If you’re looking for the perfect way to experience the Florida Keys, look no further. My 5-day Florida Keys itinerary will take you from scenic drives and waterfront resorts to laid-back beach bars and must-do Key West activities. Whether you’re into water sports, delicious food, or simply relaxing on the beach, you’ll find the perfect balance of relaxation and excitement.
Here is your ultimate 5-day Florida Keys itinerary!
Florida Keys Itinerary: Day 1
Arrival, Scenic Drive, and Lunch
Your Florida Keys itinerary starts when you land in Miami and grab your rental car. Usually, those airport-to-destination drives can feel dull, like you’re not quite in vacation mode yet. But not this time! The drive down is one of my favorite parts—it’s so beautiful! On one side, you’ve got the Atlantic Ocean; on the other, the Gulf of Mexico. It’s the perfect way to kick off your trip and feel like the vacation has begun.
For lunch, make your way to Morada Bay in Islamorada. This charming beach cafĂ© with gorgeous waterfront views immediately puts you in full vacation mode. The food is amazing—think classic American dishes with a Caribbean twist. It’s the perfect spot to unwind, sip on a drink, and take in the beauty of the Keys.
Tarpon Feeding & Check-In
As you head to Marathon, stop at Robbie’s of Islamorada to feed the tarpon. It might sound a little weird, but trust me, it’s so much fun and should be included on every Florida Keys itinerary. You can grab a bucket of fish and head out to the dock to feed these giant fish. It’s only $2.50 to get on the dock and $5 for a bucket of fish.
After tarpon feeding, check into Isla Bella Beach Resort on Marathon. This is one of the most beautiful properties in the Keys. This beachfront resort has everything you need for a relaxing stay—five oceanfront pools, bikes, kayaks, snorkeling, bocce ball, mini golf, and even giant chess. There’s also a fitness center, four restaurants and bars, and a marketplace cafĂ©.
After you settle in, have dinner at Mahina, the resort’s Polynesian-inspired restaurant. End the day with live music at their beach bar—there’s nothing better than sipping a cocktail while listening to music right by the ocean.
Florida Keys Itinerary: Day 2
Chill Out & Water Activities
Start your day with breakfast at Isla Bella, then head straight to the beach. The resort offers plenty of water activities, so kayak, paddleboard, or just lounge by the water.
Have lunch at the beach bar. The tables in the sand, strung with lights and overlooking the water, create the perfect vibe. The menu is amazing—I love the tuna nachos, mahi tacos, and beachy cocktails. It’s the ultimate spot to relax and enjoy a meal by the water!
Dinner
Later, grab dinner at Burdines Bar and Grill. It’s super casual and right on the marina—perfect for a laid-back dinner. With great views and a relaxed vibe, you can kick back, enjoy some good food, and watch the boats, and maybe dolphins, go by.
Florida Keys Itinerary: Day 3
Drive to Key West and Check-In
You’re going to Key West today! The drive is about two hours. It’s a whole different vibe in Key West.
There are many hotels, but Casa Marina and Southernmost Beach Resort are my favorite.
Casa Marina is the perfect blend of old-school charm and modern luxury. Set on Key West’s only natural beach, this historic resort offers oceanview rooms that make you feel right at home. Spend the day relaxing with a spa treatment, grab a cocktail by the pool, or swing by The Canary Room for a Hemingway Daiquiri—it’s my favorite spot. The resort has the largest private beach in Key West, two pools, a fitness center, and tons of water activities like kayaking, paddleboarding, and snorkeling. You can also rent bikes or scooters to explore the area at your own pace. It’s close to all the action but quiet enough for a relaxing stay.
Southernmost Beach Resort is an oceanfront resort with newly renovated Key West-style buildings near the best restaurants, shops, and nightlife spots. You’ll have beach access, three swimming pools, a coffee shop, three pool bars, and its popular restaurant, Southernmost Beach CafĂ©. Additionally, you can relax at the spa, visit the gym, and rent bikes to explore the area.
Looking for more great places to stay in Key West? Check out my guide on the Best Hotels in Key West.
Lunch and Explore
After checking in to the hotel, go to The Seaside Cafe at The Mansion on the Sea. It is just steps from the ocean, with tables between palm trees. This is my favorite spot in the Florida Keys. I love their mojitos and conch fritters, but they are famous for their lobster biscuits. With ocean views and delicious coastal dishes, the ambiance here is hard to beat.
Tip: There’s only outdoor seating, so be sure to dress for the weather. If it gets too hot, there’s plenty of seating under a pavilion.
After lunch, it’s time to explore Duval Street. This street is full of energy all day and night—there’s so much to see! You’ll never get bored, from historic landmarks and art galleries to cute cafes, lively bars, and unique shops. I’m not a fan of Duval’s super touristy northern end; I prefer the quieter southern end, where you’ll find chic boutiques and wine shops without all the noise. Two of my favorite spots are The Green Pineapple and Shaddow and Fish—definitely worth checking out!
Looking for more to do in Key West? Check out my Ultimate Guide to Key West.
Dinner and Drinks
Treat yourself to a special dinner at Louie’s Backyard. This is my go-to spot for a fancy waterfront dinner with stunning views of the Atlantic Ocean. Just be sure to make a reservation in advance- it’s always booked! I like to arrive early and have a glass of champagne on their lower deck, which extends right over the water. While I typically go for one of their specials, I’ve heard nothing but rave reviews about their Shrimp & Grits, so that’s definitely worth trying!
If you want an after-dinner drink, I highly recommend checking out The Canary Room at the Casa Marina if you’re looking for a classy spot. I went three times during my last trip to Key West, and every drink I had was amazing, but my favorite drinks were the Hemingway Daiquiri and the Clover Club. They’ve seriously got the best craft cocktails in town. Plus, the atmosphere is gorgeous, so it’s a great place to unwind after dinner.
Florida Keys Itinerary: Day 4
Breakfast and Water Activities
Start your day at Blue Heaven, one of Key West’s most iconic spots for breakfast. It’s always my go-to. You might have to wait for a table (they don’t take reservations), but it’s worth it. While you’re waiting, head to the bar across the street for a mimosa and live music. Don’t be surprised if you see chickens and cats roaming around—that’s part of the charm! The Lobster Benedict is a fan favorite, but I usually stick to the basics—eggs, potatoes, and bacon.
After breakfast, get out on the water! There are so many options, but these are my favorites:
Kayaking through Mangroves
The Lazy Dog kayak tour offers a 2-hour tour through mangrove tunnels for $60.
Snorkeling
Island Jane Charters offers a 3-hour snorkeling and sailing charter for $79. The price includes all necessary equipment, water, soda, white wine, beer, margaritas, and champagne.
Snuba Diving
If you want to experience snorkeling and scuba diving, try Snuba! It’s a great way to explore the reefs, see colorful fish, and check out the coral formations. Snuba Key West offers a 3-4 hour charter for $120.
Dinner and Drinks
Keep dinner casual and go to DJ’s Clam Shack. It’s a laid-back seafood shack on Duval Street with the BEST lobster roll. Seriously, the best lobster roll I’ve ever had, and I’ve tried them all up and down the East Coast. After ordering my food at the window, I sit at the front counter to see the excitement on Key West’s main strip. Head to the picnic tables in the back if you’re looking for something a little quieter.
Finish your night with drinks and live music at Hank’s Hair of the Dog. It has the best vibe, awesome music, and a lively atmosphere, perfect for winding down after a day in the sun.
Florida Keys Itinerary: Day 5
Breakfast and Drive Back to Miami
Before you head back to Miami, be sure to stop at Baby’s Coffee. Their breakfast sandwiches are delicious, and the coffee is some of the best you’ll find—a great way to wrap up your trip.
This 5-day Florida Keys itinerary is designed to help you make the most of your time in the Florida Keys. With a perfect mix of must-do activities, relaxing beach spots, and some of the best restaurants in the area, you’ll experience exactly what makes these islands so special. Whether you’re looking to explore, unwind, or enjoy a delicious meal by the water, this guide will ensure you experience the best the Florida Keys has to offer in just five days.
Need more Florida Keys tips? My Ultimate Guide to the Florida Keys has everything you need to make the most of your trip!
