4 days in Key West and the Florida Keys

The Upper Keys. A state park built around a living coral reef, an old railway quarry that cut into fossil coral, a shallow public beach with a view of the sea and a sunset in the village of Islamorada.

1. Breakfast

   A Cuban coffee and a pastry

   A tiny, strong, sweet coffee with a buttery pastry, a Florida habit. A quick start before the reef.

   Local tip Order it at a walk-up window and drink it standing, like a local.
2. 1
   MorningA morning of its own

   John Pennekamp Coral Reef State Park

   The first underwater state park in the United States, covering a long stretch of the only living barrier reef off the continental US. Snorkel or take a glass-bottom boat trip. Leave the coral alone, because it is easily harmed.

   Go when Morning, when the sea is calmest and the light is clear.

   Local tip Snorkel or take a boat trip over the reef, and book ahead in high season. Never stand on or touch coral, and check the sea conditions before you go in.

   

   About 40 min by car16.8 mi
3. 2
   MiddayWorth a short stop

   Windley Key Fossil Reef Geological State Park

   A former quarry cut into ancient fossil coral by railway builders in the early 1900s. Short trails run along the quarry walls, where you can see the coral in cross section. Shaded, quiet and interesting.

   Go when Midday, as a shady pause on the drive.

   Local tip Short trails and quarry walls with the fossil coral showing. Check ahead on opening and on any guided walks.

4. Lunch

   A fish sandwich by the water

   A fresh grilled or fried fish sandwich at a table by the water, with lime and a cold drink.

   Local tip Ask what was caught that day, because it changes.

   

   About 31 min by car or transit9.6 mi
5. 3
   AfternoonWorth the time

   Anne's Beach

   A small public beach on Lower Matecumbe Key, with shallow, warm water, a boardwalk through the mangroves and picnic tables. A calm place for children and for a quiet swim.

   Go when Afternoon, for a calm swim.

   Local tip The water is shallow for a long way out, which suits children. Shoes help on the rocky bits, and the sun is strong.

   

   About 29 min by car or transit8.1 mi
6. 4
   EveningAn evening stop

   Islamorada

   A string of islands that bills itself as a fishing capital, with a laid-back feel. Find a spot by the water at the end of the day and watch the sky change colour over the sea.

   Go when Early evening, to watch the sky over the water (about 7:36 PM).

   Local tip Find a public spot by the water and linger. The mile markers are how locals give directions.

7. Dinner

   Fresh catch for dinner

   Local fish, grilled or blackened, with rice and lime, at a table that catches the sunset.

   Local tip Tables with a view fill early, so book ahead.

A day on the road, and the road is the point. A hammock of tropical forest, a bridge that crosses the sea for seven miles, a state park with some of the best sand in the Keys, then a first evening in Key West.

1. Drive from IslamoradaAbout 59 min by car32.7 mi

   Where Day 1 ended.
2. Breakfast

   Eggs and a long drive ahead

   A hearty breakfast of eggs and toast before the long road. Fill your water bottle too.

   Local tip Eat well, because food stops are few on the stretches over the water.
3. 1
   MorningWorth the time

   Crane Point

   A nature centre and museum in Marathon on a hammock of native tropical forest, with trails, a museum of local history and a small wild bird centre. Go early, because the shade is welcome.

   Go when Morning, before the heat.

   Local tip Wear a hat and bring water for the trails. Check ahead on opening and on what is open inside.

   

   About 26 min by car or transit7.0 mi
4. 2
   MiddayWorth the time

   Seven Mile Bridge

   The long road bridge over the open water between Marathon and the Lower Keys. An old section next to it is kept as a walking and cycling path that goes on toward Pigeon Key. Check ahead on access.

   Go when Midday, as a pause in the long drive.

   Local tip Drive across slowly and stop at the pull-out rather than on the road. Check ahead on access to the old bridge, which is for walkers and cyclists.

   

5. Lunch

   Conch fritters

   Crisp balls of chopped conch, a Keys classic, served with a dipping sauce at a casual spot.

   Local tip Conch is now mostly imported, so ask where it comes from.

   About 21 min by car or transit5.3 mi
6. 3
   AfternoonWorth the time

   Bahia Honda State Park

   A state park with some of the finest sand and clearest water in the Keys, and a view of the old railway bridge. Swim, walk the beach and look across the channel.

   Go when Afternoon, for a swim and the view of the old bridge.

   Local tip The park is popular and can fill up at weekends, so go early. Check the sea before swimming, and take care on the old bridge steps.

   

   About 1 h 1 min by car35.0 mi
7. 4
   EveningWorth the time

   Mallory Square

   The waterfront at the old end of Key West, where the town gathers every evening to watch the sunset, with street performers and a lively crowd. Arrive early to get a place by the water.

   Go when About an hour before sunset (about 7:36 PM), to find a spot.

   Local tip Arrive early. The crowd cheers as the sun goes down, and the street performers keep going until after dark.

   

8. Dinner

   A late supper after the sunset

   Stone crab in season, or a simple plate of shrimp and a cold drink, when the sunset crowd thins.

   Local tip Stone crab season runs roughly from mid October to early May, so ask when it is on.

A slow day on foot. The writer's house with its cats, a lighthouse with a long view over the roofs, the house where a president stayed, then the long main street at night.

1. Breakfast

   A Cuban breakfast

   A pressed Cuban toast with strong coffee and a glass of orange juice, Key West style.

   Local tip A tiny cup of coffee is the local way to start.
2. 1
   MorningWorth the time

   Ernest Hemingway House

   The Spanish colonial house where the writer lived and worked in the 1930s, now a museum in a tropical garden full of six-toed cats. Go early, because the garden and the house fill up.

   Go when Morning, before the crowds and the heat.

   Local tip The six-toed cats roam the garden and the house, so mind your step. Check ahead on opening and on any guided tours.

   

   About 2 min walkunder 0.1 mi
3. 2
   MiddayWorth a short climb

   Key West Lighthouse

   A white lighthouse from the 1840s in the middle of Old Town, with a climb of many steps to a gallery and a view across the roofs and the sea. Go up in the morning, before the heat.

   Go when Morning, before the heat builds.

   Local tip The stairs are steep and narrow, and the top is open to the weather. Check ahead on opening and take water.

   

4. Lunch

   Key lime pie

   The local pie, tart and creamy, with a graham-cracker crust, eaten after a light lunch. Argue about whether it should be green.

   Local tip Real key lime pie is pale yellow, and plenty of people take that very seriously.

   About 11 min walk0.5 mi
5. 3
   AfternoonWorth the time

   Harry S. Truman Little White House

   A wooden house on the old naval base where President Truman spent working holidays in the years after the war. Today it is a museum of his stays and of other presidents who came here.

   Go when Afternoon, when the guided visit is cool inside.

   Local tip Visits are guided, so check ahead on times and tickets. It is a short walk from Mallory Square.

   

   About 8 min walk0.4 mi
6. 4
   EveningAn evening walk

   Duval Street

   The main street of Old Town, running from the Gulf to the Atlantic across the island, lined with shops, bars and music. Wander it after dark, then turn into a quieter side street.

   Go when After dark, when the street comes alive.

   Local tip The street is loud and lively at night. For quieter evenings turn onto a side street, and keep an eye on the heat.

   

7. Dinner

   A rooftop dinner

   A relaxed dinner with a breeze, seafood on the plate and a view over the old town.

   Local tip Rooftop tables go first, so book ahead.

A gentler day at the far end. A cemetery where the stones tell stories, the marker at the southernmost point, a fort with the best beach in town, then the old harbour at the end of the afternoon.

1. Breakfast

   Coffee and a pastry in Old Town

   A pastry and a coffee on a shady bench before the heat of the day.

   Local tip Get out early, because the streets fill by mid morning.
2. 1
   MorningWorth the time

   Key West Cemetery

   A crowded old cemetery with above-ground tombs, among them the famous joke epitaphs. Shaded and quiet in the morning, with a story on almost every stone.

   Go when Morning, in the shade.

   Local tip Look for the humorous epitaphs. Keep to the paths and be respectful, because the site is still a cemetery.

   

   About 13 min walk0.7 mi
3. 2
   MiddayA quick stop

   Southernmost Point Buoy

   A big painted concrete buoy on the corner that marks the southern end of the continental United States, with Cuba far across the water. Take a quick photo, preferably early to beat the queue.

   Go when Early morning, before the queue.

   Local tip It is a photograph and a moment. The queue grows during the day, so go early.

   

4. Lunch

   A fish taco on the road

   A simple fish taco with slaw and lime, eaten in the shade after the heat of the morning.

   Local tip Ask for the catch of the day.

   About 16 min walk0.8 mi
5. 3
   AfternoonWorth the time

   Fort Zachary Taylor

   A Civil War fort at the tip of the island with one of the town's best beaches beside it. Walk the old walls, swim and snorkel off the rocks, and stay for the sunset if you like.

   Go when Afternoon, for a swim and the old walls (about 7:36 PM).

   Local tip Bring water shoes for the rocky shore, and check the sea before swimming. The beach is one of the best in the Keys.

   

   About 22 min walk1.1 mi
6. 4
   EveningAn easy evening

   Key West Historic Seaport

   The old harbour on the Gulf side, with a boardwalk, working boats and a view over the water. A calm place to say goodbye to the island at the end of the day.

   Go when Early evening, as the boats come in.

   Local tip A good place for a slow walk on the boardwalk and a last look at the water.

   

7. Dinner

   A harbour dinner

   Grilled fish or shrimp at a table over the harbour, with the boats gently moving. A fine last dinner on the island.

   Local tip Book ahead on a weekend.