The Perfect 2-Week Florida Road Trip Itinerary + Map - The Daydream Drifters (2024)

This is the perfect Florida road trip itinerary! Having spent many years living in Florida and exploring the state extensively, I can confidently say that this road trip covers many of the must-see locations, with the option to include additional destinations if you have extra time. I recently took my husband, (who’s from Spain) on this journey, and he loved every place we visited. Even if you’re a Florida native, you’ll still enjoy this adventure!

2-Week Florida Road Trip Itinerary Overview

Day 1 + 2: Miami

Day 3, 4, + 5: Florida Keys

Day 6 + 7: Captiva Island

Day 8 + 9: Sarasota

Day 10, 11, + 12: Orlando

Day 13 + 14: Saint Augustine

Pack your bags.. it’s time for a road trip!

The starting and ending point of your Florida road trip itinerary will depend on a few factors.

• If you’re flying into Miami (like we did), I recommend renting a car at Miami aiport (MIA) and flying out of Orlando (MCO) at the end of the road trip.
  • The cost of renting a car in Miami and dropping it off in Orlando was only a $50 price difference. Almost all rental car companies will let you drop off in a different place. It made a lot more sense for us to just spend the $50 than to drive all the way back to Miami.
• If you live in Florida, then starting either in Miami or Saint Augustine (whichever is closer to your city) would be best.

Miami is known for its beautiful beaches, vibrant culture, and diverse range of attractions. There’s truly something for every kind of traveler! The peak tourist season is during the winter months, from December to April, when the weather is warm and dry. However, this is also when prices for accommodations and activities tend to be higher. If you prefer lower prices and can handle some rain, you can consider visiting during the shoulder seasons of spring (May to June) or fall (September to November).

We flew into Miami International Airport and picked up our rental car, then drove to our hotel in South Beach. After check in, we grabbed lunch and started checking off our must-do things and must-visit places in Miami!

Best things to do in Miami:

• Spend a day at Nikki Beach in South Beach (this was one of our favorite things we did in Miami)
• Explore Little Havana and eat authentic Cuban food
• Visit Wynwood Arts District
• Eat tacos at Taquiza in North Miami Beach (literally the best tacos I’ve ever had in my life)
• Walk around and admire all the pastel art deco buildings
• Grab a co*cktail at one of the many bars, nightclubs, and lounges in areas like South Beach, Downtown Miami, and Brickell
• Get brunch on Ocean Drive (we did this before heading to the Keys)

Where to Stay:

• Casa Boutique Hotel ☆☆☆ ($$)
• SLS South Beach Miami ☆☆☆☆ ($$$)
• The Savoy Hotel & Beach Club ~ Miami Beach ☆☆☆☆ ($$$$)

Make sure to get some good sleep on your last night in Miami because the next morning it’s time to grab some brunch and head down to Key West!

Driving time from Miami to Key West: approx. 3 hours, 32 mins.

On the morning of day 3, we woke up and headed straight to brunch. There are so many amazing brunch spots all over Miami, so you won’t have any difficulty finding one. Following your meal, it’s time to embark on the road trip journey to Key West! We suggest heading directly to Key West so that you can gradually make your way back to Miami while exploring the other Keys. This approach will considerably reduce the length of your next long drive, which will be on day 6.

A bit about The Florida Keys – they are a picturesque and unique chain of islands located at the southern tip of Florida, extending into the Gulf of Mexico and the Atlantic Ocean. The Florida Keys are known for their stunning natural beauty, vibrant marine life, and laid-back atmosphere.

There are hundreds of keys in the Florida Keys, but the most famous ones (listed from north to south) are:

• Key Largo
• Islamorada
• Marathon
• Big Pine Key
• Key West

Related post (for couples): A romantic getaway in Key West

Must-do things in Key West:

• Spend an afternoon at the beautiful Smathers Beach – this is a great place to take some photos!
• Wander around Downtown Key West – we loved exploring downtown without a GPS.
• Take a sunrise or sunset sailing tour – We planned to do this, but decided on taking a day trip to Bahia Honda. Next time, we definitely want to do the sailing tour. If you stay at The Perry Hotel they can arrange a sailing tour for you!
• Eat at Lobster Shack Key West – If you’re into seafood, you must try this place.
• Grab a drink at Green Parrot Bar – This bar was voted best bar in Key West and has happy hour & live music!
• Visit the popular tourist spots – Southernmost Point Buoy, Southernmost House, Key West lighthouse, etc.
• Try the Cuban food at Havana Cabana – we loved having lunch here and we thought the food was mouth-watering

The best place to stay:

• The Perry Hotel Key West ☆☆☆☆ ($$$)
  • We LOVED our stay here. It’s located on a beautiful marina about 15 minutes from downtown Key West. The hotel offers free shuttles throughout the day and night.
    • The Perry Hotel Key West is dog-friendly, if you’re bringing your furry friend along on your road trip!
  • Stay here for 2 nights and then check out early and head to Bahia Honda State Park

Driving time from Key West to Bahia Honda State Park: approx. 45 mins.

After the 45 minute drive from Key West, you’ll arrive at Bahia Honda State Park

This state park is one of the most beautiful in all of the Florida Keys. The azure waters, pristine white sand, flourishing nature—it’s a dream come true. Here’s the lowdown:

• Navigate your way there by clicking this link for Google Maps directions.
• Entrance costs $8.00* per vehicle (+.50 cents per person). The limit is 8 people per vehicle.
• Bahia Honda State Park offers a range of amenities, including camping, cabins, pavilions, picnic spots, showers, and restrooms.

We spent about 6 hours at the park. Our time mostly consisted of snorkeling, indulging in a picnic, soaking up the sunshine, and reveling in the breathtaking array of blue hues surrounding us. Camping is definitely on our agenda for the next visit!

Since we need to start making our way back north, it’s time to head to either Islamorada or Key Largo for the night. We recommend staying at Drop Anchor Resort in Islamorada, so we will use that as an example.

Driving time from Bahia Honda State Park to Drop Anchor Resort Islamorada: approx. 1 hour

Stay the night at Drop Anchor Resort in Islamorada

This super cute pastel hotel right off the main road, is also perched right on the beach. They offer 12 different kinds of rooms, many of them with ocean views. There are quite a few restaurants close to the hotel. For those seeking underwater adventures, the nearby dive shop, Key Dives, offers both scuba diving and snorkeling experiences.

Rest well because after checkout in the morning, it’s time to set off on the longest drive of the whole Florida road trip itinerary!

Driving time from Drop Anchor Resort to Captiva Island: approx. 4 hours, 38 mins.

Don’t worry too much about the long drive because there are many things to do and see along the route –

• Stop at John Pennekamp Coral Reef State Park in Key Largo and take a glass bottom boat tour or go snorkeling. There are beautiful coral reefs and lots of marine life here!
• Take an Everglades airboat tour (you can book this through lots of different companies or on GetYourGuide)
• Visit the Naples Pier
• Swim or take a looong walk on the sand at Fort Myers Beach

This is definitely one of our favorite places on the whole Florida road trip itinerary! Right when we arrived to Captiva Island, we absolutely fell in love. The peace and serenity that this island brings is unparalleled. We went straight to our hotel (South Seas Island Resort) and checked in. When we got to our room, we couldn’t believe our eyes *see photo belows*. The room was a dream!

Note: After the devastating hurricane in 2022, South Seas Island Resort has been rebuilt in many parts. Some of the hotel areas may not look the same as before.

Where to Stay:

There aren’t many places to stay on Captiva Island, but even if there were, we would still recommend South Seas Island Resort. We had an amazing stay and there were lots of things to do and many delicious food options.

Things to do on Captiva Island/South Seas Island Resort:

• Kayaking with manatees and dolphins – This was the most exciting morning of our whole road trip! We set off from the South Seas coast around 9 am and in the first 10 minutes of kayaking we were surrounded by dolphins playing. Then we paddled a bit farther and saw a few manatees under the water – they were so cute!
• Sunset dolphin boat tour – This was so much fun and we saw dolphins and manatees again, but this time more than 50 dolphins! Everyone on the boat was so excited and it was a great vibe 🙂
• Enjoy lunch on the beach at Island Tacos – The cutest little food truck with amazing Mexican food. We loved the tacos and quesadillas.
• Rent a golf cart and explore the island – Make a reservation ahead of time
• Swim, relax, and drink a co*cktail at the beautiful South Seas Island Resort ocean front pool
• Have dinner at Doc Ford’s Rum Bar & Grill on Sanibel Island – The food is delicious and they have live music often. In our opinion, we could have eaten at this restaurant every day for a week haha.
• Take a sunset walk on the beach – The sunsets are extra beautiful and colorful here!

Driving time from Captiva Island to Sarasota: approx. 2 hours, 15 mins.

Sarasota is my hometown, so it will always hold a special place in my heart! It’s a vibrant city known for its cultural richness, beautiful beaches, and artistic flair. Nestled on the southwestern coast of Florida, Sarasota frequently wins the title of having one of the best beaches in the United States, Siesta Key Beach, renowned for its powdery white sands and clear turquoise waters.

Where to Stay:

My parents still live in Sarasota, so we just stayed with them and didn’t have to get a hotel for this part of our trip! There are quite a few great hotel options in Sarasota though. I recommend staying either near Siesta Key or Lido Key area. Here are some choices:

• The Sarasota Modern, a Tribute Portfolio Hotel ☆☆☆☆ ($$)
• The Westin Sarasota ☆☆☆☆ ($$$)
• The Ritz-Carlton, Sarasota ☆☆☆☆☆ ($$$$)

Best things to do in Sarasota:

• Sunbathing and swimming at the #1 beach in the USA – Siesta Key! My husband (to remind you – he’s from Spain) had never seen a beach with sand so white and water so clear. Siesta really is amazing + the sand NEVER gets hot!
• Visit the unique The John and Mable Ringling Museum of Art – I have probably been here about 20 times in my life and it never gets old. Make sure to see the art museums, the circus museum, and the Ca’ d’Zan mansion.
• Shopping and Lunch at St. Armands Circle – Eat at Cha Cha Coconuts (they have the best fried shrimp) and then get ice cream at Kilwins (my favorite flavor is the cake batter.. yummm).
• Brunch with your feet in the sand at The Sandbar Restaurant on Anna Maria Island – This one is in Bradenton Beach area, but it’s worth the drive to eat here then explore Anna Maria Island!
• Wander around the beautiful Marie Selby Botanical Gardens in Downtown Sarasota

If you’re traveling as a couple, don’t miss 15 romantic things to do in Sarasota!

Driving time from Sarasota to Orlando: approx. 2 hours, 20 mins.

Next up on the Florida road trip itinerary is Orlando! There are e n d l e s s things to do there. It is one of the most popular places to visit in all of the USA. People usually flock here for the theme parks, but there are many other fun activities and places to see. We opted for a mix of theme parks and a nearby incredible nature landscape – the springs!

Where to Stay:

There are hundreds of hotels in Orlando! Depending on if you choose Universal or Disney, you will likely pick a hotel that’s close to the park or on park property. Often if you stay at the hotels on park property, they have guest benefits (like getting into the park early, fast passes, etc.)

We stayed at Loews Portofino Bay Hotel on Universal Orlando property and would recommend it to anyone and everyone! The hotel looks like it’s straight from Portofino in Italy, has incredible food, transport to the parks, guest benefits, and so much more. Read the post linked below for more details about this hotel and the Universal parks.

Related post: Loews Portofino Bay Hotel + Universal Orlando

Best things to do in Orlando:

• Explore the Universal Orlando Parks (Universal Studios, Islands of Adventure, and Volcano Bay)
• Visit the Disney Parks (Magic Kingdom, Animal Kingdom, Epcot, Hollywood Studios + Blizzard Beach and Typhoon Lagoon)
• Enjoy an evening at Disney Springs and eat at one of the many amazing themed restaurants
• Stroll around I-Drive (International Drive)
• Spend a day floating around Rock Springs Kelly Park (about 45 minutes away from Orlando). I go to Rock Springs every time I go to Orlando. There’s something so magical about it. Don’t forget a tube to float on!

Driving time Orlando to Saint Augustine: approx. 1 hour, 40 mins.

Saint Augustine stands out as a unique stop on the road trip, often overlooked but has SO much to offer! Nestled on the northeast coast of Florida, it holds the distinction of being the oldest continuously inhabited European-established settlement in the continental US.

Thanks to its rich history, vibrant culture, and captivating architectural beauty, Saint Augustine is a true gem and a destination that shouldn’t be missed. And let’s not forget the allure of the beautiful St. Augustine Beach!

Where to Stay in Saint Augustine:

Best things to do in Saint Augustine:

• Wander on St. George Street – This pedestrian only street is lined with shops, restaurants, and attractions.
• Get spooky with a night time haunted tour or pub crawl
• Indulge in a homemade popsicle from The Hyppo – I am obsessed with this place! The watermelon hibiscus and pink grapefruit flavors are my absolute favorite!
• Visit the historic Castillo de San Marcos National Monument
• Have a picnic at Saint Augustine Beach

For those flying out of Orlando, make your way to the Orlando Airport on the morning of Day 15 and return your rental car.

If you find yourself with some additional time, extending your stay in the Keys, exploring the Clearwater/St. Pete area, or taking a detour to Cocoa Beach are all worthwhile options!

We hope you enjoyed this Florida road trip itinerary! Have a great time and don’t forget the snacks 🙂