Florida Keys Travel Guide

By The Backseat View

Welcome to Paradise!

Visiting the quirky, colorful, and tropical paradise known as The Keys brings a peaceful reset to your life. The clear blue water draws visitors from all walks of life to snorkel and fish. Between sunrise and sunset, the time is filled with adventure.

The towering palms, charming islands, coral reefs, and tiki hut restaurants make for a dream vacation. Experiencing the ocean’s aquarium of fish, dolphins, and sea turtles makes the best memories.

Let’s open the Florida Keys Travel Guide, explore each island, find the best key lime pie, and review itineraries. The Keys can be overwhelming, so this guide is in-depth and includes mainly my favorite activities.

As we head to Hemingway’s home, he offers good advice.

“Never go on trips with anyone you do not love.” Hemingway

“When you stop doing things for fun, you might as well be dead.” Hemingway

Island Facts

• The Florida Overseas Highway from Miami to Key West is 113 miles long and takes at least 3-4 hours to travel with 42 bridges.
• The Florida Reef is the world’s third largest coral reef system, starting in Biscayne National Park and ending in Dry Tortugas National Park.
• Coral reefs worldwide are dying, and Florida’s reef is included.
• Snorkeling trips to the reef are my favorite experience in the Keys, so book trips to John Pennekamp Coral Reef State Park, Looe Key Reef, or Dry Tortugas.

• The Florida Keys are a group of 800 islands.
• The four most visited islands are Key Largo, Islamorada, Marathon, and Key West.
• The peak season with the best weather for visiting The Keys is December-March.
• Seagrass rolls in by May and stays through July. Y’all, I was unprepared for the stinky, dead grass covering the beaches. Resorts clean it up.

Welcome to Key Largo!

• The island vibe and the blue water mean you have arrived in paradise.
• Arriving at the original Ms. Mac’s restaurant at a table covered in car tags means vacation has started in the right direction. Due to crowds, there are two Ms. Mac’s restaurants. Buy the entire Key Lime Pie because you will want another piece. On every trip, Ms. Mac’s is among my top three favorite Key Lime Pies.

John Pennekamp

• The best part of Key Largo is John Pennekamp Coral Reef State Park.
• Make your reservations with the state park. Click on experiences, then boat tours to choose from snorkeling tours at $50 per person plus equipment rentals.
• The tours last 2.5 hours and run at 9 a.m., 10:30 a.m., 12 p.m., 1:30 p.m., and 3 p.m.
• The bronze statue of Christ is 9 feet tall and submerged in 25 feet of water at Key Largo Dry Rocks. I wouldn’t miss it.
• Cannon Beach and Far Beach are great places to relax.

Best of Key Largo

• The best fishing grounds, Flamingo, are near the Everglades.
• Sundowners restaurant has delicious meals, sunset views, and feeding tarpon.
• Blond Giraffe Key Lime Factory in Tavernier for award-winning Key Lime Pie.
• Biscayne Bay National Park, east of Miami, is close enough for a snorkeling trip.
• Playa Largo Resort and Baker’s Cay Resort are the top luxury resorts. If you want a luxury tropical oasis for a restful vacation, you’ve found it.
• I love Key Largo, but a two-hour drive to Key West for a day trip is too far.
• I saw gators at the docks of our Everglade side of Key Largo resort. I realize they rarely attack, but it’s still scary.
• Let’s move on.

Hello, Islamorada

• Six islands make up the village of Islamorada.
• Known as “The Sport Fishing Capital of the World”
• Home to the Bass Pro with an aquarium of fish living around their docks.

• Marker 88 is perfect for eating lunch on a swing over the water.
• The Bayside Café in Morro Bay for sunset views or Islamorada Fish Company are excellent food options.
• Theatre of the Sea is like a small sea world with dolphin and sea lion shows. It opened in 1946, and we spend 2-3 hours meeting animals.

• The Rain Barrel Village with the HUGE crab is the best place to browse handmade crafts and souvenirs.
• History of Diving Museum to explore antiques of the deep sea.
• If the sun is shining, I’m moving on to Marathon.

Marathon, I’m Home!

Finally, it always takes longer to arrive in Marathon than expected.

Marathon is MY island with a calm vibe, low crowds, and a boating paradise.

Key West is an hour’s drive for day trips. From family restaurants to animal encounters, there are plenty of activities to fill your vacation.

Marathon Activities

Snorkeling

• Our favorite snorkeling is The Rocks at Looe Key National Marine Sanctuary in Bahia Honda State Park, one island over. The State Park operates daily snorkeling trips, departing at 9:30 a.m. and 1:30 p.m. for $30 with 90 minutes of snorkeling.
• Tilden’s is my favorite small diving and snorkeling charter. It offers Looe Key tours at 8 a.m. and 1 p.m. daily, costing $150/each.
• Dive boats and private charters depart for several other nearby struggling reefs, such as Sombrero.
• Honestly, in the last two years, we visited the other reefs and found their level of damage disturbing compared to five years ago.
• Captain Hook’s was cheaper snorkeling with chaotic crowds.

Fishing

• Catch’EM All Sportfishing and Stray Cats Fishing Charters are our favorite fishing charters.
• Book fishing charters as soon as possible
• Schedule early in the vacation due to weather reschedules
• Depending on what you are fishing for, half-day vs. whole-day charters run $800 to $1,800.

Biking

• The Old Seven Mile Bridge path is two miles long and is excellent for walking, biking, and watching the enormous fish swim under the bridge in the many shades of blue water.
• The Bridge Path ends at Pigeon Key, and you can pay to tour the island.
• Biking over the ocean is a fabulous experience, especially at sunset.
• Bike Marathon Bike Rentals are near the bridge for daily or weekly rentals.

Sombrero Beach

• Sombrero Beach is the best beach in Marathon for a relaxing day and sunset.
• There are impressive playgrounds for the kids and tables for family barbeques.
• Curry Hammock State Park has a small beach where locals barbeque.

Dolphins

• The Dolphin Research Center is a must-stop for interacting with these entertaining creatures.
• Book a swim or dolphin interaction for those lifetime-lasting memories.
• For over 40 years, the dolphins have been performing high-flying acrobatics shows.
• I love that the dolphins can leave by jumping the mesh gates in the ocean. They can swim with wild dolphins and then return home.
• General Admission runs around $32.

Encounters Aquarium

• The Encounters Aquarium offers a hands-on nurse shark encounter, so it was a must-stop for my guys.
• Kids LOVE feeding gators, fish, lobsters, sting rays, and sharks, so bring extra money. Seriously, this is the best stop for kids.

Turtle Hospital

• The Turtle Hospital does fantastic work, and everyone loves turtles.
• You need reservations, and it’s a 90-minute tour.
• My teenagers understood this was an educational experience for sick turtles, so they enjoyed it. However, most small children do not.
• The hospital will have turtle release days on their website, and the entire town will show up to cheer the turtle back to the ocean.

Crane Point Nature Center

• It was a drizzling, gray day when I stumbled upon Crane Point.
• Y’all, this is stepping back in time to explore 63 acres of OLD Florida.
• I loved the nature trails with the hammock trees and old swings.
• There’s a natural fish pedicure area that’s a great laugh.
• It’s $15 for a quiet, calm walk through the forest with views.

Marathon Meals

The Butterfly Cafe

• My favorite fine dining in Marathon is The Butterfly Café, with the TDF cake for dessert.
• The tropical atmosphere located in the Tranquility Bay Beach Resort makes it worth the money.

Castaways

• Castaways can cook seafood in every way possible.
• They always have a crowd, so you need a reservation.
• It’s worth the wait.

Burdines

• Burdine’s for amazing Fried Key Lime Pie and the views.
• You can come by boat and it’s next door to Castaways.
• This is casual outdoor picnic tables and paper plates style dining.

Fish Market

• Fish Tales Market and Eatery is an affordable, local favorite with FANTASTIC food.
• It’s the oldest restaurant on the island and sells fresh seafood.
• Their Key Lime Pie served cold is my 2nd favorite in all the Keys.
• The building looks old, but finish that key lime pie, and you won’t care.

• Florida Keys Steak and Lobster House and Hideaway Cafe are rated the best for fine dining, but we travel with teenagers.
• For a moderate-priced delicious meal with a view, try Angler & Ale on beautiful Duck Island, a five-minute drive.

Marathon Lodging

• Best Luxury Hotels in Marathon: Isla Bella Beach or Tranquility Bay Beach Resort. Both resorts are luxury paradise perfection with multiple lodging options. Y’all, I dream of these resorts all year.

• The best moderate hotel is the waterfront Courtyard by Marriott, next to a marina. This is not your regular Courtyard, so have a little faith.
• Marathon has plenty of homes with boat docks, so we VRBO a house.
• A word of caution: the homes are older, and sometimes the neighborhood is sketchy, so read all the reviews.
• The water level can vary and we had a dock of mud one year.
• I only rent homes with a big hot tub or a pool. Nobody really swims in the rocky water in front of their home.

Key West is always calling, so let’s travel on!

Hi, Big Pine Key

• We enjoy a quick stop on Big Pine Key to look for the tiny Key deer in yards.

No Name Pub

• No Name Pub has pizza and a vibe. It’s more famous than it wants to be, so I love it. The Pub has the slogan, “A nice place if you can find it.” After opening in 1931, people began adding dollar bills to the walls and ceilings of the pub in the 1980s, so every inch was covered.

• Boondocks Miniature Golf and Restaurant are traditional stops. Is it even vacation if we didn’t play mini-golf?

Bahia Honda

• Bahia Honda State Park has beaches and Looe Key National Marine Sanctuary.
• It is the best place to camp.
• There are over 500 acres of trails and three beautiful beaches.
• Old Bahia Honda Bridge provides a scenic lookout and fantastic Overseas Highway views for sunset.

Welcome to the Party, Key West

“Live the full life of the mind, exhilarated by new ideas, intoxicated by the romance of the unusual.” Hemingway

When you picture the Florida Keys in your mind, it’s Key West you see.

Key West isn’t about activities; it’s about walking the streets and absorbing the relaxed vibes.

While wandering the streets, you will pass pastel island-theme homes in styles ranging from Bahamian to shotgun and Queen Anne to Colonial.

Everyone spends short weekend trips in Key West because of the atmosphere, beaches, and restaurants.

However, a day trip to Key West is enough for our family due to cruise ship crowds and high party levels. The streets will become so packed you can’t move, and weird has a new level here. Key West parking is hard to find, so it’s lots of walking or riding the Old Town Trolley to explore the town. The trolley offers several tours and runs $45 a person, so we walk.

Key West Activities

Beaches & Forts

• Smather’s beach is wide, with fluffy sand and towering palm trees, complete perfection.
• Higgs Beach is dog-friendly and usually crowded.
• Fort Zachary has a beautiful beach with a historic fort for only $6 per car.
• For a less crowded, beautiful sunset option, I love the Fort Beach.
• The U.S. Coast Guard Cutter Ingham Maritime Museum is in the Fort parking lot, and boys enjoy touring the 327-foot-long ship while learning about WWII for $15.

• Truman Little White House is nearby for a glimpse into presidential life.
• The Eco-Discovery Center is free and nearby. The center teaches environmental protection with a few aquariums.
• We drive from The Fort to Hemingway’s, then park near the Southernmost Point for the rest of the day.

Hemingway’s House

• While I appreciate the literature, history, and house architecture of Hemingway’s House, we come to see ALL THE CATS!
• The delightful 6-toed cats are on the historic furniture, watching you from the stairs and stalking you outside.

• You can feel Hemingway’s personality with his trophies, typewriters, posters, and the elegant pool area.
• There is always a crowd, so buy your tickets a day in advance.
• Across the street, the Key West Lighthouse provides island views for $17.

Butterflies & More

• Visiting the flamingos inside the Butterfly Conservation is fun.
• Butterfly tickets are walk-in access, and it’s by The Southernmost Point.
• The Southernmost Point, where we all wait hours for a photo.
• A light rain runs off the cruise ship visitors, so grab a quick photo with drizzle.
• Neighborhood streets near The Southernmost Point have parking.
• The Key West Aquarium is small and rarely makes our list.
• Key West Botanical Gardens is 15 acres of delightful gardens.

Sunset Party

• Mallory Square is packed with tourists and street performers, so arrive early.
• Key West has a constant Sunset Party on Duval Street and Mallory Square.
• Remember to bring cash to tip the entertainers.
• Sailboat Sunset Cruises are popular.

Dry Tortugas

• Boat trips to Dry Tortugas National Park leave from Key West.
• Dry Tortugas is my favorite place in all the Keys for the blue water and snorkeling.
• We reserved seats months in advance on the Yankee Freedom Ferry.
• It’s crowded and slow at 2 & 1/2 hours each way.
• Seaplane Adventures is the best way to travel 70 miles with 40 minutes of amazing views, but it’s $500/person.

• We spent an hour touring Fort Jefferson and walking on top of the walls for amazing views.
• Did I mention the snorkeling at Dry Tortugas was the best of our entire trip and worth every dollar?

“The best way to observe a fish is to become a fish.” Cousteau

Key West Restaurants

Blue Heaven

Blue Heaven is my favorite restaurant. It has an eclectic outdoor garden atmosphere, with chickens, an outdoor shower, live music, and a chicken graveyard. The food is always perfect, and I will only leave Key West after eating here.

I always call for dinner reservations weeks in advance. Dinner is open at 5 pm, and you can line up earlier without reservations. The Sunday Brunch is famous. Blue Heaven is only two blocks from Duval Street, so we walk to dinner and back to sunset in Mallory Square. It’s impossible to find restaurant parking.

Best Key Lime Pie in the Keys

I have eaten my weight in Key Lime Pie, and this is the best Key Lime Pie in all the Keys. The topping is made of spun sugar and baked meringue. The pie is as famous as the restaurant.

• Key West restaurants are great, so any place you pick is fine.
• For my 2nd Key West meal, I visit Stock Island, an inch before you reach Key West, for Hogfish Bar and Grill.
• Banana Café is my place to go for breakfast.

Key West Lodging

• I love Isla Bella in Marathon, so it’s no surprise that I love their sister resort in Key West, Ocean’s Edge Resort and Marina. With six saltwater pools and a shuttle into town, this is perfection. Rates run from $350-$500.
• For fabulous in the heart of Key West, La Mer House, also known as The Southernmost Beach Resort. It starts at $500 and is a bed-and-breakfast vibe.
• For Smathers Beach trips, Margaritaville is across the street.
• There are more hotels than you can count in Key West.
• June is PRIDE month, and the parties are larger than usual.

Whew, that’s a lot of Key’s information. To make planning easier, review a couple of itineraries in the Florida Keys Travel Guide that have worked for our family.

7-Day Marathon Itinerary

Marathon is the base with a focus on fishing and snorkeling.

• Day 1– Arrive in Miami, then drive the 2 hours to Marathon
• Book the 3 pm snorkel tour at John Pennekamp in Key Largo.
• Ms. Macs for dinner with key lime pie!
• Arrive in Marathon around 6 pm.

• Day 2– Fishing charter-Catch’EM All Sportfishing
• Option 2 is the Encounter Aquarium
• Dinner reservations at Castaways
• Enjoy Sombrero Beach for sunset.

• Day 3 -Snorkeling Charter to Loee Key
• Afternoon visit to the Dolphin Research Center.
• Dinner at the Fish Market

• Day 4– Key West for the Day
• Big Pine Key for the Tiny Deer and the No Name Pub.
• Hemingway’s House
• Fort Zachary area, time permitting
• Southernmost Point & Butterfly Conservation
• Stroll Key West & shop
• Dinner reservation at Blue Heaven with Key Lime Pie
• Sunset at Mallory Square and a stroll on Duval Street.

• Day 5– Stray Cats Fishing Charter
• Dinner at The Butterfly Cafe
• Bike the 2.2-mile section of the Old Seven Bridge for sunset views
• Alternate Plan is to visit Dry Tortuga’s for snorkeling

• Day 6 – Rest/options
• Complete any activities above that were rained out.
• Visit Bahia Honda State Park
• The Turtle Hospital reservations for the 90-minute tour.
• Lunch at Burdine’s for fried Key Lime Pie
• Boondocks for dinner and mini-golf.
• Day 7- Travel Home

The 7-Day ROAD Trip to Key West Itinerary.

• Day 1: Arrive in Miami
• Drive an hour to Key Largo and stay overnight
• Dinner at Ms. Macs

• Day 2: Snorkel John Pennekamp at 9 am or 10:30am
• Drive to Marathon for a night’s stay.
• The Rain Barrel Village is quirky shopping.
• Lunch at Morada Bay Beach Café
• Visit the Dolphin Research Center
• Dinner Reservation at Castaways
• Sunset at Sombrero Beach or
• Bike the Old Seven Mile Bridge at sunset

• Day 3: 2-hour drive to Key West
• See the Encounter Aquarium
• Stop at Big Key Pine for the tiny Key deer and the No Name Pub for lunch.
• Visit Hemingway’s House and the Key West Lighthouse
• Sunset cruise

• Day 4: Key West
• Shop Duval Street
• Lounge on Smathers Beach
• Dinner reservations at Blue Heaven
• Sunset at Mallory Square

• Day 5: Key West
• Visit the Southernmost Point for a picture
• Key West Butterfly and Nature Conservatory
• Little White House
• US Coast Guard Museum
• End the day at Fort Zachary’s Beach for a quiet sunset.

• Day 6: Key West
• Dry Tortuga’s for a snorkeling day trip
• Hogfish Bar & Grill for dinner
• Day 7: Travel Home

If you want all the tips, keep reading the Florida Keys Travel Guide.

10-14 Day Options

• If you have 10-14 days and want to drive, enjoy a few favorite road trip stops on the way to The Keys.
• Always double-check the distances and plan for accidents.
• The easiest way to ruin a vacation is too much time in the car.
• Miami offers days of activities from South Beach, shopping on Lincoln Road, South Pointe Park for beach time, and walking the legendary Ocean Drive.

• Biscayne National Park, east of Miami, is 95% underwater and offers daily snorkeling trips.
• Tampa’s Busch Gardens has roller coasters and a zoo.
• Top 15 Attractions in St. Augustine Travel Guide details my favorite city and stop.
• The Kennedy Space Center
• An Everglade trip starts at Shark Valley, an airboat ride through the glade, and ends with fishing in the Flamingo area of the Everglades.

Let’s recap.

• Make sure you set correct expectations so you aren’t disappointed.
• The Keys are half new money with millionaire homes.
• The other half has three boats in the yard with a pirate-type vibe.
• Resorts are your best option for a beautiful vacation environment with a beach.
• Perfect white sand beaches are not common in the Keys.
• Chickens and huge iguanas roam and rule the islands.
• I did not find the islands to be family bike friendly.
• Leave your fancy clothes and heels at home. This is a flip-flop vacation.

Boat rentals tips

• Renting a boat is easy because there are more boats than cars.
• Call the marina near you and ask about boat rentals.
• If you have no boating experience, don’t start on vacation.
• Hire a fishing guide at least once to ensure you catch fish.
• Most marinas rent boats from 9 am to 4 pm, which is not ideal for fishing.

First Planning Steps:

• Flight vs Drive
• Check your driving distance to The Keys. Everything is farther than you realize.
• Do you need to fly? If you only have a week, fly.
• We drive from AL and take 10-14 days.
• Flying into Fort Lauderdale is cheaper and easier than Miami and only adds 30 minutes of drive time.
• Fly into Key West and out of Miami to save on rental cars.
• Flying into Miami and leaving the car in Key West is more expensive.

• Must Do’s
• Decide on your MUST Do’s.
• A fishing and snorkeling based trip
• The beach or party in Key West trip
• Animal encounters with dolphins and turtles

• Lodging
• Pick a base island, Key West, or Marathon.
• Key Largo is too far from Key West for me.
• Key West is crowded with cruise ship passengers and partying.
• Marathon is an hour from Key West
• Pick a resort in your price range.
• If you are bringing a boat, VRBO a house with a dock.

• Basic Itinerary
• Work through a basic itinerary by picking days in the above itineraries.
• Do you have enough days?
• What stop do you want to add to your drive to the Keys?

• Reservations
• When you feel good about the trip, make those resort reservations.
• Book your fishing guide as soon as possible.
• Flights are best booked an average of three months out.
• If you are renting a boat, make that reservation early.
• Snorkeling can be booked a few weeks in advance.
• The ocean is feisty, and afternoon storms are common, so book your fishing and snorkeling trips early in your vacation and leave room for rescheduling.
• Blue Heaven for dinner in Key West needs a few weeks out for reservations or arriving at 4:45 pm.
• Turtle Hospital and dolphin swim reservations are a couple of days out.

• What to Pack
• Pack super casual clothes with flip-flops.
• A sundress is acceptable for the nicest restaurants.
• Bring HUK-type fishing clothes for the boats and water activities.

The Keys are a year round destination worth the planning!

Thanks for reading the Florida Keys Travel Guide.

“Live the full life of the mind, exhilarated by new ideas, intoxicated by the romance of the unusual.” Hemingway