5 Days Florida Keys, USA Itinerary
This 5-day itinerary explores the highlights of the Florida Keys, starting in Miami and journeying down to Key West. It balances iconic attractions with local experiences, offering a taste of island life on a moderate budget.
Duration
5 days
Budget
$750-1250
Best Time
The best time to visit the Florida Keys is during the dry season, from November to May
Activities
22
Daily Avg
$200/day
Pace
Moderate
The Florida Keys offer a unique blend of stunning natural beauty, vibrant marine life, and a laid-back island atmosphere. From snorkeling in crystal-clear waters to enjoying fresh seafood with a sunset view, the Keys provide an unforgettable escape.
Your itinerary covers 6 of 10 must-have experiences
An Underwater Wonderland
Day 2: Snorkeling/Diving at John Pennekamp Coral Reef State Park
A Sunset Spectacle
Day 4: Sunset Celebration at Mallory Square
A Key Lime Pie Pilgrimage
Day 4: Lunch at Blue Heaven
A Historic Watering Hole Tour
e.g., Sloppy Joe's Bar, The Green Parrot Bar
A Fresh Seafood Bounty
Day 3: Lunch at Lorelei Restaurant & Cabana Bar
An Island Wilderness & Wildlife Encounter
e.g., Bahia Honda State Park, National Key Deer Refuge (Big Pine Key)
A Literary & Maritime History Dive
Day 3: History of Diving Museum
An Iconic Keys Photo Opportunity
e.g., Southernmost Point Buoy, Seven Mile Bridge (Historic & New)
An On-the-Water Adventure
e.g., Kayaking through the Mangroves, Flats Fishing Charter
A Quirky Local Gem
Day 3: Dolphin Research Center
The Florida Keys offer a unique culinary experience influenced by Caribbean flavors and fresh seafood. Expect to find plenty of conch, key lime, and locally caught fish on the menus. Be prepared for a relaxed dining atmosphere, often with stunning waterfront views.
Must-Try Dishes
The quintessential Florida Keys dessert. Tart and creamy, made with key lime juice, condensed milk, and a graham cracker crust. It's a must-try for its authentic local flavor.
📍 Almost every restaurant and bakery, especially in Key West
Deep-fried balls of conch meat, mixed with vegetables and spices. They're often served with a dipping sauce, usually a spicy mayo or cocktail sauce. A great appetizer or snack.
📍 Seafood restaurants and roadside stands throughout the Keys
A hearty soup made with conch, vegetables, and spices. There are different variations, from creamy to tomato-based, so try a few to find your favorite.
📍 Seafood restaurants, particularly those with Caribbean influences
A seasonal delicacy (October 15th - May 1st). Large crab claws served chilled with mustard sauce. The crab is harvested sustainably, with the crab returned to the water to regenerate the claw.
📍 Seafood markets and upscale restaurants
Food Neighborhoods
Known for its lively atmosphere, diverse restaurants, and bars.
Known for fresh seafood and waterfront dining.
Known for family-friendly restaurants and local seafood markets.
Known for upscale dining and sport fishing-related cuisine.
Vegetarian options are available, but seafood dominates most menus. Many restaurants can accommodate gluten-free requests. Vegan options may be limited, so it's best to check menus in advance or contact restaurants directly. If you have severe allergies, always inform your server.
Dining is generally casual. Tipping is customary (15-20% for good service). Reservations are recommended, especially during peak season. Dress code is relaxed; beach attire is often acceptable at waterfront restaurants.
Key West Fantasy Fest
OctoberA large, costumed street festival in Key West. Expect large crowds and higher prices.
Conch Republic Independence Celebration
AprilA week-long celebration of Key West's secession from the US. Expect increased tourism.
🛣️Interesting Detours & Side Trips
- 🚶Arrive at Miami International Airport (MIA) and pick up rental car at Miami International Airport (MIA)$40-60/day for rental car
10:00 AM - Arrive at Miami International Airport (MIA) and pick up rental car
Collect your pre-booked rental car at the airport. Consider booking in advance for better rates. Drive to your hotel in South Beach.
- 🚗Drive from Miami International Airport (MIA) to La Sandwicherie (approx. 20 minutes)$10-15
12:00 PM - Lunch at La Sandwicherie
Grab a delicious and affordable sandwich at this popular local spot. Try the Frenchie sandwich. Expect a wait during peak hours.
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- 🚗Walk from La Sandwicherie to explore South Beach and Ocean Drive (approx. 5 minutes)Free (Bike rental: $10-15/hour)
2:00 PM - Explore South Beach and Ocean Drive
Walk along Ocean Drive, admire the Art Deco architecture, and people-watch. Take photos of the colorful buildings and vintage cars. Consider a bike rental for faster exploration.
Book on Klook - 🚗Drive from South Beach to Coyo Taco (approx. 15 minutes)$15-20
6:00 PM - Dinner at Coyo Taco
Enjoy authentic Mexican street food at Coyo Taco. Try the al pastor or carnitas tacos. It's a casual and budget-friendly option.
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South Beach, Miami Beach
Close to the beach, restaurants, and nightlife.
📅 Best Time to Visit
The best time to visit the Florida Keys is during the dry season, from November to May. Temperatures are pleasant (70s-80s°F), humidity is lower, and rainfall is minimal, making it ideal for water activities. This is also peak tourist season, so expect larger crowds and higher prices. The wet season (June-October) brings hotter temperatures, high humidity, and afternoon showers, along with the risk of hurricanes, but also fewer crowds and lower prices. Key West's popular Fantasy Fest occurs in late October, drawing significant crowds.
The weather is generally sunny and mild with low humidity. Rainfall is minimal, making it perfect for exploring the Keys.
November to May is the dry season, offering pleasant weather ideal for outdoor activities.
Major US holidays may result in increased prices and crowds.
Getting Around
Car-centric; major cities have transit
City-specific
Uber/Lyft work nationwide. Rent a car outside major cities.
Travel
$150-250 (Gas, tolls, potential bus fare)Accommodation
$300-500 (Budget-friendly hotels/motels)Food
$200-300 (Mix of casual dining and groceries)Activities
$100-200 (Snorkeling, kayaking, entrance fees)Pack a cooler with drinks and snacks for beach days and scenic stops along the Overseas Highway. This significantly cuts down on daily food and beverage expenses.
Look for happy hour specials. Many restaurants and bars, especially in Key West, offer great deals on drinks and appetizers in the late afternoon/early evening.
Utilize free activities: enjoy public beaches, watch the sunset at Mallory Square (Key West), drive the scenic Overseas Highway, or explore local nature trails.
A day trip to Dry Tortugas National Park, either by ferry or seaplane. While expensive, the pristine beauty, snorkeling, and historic fort are unparalleled and worth the cost for a unique experience.
Indulge in a sunset sailing cruise or a private fishing charter. These provide memorable perspectives of the Keys from the water, often with included amenities.
Explore beyond Key West. The Middle and Upper Keys (Islamorada, Marathon, Key Largo) offer different atmospheres, often fewer crowds, and can provide better value for accommodations and activities.
Seek out 'dock-to-dish' restaurants or local seafood markets. You'll find the freshest seafood and often better prices than more tourist-centric establishments.
- Always apply reef-safe sunscreen (required in Key West for chemical sunscreens) and wear a hat and sunglasses. The Florida Keys sun is intense year-round.
- Tipping is customary in the USA. Expect to tip 15-20% for good service at restaurants, bars, and for tour guides.
- Renting a car is highly recommended for exploring the entire length of the Keys, as public transportation is limited outside of Key West. The Overseas Highway is a scenic, but sometimes slow, drive.
- Be mindful of marine life and coral reefs. Do not touch or take anything from the water, and ensure all trash is disposed of properly to protect the fragile ecosystem.
- If traveling during hurricane season (June 1st to November 30th), monitor weather forecasts closely and be aware of potential evacuation procedures.
- Book accommodations, popular tours (like Dry Tortugas), and key activities well in advance, especially if visiting during peak season or specific events.
- Stay hydrated. Drink plenty of water throughout the day, particularly when spending time outdoors in the sun.
- 1Reef-safe sunscreen (chemical sunscreens containing oxybenzone or octinoxate are banned in Key West)
- 2Lightweight, breathable clothing (shorts, t-shirts, sundresses)
- 3Multiple swimsuits
- 4Wide-brimmed hat and sunglasses
- 5Water shoes or comfortable sandals for beaches and boat decks
- 6Insect repellent (especially for evenings and marshy areas)
- 7Light rain jacket or poncho for sudden showers
- 8Reusable water bottle to stay hydrated and reduce plastic waste
- 9Waterproof dry bag for electronics and valuables on boat trips
- 10Basic first-aid kit, including motion sickness remedies if prone to seasickness
Flights
Book 3-6 months ahead for best prices, especially for peak season (Nov-May).
Accommodation (hotels, rentals)
Book 6-12 months ahead for peak season due to high demand and limited options; 3-6 months for off-peak.
Rental Car
Book 3-6 months ahead, essential for exploring beyond a single Key. Prices increase closer to travel dates.
Dry Tortugas Ferry or Seaplane
Book 6+ months in advance; this popular day trip sells out extremely quickly.
Snorkeling/Diving/Fishing Charters
Book 1-3 months ahead, especially for prime spots and seasons, as capacities are limited.
Popular Dining Reservations
Book 2-4 weeks ahead for sought-after restaurants, especially for dinner during peak times.
Passport/ID
Ensure your passport is valid for international travelers. US citizens need valid government-issued ID.
Note: Travel conditions, regulations, and local customs may change. We recommend verifying essential details — such as visa requirements, emergency contacts, and payment options — closer to your travel date.
SIM & Connectivity
SIM Options
📍 Airalo app or website
📍 T-Mobile stores or authorized retailers (Walmart, Best Buy)
📍 AT&T stores or authorized retailers (Walmart, Best Buy)
📍 Online through Tep Wireless website (requires advance booking)
Free WiFi is widely available in hotels, cafes, and restaurants. Public WiFi hotspots are also available in some areas, but the speed and reliability can vary. Consider using a VPN for security when using public WiFi.
Useful Apps
Download offline maps before you go, as cell service can be spotty in some areas. Check your international roaming plan with your home provider before traveling. Consider purchasing a portable power bank for your devices, especially if you plan on spending long days outdoors.
Electric Socket Guide
Socket Types
Two flat parallel pins
Two flat parallel pins + round ground
120V
60Hz
Tipping Etiquette
18–20% (before tax)
15–20%
$2–5 per bag; $2–5/night housekeeping
Tipping is expected. 18–20% is standard at restaurants.
Safety & Travel Advisories
The Florida Keys are generally safe for tourists. Be aware of potential hurricane risks during the wet season.
Check official government advisories for the latest safety information, entry requirements, and travel warnings before your trip.
Emergency Numbers
911
911
911
911 for all emergencies
Payments
Cards preferred everywhere
Universally accepted
Common
Credit cards accepted everywhere. Apple Pay/Google Pay widely available.
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Trip Summary
How was this itinerary?
The best time to visit is during the dry season, from November to May. The weather is pleasant, with lower humidity and minimal rainfall. However, this is also peak season, so expect higher prices and more crowds.
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