Tampa to Key West Ultimate Florida Keys Road Trip

Trip Snapshot

• Distance/Drive Time: ~430 miles (≈7 hours direct, best split into 2–3 days)
• Best Time: Winter–Spring (dry season & mild temps); Summer is off-season (hot, humid, potential storms)
• Ideal For: Beach lovers, wildlife enthusiasts, national park explorers, island vibes
• Route Outline: Tampa → Sarasota → Naples → Everglades (US-41/Alligator Alley) → Florida Keys (US-1 Overseas Highway) → Key West
• Top 3 Highlights: Driving the Overseas Highway’s 37 bridges to Key West; spotting alligators in Everglades National Park; shell-hunting on Sanibel Island’s beaches.

Route Overview

Leaving Tampa, head south across the dramatic Sunshine Skyway Bridge spanning Tampa Bay. Follow I-275/US-41 toward Sarasota, where powdery white sands await at Siesta Key Beach. Further down the Gulf Coast, consider a stop on Sanibel Island it’s famed as one of the world’s top shelling spots (you’ll find countless colorful seashells along its shores). Continuing to Naples, you transition from Tampa’s urban energy to upscale coastal charm. Naples makes a great midway overnight with its palm-lined downtown and the nearby Audubon Corkscrew Swamp Sanctuary for a taste of the Everglades’ cypress wetlands.

From Naples, venture east on Tamiami Trail (US-41) through the northern Everglades. This scenic stretch offers roadside wildlife viewing watch for egrets, herons, and alligators lounging in canals. You can detour into Everglades National Park at Shark Valley or Everglades City for an airboat ride amid the sawgrass prairie. (The park entrance is $35 per vehicle for 7 days.) At Homestead, turn south on the famed Overseas Highway (US-1), entering the Florida Keys island chain. The road is a modern engineering feat connecting 42 tropical islands via 37 bridges including the spectacular Seven Mile Bridge, which leaps across turquoise waters and was once the world’s longest bridge of its kind. As you glide above the ocean, you’re treated to breathtaking vistas of endless sky and sea on both sides.

Arrive in Key West, the southernmost point of the continental U.S. This quirky, historic town greets you with pastel conch houses and a laid-back vibe. Park the car and explore Old Town on foot: stroll down Duval Street, visit the Ernest Hemingway Home (and its six-toed cats), and come evening, join the nightly sunset celebration at Mallory Square. Savor the reward of your journey perhaps a slice of Key Lime pie and a toast as the sun sinks into the Gulf you’ve made it from Tampa to Key West, truly an island paradise “at the end of the road”.

Top Stops & Experiences (official links)

• Everglades National Park Take an airboat tour or walk the Anhinga Trail to see wild gators, turtles, and birds in this 1.5-million-acre subtropical wilderness (7-day entry $35/vehicle).
• Sanibel Island Beaches Stroll beaches like Bowman’s Beach on Sanibel for unrivaled shelling (the island is a shell collectors’ mecca). The $6 causeway toll is well worth it for access to this natural Gulf Coast gem.
• Seven Mile Bridge & Overseas Highway Experience the crown jewel of the Florida Keys drive. This famous 7-mile stretch of US-1 hops across blue ocean straits an “open ocean” driving thrill with panoramic Atlantic and Gulf views. (Pull off at Bahia Honda State Park for a photo of the original old bridge alongside the new.)
• Mallory Square, Key West Join the festive Sunset Celebration on Key West’s waterfront. Street performers, local artists, and food carts create a lively scene each evening as the sun sets spectacularly over the Gulf.

Where to Eat & Stay

• Naples (Halfway Stop): Break up the trip with a night in Naples. Dine beachfront on fresh seafood at The Turtle Club (toes-in-the-sand dining at Vanderbilt Beach) and stay at the luxe LaPlaya Beach & Golf Resort a beachfront resort with Gulf views and top-notch amenities.
• Key West: At journey’s end, immerse yourself in island life. Savor a laid-back brunch or dinner at the iconic Blue Heaven in Bahama Village (famous for its Caribbean cuisine and Key Lime pie under shady tropical trees). For lodging, treat yourself at Ocean Key Resort & Spa, a waterfront hotel at Zero Duval Street next to Mallory Square perfect for enjoying sunsets and Old Town sights on foot.

Practical Tips

• Book Ahead: Both Naples and Key West are popular—reserve accommodations well in advance, especially for winter high season in Key West (when rates peak and rooms fill quickly).
• Weather Caution: June–Nov is hurricane season. Check forecasts and the Florida Keys Overseas Highway conditions if traveling during this period, as heavy storms can cause flooding or delays. Winter and spring offer the best weather; summer will be hot and humid (but with fewer crowds).
• Tolls & Fees: Alligator Alley (I-75 between Naples and Miami) is a tolled alternative to US-41 have a SunPass or cash ready if you choose it. If entering Everglades National Park, remember the entry fee (or use a National Parks Pass).
• Wildlife Watching: Dawn and dusk are prime times to see wildlife (birds, gators) in the Everglades, but also when mosquitoes are active pack bug repellent. Also, obey speed limits, especially in the Keys where Key deer crossings are signed (on Big Pine Key).
• Fuel Up: Gas stations are plentiful until Homestead; after that, they become sparse in the Keys. Fuel up before entering the Keys (prices jump on the islands). In Key West, park your car and rent a bike or hop on the Duval Loop shuttle it’s easier than finding parking on the narrow streets.

Rentals & Logistics

This route is entirely on paved roads and suitable for any standard vehicle. Consider renting a convertible for the full tropical experience cruising the Overseas Highway with the top down is unforgettable. If you prefer not to backtrack, you can drop off your rental in Key West (or nearby Marathon/Key Largo) and fly out, but one-way drop fees may apply. Many travelers choose to return via the same route or loop back through mainland Florida for a different scenic drive. Either way, plan your rental timing to allow a leisurely pace with overnight stops. Reserve the perfect vehicle well ahead of time, especially in peak season, to ensure you have the ideal car for your Tampa to Key West adventure.