Florida Keys Itinerary

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The Babes had such a fun trip to the FL Keys, and today I’m sharing our full Florida Keys Itinerary!

This was my first time in the Keys, and we had such a great time relaxing, soaking up the Jimmy Buffet vibes, and adventuring!

If you like water activities, eating fresh fish, and drinking yummy cocktails, you’re going to love the Keys.

There’s lots to do and see in the Keys, and of course, you can also get plenty of relaxing pool time. Those are always my favorite vacations—the ones that have the right mix of adventure and exploring, with some downtime to recharge.

Getting to the Keys

We flew into MIA so we could do a Florida Keys road trip down and visit a couple of different areas in the Keys. Plus, it’s just so much easier when you’re coming from the west coast to get a nonstop to MIA.

At the end of our trip when we departed, we left from the FL Keys airport, EYW. You’ll be hard-pressed to find a nonstop back to the west coast from EYW, so expect the journey home to take at least 8 hours. At least we gain 3 hours when we fly back to the west coast!

We arrived in Miami in the evening, before our FL Keys road trip itinerary began the next day. To make things easy on ourselves, we stayed the first night at the Hilton Miami Airport Blue Lagoon.

It’s located just four miles from Miami International Airport, offers free shuttle service to and from MIA, and has plenty of free parking if you’re renting a car. The hotel has a pool, sports courts, bike and car rental on-site, a fitness center, and a hot tub.

This could also be a great jumping-off point if you wanted to visit Everglades National Park or Biscayne National Park before continuing on with your Florida Keys itinerary.

We enjoyed a drink at the bar our first night, a dip in the pool in the AM, and then made our way out for our drive down to the Keys!

Where to Stay in the Keys

We stayed at two different resorts in the Keys so that we could experience a couple of different locations. First up was Hawks Cay Resort.

The 60-acre property is on Duck Key and has a combination of 2 or 3-bedroom villas, as well as guest rooms. With six different restaurants, a saltwater lagoon, and an adults-only pool, we had a lot of different lounge spots to choose from.

Additional onsite amenities include education-based dolphin experience with in-water and dockside programs, fishing, diving, and water sports.

We stayed in their 3-bedroom villa, right on the water. Look at how vibrant and turquoise it is! I loved relaxing on our deck and soaking up these views.

Our second resort was down in Keywest, at Southernmost Beach Resort. This spot was so cute and located in historic Old Town Key West, where Duval Street meets the Atlantic Ocean. It was super centrally located and an awesome home base for our time in Key West.

With include four bars, three heated pools, two beaches, a private tanning pier with ocean access, a fitness center, and a spa, we were pretty set.

Alright, let’s get into our girls’ trip Florida Keys itinerary!

Florida Keys Itinerary: 4-day Florida Keys Travel Guide

Day 1: Florida Keys Itinerary

Kick-off your Florida Keys road trip

On our first full day in Florida, we started our drive from Miami down to the Keys. Our first destination was Duck Key, which is about a 2-hour and 15-minute drive from Miami.

We didn’t make any stops along the way since we were excited to get to our destination, but Florida Keys Brewing Co. is a popular one, where this microbrewery serves up their favorite beers and you can grab a bite from a food truck.

We checked into Hawks Cay Resort and spent the first afternoon lounging by the lagoon and enjoying lunch and drinks. We also couldn’t miss the adorable dolphins playing and doing tricks with their trainers at the resort’s dolphin encounter area.

Dinner at Angler & Ale

We had dinner on-property at Angler & Ale, overlooking Hawks Cay Marina. It’s the resort’s casual, Keys-style restaurant, and the menu features fresh, locally sourced ingredients.

A few favs to look out for on the menu include the Whole Fried Snapper, Grouper Cheeks, ceviche of the day, and Tuna Nachos.

If you’re into fishing and plan on going out on the water while you’re staying here, guests also have the option to ‘Hook N Cook’ where you can bring in your fresh catch of the day and have the chef prepare it that evening. How cool is that?

We were also really amused by the robot waiter that brought food to some of the tables. I’ve never seen anything like that before!

Day 2: Florida Keys Itinerary

Parasailing

Our first water adventure was parasailing and we had a blast! I’ve been parasailing once before as a kid with my family in Hawaii, but that was a long time ago so it was fun to experience it as an adult and in a new destination.

The water here is so turquoise and beautiful, and I managed to snap some pics from up above. (My phone was in a case with a lanyard around my neck).

Sometimes you can spot some marine life from way up high, like sea turtles (I saw one!) and sharks. Eek.

We went out with Sundance Watersports and they did a great job. They really knew what they were doing and they ran the whole thing like clockwork.

If you get seasick, definitely bring your nausea wristbands and Dramamine if it’s a little choppy out on the water. I was pretty nauseous the whole time, including when we were up in the air.

Lunch at Robbie’s of Islamorada

Robbie’s Marina where Sundance Watersports is located is an eclectic mix of outdoor shops, food vendors, and tarpon feeding.

Never heard of a tarpon? I hadn’t either until this trip. They’re basically HUGE fish, and you can feed them from the dock. Be prepared for some aggressive pelicans to join in on the feeding frenzy.

I was beyond excited to also see a couple of manatees at the dock! I’ve only seen them at zoos so it was fun to see them in the wild. They’re one of the silliest-looking creatures ever and it was fun to see them up close.

We grabbed lunch at The Hungry Tarpon Restaurant, which has a large menu with tons of options. If you’ve been out fishing, the restaurant will also cook your fresh catch.

Tasting at Islamorada Brewery & Distillery

After lunch, we made our way over to The Islamorada Brewery & Distillery, located at mile marker 82.2 with a bright yellow-and-teal-colored tasting room.

Their outside sandbar area is the perfect Keys vibe, and we spent a while there just relaxing and tasting their different beers. The company also operates an on-site distillery creating spirits branded as Islamorada Distilling gin, vodka, and dark barrel-aged and spiced rums, so you know we had to try those too.

My favorite was their key lime colada. It was SO good. I tried a lot of key lime coladas while we were in the keys (it’s a tough job but someone’s gotta do it), and theirs was the best.

Dinner at Morada Bay Beach Café

We ended the day with dinner at Morada Bay Beach Café & Bar. The vibe is Mediterranean bistro, but set in the sand. The Café’s menu is a blend of Caribbean and American cuisines showcasing the local seafood and produce.

The ambiance is on point, and a lot of movies and music videos have been shot here. It’s the perfect place to enjoy a beautiful sunset and good food and drinks.

When we were there they had a yellowtail snapper for their whole fried fish and I had to try it. I’d never heard of yellowtail snapper (just tuna) and y’all, it was delicious. It was one of the pricier items on their menu but I really enjoyed it and was glad I tried it.

Day 3: Florida Keys Itinerary

By day 3 it was time for us to head further south on the overseas highway on our Key West drive!

Before heading out on the 1.5 hours drive to Key West, we were supposed to go on a kayaking excursion with Get Up & Go Kayaking. Sadly, the winds were too high for us to go out with them that day, but I wanted to note it here in the itinerary because it looked SO fun and we had specifically picked this company for their clear kayaks.

The kayaking adventure would have involved kayaking along mangroves, beautiful waterways, and hopefully spotting some marine life in the Florida Keys backcountry.

Drive down to Key West

If you want to break up the drive, there are more than a few things that you could make a pit stop for, including

John Pennekamp Coral Reef State Park: Located on the famous Key Largo *cue the Beach Boys*, Coral Reef State Park is known for being the first undersea park in the country. They offer snorkeling, scuba diving, and glass-bottom boat tours.

Bahia Honda State Park: This state park is known for having some of the most beautiful beaches, like Calusa Beach with its white sand and vibrant blue waters.

Turtle Hospital: The Turtle Hospital helps to rescue, rehabilitate, and release injured sea turtles. You can book a tour here to see the turtles, and your ticket helps support these rehabilitation efforts.

The Old Seven Mile Bridge: Better known as “Old 7,” you’ll cross over this bridge on your way down to Key West. There are two bridges here—one for vehicles and one that is pedestrian-only if you want to get out and stretch your legs a bit.

The older bridge was built over a century ago as the centerpiece of Henry Flagler’s Florida Keys Over-Sea Railroad. In 1938 the bridge was converted for automobiles and in 1982 the Federal government built a new span paralleling the historic one.

Check-in and lunch at Southernmost Resort

We made it down to Key West and checked into Southernmost Beach Resort. While our rooms weren’t quite ready yet, they were kind enough to give us some food/drink vouchers, so we grabbed lunch at Southernmost Beach Café.

This restaurant is located right on the beach, so it’s got that sand-in-your-toes vibe, and it features locally-inspired Key West cuisine, fresh seafood, and yummy cocktails. I of course had another key lime colada here, lol they’re just too good.

Key West Butterfly and Nature Conservatory

The Key West Butterfly and Nature Conservatory is right across the street from Southernmost Beach Resort, so we popped in this afternoon. You’ll enter into a (very humid) conservatory with around 50 different species of butterflies flying around, as well as flamingos and other exotic birds.

Sunset Sail with Fury Key West

We went out on the water with Fury Water Adventures for a sunset sail. I definitely recommend heading up top to the open-air deck—the vibe inside the cabin was very booze cruise and just not the atmosphere we were looking for.

Outdoors in the fresh air though, was lovely. They had a band playing and we danced, drank champagne, and enjoyed a gorgeous sunset.

Dinner at Half Shell Raw Bar

After your sunset cruise, walk over to Half Shell Raw Bar for an awesome seafood dinner.

Located in the Key West Historic Seaport, the casual Half Shell Raw Bar serves fresh seafood, from fish and chips to its famous Half Shell conch ceviche. Diners sit at picnic-style tables and can gaze over the water to watch boats come and go while enjoying local seafood such as Key West pink shrimp.

I ordered the lobster bake and it was totally delicious. And of course, we had oysters. If there are oysters on the menu, you know the Babes are ordering them—especially me and Iesha lol.

Day 4: Florida Keys Itinerary

Morning Vinyasa Flow Yoga Session with Salute to the Sol Yoga at The Truman Waterfront

We started our morning with a vinyasa flow yoga session with Salute to the Sol Yoga, and it was just what we needed to reset for a peaceful, relaxing day.

I loved that Rebecca, our yoga instructor, customized our session for us to be focused on light stretching and relaxation. After indulging on the sunset cruise the night before, we weren’t looking for anything intense that morning.

Salute to the Sol Yoga offers private practices or you can join Salute to the Sol at The Perry Hotel & Marina Key West every Sunday for an all-level vinyasa on the event lawn.

Hemingway Home

Ernest Hemingway lived and wrote in Key West for nearly 10 years, finding solace in the turquoise waters that surround this tiny two-by-four-mile island. At this Whitehead Street property, guests can step back in time and visit rooms and gardens where the Nobel Prize winner spent the most prolific period of his writing career.

Notable features include the island’s first swimming pool and a colony of cats, many of them six-toed, supposedly descended from a sea captain’s feline given to the author.

Hemingway wrote many of his classic works in the second-story studio that adjoins the Whitehead Street house. Among them: “Death in the Afternoon,” “For Whom the Bell Tolls,” “The Snows of Kilimanjaro” and “The Short Happy Life of Francis Macomber.” He used Depression-era Key West as the locale for “To Have and Have Not” — his only novel set in the United States.

Lunch at Fisherman’s Café Key West

Grab lunch at this local restaurant near Old Town Key West and The Historic Seaport. They serve timeless favorites and fresh ingredients like Key West shrimp, lobster, and conch in a fast-casual environment with outdoor seating.

Choose your own water adventure: Snorkeling or Jet Skiing

Our itinerary got shifted around quite a bit during our trip because of the weather—the winds were just too high in some places to stick to the original plan. So, we ended up doing both snorkeling and jet skiing on our last day.

That’s a lot of time out on the water and in the sun, so I’d recommend choosing one—or if you want to do both, plan the other water activity for a different day. We wanted to make sure we got both snorkeling and jet skiing in during our trip and the weather was finally cooperating, so that’s why we decided to pack both into our last day!

Snorkeling with Fury Water Adventures

We went out again with Fury Water Adventures, this time on their double-dip snorkel trip that stops at two different reef locations. I love snorkeling in new (to me) places—I just get really excited to see what’s out there and different than what I’m used to in Maui.

The visibility was ok (about 30 feet that day), and there weren’t a ton of different fish to check out, but we did see a pretty big (~6 foot) reef shark, lots of barracuda, and a turtle. There was also a lot of really pretty, soft fan coral.

After snorkeling, they pour you champagne for the ride back in, and we sat up top with the captain to enjoy the views.

Jet Skiing with Barefoot Billy’s

This was my absolute favorite activity of the trip—save the best for last, right?? We had SO much fun on this jet ski tour around Key West. I would definitely add this as a can’t-miss activity to put in your Florida Keys itinerary.

I had never driven a jet ski before (well, that’s kind of a lie, my dad took me jet skiing in Hawaii when I was a little kid and I cried the whole time) and I gotta say, it’s a thrill. The guys at Billy’s did such a great job getting us comfortable on the jet skis, and then we were on our way around Key West, stopping at a few interesting places (like Pablo Escobar’s former mansion) along the way.

If you’re under 35, you’ll have to get there early in order to take a boat safety quiz. It’s open book (and open internet for that matter), and you can do it as a group to help each other find the correct answers. They’ll give you all the details when you make your reservation, but it’s definitely something to be aware of so you can plan accordingly.

I would say wear shorts or stand up for some of the ride (bouncing around on the seat in a wet swimsuit starts to get pretty uncomfortable after a while), and definitely wear sunscreen.

This adorable long sleeve swimsuit arrived in my mailbox after my trip, but this suit or a long sleeve UV-protectant top would have been perfect for jet skiing. I did end up getting a little burnt on my shoulders because you’re out there for a while and there’s not really a way to reapply sunscreen.

Dinner at The Docks Stock Island

The Docks is Stock Island’s newest restaurant, serving up fresh sustainably sourced seafood. The décor is upcycled island style with views overlooking Stock Island’s working marina.

I had the local sauteed snapper and it was soo good. We also enjoyed the east coast oysters they had on the menu (because, duh), and I was pretty pumped about those because ultimately I like those better than Gulf Coast oysters (but I was glad I tried them at Half Shell Raw Bar.

My only regret was not getting their key lime pie, because it looked awesome and we hadn’t had a chance to try key lime pie in the Keys, but we had to get to our next activity…

Drag Show at 801 Bourbon Bar

We rounded out our FL Keys trip with a drag show at 801 Bourbon Bar and had a blast! Megan had been before so she recommended it and we had such a fun night.

Be sure to buy your tickets in advance and get lots of dollar bills for the show (they can also make change for you at the bar)!

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That’s our Florida Keys itinerary! The Keys are such a great destination for a girls’ trip, couple’s trip, or even a family vacation. There’s just so much fun stuff to do here.

I’ll be writing up more posts from our trip including what to wear and more restaurant recommendations, so be on the lookout for those!

In the meantime, if you’ve been to the Keys, I’d love to know, what are some of your other favorite spots? I’d love to know because I’ll definitely be back someday! Next time, I’d love to extend my trip and head even further south to check out Dry Tortugas National Park.

If you’re spending more time in Florida and looking for more trip-planning inspo, be sure to hit up the best beaches in South Florida.

If you hit up any of these recommendations on your next FL Keys trip, tag me in a Story @wtfab, I’d love to see it!

Huge thank you to the Florida Keys Tourism Board for hosting the Babes on this epic trip! You can visit their website for more resources when you’re planning your trip.

Looking for more travel inspo? Check out my other travel guides here!

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