Travel Guide

First Timer’s Guide to the Florida Keys

First Timer’s Guide to the Florida Keys

Located on the southern tip of Florida lies a string of tropical islands called the Florida Keys. With more popular destinations in Florida like Orlando, Palm Beach and Miami, the Keys are occasionally overlooked by some . It’s a real shame because I think it’s one of the most beautiful destinations in the United States! I remember seeing it for the first time while watching one of Netflix’s popular series, Bloodline and thinking to myself “Wow that place is stunning”. The gorgeous scenery and tropical vibes sparked my interest right away and next thing you know, I’m already plotting a visit to the Florida Keys!

First Timer's Guide to the Florida Keys

How to get here:

There are three airports you can fly into: Miami International Airport, Fort Lauderdale-Hollywood International Airport and Key West International Airport. Although it is the furthest out of the three airports, me and my friend Mariana from Mariana’s Postcards chose to land in Fort Lauderdale because of the cheaper flights.

How to get around:

The Keys are divided into five regions: Key Largo, Islamorada, Marathon, Big Pine & Lower Keys, and Key West.  For our trip, we mainly focused on Key Largo, Islamorada and Key West. The best way to get around is to rent a car and go on a road trip! Although it takes about 4 hours to get to Key West from Fort Lauderdale, we didn’t mind the drive thanks to the scenic, 113-mile long Overseas Highway that boasts 42 bridges that connect the islands, including the renowned seven-mile bridge. Once you get to Key West, most hotels offer free shuttle services if you want to explore Old Town Key West.

When to visit:

We visited at the end of August and it was really hot and humid. Weather forecast predicted a lot of rainy days but it only rained one day during our trip to the Keys. For the best weather,  you should visit between March and May. However, an off-season visit from June to November (hurricane season) is the best time to go budget wise.

Key Largo and Islamorada

Key Largo was our first stop during our 5 day trip to the Florida Keys. It has a long history of marine conservation since the 1960’s and has been protected from spearfishing and coral collection for four decades. Nowadays, it is regarded as the Diving Capital of the World!

If Key Largo is famous for its diving spots, Islamorada is known as the Sport Fishing Capital of the World. It is where backcountry sport fishing and saltwater fly-fishing were pioneered.

 Where to Stay:

Kona Kai Resort , Gallery and Botanic Gardens

97802 Overseas Highway Key Largo, FL 33037

Website: Kona Kai Resort

Our first night in Florida Keys was spent in this quaint resort located in Key Largo. Since it’s reserved exclusively for adults, this 13-suite boutique resort is perfect for those looking for a more intimate and relaxed setting. Aside from having a gorgeous waterfront location, Kona Kai also incorporated a botanic garden that has a collection of over 250 tropical species.

During our stay we enjoyed several on site amenities such as: waterfront freshwater pool and jacuzzi, beachfront hammocks, ping-pong by the beach, complimentary kayaks, stand up paddle boards and paddle boats. If that’s not impressive enough, they also have a tennis and shuffleboard court, BBQ grills, complimentary bottled water and fruits served poolside and in-suite or beachfront massage as well as private yoga.

First Timer's Guide to the Florida Keys

First Timer's Guide to the Florida Keys

One of the things that I absolutely loved about Kona Kai was how cute and charming the guest rooms are! Our suite had an adorable cottage style decor complete with island inspired furnishings, living room, dining room and a fully equipped kitchen. The best part? The bed was super comfy and made it easy for me to fall asleep especially after a long day of travel!

First Timer's Guide to the Florida Keys

Things to Do:

Snorkeling Excursion at John Pennekamp Coral Reef State Park

102601 Overseas Highway (MM 102.5) Key Largo, FL 33037

Website: John Pennekamp Coral Reef State Park

John Pennekamp Coral Reef State Park is the first undersea park in the United States and encompasses approximately 70 nautical square miles. There are several activities you can do which includes scuba, glass bottom boat tours, snorkeling tours and boat and kayak rentals. One of the main attractions inside the state park is the famous statue called “Christ of the Deep” that is a replica of a statue called “Il Christo Degli Abissi” that is located in the Mediterranean Sea of Italy.

Unfortunately, due to low visibility we weren’t able to see the statue. However, the boat captain and crew brought us to another snorkeling spot and it was absolutely amazing! I saw a variety of sea creatures plus some of the most beautiful coral reef. You guys definitely have to see it for yourselves!

  • Snorkeling Tour (lasts 2 1/2 hours): $29.95 per person. Equipment rental available on-site.

First Timer's Guide to the Florida Keys

(GoPro photos from Mariana)

Tarpon Feeding at Robbie’s of Islamorada

77522 Overseas Hwy, Islamorada, FL 33036

Website: Robbie’s of Islamorada

Robbie’s Marina is a must stop during your road trip to Key West! It has an eclectic mix of outdoor shops, food vendors and of course the popular tarpon feeding. You can stop by The Hungry Tarpon Restaurant and Bar for lunch or you can go straight to the dock and grab a bucket of fish to feed the tarpon. It was definitely one of the highlights of our trip!

  • Admission to dock: $2.25 per person.
  • Bucket of fish: $4.00 (5-8 pieces).

First Timer's Guide to the Florida Keys

Where to Eat:

Mrs. Mac’s Kitchen

99336 Overseas Highway, Key Largo FL 33037

Website: Mrs. Mac’s Kitchen

This Key Largo eatery is a local’s favorite spot and features a hearty menu ranging from biscuits and gravy to fresh fish straight off the dock. Aside from the delicious food, I also enjoyed looking through license plates that were donated by guests and now serves as decoration all over the restaurant.

  • What to order: Paula’s Texas Benedict, World Famous Homemade Chili, Award Winning “Konk” Chowder and The “Mac” Attack.
Ciao Hound at Postcard Inn

84001 Overseas Highway, Islamorada FL 33036

Website: Ciao Hound 

My taste buds were absolutely surprised at how delicious the food was at Ciao Hound. Don’t get me wrong but who knew that Key Largo would have one of the best Italian food I’ve ever tasted. The service was outstanding and the ambiance was laid back, which made the experience even more amazing. Every dish we ordered was so flavorful including the bread! My mouth is watering right now just thinking of it. I love that they paired authentic Tuscan flavors with fresh Keys-sourced ingredients.

  • What to order: Mahi-Mahi Puttanesca (an absolute must! trust me on this), Mussels Arrabbiata, Crispy Calamari and Lobster Ravioli.

First Timer's Guide to the Florida Keys

Morada Bay Beach Cafe

81600 Overseas Highway, Islamorada FL 33037

Website: Morada Bay Beach Cafe

Located in the heart of Islamorada, this Mediterranean bistro cafe offers a laid back and relaxed atmosphere. The white sandy beach filled with palm trees and Adirondack chairs is the perfect setting to watch the famed Florida Keys sunset. Their menu is a blend of Caribbean and American cuisines showcasing fresh local seafood and produce. If you’re a fan of Netflix’s popular series Bloodline, you will recognize the Rayburn inn along with the other film locations in and around the beach cafe.

First Timer's Guide to the Florida Keys

First Timer's Guide to the Florida Keys


Other recommendations:

  • Key Largo Conch House (100211 Overseas Highway, Key Largo FL 33037)
  • Key’s Fisheries (3502 Louisa St. Marathon, FL 33050)


Key West

Key West is the southernmost point in the continental United States and is considered by some as the heart and soul of the Florida Keys. It’s home to such literary greats as Ernest Hemingway and Tennessee Williams, who wrote some of their best-known works while living on the island.

Interesting facts about Key West:

  • To get to Key West from Miami, it’s a 150-mile drive down the Overseas Highway but only 90 miles to Cuba.
  • Key West is home to the third largest barrier coral reef in the world! Known as the Florida Straits, Key West’s coral reef extends 150 miles north towards Miami and 70 miles west to the Dry Tortugas. It’s the largest in North America and the third largest in the world behind Belize and the Great Barrier Reef in Australia.

Where to Stay:

The Perry Hotel Key West

7001 Shrimp Road Drive, Key West FL 33040

Website: The Perry Hotel

For three nights, The Perry Hotel was our home base while we explored the rest of Key West. Tucked away in Stock Island, this charming boutique hotel blends smooth wood finishes with rustic metal details that recall the area’s iconic maritime heritage. It’s located beside a state-of-the-art 220 slip marina and features 100 rooms, a pool deck that overlooks the working waterfront, two boat-to-table seafood driven restaurants (Matt’s Stock Island Kitchen and Bar and The Salty Oyster Bar and Grill), outdoor fire pits and on-site scooter and bike rentals. Aside from having amazing amenities, the staff (shoutout to James especially) made our time at the hotel even more special! They were so kind and helpful to us and made sure we felt welcomed throughout our stay.

  • The daily resort fee covers: welcome glass of champagne at check-in, shuttle service to Old Town, wifi, concierge, fitness center and on site and valet parking.

First Timer's Guide to the Florida Keys

Dress from Lulus. Click HERE to shop!

Our room was clean, spacious and had an amazing balcony view of the marina. I love how they incorporated contemporary furnishings along with some rustic touches throughout the the whole suite. Other in-room amenities include: bath and body essentials, flat screen tv, wifi, in-room refrigerator, coffee maker, work space with desk and chair and secure in-room safe.

Things to do:

Visit  the Key West Butterfly and Nature Conservatory

1316 Duval St. Key West, FL 33040

Website: The Key West Butterfly and Nature Conservatory

Filled with hundreds of nature’s most beautiful winged creators, The Key West Butterfly and Nature Conservatory allows you to walk through a climate controlled, glass enclosed habitat and see 50-60 butterfly species along with 20 exotic bird species. It was definitely a one-of-a-kind experience to see them up close and personal! I was able to get a few shots of them in their natural habitat and I love how they all turned out!

  • General Admission: $12.00
  • Conservatory Hours: 9 am-5 pm daily. Last admission to conservatory is at 4:30 pm.

First Timer's Guide to the Florida Keys

Explore the Ernest Hemingway Home and Museum

907 Whitehead St. Key West, FL 33040

Website: Ernest Hemingway Home and Museum

For fans of Ernest Hemingway, this property is a must see when visiting Key West. He lived and wrote here for nearly 10 years, finding solace in the turquoise waters that surround this island that he called home. Everything in the property was well taken care of and it felt like we had stepped back in time while we explored the rooms and gardens of the prolific writer.

  • Admission: $14.00. No reservations required.

First Timer's Guide to the Florida Keys


Ultimate Adventure with Fury Water Adventures

631 Greene St. Key West, FL 33040

Website: Fury Key West

If you’re an adrenaline junkie or just want to do something adventurous during your time in Key West, then you have to go on the Ultimate Adventure tour with Fury. We sailed on a state-of-the-art catamaran that took us on an all-day adventure that includes reef snorkeling, parasailing, jet skiing and their very own state certified water park. It was our first time parasailing and the crew made sure we had the proper equipment, which made me feel safe throughout the whole experience.

  • Ultimate Adventure: $143.95; includes snorkeling gear, life vests, reef safe sunscreen, breakfast, buffet lunch and complimentary beverages.
  • What to bring: photo id (for 16+), towel, bathing suit, sun protective clothing, waterproof camera, refillable water bottle.

First Timer's Guide to the Florida Keys

Sunset Celebration at Mallory Square

400 Wall St. Key West, FL 33040

Website: Mallory Square

Sunset Celebration is a nightly “street carnival” in Mallory Square that features arts and crafts, exhibitors, street performers, food carts, psychics, musicians and other entertainers. Tourists and locals alike flock to this spot to watch the world famous Key West sunset. We didn’t make it here in time for sunset but we did enjoy checking out the booths and street performers. It’s definitely one of the unique ways to experience the nightlife in Key West.

Go on a Conch Tour Train

501 Front St. Key West, FL 33040

Website: Conch Tour Train

Even though we initially didn’t plan to go on the conch tour train, I ended up enjoying it more than I expected. Our tour guide Kenny (a former chef of 30 years) was very funny and informative. He had so much passion for Key West that he made the 75-minute trip around Old Town enjoyable. I learned so much about the history of Key West through this tour.

  • Online Price: $28.30.
  • Departs at least every 30 minutes from 9 am-4:30 pm daily.
Sunset Sail with Sebago Watersports

205 Elizabeth St. Key West, FL 33040

Website: Sebago Watersports

On our last night in Key West, we went on a sunset sail aboard a fast 69′ sail catamaran with Sebago Watersports. Throughout the tour they served complimentary Hors d’Oeuvres, champagne, sangria, wine, beer, sodas and filtered water. The catamaran had plenty of seating and an expansive deck where you could enjoy the sunset without overcrowding. It’s the perfect way to end our trip to Key West!

  • Tour duration: 2 hours and departs daily (winter-4:30 pm, summer-6:30 pm)
  • Adults: $59.95

First Timer's Guide to the Florida Keys


Other Recommendations:

  • Key West Eco Tours (231 Margaret St. Key West, FL 33040)
  • Sunset Pier (0 Duval St.)
  • Key West Aquarium (1 Whitehead St. Key West, FL 33040)


Where to Eat:

Hot Tin Roof

0 Duval Street, Key West FL 33040 at Ocean Key Resort and Spa

Website: Hot Tin Roof

Located in Ocean Key Resort and Spa, Hot Tin Roof offers the best waterfront dining in Key West. Apart from the amazing and delicious menu, you can also enjoy the world famous Key West sunset either from a romantic banquette in the dining room or the al fresco dining on the veranda.

  • What to order: Spicy Tuna Tacos, Oysters on the Half Shell, Charred Octopus, Seafood Paella (so delicious!!!), Thyme and Butter Poached Lobster and Cuban Coffee Creme Brulee.


Lucy’s Retired Surfers Bar and Restaurant

221 Duval St. Key West, FL 33040

Website: Lucy’s Retired Surfers Bar and Restaurant

Lucy’s Retired Surfers Bar and Restaurant offers a coastal menu that features some of their most popular dishes such as fish tacos, ceviche and queso blanco dip – all made with the freshest local ingredients. The vibe at Lucy’s is very laid back, beachy and full of color! BTW they have the cutest outdoor patio. It’s perfect for events or just a casual hang with friends.

  • What to order: Shaka Ceviche, Sue’s Spicy Queso Blanco, Surf’s Up Jerk Chicken Wings (my FAVE), Jamaican Jerk Chicken and Catch of the Day.
Bistro 245

245 Front St. Key West, FL 33040

Website: Bistro 245

Probably one of the best Sunday buffet brunches I’ve had in awhile. And that’s saying something because I live in Vegas, home of the best buffets. They had an amazing buffet spread which included an omelet and eggs made to order section, seafood area, fresh baked goods, fruits and desserts, complimentary champagne service and THEE BEST lobster mac and cheese!

First Flight Island Restaurant and Brewery

301 Whitehead St. Key West, FL 33040

Website: First Flight Island Restaurant and Brewery

First Flight Island Restaurant and Brewery is located in the heart of downtown Key West. It’s well known for being the birthplace of Pan American World Airways. In Fact, Pan-Am’s first tickets were sold out of this very building in 1927! First Flight’s main level includes soaring trees that arch and create a living canopy in the main garden by day and sparkle with lights at night – the perfect ambiance for a romantic evening.

I can’t rave enough about the fresh seafood in Key West and First Flight was no different. I literally finished a whole yellowtail snapper because it was that delicious!

  • What to order: Whole Yellowtail Snapper, Seared Tuna, Seafood Linguini and Mutton Snapper.


Other Recommendations:

  • Matt’s Stock Island (7001 Shrimp Road, Stock Island FL 33040)
  • Hogfish Bar and Grill (6810 Front St, Stock Island FL 33040)
  • Fisherman’s Cafe (205 Elizabeth St, Key West FL 33040)

I hope you guys enjoyed reading this post and that it made you excited to explore this part of Florida. From the amazing scenery to the fresh and delicious food, I honestly have nothing but praises for the Florida Keys.  I’m looking forward to hopefully visiting again someday!

To learn more about the Florida Keys, check out the Florida Keys Visitor Website HERE.

Disclaimer: Thank you to The Florida Keys and Key West Tourism Board for sponsoring our press trip. 

As always, all opinions on my “First Timer’s Guide to the Florida Keys” blog post are honest and my own. 

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