Photo by Zoshua Colah on Unsplash
The 4-day plan, rearranged for 5 days: every place stays and a few more are added, and each day keeps to one part of town.
From average weather, 2021 to 2025: warm, sunny days with little rain score highest (the air stands in for the sea, which is not included). Crowds and prices change through the year, so check them before you book.
Built from the plan’s must-sees, grouped so each day stays close together and ordered by time of day.
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.
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.
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.
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.
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.
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.
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.
Built from the plan’s must-sees, grouped so each day stays close together and ordered by time of day.
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.
A restored captain's house in Old Town with period furniture and a tropical garden, named for the bird painter John James Audubon.
Go when Morning, with the gardens in the shade.
Local tip An old captain's house with a tropical garden in Old Town. Check ahead on opening.
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.
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.
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.
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.
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.
Built from the plan’s must-sees, grouped so each day stays close together and ordered by time of day.
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.
A small island once a trading town, reached only by water, with the ruins of its streets and cisterns under the trees.
Go when Morning, by boat or kayak.
Local tip The old island town is reached only by water, so check ahead on how and when. Wear shoes and take 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.
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.
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.
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.
Built from the plan’s must-sees, grouped so each day stays close together and ordered by time of day.
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.
A small island under the old Seven Mile Bridge that once housed railway workers, now a museum of the railway and the sea.
Go when Morning, on a walk or a bike ride.
Local tip A small island once home to railway workers. Check ahead on how to get there, and on any tours.
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.
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.
Built from the plan’s must-sees, grouped so each day stays close together and ordered by time of day.
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.
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.
A refuge on Big Pine Key for the Key deer, a tiny deer found nowhere else, with short trails and a freshwater pool.
Go when Early morning or evening, when the deer come out.
Local tip Key deer are tiny and shy. Never feed them, and drive slowly at dawn and dusk, because they cross the roads.
By average weather from 2021 to 2025, March to May and November are the best months for a beach trip to Key West. This plan is built for mid March, which is one of the best months. Crowds and prices change through the year, so check them before you book.
It covers 5 days in Key West, planned for mid March. Each day is built around a small number of stops, with room to rest.
It was planned for most travelers. The pace and the places reflect that, so check it fits how you travel.
No. Places marked "book ahead" need a reservation. Hours, prices and availability change, so confirm before you go.
Yes. Archie drafts a day by day plan for your dates and takes your pace, the weather and who is travelling into account. You can start one from the Archie app.
Yes. It is a starting point you can change to fit your own trip: swap a place, add a day or move the pace.
Each day has about 1.6 to 35.4 miles between its stops, and 86.7 miles in all across 5 days. A short hop is a walk and a longer one a ride. Distances are straight-line estimates, so allow extra for the streets.
3 days of neon, salsa and sunrise in MiamiAbout 110 miles awayAn easy add-on
5 days in OrlandoAbout 260 miles away
4 days on the Georgia coast and in the OkefenokeeAbout 430 miles awayMake it yours in a minute, then move days around and add what you want.
A trip idea · Updated November 2026
Want your own days planned like this? Plan your own trip on the web or get the Archie app.
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