Key West and Key Largo, Florida

Deep dives into local history, extended activity suggestions, budgeting strategies, packing checklists, and insider tips. Whether you have three days or three weeks, families in tow or solo explorers, honeymooners or retired couples, this in-depth roadmap will ensure you make the most of every mile in paradise.

Why Choose a Keys Road Trip?

The Overseas Highway is more than a way to get from point A to point B—it’s a journey through tropical landscapes, historic landmarks, and vibrant communities set against the backdrop of the Atlantic Ocean and Gulf of Mexico. A Keys road trip offers:

• Flexibility: Stop when a hidden beach beckons, linger for a sunset over a sandbar, or detour to a wildlife refuge at will.
• Immersion: Dive into local culture—from Cuban cafés and family-run seafood shacks to art galleries showcasing Keys-inspired works.
• Scenic Variety: Travel over aquamarine waters on bridges like the Seven Mile Bridge, wind through mangrove tunnels, and witness island jungles.
• Personalization: Customize your vacation length, pace, and activities according to your interests—whether that’s fishing, snorkeling, history, or simply relaxing.
• Value: With advanced planning, smart budgeting, and multi-stop lodging deals, you can stretch your travel dollars further than you might expect.

In short, a Keys road trip maximizes freedom, discovery, and adventure—qualities that define the ultimate American vacation.

Best Time to Travel

Choosing when to hit the road is crucial for balancing weather, crowds, and costs. Here’s a seasonal breakdown:

• Spring (March–May): Warm temperatures (mid-70s to mid-80s°F), low rainfall, excellent snorkeling clarity, and fewer afternoon storms. Peak wildlife activity—ideal for birdwatching and turtle nesting season.
• Summer (June–August): Hot and humid (80s to 90s°F), daily afternoon thunderstorms, hurricane season officially starts June 1. Lodging rates drop but pack for heat, bring bug repellent, and plan water-based activities in mornings.
• Fall (September–November): Off-peak deals, mild temperatures returning (80s°F), chance of tropical storms. Watch weather forecasts and purchase travel insurance. Great for budget-minded families once kids are back in school.
• Winter (December–February): Peak tourist season—temperatures in 60s–70s°F, dry weather, popular for snowbird vacations. Book car rental and overnight stays 3–6 months in advance to lock in rates.

Insider Note: Late May and early October often hit the sweet spot: manageable crowds, decent weather, and shoulder-season prices on accommodations and rentals.

Car Rental Essentials

Your choice of car rental can make or break your journey. Consider these factors when booking:

Vehicle Type

• Convertibles: Bask in sea breezes, perfect for couples or small groups.
• SUVs & Crossovers: Ample cargo space for snorkel gear, coolers, beach chairs, and family luggage.
• Vans & Minivans: Ideal for large families or multi-generational vacations with extra passengers.

Rental Logistics

• Pick-Up & Drop-Off: One-way rentals (Miami to Key West) save time but often include drop-off fees—compare round-trip vs. one-way pricing.
• Insurance: Verify that collision, theft, and roadside assistance are included or add supplemental coverage. Check exclusions for water damage if you plan to boat.
• Fuel Policy: Full-to-full is standard; budget for higher fuel prices south of Marathon. Fill up before remote legs.
• Extras to Avoid: Decline costly GPS units—download offline maps. Skip airport add-ons by booking at off-airport locations if convenient.
• Driver Requirements: Minimum age usually 21–25; underage fees can be steep. Bring a valid driver’s license and credit card.

Sample Itineraries

Whether you have three days or two weeks, here are itinerary templates you can adapt to your interests and pace. Distances and drive times assume non-stop travel; factor in stops and traffic, especially in season.

Three-Day Express Road Trip

• Day 1: Miami → Key Largo (56 miles, ~1 hr). Morning snorkel at John Pennekamp; lunch at a waterfront café; kayak mangroves in the afternoon; check into Key Largo vacation rental or hotel; sunset fishing charter or beach stroll.
• Day 2: Key Largo → Islamorada (25 miles, ~30 min). Breakfast at a café; stop at the African Queen boat; join a mid-morning fishing or snorkel charter; lunch at a sandbar tour; spend afternoon at Windley Key Fossil Reef; overnight in Islamorada; dinner at a local seafood grill; evening tarpon feeding at Robbie’s Marina.
• Day 3: Islamorada → Key West (80 miles, ~1 hr 45 min). Sunrise drive across Seven Mile Bridge with photo stops; brief Marathon stop for Turtle Hospital tour; lunch on the go; arrive Key West by afternoon; visit Hemingway Home & Museum; stroll Duval Street; end with Mallory Square Sunset Celebration; depart or stay overnight.

Five-Day Balanced Adventure

• Day 1: Miami → Key Largo. Morning snorkeling; tour on glass-bottom boat; dinner at local grill; overnight in Key Largo.
• Day 2: Key Largo → Islamorada. Private reef fishing charter; lunch aboard; afternoon brewery/distillery tour; sunset sandbar party; overnight in Islamorada.
• Day 3: Islamorada → Marathon. Early morning tarpon feeding; stop at Florida Keys History & Discovery Center; snorkel Sombrero Reef; Turtle Hospital visit; overnight in Marathon.
• Day 4: Marathon → Lower Keys (Big Pine Key & Bahia Honda). Morning bike ride on Seven Mile Bridge; beach day at Bahia Honda State Park; picnic or beachside BBQ; overnight Lower Keys cottage or resort.
• Day 5: Lower Keys → Key West. Wildlife spotting in National Key Deer Refuge; lunch in Big Pine Key; arrive Key West afternoon; choose either Dry Tortugas day trip or explore Key West attractions; overnight in Key West.

Seven–Fourteen Day Leisure Road Trip

• Include extended stays at Duck Key, Little Palm Island (adults-only luxury), and No Name Key for secluded nature retreats.
• Add eco-tours: Everglades airboat experience before entering the Keys; nighttime bioluminescence kayak excursion off Islamorada.
• Plan a two-day camping excursion in Dry Tortugas National Park—book beach campsites and ferry or seaplane.
• Factor in spa and wellness days at Cheeca Lodge, food and wine pairing events at local vineyards or distilleries, and golf rounds at Keys’ championship courses.
• Reserve sunset sails, private yacht charters, and eco-photography workshops to diversify experiences.

Key Largo (Mile Markers 106–90)

Overview

Key Largo, the first major island encountered after leaving the mainland, is renowned for its marine conservation areas, underwater sculptures, and easy-access diving and snorkeling. It earned its nickname “Diving Capital of the World” thanks to the landmark John Pennekamp Coral Reef State Park, established in 1963 as the first undersea park in the U.S.

Marine & Water Activities

• John Pennekamp Coral Reef State Park: Covering 70 square miles of coral reefs, seagrass beds, and mangrove swamps, the park offers guided snorkeling trails, kayak rentals, and glass-bottom boat tours. Must-see sites include the Christ of the Abyss statue and the Alligator Reef Lighthouse.
• Glass-Bottom Boat Tours: Non-swimmers and families enjoy narrated tours that reveal reef life through boat windows without getting wet.
• Kayak & SUP Adventures: Paddle through mangrove tunnels, backcountry bays, and creeks teeming with fish and birds. Don’t miss the Blackwater Sound for calm paddling.
• Nighttime Bioluminescence Tours: On moonless nights, kayak excursions offer glimpses of plankton glowing under paddles—nature’s own light show.

Cultural & Historic Attractions

• African Queen: The original 1912 steam-powered paddlewheeler made famous by the movie “The African Queen” is docked near the park. Cruises run daily and include narration on the vessel’s storied past.
• Florida Keys Wild Bird Rehabilitation Center: A nonprofit that treats injured wild birds—visitors can tour the facility, see resident raptors, and learn about local bird species.
• Florida Keys History & Discovery Center: Interactive exhibits covering everything from watershed science to pirate lore to space-age missile testing on Key Largo during the Cold War era.

Dining & Local Flavors

• Fresh-caught Yellowtail Snapper sandwiches and conch fritters at casual bayside shacks.
• Cuban-inspired seafood dishes—think garlic mojo shrimp and black bean soup—in family-run Cuban diners.
• Key lime pie with graham cracker crust at roadside bakeries.

Accommodation Options

• Budget: Small motels along US-1 with bay views offer basic rooms and easy access to snorkeling launch points.
• Mid-Range: Resorts with private docks, pools, and in-house dive shops; ideal for combining lodging and marine activities.
• Vacation Rentals: Waterfront condos and homes with full kitchens—perfect for families or groups planning multi-day stays.

Islamorada (Mile Markers 90–74)

Overview

Often called the “Sportfishing Capital of the World,” Islamorada offers top-tier fishing charters alongside art galleries, artisan markets, and a burgeoning craft beer and rum scene. The blend of angler culture and island artistry makes Islamorada a cornerstone stop on any Keys road trip.

Fishing & Boating Excursions

• Backcountry & Reef Charters: Half-day or full-day excursions target species from permit and bonefish in the flats to snapper and grouper on offshore reefs, and sailfish further out.
• Sun Seeker Private Charters: Customized trips combining snorkeling over coral reefs, offshore trolling for big game, and guided reef fishing.
• Sandbar & Dolphin Tours: Social boat excursions to shallow sandbanks for sunbathing, swimming, and dolphin spotting at play.
• Kayak & Paddleboard Rentals: Explore mangrove islets and quiet canals at your own pace.

Arts, Culture & Shopping

• Local Galleries & Studios: Discover seascape paintings, glass art, jewelry, and driftwood sculptures—many by Florida Keys–based artists.
• Monthly Artisan Markets: Pop-up events featuring handmade crafts, local honey, tropical jams, and street food.
• Islamorada Brewery & Distillery: On-site tours and tastings of small-batch ales, lagers, and rum spirits crafted with local sugarcane.

Dining & Nightlife

• Waterfront seafood grills offering stone crab claws, mahi-mahi tacos, and peel-and-eat shrimp.
• Casual tiki bars with craft cocktails infused with Keys citrus and rum.
• Sunset happy hours at beachside lounges with live music.

Lodging Choices

• Fisher Inn Resort & Marina: Economical cottages and rooms overlooking the Atlantic, with boat slips and easy access to fishing charters.
• Cheeca Lodge & Spa: A 27-acre beachfront resort with championship golf, full-service spa, tennis courts, and multiple on-site dining venues.
• Boutique Cottages & Inns: Quaint, secluded rentals set amid tropical landscaping for couples and small groups.

Marathon (Mile Markers 53–47)

Overview

Marathon sits roughly halfway along the Overseas Highway, offering a blend of local community charm, resort comforts, and family-friendly attractions. It’s a prime spot to refuel your car rental, your belly, and your sense of wonder.

Marine & Wildlife Encounters

• Sombrero Reef: Part of the Florida Keys National Marine Sanctuary, this offshore reef features shallow snorkeling depths and abundant coral formations.
• Turtle Hospital: A nonprofit rehabilitation center where visitors can learn about injured sea turtles and the rescue process.
• Florida Keys Aquarium Encounters: Interactive touch tanks, shark feedings, and behind-the-scenes animal encounters.

Historic & Cultural Sites

• Marathon Air Museum: Displays restored WWII aircraft and artifacts, honoring the area’s aviation history.
• Crane Point Hammock: A 63-acre nature center with nature trails, historic homes, and an interpretive museum showcasing Keys pioneer life.

Dining Highlights

• Local fish tacos and lobster Reuben sandwiches at waterfront cafés.
• Caribbean-inspired seafood platters with tropical salsas.
• Key lime pie milkshakes and gourmet ice cream shops.

Accommodation Options

• Tranquility Bay Beachfront Resort: Spacious beach houses with full kitchens, private docks, and multiple pools.
• Isla Bella Beach Resort: Luxury oceanview suites, full-service spa, and in-house marina services.
• Courtyard by Marriott Faro Blanco: Family-friendly amenities including game rooms, pools, and waterfront dining.

Lower Keys & Big Pine Key (Mile Markers 30–0)

Overview

South of Marathon, traffic thins and island life slows. Big Pine Key’s lush environment is home to the endangered Key deer, while Bahia Honda State Park offers some of the Keys’ most pristine white-sand beaches.

Wildlife & Nature

• National Key Deer Refuge: Drive slowly at dawn or dusk to spot tiny Key deer grazing near the roadside.
• Birdwatching: Mangrove shorebirds, herons, egrets, and migratory species frequent the area’s salt ponds.

Beach & Outdoor Fun

• Bahia Honda State Park: Two main beaches—Calusa and Sandspur—offer snorkeling, swimming, and picnicking under pavilions.
• Historic Old Seven Mile Bridge: Pedestrian and bike path with panoramic views; sunset visits are spectacular.
• Mangrove Kayaking: Launch from shallow coves to explore hidden waterways and spot fish, crabs, and juvenile sharks.

Lodging & Camping

• Little Palm Island Resort & Spa: Ultra-luxury adults-only retreat accessible only by boat, featuring private bungalows and gourmet dining.
• No Name Key Cottages: Rustic waterfront cabins with kayaking access and fire pits.
• Bahia Honda Campground: Beachside tent and RV sites inside the state park—book months in advance for prime sites.

Key West (Mile Marker 0)

Overview

Reaching Key West marks the culmination of your road trip - a lively island town known for its vibrant nightlife, historic architecture, and cultural melting pot. From pastel conch houses to Cuban cafés and nightly street celebrations, Key West pulsates with energy.

Historic Landmarks

• Ernest Hemingway Home & Museum: Tour the Spanish Colonial-style house where Hemingway wrote classics; meet the famous six-toed cats roaming the grounds.
• Harry S. Truman Little White House: Presidential retreat turned museum, showcasing exhibits on Truman’s wartime leadership and Keys life.
• Fort Zachary Taylor Historic State Park: Civil War–era fort with guided tours and adjacent beach for snorkeling and picnicking.
• Southernmost Point Buoy: Iconic sundial-like marker denoting the southernmost point of the continental U.S. (and 90 miles to Cuba).

Duval Street & Nightlife

• Duval Street’s bars and pubs—Sloppy Joe’s, Green Parrot, and Irish Kevin’s—offer live music, open mic nights, and craft cocktails.
• Food truck parks and night markets feature local bites from shrimp tacos to rum cake.
• Mallory Square’s Sunset Celebration hosts street performers, artisans, and communal “sunset countdowns.”

Arts & Culture

• Galleries & Museums: Waterfront museums showcasing maritime history, shipwreck artifacts, and local art.
• Fantasy Fest: Annual costume festival in October with parades, themed parties, and charity events.
• Hemingway Days: July festival celebrating the author’s legacy with lookalike contests, readings, and fishing tournaments.

Accommodation Spectrum

• Historic bed & breakfasts in Old Town—quaint rooms with porches shaded by bougainvillea.
• Luxury waterfront resorts with private beaches and pools.
• Vacation rentals in quiet residential neighborhoods for families or groups.

Optional Dry Tortugas Day or Overnight Trip

For history buffs and snorkeling enthusiasts, Dry Tortugas National Park is an unforgettable side journey. Located 70 miles west of Key West, Fort Jefferson’s massive brick walls guard crystal-clear waters and thriving coral reefs.

• Ferry vs. Seaplane: Yankee Freedom III ferry (2 hr 15 min each way) departs early; seaplane (40 min) lands on water near the fort—book well in advance.
• Fort Jefferson Tour: Self-guided or ranger-led walks around the moat, parade grounds, and historic gun platforms.
• Snorkeling: Gear available onboard or bring your own; encounter parrotfish, angelfish, and sea turtles in pristine reefs.
• Camping: Primitive campsites inside the moat—reserve via recreation.gov; bring all supplies including water and shade.

Top Activities & Experiences

• Watersports: Stand-up paddleboarding, jet-skiing, kiteboarding, parasailing, flyboarding for thrill-seekers.
• Fishing: Backcountry flats charters for permit and bonefish; reef charters for snapper and grouper; offshore trolling for mahi-mahi and marlin.
• Eco-Tours: Everglades airboat day trips before entering the Keys; guided mangrove photography workshops; night kayaking among bioluminescent organisms.
• Sunset Sails & Dolphin Cruises: Catamaran and schooner tours featuring champagne toasts and pod-spotting excursions.
• Cultural Festivals: Lobsterfest in August, Hemingway Days in July, Fantasy Fest in October, and Key West Food & Wine Festival in January.
• Scenic Photography: Sunrise atop Seven Mile Bridge, mangrove reflections at golden hour, pastel hues of Key West conch houses.
• Nature Trails: Self-guided hikes at Curry Hammock State Park and Main Park Trails in Marathon.

Where to Stay: Hotels, Resorts & Vacation Rentals

The Keys offer lodging options for every budget and travel style:

• Key Largo: Budget motels along US-1, mid-range waterfront resorts, full-service vacation rentals.
• Islamorada: Cottage-style inns, luxury resorts with spas, boat-accessible private rentals.
• Marathon: Beachfront houses, family-friendly resorts, boutique hotels.
• Lower Keys: Secluded island retreats, state park campgrounds, remote luxury bungalows.
• Key West: Historic bed & breakfasts, upscale waterfront hotels, self-catering apartments.

Pro Tip: For longer stays, consider weekly or monthly rates on vacation rentals for significant savings. Always verify cancellation policies and deposits, especially during hurricane season.

Dining & Local Cuisine

Florida Keys cuisine blends fresh seafood, Caribbean influences, and Southern comfort:

• Fresh-Caught Seafood: Conch fritters, stone crab claws (seasonal Oct–May), fresh lobster Reubens, mahi-mahi and yellowtail snapper tacos.
• Cuban & Caribbean Flavors: Café Cubano, pressed medianoche sandwiches, plantain mofongo, black bean soup.
• Key Lime Pie: Must-try dessert available in myriad variations from classic to frozen custard.
• Farm-to-Table & Organic: Growing local movement with produce stands, artisanal cheeses, and craft breweries.
• Fine Dining: Waterfront steakhouses, sushi bars with ocean views, upscale island-fusion tasting menus.

Reserve tables in advance for popular spots during peak season and weekend nights.

Budgeting Your Road Trip

Estimate costs for a mid-range vacation per person (not including airfare to Florida):

• Car Rental: $40–$100 per day depending on vehicle type, plus insurance and one-way fees.
• Fuel: Approx. 200–250 miles round-trip; budget $3–$4 per gallon; expect $50–$80 total.
• Accommodations: $100–$500 per night based on season and property class; average ~$200–$300.
• Meals: $15–$30 per person for casual; $40–$70 for upscale dining; budget $50–$75 per person daily.
• Activities: Snorkel charters $50–$100; fishing charters $150–$300; park fees $10–$20; museum tours $5–$30.
• Miscellaneous: Souvenirs, tips, parking fees ($2–$5 per hour in Key West), emergency fund.

Packing Checklist

• Lightweight, breathable clothing; quick-dry swimwear; rash guard or wetsuit for long snorkels.
• Reef-safe sunscreen, aloe vera gel, lip balm with SPF.
• Snorkel gear if you prefer your own; otherwise plan rental fees.
• Wide-brimmed hat, polarized sunglasses.
• Reusable water bottle, insulated cooler bag for beach snacks.
• Beach towel, water shoes or reef booties.
• Portable charger, waterproof phone case.
• Driver’s license, printed reservations, travel insurance documents.
• Prescription medications, first-aid kit, insect repellent.
• Light jacket or cover-up for breezy nights.

Road Trip Safety & Driving Tips

• Speed Limits: Generally 45–55 mph; slow down for pedestrian areas and wildlife crossings.
• Watch for Wildlife: Key deer and other animals roam roads, especially at dawn and dusk—drive cautiously.
• Bridge Crossings: Pull offs on old Seven Mile Bridge for photography—do not stop on active lanes.
• Weather Hazards: Afternoon thunderstorms common in summer; slow down on wet roads and avoid low-lying areas during heavy rain.
• Cell Coverage: Spotty in Lower Keys; download offline maps and keep printed directions as backup.
• Emergency Services: Key West hospital in southernmost island; Florida Keys Memorial Hospital in Marathon; cell 911 calls route through Monroe County dispatch.

Insider Tips & FAQs

• Gas Stations: Fill up before leaving Marathon—next reliable station in Key West.
• Parking in Key West: Meters (up to 2 hrs) and garages fill quickly; consider remote lots with free shuttle service.
• Best Photography Spots: Sunrise on Seven Mile Bridge, sunset at Mallory Square, mangrove reflections at Curry Hammock.
• Budget vs. Luxury: Mix high-end resorts with budget guesthouses for balanced cost; mid-week stays often cheaper.
• Pet-Friendly Options: Many vacation rentals and some hotels allow pets—verify fees and restrictions.
• Hurricane Season Prep: June–November; book refundable rates, subscribe to NOAA alerts, have emergency kit with water and nonperishables.
• Meal Timing: Lunch specials often cheaper; dinner reservations essential in peak season.
• Local Etiquette: Respect wildlife rules, avoid stepping on coral, tip tour guides and restaurant staff 15–20%.
• Mobile Apps: Download Tide charts, reef-safe sunscreen guides, parking pay apps, offline GPS like Maps.me.
• Credit Cards vs. Cash: Most places accept cards; carry small cash for tips, parking meters, and food trucks.

History & Culture of the Florida Keys

The Keys’ story spans Native peoples, Spanish exploration, Cuban influence, railroad ambition, and maritime lore:

• Indigenous Heritage: Tequesta and Calusa tribes inhabited the islands before European contact, leaving shell mounds and fishing traditions.
• Spanish & Pirate Era: In the 16th–17th centuries, Spanish galleons wrecked on reefs, leading to treasure salvage and pirate legends.
• Flagler’s Overseas Railway: Built 1905–1912 by industrialist Henry Flagler, linking islands to Miami—destroyed by the 1935 Labor Day Hurricane, its bridge remnants repurposed into the highway.
• Cuban Immigration: Proximity to Cuba fostered cultural exchange—Cuban coffee, cigars, and architecture shaped Key West’s character.
• Call of the Sea: From sponge diving to commercial fishing, maritime industries defined economies; today sportfishing and ecotourism continue traditions.
• Literary Legacy: Ernest Hemingway, Tennessee Williams, and other artists found inspiration here—tribute festivals celebrate their work annually.

Wildlife, Conservation & Eco-Tourism

The Florida Keys are a biodiversity hotspot, home to coral reefs, mangroves, seagrass beds, and unique species:

• Coral Reefs: Third-largest barrier reef system in the world; under restoration efforts by the Coral Reef Conservation Program.
• Key Deer: Endangered subspecies found only on Big Pine Key—view from designated drives in the refuge.
• Sea Turtles: Loggerheads, greens, and Kemp’s ridleys nest on Lower Keys beaches—support local hatchling conservation projects.
• Mangrove Ecosystems: Nurseries for juvenile fish and natural storm surge buffers—guided eco-kayak tours highlight their importance.
• Birdlife: Over 200 migratory and resident species, including roseate spoonbills, ospreys, and peregrine falcons—prime birding spots at Curry Hammock and Key West Wildlife Center.
• Responsible Tourism: Follow “Take nothing but pictures, leave nothing but footprints,” use reef-safe sunscreens, and choose certified eco-tours.

Conclusion: Your Unforgettable Keys Vacation

A Key West road trip is more than a drive—it’s a journey through natural wonders, historic tales, and island cultures woven together by turquoise seas and tropical breezes. By planning your car rental logistics, choosing the right season, customizing an itinerary, and diving deep into each island’s offerings, you’ll craft a Florida Keys vacation that resonates long after the final sunset fades. Embrace spontaneity, respect local environments, and share island hospitality with every encounter. Now, pack your bags, load the cooler, and set your GPS for Florida’s island paradise - Key West awaits.