe, a family-owned Cuban restaurant near Mallory Square. Be sure and go to the square right before the sun drops below the horizon of the Gulf of Mexico. It truly is like a painting in the sky. But beware, it is crowded!


Day #3

The Most Exciting Day You Will Have in the Keys!

Blue Heaven Restaurant, 8 a.m.

There is nothing quite like the Blue Heaven for breakfast. The blue house where you can have “breakfast with the roosters”! I loved the Lobster Eggs Benedict and Chef Guillaume is famous for his key lime pie as well! Here, they eat it for breakfast. All that food for breakfast is to get you ready for the ride of your life coming up next.

Key West Seaplane Adventures, 9:30 a.m.

Take a sea plane to Fort Jefferson, where you will have the thrill of your life, as you buckle yourself in, put your headset on and become the copilot on a seaplane over to Dry Tortugas! What a ride! I can guarantee you will enjoy this!



Dry Tortugas Islands for the Day, 10:30 a.m.

Wear your swimsuit under your clothes and get ready for a fabulous day exploring the Old Fort and swimming the gorgeous crystal clear, turquoise blue water of the Tortugas Islands. It will be one of the best days you have! Bring your snacks and water, as there is nothing here but an island and a fort!


Dinner at Latitudes on at Sunset Key Guest Cottages, 7:45 p.m.  

Kick back and grab a bite at this unique resort island, only a quick boat ride away in the Key West Harbor. It’s the perfect setting for an eloquent evening of outstanding food and drink to enjoy your final sunset.

Sunset, 8:19 p.m.

You may never go back home.


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