At a glanceThree nights in Miami Beach, three in Islamorada and three in Key West or the Lower Keys, driving the Overseas Highway and flying home from Key West. It suits couples who want a tropical honeymoon without a passport, with city energy first and island time after. December to April brings dry, mild weather, with May and June quieter and good for snorkeling.
This is a tropical honeymoon that starts with a nonstop flight to Miami and needs no passport. Over ten days you spend three nights in Miami Beach, then drive the Overseas Highway into the Florida Keys for six nights, split between Islamorada and Key West or the Lower Keys, before flying home from Key West.
Miami Beach is the lively opening, with Art Deco hotels, Cuban coffee, stone crab claws in season and some of the best restaurants in Florida. Islamorada is the calm middle, with a palm-shaded resort, fishing piers, kayaks in the mangroves and boat days on the reef. Key West is the colorful end of the road, with Victorian inns, bike rides to dinner and the sunset celebration at Mallory Square. Couples who want total quiet can swap it for Little Palm Island, reached only by boat.
The drive is the hinge of the trip. Take it in daylight, stop often and treat the Seven Mile Bridge as an event. Flying home from Key West means you never drive the highway twice.
The route
- Miami BeachUnited States · 3 nights
- Florida KeysUnited States · 6 nights
- Best months
- December to April, or May and June for quieter, clearer water
- Trip length
- 10 days
- Budget
- About $350–900 a night for two in boutique hotels and resorts, much more on a private island (approximate)
Day by day
Days 1–3: Miami Beach
Fly into Miami International Airport (MIA), about 20 to 30 minutes from the beach, or Fort Lauderdale (FLL), about 45 minutes. You do not need a car yet. For the splurge, The Setai in South Beach has a calm design, three pools and a quiet stretch of sand. The Four Seasons Hotel at The Surf Club in Surfside is quieter and more refined. The Faena Hotel Miami Beach in Mid-Beach is the theatrical choice.
On day one, swim, rest and walk Ocean Drive's Art Deco hotels after dark, when the neon comes on. On day two, see the murals at Wynwood Walls and eat your way along Calle Ocho. On day three, bike to the lighthouse on Key Biscayne or take a sunrise swim off a quiet Mid-Beach stretch.
The romantic moment is a long dinner with stone crab claws in season, followed by a nightcap on a rooftop. Swim near lifeguard towers and check the flags for rip currents.
Days 4–6: Islamorada
On day four, pick up a rental car and drive about 90 minutes to Islamorada. Cheeca Lodge and Spa, on a stretch of beach with a long fishing pier and palm-shaded grounds, is classic Keys luxury without the scene. Smaller waterfront inns cost less.
This is the slow stretch. Kayak or paddleboard through the mangroves at sunrise, book a morning snorkel trip on the reef before the wind rises and spend afternoons by the pool. If either of you fishes, Islamorada calls itself a sportfishing capital. A half-day charter is easy to arrange. Stop for key lime pie along the highway and compare a few versions.
The romantic moment is sunset from the end of a pier on the Florida Bay side, where the sky reflects in calm, shallow water. Pack insect repellent for dusk near the mangroves.
Days 7–9: Key West or the Lower Keys
On day seven, drive about two to two and a half hours to Key West. Time the Seven Mile Bridge for golden hour if you can. Stop at Bahia Honda for a swim on one of the best beaches in the Keys. Watch for endangered Key deer in the Lower Keys at dusk.
In Key West, stay at a boutique inn in Old Town, where restored Victorian houses have private pools and tropical gardens. Sunset Key Cottages, a short launch ride from town, give you quiet nights with quick access to dinner. For complete quiet, Little Palm Island Resort and Spa, off Little Torch Key, has thatched bungalows and no cars at all.
Snorkel the reef at Looe Key and take the ferry to Fort Jefferson in Dry Tortugas National Park for a full day. The romantic moment is the sunset celebration at Mallory Square, then a slow bike ride back to your inn.
Day 10: Key West and Home
Return the rental car at Key West International Airport (EYW), which has service from several East Coast and Southern hubs, often with a connection. Check rental drop-off fees when you book, since a one-way rental between Miami and Key West can add a charge. Flying out of Key West means you drive the Overseas Highway only once.
If your flight is in the afternoon, have a last breakfast in a garden café, walk the quiet streets of Old Town before the day-trippers arrive and buy a key lime pie to take home if your airline allows it.
If flights from Key West are limited on your date, drive back to Miami instead, about three and a half to four hours, then fly home from MIA. Leave early and allow time for traffic on the two-lane stretches. Either way, keep reef-safe sunscreen and a hat in your bag until the very end.
Getting Between Stops
Miami Beach to Islamorada is about 90 minutes by car, longer in Friday traffic heading south. Pick up a rental on the morning you leave the beach, since parking in Miami Beach is expensive.
Islamorada to Key West is about two to two and a half hours along US 1, the Overseas Highway. It is two lanes for long stretches, so be patient with slow traffic and pass only where marked.
Drive in daylight. The views from the bridges are the point of the trip. Mile markers on small green signs count down to 0 in Key West. Locals give directions by them.
Key West International (EYW) has flights to East Coast and Southern hubs, often with a connection. Fly in to Miami and out of Key West to avoid backtracking. Compare one-way car drop fees before you book.
Where to Stay
In Miami Beach, The Setai and 1 Hotel South Beach are the South Beach splurges. Faena Hotel Miami Beach and the Fontainebleau sit in Mid-Beach. The Four Seasons Hotel at The Surf Club in Surfside is the most refined option. Mid-Beach and Surfside are quieter than South Beach, especially in March.
In Islamorada, Cheeca Lodge and Spa is the classic choice for calm, with a long fishing pier. Smaller bayside inns and cottages cost less.
In the Lower Keys, Little Palm Island Resort and Spa is the famous private-island splurge, reached only by boat. In Key West, a boutique inn in Old Town lets you walk to dinner. Sunset Key Cottages offer quiet nights a short launch ride from town. Book Key West early for winter weekends.
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When to Go
December to April is high season, with dry weather, highs in the mid to upper 70s in the Keys and calm seas. Prices peak around the holidays, Art Basel Miami Beach in early December and spring break in March.
May and June are warmer and quieter. The water is often at its clearest for snorkeling. July and August are hot and humid with brief afternoon thunderstorms.
Hurricane season runs from June 1 to November 30, with the main risk from about mid-August through October. If you travel then, buy travel insurance, book refundable rates and watch the forecast. Some smaller Keys restaurants and inns close for a few weeks in September.
Late October and November can be lovely, with fewer people and stone crab season starting in mid-October.
Budget and Booking
This is not a budget route in high season. As an approximate guide, good boutique hotels in Miami Beach run roughly $300 to $600 a night, while top resorts can top $1,000. Cheeca Lodge and good Key West inns often run several hundred dollars a night in winter. Little Palm Island runs well into four figures. Summer rates drop sharply. All prices are approximate.
Book Key West and Little Palm Island first for winter dates, then Islamorada, then flights. Reserve the Dry Tortugas ferry early, since it sells out.
Save on parking by skipping the car in Miami Beach. Hotel valet can add a lot per night. Budget for resort fees, which many Florida hotels charge on top of the room rate.
Staying Comfortable and Safe
The sun is the main hazard. Use reef-safe sunscreen, wear hats and rash guards on the water and drink plenty of water, even in winter.
In Miami Beach, swim near lifeguard towers and check the flag colors, since rip currents can be strong after storms. Watch belongings on the beach and in crowded bars and use rideshares late at night. Nicer restaurants expect smart resort wear for both of you.
Mosquitoes are active year-round in South Florida, more so in summer. Local cases of dengue have been reported in recent years. If you're pregnant or hoping to be soon, check CDC travel health notices and Florida Department of Health guidance.
In the Keys, book boat trips for the morning, before winds rise. Obey reduced speed limits for Key deer.
Make It Shorter or Longer
For a 7-day trip, skip Islamorada. Spend two nights in Miami Beach and four in Key West or on Little Palm Island, stopping in Islamorada for lunch on the drive down.
For 12 to 13 days, add a night at Fort Jefferson by booking a campsite in Dry Tortugas National Park, or add Marathon for Sombrero Beach and the turtle hospital. A day in Everglades National Park, about an hour from Miami, works well before you head south.
If you want a quieter honeymoon, swap Miami Beach for two extra nights in Islamorada and fly into Fort Lauderdale. If you want more city, add a night in Miami's Brickell or Coconut Grove for restaurants away from the beach.
FAQPlanning this trip
How long is the drive from Miami to Key West?
About three and a half to four hours without long stops, depending on traffic. Key Largo is about 90 minutes from Miami and Islamorada is a little farther. Breaking the drive with three nights in Islamorada turns it into two easy, scenic legs.
Are there good beaches in the Florida Keys?
There are a few, but do not expect wide sandy beaches everywhere. Bahia Honda, Sombrero Beach in Marathon and Smathers Beach in Key West are the best. The Keys are more about boats, snorkeling, sunsets and pools. Miami Beach covers the classic beach days on this route.
Is Little Palm Island worth the splurge?
For couples who want total quiet, yes. It is a five-acre island off Little Torch Key, reached only by boat, with thatched bungalows, outdoor showers and no cars. The main activity is doing very little. It costs well into four figures a night, so many couples book it for just two or three nights.
When is hurricane season in Miami and the Keys?
June 1 to November 30, with the main risk from about mid-August through October. If you travel then, buy travel insurance, book refundable rates and watch forecasts in the week before you leave. December to April is the safest and driest time.
Do we need a car for this honeymoon?
Only for the Keys. In Miami Beach, walking, the free trolley and rideshares cover everything. Parking is expensive. Pick up a rental the morning you leave for Islamorada and drop it at Key West's airport, checking one-way fees when you book.
