The Miami to Key West drive stretches before us like a ribbon of dreams, the morning sun glinting off our rearview mirror as we leave the city behind. Ahead lie 42 bridges connecting a string of tropical islands through the Florida Keys, each one a stepping stone to paradise.

We could have flown directly to Key West, caught the express bus, or taken one of the daily boat tours to Key West. But there’s something magical about driving the Keys that no other mode of transport can match.

Where else can you cruise with the Atlantic Ocean on one side and the Gulf of Mexico on the other, crossing bridges that seem to float above turquoise waters?

While Google Maps confidently declared our destination was just four hours away, we’d planned a full week to explore this archipelago of 800 islands.

Each key has its own personality, from the diving mecca of Key Largo to the quirky charm of Key West, with countless hidden treasures in between.

Our rental car was stocked with snorkel gear, beach towels, and an old-fashioned paper map marked with local recommendations. Sure, we had our must-see stops planned, but we also left plenty of room for spontaneous detours.

After all, some of the best memories come from those unplanned moments – like when a hand-painted sign for fresh stone crab leads you to the best seafood lunch of your life.

Best Time to Do the Miami to Key West Drive

After three trips through the Keys in different seasons, we discovered early spring is pure magic. Our April journey blessed us with perfect blue skies, gentle breezes, and noticeably thinner crowds than our previous winter adventure.

Spring (March to May) brings ideal temperatures in the mid-70s to low 80s and crystal-clear waters perfect for snorkeling.

Winter offers gorgeous weather but expects peak crowds and prices – we learned this the hard way crawling through Seven Mile Bridge traffic during a holiday weekend.

Summer trades afternoon thunderstorms for great hotel deals, while fall (September-October) offers the lowest prices of the year if you’re willing to gamble with hurricane season.

Our tip? Pick early spring. You’ll get the best of everything: comfortable weather, calm waters, reasonable rates, and room to breathe at popular spots.

Before our Keys adventure began, we spent two days diving deep into Miami’s vibrant neighborhoods. Each area pulses with its own unique rhythm, and we’re so glad we took the time to explore before heading south.

Miami Beach: Beyond the Tourist Trail

Sure, everyone knows about the white sand beaches and art deco buildings, but Miami Beach offered us so much more. We started our morning at The Local House on Ocean Drive, where the avocado toast comes with a side of people-watching. For the best beach experience, head to South Pointe Park – the locals’ preferred spot away from the tourist crowds.

Hidden Gem: Check out the Holocaust Memorial. It’s a moving and powerful site that many visitors miss, tucked away just steps from the shopping bustle of Lincoln Road.

Must Eat: Puerto Sagua on Collins Avenue for authentic Cuban food. Their midnight sandwich (Cubano) and café con leche are the real deal.

Must Do: Take an early morning walk along Ocean Drive before the crowds arrive. The art deco buildings look their best in the soft morning light, and you can actually hear the ocean instead of the party music.

Little Havana: Cuba’s Heart in Miami

Calle Ocho (8th Street) is the backbone of Little Havana, but the real treasures lie in the side streets. For foodies, I suggest the Little Havana Walking Food Tour complete with tastings! We found Lung Yai Thai Tapas, a tiny spot serving some of the best Thai food we’ve had outside Thailand, hidden among the Cuban restaurants.

Must Visit: Domino Park, especially in the late afternoon when local seniors gather for intense domino games. The conversations might be in Spanish, but the competitive spirit needs no translation.

Hidden Gem: Los Pinarenos Fruteria, a family-run fruit stand that’s been serving tropical smoothies and fresh guarapo (sugarcane juice) since 1963. The mamey smoothie changed our lives.

Must Do: Take a morning walk through the neighborhood to spot the painted roosters scattered throughout the streets. Each one tells a different story about the community.

Little Haiti: Caribbean Soul

This neighborhood surprised us with its vibrant art scene and incredible food. The Caribbean Marketplace, with its distinctive gingerbread architecture, serves as the cultural heart of the area.

Must Visit: The Little Haiti Cultural Complex – we caught an impromptu drum performance that had everyone dancing.

Hidden Gem: Chef Creole. Look for the little pink building serving the most authentic Haitian food in Miami. The griot (fried pork) and pikliz (spicy slaw) are unforgettable.

Local Tip: Stop by Libreri Mapou, a bookstore that’s been the neighborhood’s cultural cornerstone for decades. Even if you don’t read French or Creole, the owner’s stories about the community are worth the visit.

Downtown Miami: Urban Energy

Downtown surprised us with its mix of historic architecture and modern skyscrapers. The free Metromover gave us a perfect overview of the area – and great photo ops.

A fantastic experience to enjoy while in Miami is the Biscayne Bay Millionaire’s Row Sightseeing Cruise. This boat tour offers a scenic journey through Biscayne Bay, where you’ll get a glimpse of luxurious waterfront estates. These extravagant mansions are truly a spectacle, showcasing the lavish lifestyle of the city’s elite.

Must Visit: Pérez Art Museum Miami (PAMM). The hanging gardens outside are as impressive as the art collection inside, and the waterfront café offers one of the best views in the city.

Hidden Gem: The Historic Alfred I. DuPont Building. Step inside this Art Deco masterpiece to see the original 1939 marble floors and brass elevator doors.

Must Do: Take an afternoon stroll through Bayfront Park. The views of cruise ships and Biscayne Bay make for perfect photo opportunities.

Must Eat: Sparky’s Roadside Barbecue. In an area full of upscale restaurants, this laid-back spot serves amazing pulled pork and craft beers.

Local Tips for Exploring Miami:

• Use the Metrorail and Metromover to avoid parking hassles
• Early mornings (before 10 am) and late afternoons (after 4 pm) are best for exploring outdoor areas
• Many museums offer free admission days – check their websites
• Street parking is generally cheaper than garages, but read signs carefully
• Keep cash handy for small local shops and food stands

After two days exploring Miami’s neighborhoods, we were ready to start our Keys adventure. But these vibrant communities gave us the perfect cultural launch pad for our journey south.

Leaving Miami’s skyline behind, we hit the Overseas Highway where our Keys adventure officially begins at Mile Marker 118. The roadway stretches ahead like a ribbon through the ocean, with the Atlantic on one side and the Gulf of Mexico on the other.

The Journey South: First Stop – Coral Castle

Before diving into the Florida Keys, we made a fascinating detour to one of Florida’s most mysterious attractions. Just 30 minutes south of Miami, in Homestead, sits the enigmatic Coral Castle.

This stone structure isn’t actually in the Keys, but it’s a must-see stop on your Miami to Key West drive.

Built single-handedly by Edward Leedskalnin between 1923 and 1951, this architectural marvel remains a source of mystery and wonder.

Ed, who stood barely 5 feet tall and weighed 100 pounds, somehow carved and moved massive blocks of coral rock, some weighing several tons, using only primitive tools. How he accomplished this feat remains unexplained to this day.

We spent about an hour exploring the grounds, marveling at features like:

• A 9-ton gate that moves with just a touch of your finger
• Rocking chairs carved entirely from stone
• A 30-ton telescope aligned perfectly with the North Star
• Heart-shaped tables that tell a story of lost love

Local Tip: Visit in the morning before the South Florida heat kicks in. The castle is mostly outdoors, and the coral stone reflects quite a bit of sun.

After having our minds blown by this incredible site, we continued south toward Key Largo, where our Keys adventure would officially begin at Mile Marker 118.

Next Stop: The Wild Everglades

After Coral Castle, we couldn’t resist the call of Florida’s most famous wilderness. The Everglades National Park entrance is just minutes away in Homestead, easily accessible off US 1 on Palm Drive. Watch for the brown park signs – they’ll lead you straight there.

The Everglades airboat tour is a must-do Florida experience. The one-hour tour might seem short, but trust me – the thrill of gliding across the “River of Grass” while spotting alligators and exotic birds makes it worth every minute.

Our guide, a third-generation Everglades native, shared fascinating stories about this delicate ecosystem while expertly navigating the waterways.

If you’ve got time (and we recommend making time), the three-hour mangrove tunnel kayak tour offers a completely different perspective.

Silently paddling through narrow channels beneath a natural canopy of mangroves, we felt like real explorers. The only sounds were our paddles dipping into the water and the occasional splash of jumping mullet fish.

Park Highlights:

• Anhinga Trail: Easy boardwalk where we spotted dozens of alligators
• Gumbo Limbo Trail: Shaded walk through jungle-like hardwood hammock
• Observation tower: Perfect for spotting wading birds
• Wildlife show: Educational presentation featuring local species

Tips for Your Visit:

• Arrive early to beat both the heat and crowds
• Bring bug spray, water, and sunscreen
• Wear closed-toe shoes that can get wet
• Pack a hat and sunglasses
• Don’t forget your camera!

Time Needed:

• Quick Visit: 2-3 hours (airboat tour + wildlife show)
• Full Experience: 4-6 hours (adding kayak tour or hiking)

Whether you choose the adrenaline rush of an airboat ride or the serenity of a kayak tour, the Everglades offers a glimpse into Florida’s wild heart. It’s hard to believe that this vast wilderness exists so close to Miami’s bustling streets.

Key Largo: Diving Capital of the World (MM 108-99)

Our first real taste of Keys life came in Key Largo, and what a perfect introduction it was. Known as the “Diving Capital of the World,” this island offers an underwater playground that kept us busy for days.

Water Adventures

John Pennekamp Coral Reef State Park (MM 102.5) was our first stop, and it’s a must-visit. As America’s first underwater park, it offers:

• Snorkeling tours to vibrant coral reefs
• Glass-bottom boat trips (perfect if you don’t want to get wet)
• Kayak rentals for exploring mangrove trails
• Scuba diving trips to the famous Christ of the Abyss statue

We also tried paddle boarding with Keys Paddle (MM 103.6) – a peaceful way to explore the calm morning waters and spot manatees.

Where to Eat

Breakfast:

• Doc’s Diner (MM 99.6): Try their lobster eggs benedict
• Harriette’s Restaurant (MM 95.7): Famous for homemade biscuits and key lime muffins

Lunch:

• Mrs. Mac’s Kitchen (MM 99.4): Best conch fritters and key lime pie
• Key Largo Fisheries Backyard Café (MM 99.5): Fresh catch sandwiches right on the water

Dinner:

• The Fish House (MM 102.4): Local favorite for fresh seafood
• Skipper’s Dockside (MM 100): Perfect sunset views with your dinner
• Alabama Jack’s (Card Sound Road): Worth the detour for the best conch fritters in the Keys

Where to Stay

Luxury:

• Baker’s Cay Resort (MM 97): Private beach and multiple restaurants
• Playa Largo Resort (MM 97.5): Modern luxury with excellent amenities

Mid-Range:

• Key Largo Bay Marriott Beach Resort (MM 103.8): Great location and marina views
• Holiday Inn Key Largo (MM 100): Reliable comfort with a tiki bar

Budget-Friendly:

• Rock Reef Resort (MM 98): Old Florida charm with a private beach
• Sunset Cove Beach Resort (MM 99): Clean rooms and a good location

For RV Travelers:

• Key Largo Kampground (MM 101.5): Full hookups and boat ramp access

Local Tips:

• Book water activities early in the morning when the water is calmest
• Most restaurants offer early bird specials between 4-6 PM
• The Caribbean Club (MM 104) offers the best sunset views with a dose of Hollywood history
• Many hotels offer dive packages – ask when booking
• Keep an eye on the weather – morning activities generally have better conditions

Whether you’re an experienced diver or just getting your feet wet, Key Largo’s crystal-clear waters offer something for everyone. We spent two nights here and could have easily stayed longer, exploring a new reef or trying a different water sport each day.

Islamorada: Sport Fishing Capital of the World (MM 90-65)

The drive from Key Largo to Islamorada treats you to some of the most stunning views along the Overseas Highway. Known as the “Sport Fishing Capital of the World,” Islamorada is actually a village of six islands where backcountry and deep-sea fishing dreams come true.

Must-Do Activities

Robbie’s Marina (MM 77.5):

• Feed the massive tarpon (bring dollar bills to buy fish bait)
• Browse local artisan stands
• Book fishing charters or water sports
• Grab lunch at the Hungry Tarpon Restaurant

History of Diving Museum (MM 83):

• Fascinating collection of diving helmets and gear
• Interactive exhibits about coral reef protection
• Perfect activity for a rainy afternoon

Theater of the Sea (MM 84.7):

• Swim with dolphins and sea lions
• Watch marine life shows
• Take a bottom boat tour

Where to Eat

Breakfast:

• Midway Café (MM 80.4): Home of the “lobster egg benedict”
• Bob’s Bunz (MM 81.6): Fresh-baked pastries and hearty breakfast plates

Lunch:

• Lorelei Restaurant & Cabana Bar (MM 82): Waterfront lunch with incredible views
• Islamorada Fish Company (MM 81.5): Fresh local catch with marina views

Dinner:

• Chef Michael’s (MM 81.6): Upscale dining with fresh fish
• Islamorada Shrimp Shack (MM 69): Local favorite for fried seafood
• Marker 88 Beach Bar & Restaurant (MM 88): Perfect sunset di

Where to Stay

Luxury:

• Cheeca Lodge & Spa (MM 82): Historic luxury resort with private beach
• The Islander Resort (MM 82.1): Guy Harvey Outpost with oceanfront rooms

Mid-Range:

• Postcard Inn Beach Resort & Marina (MM 84): Recently renovated with great amenities
• La Siesta Resort & Marina (MM 80.5): Comfortable rooms with kitchen options

Budget-Friendly:

• Pelican Cove Resort (MM 84.5): Clean rooms with ocean views
• Sunset Inn (MM 82): Old Florida charm at reasonable prices

For RV Travelers:

• Islamorada Marina & RV Resort (MM 80): Full hookups with boat access

Local Tips:

• Book fishing charters in advance, especially during peak season
• The best sunset views are from the beach bars on the gulf side
• Many restaurants will cook your catch if you go fishing
• Arts & Crafts Show at Founder’s Park (MM 87) happens monthly
• Indian Key Historic State Park is accessible by kayak for a unique adventure

Hidden Gems:

• Florida Keys Brewing Company (MM 81.6): Local craft beer with a tropical garden
• Library Beach (MM 81.5): Small but peaceful public beach
• Windley Key Fossil Reef Geological State Park (MM 84.9): Ancient coral turned decorative stone

Islamorada perfectly balances tourist amenities with authentic Keys charm. Whether you’re here to fish, relax on the beach, or explore the local culture, plan at least two nights to really experience what makes this village of islands special.

Marathon: Heart of the Keys (MM 65-45)

Driving across the iconic Seven Mile Bridge feels like gliding over an endless expanse of turquoise water. As the morning sun dances across the waves, you’ll spot boats of all sizes navigating the channels below, their wakes creating patterns in the crystalline waters. Marathon sits at the heart of the Florida Keys, offering a perfect blend of marine life encounters, pristine beaches, and authentic Keys culture.

The Famous Seven Mile Bridge

The bridge itself is an engineering marvel, stretching across the ocean like a ribbon of concrete and steel. For the best experience:

• Drive south at sunset for spectacular views
• Park at the north end to walk the restored “Old Seven” bridge
• Look for sea turtles and rays in the clear waters below
• Stop at the pull-offs for photo opportunities you won’t forget

Marine Life Encounters

Marathon quickly became our favorite surprise of the trip. While Key West might get all the fame, this laid-back community at Mile Marker 50 captured our hearts with its authentic Keys character.

Our first stop was the Turtle Hospital, where we met Bernie, a rescued sea turtle missing one flipper but full of personality. The dedicated staff shared stories of rescue and rehabilitation that left us with a deeper appreciation for these gentle creatures.

Sombrero Beach became our daily ritual. Unlike the rocky shores found elsewhere in the Keys, this sandy paradise offered soft sand and crystal-clear waters.

We spent one memorable morning watching a family of manatees slowly cruise past swimmers, their gentle presence adding magic to an already perfect day.

A hidden gem among Keys beaches, offering:

• Soft sandy shores (rare in the Keys)
• Crystal clear swimming waters
• Sea turtle nesting grounds (in season)
• Perfect sunrise viewing spot
• Clean facilities and plenty of parking

Where To Eat In Marathon Keys

For lunch, we followed a local’s tip to Keys Fisheries. Sitting at their casual outdoor tables, we feasted on stone crab claws and watched commercial fishing boats unload their daily catch.

The fishermen’s stories of life on the water gave us a glimpse into the real Florida Keys, far from the tourist brochures.

As evening approached, we found ourselves at Sunset Grille, perched at the edge of Seven Mile Bridge. With our feet in the pool and frozen drinks in hand, we watched the sun paint the sky in brilliant oranges and pinks.

A local musician played Jimmy Buffett covers, and for a moment, we understood why people come to the Keys and never leave.

Where to Rest Your Head

We chose to stay at Tranquility Bay Resort, where our beach house offered front-row seats to spectacular sunrises. But Marathon offers plenty of options, from luxury resorts to charming guesthouses, each with its own piece of paradise.

Luxury: Isla Bella Beach Resort (MM 47)

• Private beach access
• Multiple pools
• On-site marina
• Luxurious spa services

Mid-Range: Tranquility Bay Resort (MM 48)

• Beach house accommodations
• Three swimming pools
• Private beach
• Full kitchens available

Budget-Friendly: Banana Bay Resort (MM 49.5)

• Waterfront views
• Pool access
• Clean, comfortable rooms
• Great value for location

Local tip we wish we’d known earlier: The best time to drive Seven Mile Bridge is at sunset, heading south. The views of the sun sinking between the old and new bridges create photos that no filter could improve.

The Lower Keys: Where Nature Takes Center Stage

As we crossed the Seven Mile Bridge, the rhythm of the Keys seemed to slow even further. The Lower Keys, stretching from Mile Marker 45 to the outskirts of Key West, reveal a different side of the Florida Keys – one where nature rules and development takes a respectful step back.

Our first stop was Bahia Honda State Park at Mile Marker 37, and we immediately understood why it’s often called the Keys’ best beach. Unlike the rocky shores common throughout the islands, Bahia Honda welcomed us with soft, sandy beaches and crystal-clear waters.

We spent the morning snorkeling right off the beach, spotting tropical fish darting around our feet. The park’s position alongside Bahia Honda Bridge, an abandoned overseas railway bridge, created perfect photo opportunities as the old bridge stretched toward the horizon.

Further down the highway, Big Pine Key introduced us to some of the Keys’ most charming residents – the tiny Key deer. No larger than a dog, these endangered deer roam freely through the National Key Deer Refuge.

We spotted several during our early evening drive, their delicate forms browsing peacefully in residents’ yards. The refuge itself offers serene walking trails where the only sounds are rustling palms and calling birds.

Hungry from our adventures, we followed a local’s tip to No Name Pub, hidden away on Big Pine Key. Finding this historic spot felt like a treasure hunt, but the reward was worth it.

Dollar bills cover every inch of the walls and ceiling, each telling its own story, while the aroma of their famous pizza filled the air.

We learned that fishermen started the tradition of signing dollar bills decades ago, ensuring they’d have money for a drink when they returned from sea.

The natural wonders continued at Looe Key National Marine Sanctuary, where we joined a snorkeling tour to one of the most pristine coral reefs in the Keys.

The water clarity was remarkable, offering perfect views of parrotfish, angelfish, and even a peaceful nurse shark resting under a coral ledge.

For those seeking solitude, Little Palm Island at Mile Marker 28.5 offers the ultimate escape. While we didn’t stay at this exclusive resort, we watched the private boats ferry guests to and from the island, imagining the luxury that awaited them.

For our overnight stay, we chose Parmer’s Resort, a charming mid-range option that perfectly captured the old Florida Keys atmosphere with its waterfront rooms and peaceful gardens.

One unexpected highlight was the Blue Hole on Big Pine Key, an abandoned quarry turned wildlife sanctuary. The freshwater lake attracts all sorts of wildlife, and we spent a peaceful hour watching an alligator sun itself while ospreys circled overhead.

A word of caution for fellow travelers: drive carefully through this stretch, especially at dawn and dusk. The protected Key deer have no fear of cars, and they frequently cross the highway.

But this is part of the Lower Keys’ charm – it’s a place where wildlife takes priority and humans are just grateful visitors.

As we approached Key West, we found ourselves already missing the tranquil beauty of the Lower Keys. This stretch of islands offers a glimpse of what the entire Keys must have been like decades ago – wild, peaceful, and full of natural wonders.

It’s the perfect counterpoint to the festivities that await in Key West, and we were glad we took our time to explore.

Key West: The End of the Road, The Beginning of Adventure

Crossing the final bridge into Key West, we watched the Mile Markers tick down to zero. The island’s energy was palpable even from the car – a vibrant mix of history, culture, and celebration that makes Key West unlike anywhere else in the Florida Keys.

Historic Old Tow

We chose to stay in the heart of Old Town, just a few blocks from Duval Street in a restored conch house turned guest house. These historic homes, with their white wooden porches and gingerbread trim, tell stories of the island’s rich past.

Our mornings began with coffee in the courtyard, sharing travel tips with other guests while resident roosters strutted past, the unofficial mascots of Key West.

Must-Visit Historic Sites:

• Ernest Hemingway Home: Six-toed cats roam freely through the Spanish Colonial mansion
• Truman Little White House: Former president’s winter retreat
• Oldest House Museum: Peek into Key West’s earliest days
• Fort Zachary Taylor: Civil War-era fort with the best beach in Key West

We discovered that Key West is best explored on foot or by bike. The narrow streets of Old Town revealed something new at every turn – artist studios tucked into tropical gardens, tiny bars claiming to be the “original” something or other, and local cafes serving Key lime pie that sparked friendly debates about whose recipe was best.

Blue Heaven won our hearts with its outdoor seating under the trees, where roosters roamed between tables and the Key lime pie came topped with a towering meringue.

Sunset in Key West is more than just a time of day – it’s a celebration. While crowds gathered at Mallory Square for the famous Sunset Celebration, we followed a local’s advice and headed to Fort Zachary Taylor State Park.

Here, we found a quieter spot to watch the sun sink into the Gulf of Mexico, the sky painted in impossible shades of orange and pink.

The fort itself, a Civil War-era structure, offered fascinating tours during the day and some of the best views of the island.

Best Viewing Locations:

• Mallory Square: Famous sunset celebration with street performers
• Fort Zachary Taylor: Quieter beach setting
• Sunset Pier: Waterfront dining with a view
• Louie’s Backyard: Upscale dinner with sunset views
• Sunset Key: Take the ferry for dinner at Latitudes

Food & Drink Discoveries

The food scene surprised us with its diversity. One evening, we feasted on fresh catch at Half Shell Raw Bar, sitting at wooden tables overlooking the historic seaport.

Another night found us at Santiago’s Bodega, where Spanish tapas and sangria made us forget we were in the Florida Keys altogether.

For lunch, we couldn’t resist the Cuban sandwiches at Five Brothers, a tiny corner store where locals lined up for their caffeine fix.

Local Favorites:

• Blue Heaven: Best Key lime pie under a canopy of trees
• Half Shell Raw Bar: Fresh seafood at the historic seaport
• Santiago’s Bodega: Spanish tapas in a romantic setting
• Five Brothers: Cuban sandwiches and café con leche
• First Flight Restaurant: Original Pan Am Airways building

Water Adventures

Water adventures called to us daily. We took a morning snorkel trip to the coral reef, where parrotfish darted through crystal clear waters.

A sunset sail brought us close to playful dolphins, while a kayak tour through the mangroves revealed a quieter side of the island. Each adventure showed us a different perspective of Key West’s relationship with the surrounding waters.

The island’s most colorful stories came alive during a ghost tour through Old Town. Our guide, a local historian, shared tales of haunted dolls, tragic love affairs, and the infamous Robert the Doll, whose home at Fort East Martello Museum still draws curious visitors.

Popular Activities:

• Dry Tortugas National Park: Day trip to the remote fort and snorkeling paradise
• Sunset sail: Choose from dozens of evening cruises
• Mangrove kayak tours: Explore the quiet backwaters
• Coral reef snorkeling: See tropical fish in crystal clear waters
• Jet ski island tour: Circle the entire island

Cultural Experiences

The island’s artistic spirit comes alive in its galleries and museums.

Don’t Miss:

• Key West Butterfly Conservatory: Magical encounter with hundreds of butterflies
• Custom House Museum: Local history and art
• The Studios of Key West: Working artists and exhibitions
• Mel Fisher Maritime Museum: Treasure hunting history
• Ghost Tours: Evening walks through haunted Old Town

Hidden Gems

Away from the Duval Street crowds, we found quiet corners that captured Key West’s true spirit.

Local Secrets:

• Nancy’s Secret Garden: Peaceful café tucked away on Elizabeth Street
• The Key West Cemetery: Fascinating historical plots with famous epitaphs
• Elizabeth Street Garden: Beautiful tropical garden open to the public
• The Green Parrot: Authentic local bar away from tourist crowds
• Coast Project: Artist collective with unique local works

Practical Tips

Experience taught us some valuable lessons about visiting Key West.

Smart Travel Tips:

• Book accommodations in Old Town to walk everywhere
• Visit popular attractions early morning or late afternoon
• Rent bikes instead of dealing with parking
• Carry cash for small local shops
• Make dinner reservations, especially during sunset hours
• Stay hydrated – the island heat can be intense

Whether you’re here for the history, the beaches, the food, or the famous Key West sunset, this small island packs an incredible number of experiences into its 2-by-4-mile area. The key is to balance the must-see attractions with quiet moments that let you discover your own slice of Key West magic.

Where to Stay in Key West

Finding the right place to stay can make or break your Key West experience. We discovered that each neighborhood offers its own unique charm and advantages.

Old Town Accommodations

The heart of Key West’s historic district puts you within walking distance of major attractions.

Luxury Options:

• Ocean Key Resort & Spa: Prime location at the foot of Duval Street
  • Stunning sunset views from the pier
  • Zero Duval restaurant for fine dining
  • Beautiful pool overlooking the Gulf
• La Concha Hotel: Historic landmark on Duval Street
  • Rooftop spa with panoramic views
  • Central location for shopping and dining
  • Historic architecture with modern amenities

Boutique Guesthouses:

• Marquesa Hotel: Restored 1884 conch houses
  • Four swimming pools
  • Peaceful gardens
  • Award-winning restaurant
  • Adults only
  • Artist House: Famous Victorian mansion
  • Reportedly haunted
  • Stunning architecture
  • Wine and cheese happy hour
  • Walking distance to attractions

Mid-Range Choices:

• Cypress House Hotel: Adult-only historic inn
  • Daily poolside breakfast
  • Afternoon cocktail hour
  • Three blocks from Duval
  • Eden House: Key West’s oldest hotel
  • Hammocks and gardens
  • Free shuttle service
  • Heated pool

New Town Area

Better value but requires transportation to attractions.

Family-Friendly Options:

• The Gates Hotel
  • Modern rooms
  • Food truck by pool
  • Free shuttle to Old Town
  • Rum tastings

Budget-Friendly:

• NYAH (Not Your Average Hotel)
  • Build-your-own room concept
  • Multiple pools
  • Continental breakfast included
  • Adult only

Key West Harbor

Perfect for boat enthusiasts and water activities.

Waterfront Options:

• Perry Hotel
  • Modern marina setting
  • Multiple restaurants
  • Pool with harbor views
  • Free shuttle service
  • Stock Island Marina Village
  • Authentic working harbor
  • Fresh seafood restaurants
  • Away from tourist crowds
  • Great for fishing enthusiasts

Local Tips for Booking

Timing Matters:

• Book well in advance for winter months (December-April)
• Best rates found in September-November
• Holiday weekends require earliest bookings
• Consider shoulder season (April-May) for good weather and rates

Location Strategy:

• Stay in Old Town if you want to walk everywhere
• New Town offers better value but requires transportation
• Harbor area best for boating activities
• Consider noise levels near Duval Street

Money-Saving Tips:

• Many guesthouses offer free breakfast
• Look for properties with included airport shuttles
• Some hotels offer free parking (rare in Old Town)
• Check for packages including water activities

Getting Around Key West & Day Trips

The beauty of Key West lies in its compact size, but knowing how to navigate the island and explore beyond it can transform your experience from good to unforgettable.

Getting Around the Island

Walking:

• Most attractions within 15-minute walk in Old Town
• Duval Street is just over a mile long
• Pick up a free walking map from visitor center
• Early morning walks best for photo opportunities

Biking: Local’s Tip: We found biking to be the perfect way to explore. The flat terrain and bike-friendly streets make it ideal for cyclists of all levels.

• Bike rentals available throughout the island ($15-25/day)
• Many hotels offer free or discounted bikes
• Lock your bike – even in Key West theft happens
• Popular bike rental spots:
  • Eaton Bikes: Great service, multiple locations
  • Island Bikes: Competitive rates
  • WeCycle: Delivers to your hotel

Free Duval Loop Bus:

• Runs through Old Town
• Air-conditioned comfort
• Stops at major attractions
• Track bus location via mobile app

Ride Share & Taxis:

• Uber and Lyft readily available
• Local taxis cluster at popular spots
• Fixed rates to/from airport ($20-25)
• Pedi-cabs popular for short trips

Final Thoughts: Making the Most of Your Keys Adventure

Our journey from Miami to Key West revealed why this string of islands captures so many hearts. Each key has its own personality: Key Largo’s underwater wonders, Islamorada’s fishing culture, Marathon’s family-friendly charm, the Lower Keys’ natural beauty, and Key West’s vibrant spirit.

Trip Planning Essentials

Best Times to Visit:

• Spring (March-May): Ideal weather, moderate crowds
• Winter (December-February): Perfect temperatures but peak crowds
• Fall (September-November): Best deals, hurricane season
• Summer (June-August): Hot but great hotel rates

Road Trip Tips:

• Allow at least 4 days for the journey
• Keep a flexible schedule for spontaneous stops
• Download offline maps – cell service can be spotty
• Always have cash on hand
• Fill up gas when tank hits half – stations can be far apart

Don’t Miss:

• Sunrise on the Atlantic side
• Sunset on the Gulf side
• Fresh seafood at local spots
• At least one water activity per location
• Quiet moments away from tourist areas

Whether you’re seeking adventure, relaxation, or a bit of both, the Florida Keys offer an escape unlike anywhere else. The journey from Miami to Key West isn’t just a drive – it’s a transition from everyday life to island time, where the only schedule that matters is the sunset.

Remember, the real magic of the Keys often happens when you slow down, take that random turn, or stop at that interesting-looking roadside stand. After all, you’re not just driving to a destination; you’re experiencing one of America’s most unique and beautiful road trips.

Safe travels, and enjoy paradise! 🌴🌊🌅

Last Updated: February 2025