Planning Your Trip
Best Time to Go
The ideal time for your St. Augustine to Key West road trip depends on your preferences and priorities. Winter (December to April) offers pleasant temperatures and low humidity, perfect for outdoor activities and exploring historic sites[1]. However, this is also peak tourist season, so expect higher prices and larger crowds. Summer (June to August) brings hot, humid weather and occasional afternoon thunderstorms, but it's an excellent time for water activities and enjoying the beaches.
For a balance of good weather and fewer crowds, consider visiting during the shoulder seasons of spring (April to May) or fall (September to November). Keep in mind that hurricane season runs from June to November, with September and October being the most active months.
How Long to Spend
The driving distance from St. Augustine to Key West is approximately 460 miles, which can be covered in about 8-9 hours without stops. However, to truly appreciate the journey and make the most of your Florida road trip itinerary, we recommend allocating at least 5-7 days for your adventure.
Here's a sample itinerary:
- Day 1-2: Explore St. Augustine
- Day 3: Drive to Islamorada, stopping at points of interest along the way
- Day 4: Islamorada to Marathon
- Day 5: Marathon to Key West
- Day 6-7: Discover Key West
Transportation
Renting a car is the most convenient option for your St. Augustine to Key West road trip. Many major car rental companies operate in both cities, offering a range of vehicles to suit your needs and budget. When driving the Overseas Highway, be aware of speed limits, which can change frequently, and watch for cyclists and pedestrians.
For a unique experience, consider renting a convertible to fully enjoy the scenic coastal drive Florida offers. Alternatively, RVs and campervans are popular choices for those who want to combine transportation and accommodation.
Accommodation
The Florida Keys offer a wide range of accommodation options to suit every budget and preference. In St. Augustine, consider staying in a charming bed and breakfast in the Historic District for an authentic experience. As you make your way down the Keys, you'll find everything from budget-friendly motels to luxurious beachfront resorts.
Key West, in particular, offers a variety of unique lodging options, including historic inns, boutique hotels, and vacation rentals. Popular areas to stay include Old Town, which puts you close to major attractions, and the waterfront for stunning views.
St. Augustine: The Historic Coast
Your journey begins in St. Augustine, the oldest continuously occupied European-established settlement in the United States. Founded in 1565, this charming city is a treasure trove of history and culture.
Top St. Augustine Attractions
- Castillo de San Marcos: This 17th-century Spanish fort is a must-visit landmark, offering stunning views of the Matanzas River and insights into the city's military history.
- St. Augustine Lighthouse: Climb 219 steps to the top of this iconic black-and-white striped lighthouse for panoramic views of the Atlantic Ocean and the city.
- Flagler College: Admire the stunning Spanish Renaissance architecture of this former luxury hotel turned college campus.
- St. George Street: Take a stroll down this pedestrian-only thoroughfare lined with shops, restaurants, and historic buildings.
- Ponce de Leon's Fountain of Youth Archaeological Park: Explore the site where Spanish explorer Ponce de Leon allegedly searched for the mythical Fountain of Youth.
St. Augustine History and Culture
Immerse yourself in the rich history of St. Augustine by visiting its numerous museums and participating in guided tours. The St. Augustine Pirate & Treasure Museum offers an interactive look at the city's swashbuckling past, while the Lightner Museum showcases an impressive collection of 19th-century art and artifacts.
For a spine-tingling experience, join one of the popular St. Augustine ghost tours, which combine history with tales of the supernatural.
St. Augustine Beaches
After exploring the historic sites, relax on St. Augustine's beautiful beaches. Anastasia State Park offers pristine shorelines and opportunities for swimming, surfing, and wildlife viewing. For a more lively beach scene, head to St. Augustine Beach, where you'll find restaurants, shops, and a fishing pier.
Down the Keys: Must-See Stops and Hidden Gems
As you leave St. Augustine and embark on your coastal drive Florida adventure, you'll encounter numerous attractions and scenic spots along the way. Here are some must-see stops and hidden gems in the Florida Keys:
Upper Keys
Islamorada
- Theater of the Sea: Swim with dolphins, sea lions, and rays at this marine mammal park.
- Robbie's Marina: Feed the massive tarpon that gather at this quirky roadside attraction.
- Florida Keys Brewing Company: Sample locally crafted beers in a tropical setting.
Key Largo
- John Pennekamp Coral Reef State Park: Explore the first underwater state park in the U.S. through snorkeling, diving, or glass-bottom boat tours.
- African Queen Canal Cruise: Take a ride on the original steamboat from the classic Humphrey Bogart film.
Middle Keys
Marathon
- Turtle Hospital: Learn about sea turtle conservation and rehabilitation efforts.
- Dolphin Research Center: Interact with dolphins and sea lions in a natural lagoon setting.
- Sombrero Beach: Enjoy one of the best public beaches in the Keys, perfect for swimming and picnicking.
Seven Mile Bridge: Drive across this engineering marvel, one of the longest bridges in the world, offering stunning views of the surrounding waters.
Lower Keys
Big Pine Key
- National Key Deer Refuge: Spot the endangered Key deer, a miniature subspecies of white-tailed deer found only in the Florida Keys.
Bahia Honda State Park: Relax on award-winning beaches, snorkel in crystal-clear waters, and take in breathtaking views of the old Bahia Honda Bridge.
Key West: The Conch Republic
Your journey culminates in Key West, a vibrant island city known for its laid-back atmosphere, colorful architecture, and rich history.
Key West Landmarks and Attractions
- Southernmost Point Buoy: Snap a photo at this iconic concrete buoy marking the southernmost point of the continental United States.
- Duval Street: Explore this lively thoroughfare lined with bars, restaurants, shops, and galleries.
- Ernest Hemingway Home and Museum: Visit the former residence of the famous author, home to descendants of his six-toed cats.
- Mallory Square: Join the nightly Sunset Celebration, featuring street performers and food vendors.
- Fort Zachary Taylor Historic State Park: Explore a Civil War-era fort and enjoy one of Key West's best beaches.
Water Activities in Key West
Key West offers a plethora of water-based activities for all ages and skill levels:
- Snorkeling and diving at the Florida Keys National Marine Sanctuary
- Kayaking through mangrove tunnels
- Parasailing for a bird's-eye view of the island
- Jet skiing around the island
- Sunset sailing cruises
Key West Nightlife and Cuisine
As the sun sets, Key West comes alive with a vibrant nightlife scene. Duval Street is the heart of the action, with numerous bars and live music venues. Don't miss the chance to sample some local specialties:
- Key Lime Pie: Try this tangy dessert at numerous spots around town
- Conch Fritters: A local delicacy made from queen conch meat
- Fresh Seafood: Enjoy the catch of the day at waterfront restaurants
- Cuban Coffee: Start your day with a strong and sweet "bucci"
The Return Journey: Key West to St. Augustine
As your Florida Keys road trip comes to an end, consider taking a different route back to St. Augustine for a fresh perspective. One option is to drive through the Everglades National Park, America's largest tropical wilderness. This detour offers opportunities for wildlife viewing, airboat rides, and hiking through unique ecosystems.
Alternatively, you could explore some of Florida's charming small towns along the way, such as Naples, Sarasota, or St. Petersburg, each offering its own unique attractions and character.
Budgeting for Your Trip
The cost of your St. Augustine to Key West road trip can vary widely depending on your travel style and choices. Here's a rough estimate of daily costs per person:
- Accommodation: $100-$300
- Food: $30-$60
- Activities: $50-$100
- Transportation: $30-$50 (including gas and car rental)
To save money, consider:
- Camping in state parks or RV resorts
- Cooking some meals instead of eating out
- Taking advantage of free activities like beach visits and self-guided walking tours
- Traveling during the off-season for better rates on accommodation
Responsible Travel Tips
As you enjoy your Florida road trip, it's important to be mindful of the fragile ecosystems you'll encounter:
- Use reef-safe sunscreen to protect marine life
- Avoid touching or stepping on coral when snorkeling or diving
- Properly dispose of trash and recycle when possible
- Support local businesses and eco-friendly tour operators
- Respect wildlife and maintain a safe distance when observing animals
Conclusion
A St. Augustine to Key West road trip offers an unparalleled opportunity to experience the best of Florida's history, natural beauty, and vibrant culture. From the historic streets of St. Augustine to the tropical paradise of Key West, this journey along the Florida Keys is filled with unforgettable experiences and breathtaking scenery.
As you plan your adventure, remember to be flexible, take your time to explore off-the-beaten-path destinations, and immerse yourself in the unique atmosphere of each stop along the way. Whether you're seeking relaxation on pristine beaches, thrilling water activities, or a deep dive into American history, this ultimate Florida road trip has something for everyone.
So pack your bags, hit the road, and get ready for an epic journey through one of America's most iconic coastal regions. Your St. Augustine to Key West road trip awaits, promising memories that will last a lifetime and stories you'll be eager to share. Don't forget to document your adventures and share them with fellow travelers – your experiences might just inspire someone else's dream vacation!