Florida Keys Travel Guide | Ultimate Vacation Itinerary

Location: United States, East Coast,
Key West Family Resorts Hawks Cay

ABOUT Florida Keys

The state of Florida offers so much for travelers. There are so many cities to visit around the state for families, girl’s trips, solo trips, and couple’s vacations. All you have to do is pick what type of experience you are looking for, and then let that decide where you’ll be headed.

The Florida Keys is an ultimate destination. It’s a paradise that you can go to where you’ll find clear blue waters, tropical sunsets, and you’ll be able to get the Caribbean island vibe without having to leave the United States.

To visit, just fly into the Miami airport and grab yourself a rental car, and take a nice road trip down the to the Florida Keys where you’ll have the option to stop through places like Islamorada or keep going down the coast and make it all the way to Key West to complete your Florida Keys & Key West getaway.

The Florida Keys is a destination where you’ll be able to take multiple types of vacations such as the girl’s getaway or a family vacation. And to give you a full travel guide on vacationing in the Florida Keys, I’ve provided this epic vacation itinerary.


Travel to the Florida Keys is not as difficult as you may think, but do keep yourself aware that the drive does turn into one lane where you aren’t able to access a large multi-lane highway. So make sure that you bring the Florida Keys vibe and just enjoy the ride and the amazing view. You can travel to the Florida Keys by either starting in Miami or if you are doing an epic family vacation, you can start from Orlando. Driving from Miami to the Florida Keys is about a 2 hour drive depending on traffic. With heavy traffic, I would add an additional 30 minutes, but if it’s a lighter day, you can probably get there sooner. If you’re looking to go from Orlando to Key West, you’re looking at a 3-4 hour drive with minimal traffic, but you don’t have to do it straight through. Stop in the Keys and enjoy the area of Islamorada and Duck Key. As you travel around the Florida Keys, you can reference this map of the Keys of Florida as your guide.

Trip map courtesy of Wanderlog, a trip planner app on iOS and Android

What to Pack for THE FLORIDA KEYS

When packing for visiting the Florida Keys, you’ll want to bring swimwear, comfortable shoes along with sandals that are easy to take off and store for watersports, casual vacation wear, and also a jacket or sweatshirt for the cool evenings when you want to be outside but it begins getting a little chilly. The Florida Keys is a very casual, but bright area, so don’t feel like you have to bring super dressy outfits.

For the women, summer dresses are a great go-to, especially looser ones that flow in the breeze. For the men, a nice pair of shorts is great for walking around and experiencing Florida Keys and also for dining.

What I like to do for all of my trips is I rent from Nuuly. It’s a great way to get outfits for your entire trip that fit your personal style for one very low price compared to the value of each of the pieces that you get. So, don’t shop, instead, rent from Nuuly (and get $20 off your first rental).

Summer TravelShop

Key West Family Resorts Hawks Cay


Villa At Hawks Cay Resort

Hawk’s Cay Resort

Hawk’s Cay Resort in the Florida Keys is located on Duck Key and offers 250 two- and three-bedrooom villas as well as a hotel. This resort is both family friendly and adult friendly in the aspect that, if you’re traveling with kids, there is a pool that is great for the little ones, the Coral Cay Activities Center, as well as dolphin experiences and in-water and dockside experiences that the entire family can enjoy. And for those who aren’t into sitting by the pool with little ones running around, there is the Oasis Cay adults-only area that is fit with comfortable cabanas and poolside service where you can order cocktails and bites from the pool. I highly recommend staying in a villa as they are immaculate and give you plenty of balconies to sit out on and get a great view of the docks while feeling the cool breeze and sounds of the ocean. The villas are equipped with a full kitchen, living room area, and multiple bathrooms to fit the entire family. The three bedroom villas have a master bedroom with a full bathroom and walk out patio and two additional bedrooms, one being on the second floor with two full beds and the second on the main floor with one bed.
Hawks Cay Resort Villa
Swimming With The Dolphins Florida Keys
Enjoy the OASIS POOL at Hawk’s Cay

If you’re traveling to the Florida Keys on a girl’s getaway, solo travel, or a couple’s vacation, you’re probably looking for some adult-only time. Hawk’s Cay Resort provides that experience with the Oasis Pool that is an adults-only pool where you can sit in a cabana or in the lounge chairs and enjoy the sunshine and sounds of the water while ordering bites and tasty cocktails. On my girl’s getaway with the Babes That Wander, we spent great times by at the Oasis Pool during the day as we swam around the large pool, and then later in the evening where we were able to come back and enjoy time in the hot tub. So when you’re looking to just have some downtime in Florida Keys without having to leave the resort, the Oasis Pool is where you’ll want to visit.

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Morado Bay Beach Cafe Florida Keys
Morado Bay Beach Cafe

Morada Beach Cafe

The Morada Bay Beach Café & Bar is an outdoor bistro café set on the sand right off the water where you can enjoy tastes of the islands while watching the beautiful sunset late in the evening as you dine. When you dine at this restaurant, make sure that you ask about the seafood specials because you’ll want to order just that. And if you’re looking for a little extra, there is also the sister restaurant, Pierre’s, which is also right there and is located in the most picturesque beach house that I have seen.
Morado Bay Beach Cafe Dinner
Hungry Tarpon Restaurant

When visiting Robbie’s of Islamorada, make sure that you stop over to the Hungry Tarpon Restaurant and Bar that is a great go-to place for breakfast, lunch, and dinner for the entire family. The restaurant is located right on the dock, so if you get there early enough, you can get a great table right next to the water where you can look out to see the tarpons swimming close to the dock along with the manatees that tend to pop in from time to time to check out what is going on and to steal some fish from the tarpons. The menu itself is vast and offers options for everyone. If you go for breakfast, make sure to order their signature Trash Can Bloody Mary. I’m not a person who typically likes Bloody Mary’s but theirs was actually quite tasty and I enjoyed all of the little bites that came in it such as the bacon, jerky, and olives.

Florida Keys Angle And Ale

Angler & Ale

At Hawk’s Cay Resort, you can enjoy food at the casual, Key-style restaurant, Angler & Ale, that overlooks the Hawk’s Cay Marina. With the fresh menu that includes whole fried snapper and ceviche of the day, you’ll eat some great seafood that you won’t be able to find other places. Even if you are not staying at the resort, you can still come and dine at this restaurant, but if you are staying at the resort, the restaurant is in walking distance from the hotel and villas or you can catch the complimentary trolley that ill take you to and from. Along with the fresh, delicious food and great marina ambiance, also make sure to take a look at the craft cocktail menu and extensive beer selection. The food and drink menu make Angler & Ale a great dining location to spend late evenings enjoy the company of those you are traveling with.
Angle And Ale Florida Keys


Parasailing In Key West

On the days where the wind is a little too strong to go kayaking or snorkeling, make sure to book yourself a parasailing experience as it is one of the most epic things to do in the Florida Keys. While in the Florida Keys, you can book a parasailing experience with Sundance Watersports, where they will meet them on the docks at Robbie’s and board the boat to be taken out on the ocean to fly up tandem with a partner for an thrilling and unforgettable parasailing experience. Parasailing doesn’t require any previous experience and you don’t necessarily need to know how to swim. They’ll equip you right on the boat and attach you to the parasail and then up you’ll go for one of the most epic experiences that you can have in the Florida Keys. While in the air, you can look at over the crystal-clear waters and see some of the marine life such as the possibility of sighting dolphins or turtles that like to swim close to see what is going on. This is a great experience for the entire family and is super safe.

Sundance Watersports offers other exciting experiences such as snorkeling and sunset cruises, so there are options for all ages and thrill seeking levels.

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Manatees In Florida Keys

Right on the dock at Robbie’s on Islamorada, you can grab yourself a bucket of fish, for free, and feed the tarpons that that swim up right to the dock and wait for those out there to feed them. It’s a fun and funny experience especially because you’re feeding fish to fish while also trying to avoid feeding any manatees that may swim up and try to get the fresh water off the fish and avoiding the large pelicans that are also out there trying their hardest to take the fish from the tarpons as well.


At Hawk’s Cay Resort, you can find a pod of friendly and loveable bottlenose dolphins. Not only can you walk by and watch these friendly dolphins swim about, you can also take part in the Dolphin Connection program. This experience allows you to view, interact, and learn about the dolphins in a safe, humane manner. When you make a reservation, you’ll pick the experience that you are looking to have which can be anything from seeing and learning about the dolphins, swimming with them, learning to be a dolphin trainer, or having an intimate encounter.


If you’re an early riser and looking to have an experience that starts your day off with peace and deep connection to yourself, make sure to book yourself sunrise yoga. Depending on where you are staying, your yoga session can take place right at your resort, so you can just wake up and walk right over. Hawk’s Cay Resorts has sessions that take place that overlook their Saltwater Lagoon. One popular option in the area for sunrise yoga is Island Flow Yoga. They offer group sessions as well as private sessions where you can have your session on the bay front pier, under the gazebo, or on the beach.


One of the must-stop places while in the Florida Keys is Islamorada Brewery & Distillery. This brewery and distillery is a renowned and well known company that stands out at mile marker 82.2 with its bright yellow and teal colored tasting room. You can stop in for their craft beer or taste their spirits made right at the on-side distillery which includes gin, vodka, and rums. Make sure to sit outside in their back patio area and enjoy a flight of beers or their craft cocktails and play games with friends. After a flight, stay longer and keep drinking the cocktails and brews responsibly as you enjoy the fun atmosphere and play games available right in the back patio area.

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