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The Ultimate Road Trip: How to Spend 5 Days in the Florida Keys

  • September 25, 2019
  • By Jackie
The Ultimate Road Trip: How to Spend 5 Days in the Florida Keys


WOW this might be the longest, biggest, juiciest post I’ve EVER written so I hope you’re ready for it! My Instagram is FLOODED with photo from our trip to the Florida Keys and my Instagram Highlight from the trip is pretty amazing, but now I’ve put together the ULTIMATE Road Trip Guide! How to Spend 5 Day in the Florida Keys! Where to eat, where to stay, what activities to do – literally EVERYTHING. And since you guys seem to love my itinerary type travel posts that is exactly how I set this one up!

I broke everything out by day so you can easily see how much Megan and I go do in the 5 days we spent in the Florida Keys! I’m warning you it’s a long one, but it’s definitely worth it, especially if you’re planning a trip to the Keys. And if you’re not, maybe you will after reading this post!


Day 1:


We took a 7AM flight out of NY and landed in Miami around 10AM, took the shuttle to our Mazda Rental Car c/o DriveShop and were on the road to the Florida Keys before 11AM! It was my first time going to the Keys and I was honestly SO surprised how fast the ride from Miami to Key Largo was. I think the main reason why I never visited before was because I thought the trip would be much longer, but we pulled into Key Largo (Key Largo Chocolate specifically) by 11:30AM for our first piece of Key Lime Pie of the trip! This is a must visit on your trip because who doesn’t want a slice of key lime pie to kick off their Florida Keys Road Trip, but also because they have Key Lime Pie ON A STICK and because the lime green and pink exterior of the building is super Instagrammable!


After getting our key lime pie fix we headed to Kona Kai Resort in Key Largo to check in! Kona Kai is a intimate adults-only resort on Florida Bay with only 13 guest rooms and suites. I absolutely loved how quite and serene the resort was, plus it was beyond beautiful. Private white sand beach, waterfront pool and jacuzzi, hammocks and beach chairs scattered around the property all surrounded by a tropical botanic garden. The staff was also beyond accommodating and went above and beyond for everything we needed while we were there plus gave us great suggestions for exploring Key Largo and surrounding towns.

fruit-print-dress-ultimate-road-trip-5-days-florida-keys-itinerary-what-to-do-key-west-key-largo-islamorada-marathon-miami-vacation-guideShop my sunglasses, The Bagtique Lemon Earrings c/o & SHEIN Fruit Print Dress c/o (Use Code: JACKIEG15Q3 for 15% off)

After dropping off our luggage and changing into vacation clothes we headed to Marker 88 for brunch, this waterfront restaurant known for their crazy Southern Bloody Mary so we knew it was the perfect place to stop for Sunday Brunch!

hammock-nap-ultimate-road-trip-5-days-florida-keys-itinerary-what-to-do-key-west-key-largo-islamorada-marathon-miami-vacation-guideShop my Wyeth Bardot Hat c/o

We explored Kona Kai a little bit after lunch (and by explored I mean took a nap in the hammock) then headed to Florida Keys Brewing for a tour and tasting! Not going to lie this was one of my favorite parts of the trip. The Brewery itself is so cool and colorful and totally on brand for me plus every single beer we tried (PS we sampled ALL of them) was delicious! Not sure if I can pick a favorite, but the Smuggler’s Moon Oatmeal Stout was up there and the Jala-Mango Jalapeno Mango Wheat was right behind it. We definitely could’ve hung out there for a couple hours and I can’t recommend it enough if you’re in the area! They have an inside bar area and outdoors beer garden with live music so it’s definitely THE place to hang out in the Upper Keys.

florida-keys-brewing-ultimate-road-trip-5-days-florida-keys-itinerary-what-to-do-key-west-key-largo-islamorada-marathon-miami-vacation-guideShop my Kendra Scott Earrings c/o and ASOS Dress.

Then we ended the night with a quick dinner at Tides Beachside Bar & Grill at the Islander Resort. The Islander Resort grounds are so beautiful and I wish we would’ve been able to have lunch here to see it during the day, so keep that if you’re planning to visit. Order the Blackened Fish Sandwich and obviously, Key Lime Pie!

Day 2:

We explored our hotel and relaxed in the morning then headed out to Key Largo Conch House for lunch. We heard so many great things about this restaurant so we knew we needed to check it out and it didn’t disappoint! Order the Grilled Mahi Tacos!


After lunch we headed to John Pennenkamp Park to go snorkeling, but the water was so rough that we sadly weren’t able to go! If you plan on snorkeling in the Keys though THIS is the place to do it. John Pennenkamp Coral Reef State Park is the first undersea park in the US and the shallow water coral makes it great for snorkeling (depending on the weather your snorkeling tour may go to the “Christ of the Deep” statue). They also offer kayaking, scuba diving and glass bottom boat tours.


Since our plans got changed for the afternoon we stopped at a farmers market and picked up some snacks then headed back to Kona Kai and relaxed by the pool with some Risata Moscato! Did you know that September is National Self Care Awareness Month? Over the past few years I’ve made it a point to do a little bit of both – traveling and vacationing – on all of my trips because while I love to see ALL the things, I’ve found that I don’t fully enjoy myself if I’m constantly on the go, so being able to relax for the afternoon with a glass of Moscato was a blessing in disguise!

sunset-ultimate-road-trip-5-days-florida-keys-itinerary-what-to-do-key-west-key-largo-islamorada-marathon-miami-vacation-guideShop my dress, Melie Bianco bag c/o The Bagtique & Kendra Scott earrings c/o!

For dinner we headed down to Islamorada to Robbie’s and ate at Hungry Tarpon! Robbie’s is a Florida Keys institution and a must visit if you’re headed there. If you’re there during the day make sure to sign up for a tarpon feeding and then make sure to eat at Hungry Tarpoon for either lunch or dinner! We asked our waiter for suggestions as to what to order and everything was BEYOND delicious! I suggest a Blueberry Mojito to drink and Chef’s Peel & Eat Shrimp, Thai Fish Fingers, Ahi Tuna Tacos to eat!


Day 3:

After breakfast at Kona Kai (did I mention that complimentary light breakfast is served every morning – bagels, pastries, fruit, coffee), we reluctantly checked out and started our drive south to Key West!


We stopped along the way at Drop Anchor Resort (purely because it was super colorful and Instagrammable) and then at Isla Bella Beach Resort because it was highly recommended by so many people and once we got there we understood why. I wish we were staying 2 more days in the Keys so we could’ve done 2 days here because it was beyond beautiful! Then we stopped for lunch at Mangrove Mama’s on Sugarloaf Key! Such a great spot if you’re looking for somewhere to stop to eat on the drive, I suggest the Blackened Mahi Tacos (I know I’m suggesting them everywhere, but these might have been my favorite – mahi, bacon and slaw!! SO delicious).


We checked in The Perry Hotel on Stock Island and we welcomed with open arms…and by open arms I mean champagne and the best view of the harbor in the whole hotel. While The Perry Hotel isn’t in Key West (it’s just before it on Stock Island) I highly recommend it. It has a waterfront pool, marina views, scooter rentals and it’s dog friendly!


Then we headed into Old Town Key West for a sunset sail with Fury (we did Commotion on the Ocean Sunset Cruise to be exact)! This was another one of my favorite parts of the trip! It was so relaxing just hanging out on the water and we had a great night and a perfect sunset. The 2 hour cruise includes live music, drinks (margaritas, champagne, beer & wine) and appetizers! I honestly can’t recommend it enough, this is one of those excursions that no matter how many times I visit Key West I think I’ll do it!

 fury-sunset-cruise-ultimate-road-trip-5-days-florida-keys-itinerary-what-to-do-key-west-key-largo-islamorada-marathon-miami-vacation-guideShop my heart sunglasses & Kendra Scott earrings c/o!

After our sunset cruise we stopped for a quick dinner at Azur. Megan and I weren’t too hungry so we ended up splitting a few appetizers! I highly recommend the Steamed Mussels, Pulpo (definitely my favorite), Steamed Clams & Chorizo and Goat Cheese Salad!

Day 4:

We woke up bright and early for our last full day in the Florida Keys to go parasailing with Fury. Of course I was a little nervous (it was my first time parasailing), but it was 100% worth it! Honestly I think sitting on the boat is more rough then being up in the air on the parasail! Fury parasailing boats leave pretty much every hour, but I definitely still recommend booking this excursion in advance so you’re guaranteed a spot on a boat! There were 6 people on our boat and we went up in groups of 2 and were all able to parasail for about 12 minutes. I highly recommend it and would definitely do it again!


After parasailing we finally got a chance to explore Old Town Key West! First, we grabbed some coffee and took the Conch Train Tour, I love doing these kind of tours when I first get to a new location (we did a similar one when we got to Charleston) because not only do you learn some history about the area, but you also learn where everything is!

blue-macaw-restaurant-rum-runner-ultimate-road-trip-5-days-florida-keys-itinerary-what-to-do-key-west-key-largo-islamorada-marathon-miami-vacation-guideShop my hat, sunglasses, dress & Megan’s lobster phone case!

Then we hopped on the Old Trolley Tour to the Bahama Village area of Key West for lunch! We originally wanted to go to Blue Heaven, but it was closed so we ended up at Blue Macaw instead! Atmosphere, drinks and food were great and I definitely recommend it. It was insanely hot this day so that might have influenced what I ordered, but everything was so good. Try the Rum Runner, Peel & Eat Gulf Shrimp and Tomato & Watermelon Salad! PS Blue Macaw is known for their Build Your Own Bloody Mary Bar and if it wasn’t so hot I definitely would’ve taken advantage of this because I LOVE bloody marys and this one looked insane!


You can’t go to Key West and not visit Hemingway Home! It was the residence of Ernest Hemingway in Key West and just as beautiful now as I’m sure it was in the 1930s when he lived there. A few fun facts about Hemingway Home – it was one of the first houses on the island to be fitted with indoor plumbing, it has the first pool in Key West, and the six and seven toed cats that can be found at the house are descendants of Hemingway’s cats!


After being out in the heat all day we headed back to the hotel to enjoy the waterfront pool a little and get ready for dinner at Matt’s Stock Island Kitchen, which was conveniently at our hotel! We had a table overlooking the marina which was perfect for watching the sunset and the food was not to be missed. Order a Pineapple Jalapeno Mojito (or two) to drink and the Commodore Tower as an appetizer and the Black Grouper for dinner (I’m literally still thinking about this dinner!)

tropical-dress-stock-island-marina-ultimate-road-trip-5-days-florida-keys-itinerary-what-to-do-key-west-key-largo-islamorada-marathon-miami-vacation-guideShop my sunglasses, SHEIN Tropical Cold Shoulder Dress c/o (Use Code: JACKIEG15Q3 for 15% off) and bag c/o!

After dinner we booked it back to Key West to go on the Ghosts and Gravestones Tour. This is becoming a bit of a tradition for us to go on one of these in every place we visit and this one was just as fun as tours past.

Day 5:


We checked out of The Perry Hotel, then headed into Key West for breakfast at Fisherman’s Cafe. We definitely went out with a bang with this meal because it was definitely memorable. Honestly we walked past it SO many times during our stay in Key West and didn’t think anything of it, but boy were we wrong. It was BEYOND delicious! Order a “El Cubano” Breakfast Sandwich, Yuca Fries and Plantains and be prepared to be full for a week! Definitely another meal I’m still thinking about.


We did a little more exploring in Old Town Key West. We walked down Duval Street, snapped a photo with the Mile 0 sign, explored Truman’s Little White House and just got lost in the perfect little streets of Key West. Before we knew it, it was time to trek back to Miami for our flight home. We didn’t get to see everything I wanted, but I’m grateful that we got to see a ton during our tours the day before and that just means I’ll have come back! The drive from Key West to Miami is about 3 hours, but it’s such a beautiful ride it doesn’t seem that long at all. And just like that we were on our 7pm flight back to New York.

ultimate-road-trip-5-days-florida-keys-itinerary-what-to-do-key-west-key-largo-islamorada-marathon-miami-vacation-guideShop my hat, sunglasses, earrings, dress & bag c/o!

Things we didn’t get to visit & restaurants we didn’t get to eat at, but were HIGHLY recommended:

  • Breakfast at Blue Heaven (Key West) – SO many people recommended this place so if it’s open when you’re there definitely go!
  • Dinner at Santiago’s Bodega (Key West)
  • Sandy’s Cafe apparently has the best Cuban Sandwich on the island! (Key West)
  • Sunset dinner at Latitude’s Restaurant (Sunset Key)
  • Mrs. Macs Kitchen (Key Largo)
  • First Flight Island Restaurant & Brewery (Key West) – The birth place of Pan American Airways
  • Sloppy Joe’s (Key West)
  • The Green Room Eco Bar (Key West)
  • The Fish House (Key West)
  • Holiday Isle Tiki Bar (Islamorada) – The Rum Runner was invited here!


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Thank you Kona Kai Resort for hosting us in Key Largo and thank you The Florida Keys for organizing some meals, excursions and our accommodations in Key West! All opinions are my own, thanks so much for supporting companies that make this blog possible.

Location: The Florida Keys | Photos: Megan Zietz & myself
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By Jackie, September 25, 2019
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