A Florida Girl's Guide to The Keys

A Florida Girl's Guide to The Keys

Although our family recently moved to Nashville, my heart is happiest along Florida’s saltwater shores. I spent most of my life along the gulf coast and have vacationed in the Keys for as long as I can remember. Some of my most memorable outdoor moments as a child are the ones I am now reliving as an adult with my children.

The Florida Keys are a chain of roughly 120 miles of 44 islands and 42 bridges that begin 15 miles south of Miami. It’s a beautiful, tropical destination known for sport fishing, historic sites, boating, blue waters and outdoor dining. Unlike the high-dollar luxury seen in areas like Rosemary Beach or Palm Beach, The Keys offer more of an “old Florida charm” void of chain restaurants or even a Walmart. There’s no real beach area like you may be used to, outside of resort beaches, but more areas off the causeway where you can pull off for a swim..or even camping.

With so many islands and activity offerings, I thought it would be best to offer up a five day guide of what to do and where to stay in The Keys. The map below shows how the area is divided into the Upper Keys, Middle Keys, Lower Keys and Key West. We always stay in the Middle Keys because it is most convenient for family activities and a little less busy than Key West. These are my personal favorites and the places we return to year after year.


You have two options ….you can fly into Miami or into Key West. (Marathon has an option for private planes.) Due to expense, we always fly into Miami, rent a car and then drive the 2.5 hours to the Middle Keys.


Our family prefers to stay in the Middle Keys, either Islamorada or Marathon/Duck Key. The Upper Keys are fine but a bit more commercial and crowded for me. John Pennekamp Reef is there, famously known for the underwater Jesus statue, but other than that, not my preferred area. The Middle Keys are more enjoyable for us simply due to the activities available, the restaurants we like and the proximity to the other islands within a short drive. Key West is great for a day trip but since we prefer to do more active, outdoor activities rather than tour/walk, it’s better for us to stay elsewhere. There are fabulous things to do in Key West, which I will list below.


Hawk’s Cay Resort - Located in the Middle Keys area, our family has stayed here for nearly 10 years and it is the resort I recommend the most if you have children. Their kids club and pirate pool cannot be beat. They also have a saltwater lagoon where you can rent paddle boards, a marina for fishing, multiple pools, resort shuttles, dolphins on site, a relaxing spa, restaurants and a great fitness center. There are several accommodations to choose from…hotel room to waterfront villa to villa with a pool. (Many people tow their own boats and dock them behind their villa.) We prefer to stay at the villas with individual, small, private pools because at the end of the day when we’re exhausted and the kids still have energy….into the pool they go! They also have special rates for Florida residents, past and present military, first responders and medical personnel. In my opinion, this has the most engaging offerings for active kids ages 4-16. Years ago, I wrote a blog post on the resort so I’ll link that again here.

Isla Bella Resort – This is the newest resort on my list and is where I recently chose to host an influencer retreat. Situated on over 24 acres of oceanfront property with white sand walkways, Isla Bella is a luxury resort in the heart of the Keys. Every room has an ocean front view and there are several rooms, suites and 2 bedroom options to choose from. There’s an incredible grocery/ gift market on property as well as a marina with charter boats, kayaks and jet skis. Their fitness center has Pelotons available and their spa is highly rated. There are five pools to choose from and there are scavenger hunt and art activities for the little ones. Although this resort is great for kids, I think this one is best for couples, girls trips and trips with toddlers or older teens.

Cheeca Lodge & Spa – My father’s favorite resort in the Keys, Cheeca Lodge features 27 acres of lush gardens and coastline with a Jack Nicklaus 9 hole, par 3 golf course. With a marina on site, a family pool and separate adult pool, Cheeca is the perfect blend of luxury living and outdoor adventure. Located in Islamorada, the sport fishing capital of the world, Cheeca is famed for their on-site fishing charters and fine dining. They also have Camp Cheeca, an environmental program for kids as well as a fitness center for those early morning workouts. This resort is the happy medium between the two resorts above and I definitely recommend this one if you have a serious fisherman or golfer in your family.

Rainbow Bend – Let me preface this recommendation by stating that I haven’t been here since college however for the price, it still seems to be one of the least expensive options for those traveling on a budget. This isn’t a luxury resort but rather a quaint little motel with its own beach, kayak rental, free breakfast and suites that have kitchenettes. With its Marathon location, its centered right in the middle of the Keys which makes exploring the islands very easy.

The Mermaid & The Alligator – My favorite bed and breakfast in Key West, this 1904 Victorian home is tucked away in the heart of Old Town Key West, just a short bike ride to some of the biggest attractions. Enjoy a complimentary, homemade breakfast each morning and bike rentals to get you around.


FISHING: There are three main types of fishing in The Keys…. 1) inshore, 2) reef and 3) offshore.

Inshore fishing is my personal favorite due to the size of the fish you can catch in relatively shallow water. You don’t need an all-day trip for these excursions and for those who get seasick, this shouldn’t give you too much trouble. Since you stay inshore and can still see land, waters are generally calm and blue. Flats boats typically can only hold 3 other guests besides the captain so keep that in mind when booking your trip. Our go-to guide, for nearly a decade, is Captain Ted Wilson, a UF graduate with an animal science degree who can teach you about the fish as much as he can put you on them. He’s a great family guy who always is a joy to fish with. Most people fish for tarpon, snook, bonefish and redfish on these trips but we always manage to get sharks as well! Fishing is prime in March, April and May, still great through the summer and sees action into October (a great fall break option for my Nashville friends.) 

Reef fishing and off-shore fishing are typically a bit longer of a day where you go a bit farther out in the ocean. You can get a lot of snapper and grouper reef fishing and then ask your guide to filet them for your dinner. Most people go off-shore fishing for mahi mahi, tuna, wahoo and snapper in The Keys. These boats can hold more people than inshore boats; maximum is 6.

Many resorts have their own marinas however, Two Conchs charters are now found all over The Keys and have their own TV show on the World Fishing Network. Bud n Mary’s  marina is a trusted marina that is home to reputable guides that fish for all of the above. If you have no idea where to start, call there first. They are located in Islamorada, about 30 minutes north of Marathon.

* Captain Ted and I discussed, and agreed, that we thought age 7 or 8 is really the youngest child we would bring on fishing trips. These are long days, sometimes with no shade, and it’s just a lot for little ones.

** After you book your hotel, book your charter. These book up fairly quickly.

ROBBIE’S MARINA : Located in Marathon, this is the famed spot where you can hand feed tarpon. It started with one fish named Scarface and then blossomed into a full-fledged tourist attraction. The Hungry Tarpon is a great restaurant that is also there and now there are local artisans and food trucks that set up shop within the marina grounds. Add this to your Keys bucket list. You can snorkel, kayak, jet ski and parasail out of here. 

SNORKELING: For years, we have taken the 10am snorkeling trip to Alligator Reef out of Robbie’s with Sundance Sports. (There is also an afternoon trip but given the thunderstorms, we like to take our chances with the earlier trip.) For roughly $36 a ticket, includes gear, you can take a 2.5 trip to snorkel the turquoise waters by the lighthouse. Despite the name, there are no alligators but you will see reef fish, sea turtles and harmless nurse sharks and barracuda. You can also see dolphin on a good day!

DOLPHIN RESEARCH CENTER – When visiting Marathon, stop by the dolphin research center to learn more about the ocean’s favorite mammal. Although you can simply walk the grounds for about $25, the real experience is with the dolphin encounters. We had a great time in the water learning how dolphins communicated, how they played and how they enjoyed interacting with us. We also got to see very distinct dolphin personalities which was a great lesson in animal science!

Turtle Hospital – Also in Marathon, the Turtle Hospital, is a non-profit organization that rescues, rehabilitates and releases injured sea turtles. The hospital is run out of a converted motel where rooms serve as living quarters for the staff. They educate the public through outreach programs at schools and assist with research in conjunction with state universities. *You’ll also notice that a lot of street lights are red in The Keys. This is so turtles don’t mistake the lights for the moon ; the city will change the light color during turtle season.

World Wide Sportsman - This two-story fishing and outdoor store in Islamorada is one of our favorite spots to shop. The saltwater version of Bass Pro, WWS features Hemingway’s boat, Pilar, the sister ship of his famous Pilar housed in a museum in Cuba. There is a marina out back where you can book fishing charters and one of our favorite outdoor restaurants is also located there.

Hemingway’s Home & Museum – As a former English teacher and mother of seven, Ernest Hemingway’s home in the Florida Keys is a must see! There are guided walking tours, audio tours and self -guided tours you can take to view this literary master’s private home. You can see his private pool and where he wrote some of his most favorite novels. Also on site, Hemingway’s famous six-toed cats, descendants of his original six-toed cat, Snow White. This is a great educational tour for kids because most will read at least one his stories at some point in middle school or high school.

The Shipwreck Museum – For pirate and treasure lovers, be sure to check out this museum to hear true stories of much of Key West’s history and see real artifacts pulled from famous shipwrecks in the area.

Southernmost Point – You’ve probably seen this famous buoy….it’s the brightly colored marker that marks the lowest latitude in the USA, just 90 miles from Cuba. Tip : Get there early, the line forms quickly and it can be a long one! 

Mallory Square - Sunsets at Mallory Square is one of the most popular things to do in Key West. Two hours before sunset, this Key West sunset celebration hosts musicians, artists and food vendors for an incredible tropical experience.

**Note, we typically just drive to Key West from Marathon or Islamorada in the morning, spend the day and then go home after sunset.


You won’t find many chain restaurants in the Keys…maybe a McDonald's here and there but don’t expect too many Starbucks or Chick-Fil-A. Most of the restaurants are right off the main stretch, Overseas Highway, and are mom and pop type restaurants.

Some of our favorites include:

Harriet’s – Key Largo – Known for its ability to make you feel at home, Harriet’s is a local favorite known for its homemade muffins, especially their key lime muffin. Consistently rated #1 on Yelp and Trip Advisor, this is lovely restaurant to stop at in the Upper Keys..either on your way in or out. 

Tower of Pizza  – Key Largo – This is our go-stop on the drive in from the Miami airport. I’ve been coming here since I was a kid and still love their pizza and salads as much as I did when I was a kid. They also have really great garlic knots..the best I’ve ever had!

Lazy Days – Islamorada - Arguably one of the most popular restaurants in The Keys, Lazy Days is an award winning restaurant known for steak, seafood, pasta…and will cook the fish you catch if its filleted. The wait can be long so call ahead or eat earlier in the day to ensure a great experience!

Islamorada Fish Company – Islamorada - Located right next to World Wide Sportsman, this is also a family favorite that offers oceanfront dining. You can see tarpon swim in the bayou in the middle of the restaurant, they have a great kids menu and wonderful, homemade key lime pie!

Island Fish Company - Marathon – Our family eats here often because of its incredible fresh fish and kid friendly menu. Located next to a marina, you get the feeling of being outside but its covered with fans so very comfortable. 

Driftwood Pizza - Marathon - Family owned and operated, this pizza, sub and salad shop has a great family menu for kids that also include mac’n’cheese and key lime pie sticks!

Glazed – Key West - Formerly a local favorite, now the most popular place for donuts, including their key lime pie donut!

Blue Heaven - Key West – One of The Keys most eclectic restaurants, Blue Heaven is known for its Caribbean spices and Keys flavors. They also have a great filet mignon and pork tenderloin.

Café Marquesa – Key West - Set just a bit off the main tourist drag on Duval Street, Marquesa is a 50 seat restaurant that has a lot of classic dishes with an elevated feel. Shrimp and grits is a favorite here.

Bad Boy Burrito - Key West – There are a ton of Mexican restaurants throughout They Keys but this one has several high-end ingredient options that serve up Mexican with a twist. Their Kobe beef, squash and zucchini burritos are popular as is the pineapple habanero. 

Our five/six day trips typically look like this:

  • Day 1 – Travel in, stop in Upper Keys, Instacart groceries/trip to Publix and settle in
  • Day 2 – Resort day – Paddleboards, poolside lunch, on-site activities. Maybe Turtle Hospital or Dolphin Center
  • Day 3 – Robbie’s Marina, snorkeling, lunch at The Hungry Tarpon
  • Day 4 – Fishing - Resort day
  • Day 5 – Key West
  • Day 6 – Local attractions or restaurant. I aim for a flight after 12 so I’m not rushing to drive to Miami airport super early in the morning.

If you have more questions or want to see videos, you can find me on Instagram, @jennyreimol, and check out my Keys highlight!

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