This Florida Keys road trip is built for American travellers who want a realistic, well-paced plan: what to see each day, where to sleep, how long the drives take and what to book in advance. Key West is the southernmost point of the continental US, a laid-back island of pastel houses, sunset celebrations and turquoise water.
Use it as a framework rather than a rulebook. Swap days around for weather, slow down where you fall in love with a place, and keep at least one flexible half-day for the unexpected.
Itinerary overview
- Length: 3 days
- Main stops: Miami and Key West
- Best season: December to May
- Getting there: fly into Key West International (EYW) or Miami (MIA)
Day-by-day itinerary
Day 1: Miami to Islamorada
Drive the Overseas Highway, snorkel at John Pennekamp Coral Reef State Park and eat at Islamorada. Read our Miami travel guide.
- Stay: South Beach (the classic beach-and-nightlife base).
- Don’t miss: South Beach and Ocean Drive, Wynwood Walls and Little Havana.
Day 2: Marathon and Bahia Honda
The Turtle Hospital, Seven Mile Bridge and Bahia Honda’s beaches.
Our road trip gear picks
- Best dash cams for road trips VerdictFox
Record scenic drives and protect yourself if something happens on the highway. - 12V car fridges for road trips VerdictFox
Keep drinks and picnic food cold on long road trips without buying ice every day. - Best portable power stations VerdictFox
Run a cooler, charge cameras and power a CPAP at campsites without hookups.
Partner links: these go to our sister review sites, which may earn a commission at no extra cost to you.
Day 3: Key West
Hemingway Home, Southernmost Point and the Mallory Square sunset. Read our Key West travel guide.
- Stay: Old Town (walkable historic area).
- Don’t miss: Mallory Square sunset, Ernest Hemingway Home and Museum and Southernmost Point buoy.
Where to stay along the way
- Miami: South Beach (the classic beach-and-nightlife base); Mid-Beach (quieter resorts on the sand); Brickell and Downtown (high-rise hotels and city dining)
- Key West: Old Town (walkable historic area); New Town (better value); Stock Island (cheaper rooms nearby)
What to pack for Key West
- Breathable clothing and a sun hat
- High-SPF reef-safe sunscreen
- A reusable water bottle
- Sandals and comfortable walking shoes
- A light rain jacket for afternoon storms
- Insect repellent
For a complete checklist, see our road trip packing list.
Common mistakes to avoid
- Visiting only on peak weekends, when parking and restaurants are packed.
- Not booking accommodation early enough in high season.
- Skipping the quieter trails and viewpoints just outside town.
- Driving tired after a long day outdoors.
- Forgetting that some shops and restaurants keep short seasonal hours.
Accessibility and family travel
The town centre is generally walkable and accessible, though trails and viewpoints vary. Families will enjoy the relaxed pace, and many accommodations offer family rooms or kitchenettes.
Best time for this trip
| Season | Months | What to expect |
|---|---|---|
| Winter | December–February | Dry, sunny, 60–78°F; peak season and higher prices. |
| Spring | March–May | Warm and dry; spring break crowds in March. |
| Summer | June–August | Hot, humid, daily thunderstorms; hurricane season begins June 1. |
| Fall | September–November | Still hot early, peak hurricane risk in September; pleasant by November. |
Book the most popular experiences (timed entries, tours and shows) as soon as your dates are fixed.
Getting around
A rental car gives you the most freedom on this route; pick it up at Key West International (EYW) or Miami (MIA) and keep an eye on one-way drop-off fees. Gas prices vary widely by state; California and Hawaii are usually the most expensive.
Sample 3-day budget for two
| Item | Mid-range estimate |
|---|---|
| Hotel (3 nights) | $780–$1,350 |
| Food and drink | $540–$864 |
| Activities and entry fees | $140–$280 |
| Local transport or car | $180–$270 |
| Total | $1,640–$2,764 |
Estimates exclude flights and assume a mid-range hotel; travelling in shoulder season can cut accommodation costs by a third or more.
Budget
| Travel style | Per person per day | Covers |
|---|---|---|
| Budget | $120–$180 | motel or hostel, casual meals, self-drive or transit |
| Mid-range | $250–$400 | good hotel, sit-down meals, some tours |
| Luxury | $600–$1,200 | resort or boutique hotel, fine dining, private tours |
For 3 days, a mid-range traveller should budget roughly $750–$1,200 per person, excluding flights.
Tips for this itinerary
- Book Dry Tortugas ferries well in advance.
- Hotels are pricey; consider the Middle Keys.
- Hurricane season runs June to November.
- Keep the first evening light if you are arriving after a long flight or drive.
- Download offline maps for areas with patchy coverage.
Planning tips for your trip
- ID for flights: Domestic flights require a REAL ID-compliant licence or another accepted ID such as a passport. See our guide to REAL ID and TSA rules.
- Money: Sales tax is added at the register and varies by state and city; tipping 18–20% at sit-down restaurants is expected.
- Insurance: Your health plan may have limited out-of-network cover in another state, and trip-cancellation cover is worth having for expensive bookings, especially in hurricane season.
- Driving: Most visitors drive; rental cars are widely available, and a US licence is all you need. Gas prices vary widely by state; California and Hawaii are usually the most expensive.
- Saving money: our budget vacation and cheapest places to travel guides have dozens of practical ideas.
Responsible travel tips
Popular places are under pressure from crowds. Visit on weekdays or in shoulder seasons, carpool or use shuttles, refill a reusable water bottle, and buy from local businesses. Respect Indigenous lands and cultural sites, follow posted closures, and keep a safe distance from wildlife.
Safety basics
Carry water and layers on outdoor outings, check weather and road conditions before long drives, and tell someone your plans in remote areas, where mobile coverage can be patchy. In cities, use normal precautions with valuables at night. The emergency number is 911.
Travel gear we trust
- Travel backpacks for weekend trips BuyrSkip
A 30–40 litre backpack handles a long weekend and fits under most airline seats. - Airline-safe power banks BuyrSkip
Navigation, photos and cold weather drain phones fast; a 20,000 mAh bank keeps you going. - Best travel accessories BuyrSkip
Packing cubes, neck pillows and organisers that make travel days easier.
Partner links: these go to our sister review sites, which may earn a commission at no extra cost to you.
Frequently asked questions
Is 3 days enough?
Yes, for the highlights. With extra days, slow down at your favourite stop rather than adding more places.
Do I need a car?
Yes, for road trips and park-based plans. For city itineraries, transit and walking are easier.
What should I book ahead?
Hotels, timed-entry permits or reservations, popular tours and shows.
What is the best time to do this trip?
December to May.
How much does it cost?
Roughly $250–$400 per person per day for mid-range travel, plus transport to the start.
Plan the rest of your trip
- Miami Travel Guide: Beaches, Neighbourhoods and Food
- Key West Travel Guide: Things to Do, Where to Stay and Tips