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Keys and Key West

Photo by Roman Boed

Keys and Key West Itineraries

Key West in 48 Hours

Key West on a Budget

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It’s a slice of the Caribbean in America, this scattering of coral rock islands in shallow seas, kissed by the tradewinds, topped with tropical forests, and blessed with pleasant weather year-round. The Florida Keys arc southwest from the tip of the Florida peninsula, south of Miami, ending at the Tortugas, less than a hundred miles by sea from Havana, Cuba. The Keys are a special place, mostly disconnected from the rest of Florida and absolutely disconnected from the most of the world. Life is on “island time” and the atmosphere is casual everywhere you go.

Unless you’re flying directly in to Key West, you’ll pass everything twice along the 125 miles of US 1 between Florida City and Mile 0. Known as the Overseas Highway throughout the Keys, built on the remains of the Overseas Railroad, an incredible project started in 1905, the highway is the only main road connecting the islands. It’s a Florida Scenic Highway and an American Byway, arguably one of the most beautiful drives in America when you’re island-hopping through the Middle and Lower Keys, with Florida Bay stretching out to the northwest and the Atlantic Ocean to the southeast. US 1 ends in Key West in front of the courthouse, where Mile Marker 0 is a popular spot for selfies.

Most visitors to the Keys are headed to Key West – even if only to say they’ve been there – but there is much to see along the entire island chain. Here are some of the highlights.


Upper Keys: Key Largo

At 27 miles long, Key Largo is the largest of the Keys, first settled at Rock Harbor in 1870. Thanks to local support and agressive land purchases over the past fifty years, much of the island will remain tropical forever, protecting the coastal mangrove forests at John Pennekamp Coral Reef State Park, the northernmost Caribbean forests at Key Largo Hammocks Preserve State Parks, and the vast salt lakes at Crocodile Lakes National Wildlife Refuge, where indeed, there are crocodiles.

Divers flock to Key Largo for the easily accessible coral reefs, and there are dive shops and dive resorts to cater to them. The easiest way to get your coral fix is a visit to Pennekamp – reservations suggested – for a snorkel, dive, or glass-bottomed boat trip over Molasses Reef. It’s on Key Largo you’ll first notice the bicycle paths alongside US 1. The Florida Overseas Heritage Trail starts (or ends, depending on your direction) here, mostly following the route of the old Overseas Railroad to Key West. You’ll find this section of US 1 crowded with businesses and strip malls in clusters, with welcome breaks of tropical forest now and again, on the way to Tavernier, at the south end of the island.


Middle Keys

Islamorada
Islamorada is the “City of Islands,” and it’s here where you first feel like you’re driving in the tropics. Called the purple islands (morada) by Spanish explorers, most of these islands still sport their tropical forests, with resort hotels tucked under the trees or along the beachfronts. The four major islands of this chain include Plantation Key, Windley Key, Upper Matecumbe, and Lower Matecumbe. It’s on Upper Matecumbe that you’ll find most services.

From Craig Key to Grassy Key, enjoy the views. With more residents than visitors, these Keys offer delightful small-scale Mom & Pop motels and resorts, many established more than fifty years ago. Placid aquamarine waters stretch off to the horizon as you drive across each causeway and bridge.

Seven Mile Bridge. Photo by John Keatley

Marathon
Settled in the 1830s by Bahamian immigrants, who began farming on Vaca Key, Marathon is the most urban of the island centers, with department stores and an airport. Much of the that island is developed, but Crane Point Hammock – a privately-owned preserve – protects 63 acres of tropical forest and mangroves in the heart of Marathon, as well as the remnants of Adderly Village, the original settlement, including the first home built in the Keys.

Marathon owes its explosive growth to the building of the Overseas Railroad. First, for the workers, gathered here to cross seven miles of open ocean with a railway trestle. The marathon of work they put in to complete the railroad on time gave this chain of 13 islands its name. Then, for the fishing. The piers of the Seven Mile Bridge created eddies that attracted tarpon, which in turn attracted sportsmen. Fishing is big throughout the Keys, but especially here in Marathon.

South of the Seven Mile Bridge, the next series of bridges and causeways connect small islands with very few services or residents. The big exception is Bahia Honda Key, which is entirely a Florida State Park and is home to the most beautiful beaches in the Keys. Since the sand on these islands is organic, most of the natural beaches aren’t very pleasant. The beaches of Bahia Honda are a big exception, thanks to the coral reefs offshore. This is a departure point for divers headed to Looe Key.


Lower Keys

It’s on Big Pine Key that you encounter the diminutive Key deer. That’s why there are chain link fences along US 1 as you drive through the tropical forest. The smallest deer species in America, these deer aren’t much larger than a German Shepherd. National Key Deer Refuge protects the wild habitats which the deer need for survival, on Big Pine Key and the islands surrounding it.

Driving through the Lower Keys, you’ll find them heavily forested and lightly populated. If you’re looking for an escape, some of the most pleasant small resorts and campgrounds can be found on these islands, where fishing, kayaking, and snorkeling are the only pursuits that might pull you away from the pool or a good book. And yes, there are tiki bars. Lots of them. For cyclists, this section of the Overseas Heritage Trail offers outstanding views, decent watering holes, and the least hassle for road crossings and driveways as you bike between Big Pine Key and Stock Island, the gateway to Key West.


Key West

At Key West you’ll find the southernmost of everything – the Southernmost Point (expect a long wait for that photo), the Southernmost House, the Southernmost Beach Resort, the Southernmost Beach Cafe … you get the picture. Key West has a well-earned ribald reputation, from its days as a port-of-call during the wrecker and pirate era to its “come as you are” vibe today. It was one of the earliest cities to embrace LGBTQ tourism, with some clubs and hotels catering just to LGBTQ visitors. Today, cultural diversity is celebrated year-round, and no event draws more visitors then Fantasy Fest, which started in 1979 as a ploy to fill hotels in the off-season. It’s blossomed to a thematic annual bacchanalia with one of the most colorful costume parades you’ll ever see, burlesque shows and body painting, and a bevy of parties at the bars of Key West during the last week of October.

Photo by John Keatley

As one of Florida’s oldest cities, Key West still retains much of the granduer of the past in its architecture and its mature tropical forest, which shades much of the city. Once you’ve arrived, park the car at your hotel and don’t move it again. You’ll find this is a very walkable city, although there are lots of bike, scooter, and electric car rentals on the island, if you wish to go farther afield.

A walk down Duval Street will take you to art galleries and fine restaurants, t-shirt shops, and the many bars that the city is known for. It’s never a problem to do a pub crawl in Key West, since the distance between bars is so small. Captain Tony’s Saloon – where Ernest Hemingway hung out, and Harry Truman was known to have a drink or two – was the original Sloppy Joe’s Bar, which you’ll now find just around the corner. Jimmy Buffet discovered Key West in his early days, and when you see the seat with his name painted on it at Margaritaville, he might just be sitting in it.

Whitehead Street connects you with some of the must-see attractions of Key West: the Hemingway Home, the Audubon House, the Little White House, and the Mel Fisher Maritime Museum, on your way to the Key West Aquarium and Mallory Square, where every sunset is a celebration.

There is much more to see and do in Key West alone; you can easily spend a week here, and a week is a good budget for any visit to the Florida Keys. Check out our itineraries for exploring the islands.


Explore a Keys and Key West Itinerary:

Key West in 48 Hours … Get in tune with ‘Island Time’
Key West on a Budget … How to do it free and cheap


When To Go

At bare minimum, you should spend no less than three days in the Florida Keys: one day to travel to Key West, a full day in Key West, and a full day to come back. You’ll want to stop and do something along that down-and-back drive, whether it’s to take a guided ecotour, relax on a beach, or pop into some art galleries. Plus, you need to pad your time: driving the island chain can take longer than expected at times, so you can’t expect to pull it off in a day. You’ll miss out on experiencing Key West if you don’t spend at least a full day, even if you stay north of the island.

For optimum enjoyment, three to five days in Key West gives you enough time to experience most of what the island has to offer. Add an extra day if you plan a trip to Fort Jefferson on the Dry Tortugas, or any other boating / outdoor excursion that’ll take a day on the water. The same goes for any stops along the Keys where diving, snorkeling, or kayaking is involved. Take a day for Looe Key, and a day or two at Key Largo. You’ll spend a minimum of half a day just getting out to the reefs and swimming around, and the rest of the day to relax after all that activity. That’s what those oceanfront tiki bars are all about.

You can easily fill a week in the Keys, especially if you love the outdoors. Whether you’re there to fish, go birding, or just look for beauty spots to photograph, you can take the tours, ramble on your own, and relax at your resort or campsite. The idea of being here is not to be in a hurry.

High and Low Season

When should you travel to the Florida Keys? It depends on what you’re looking for.

If you’re coming here for the fishing, pay attention to seasons. Most anglers are looking to catch the Big Three: tarpon, bonefish, and permit. Tarpon are best April to June, and bonefish and permit from spring through the fall. The Keys have the highest concentration of Florida spiny lobster, for which the two-day recreational season opens in late July, and the general commercial season from August through March. Be sure to read up on fishing regulations before planning your trip.

If you want to run into hordes of people, join the crowds that descend on the islands between Christmas and Easter. The weather is at its best this time of year, but the rates are also at their highest and it can be tough to find a room. Even campsites will run you more than $70 a night, if you can find one. There’s another bubble of high season in the summer between June and August, when families are traveling and the fishing is good.

If you want some quiet time, show up during late September or early October. Some family-owned resorts and restaurants shut down during this time, since business and slow and it’s hurricane season. A lesser-known lull is during the first couple weeks of December, during the week. Rates are especially good at this time and the weather is quite pleasant.

Tip: A side effect of the special events that go on almost every weekend in the Florida Keys is that hotels and resorts will double or triple their normal room rates during the event. Especially for weekend events. So unless you really want to attend that particular event, avoid weekends and event weeks in the Keys, since US 1 is jammed with day-trippers who can’t, or won’t, pay those high prices for a room.

Weather and Climate

The Florida Keys are the tropics, so weather swings towards the hot end of the spectrum most of the year. Thankfully, sea breezes help temper the blazing sun. Average daily temperatures are in the 70s during the winter, and the high 80s in the summer, although it can top 90°F with ease on a summer’s afternoon. Keep well-hydrated if you’re playing outdoors, especially if you are involved in a very physical activity like paddling or bicycling.

Just like in the Caribbean, thundershowers are normal May through October. They tend to be torrential but brief, and often leave rainbows in their wake. Hurricane season runs from June through November. Since there’s only one way in and out of the islands by road, do keep alert to tropical weather conditions by using a weather app on your phone with push alerts. Follow any instructions to evacuate the islands with all seriousness. When an evacuation is necessary, visitors are usually asked to leave in advance of general warnings to residents.

Events and Holidays

Over the past forty years, the Florida Keys have developed a parade of festivals and events that keep the islands hopping all year long. Here are some of the largest and most well-established ones, most of which are held in Key West. Find many more events on the Florida Keys & Key West calendar of events.

January (second week): Key West Literary Seminar
January (second Saturday): Art Under the Oaks, Tavernier
January (second Sunday): Key West Half Marathon
Apr-Nov: Key West Fishing Tournament
Apr (second Saturday): Seven Mile Bridge Run, Marathon
Apr (last week): Conch Republic Independence Celebration, Key West
May (first week): Key West Songwriters Festival
May (second week): Key Largo Music Festival
June (second week): Key West Pride
June (last weekend): Marathon Super Boat Grand Prix
July (second Saturday): Underwater Music Festival, Looe Key
July (second weekend): Key Lime Festival, Key West
July (third week): Hemingway Days, Key West
Aug (third Saturday): Anything That Floats Race, Key Largo
Sep (first week): Key West Brewfest
Sep (second week): Key West Womenfest
October (second week): Islamorada Fall All-Tackle Bonefish & Permit Championship
October (second week): Humphrey Bogart Film Festival, Key Largo
October (last week): Fantasy Fest, Key West
November (second week): Key West World Championship Races
November (last week): International Sand Art Competition, Key West
Dec 31: New Year’s Eve Shoe Drop Celebration, Key West

National & State Holidays
January 1: New Year’s Day
January (third Monday): Martin Luther King Jr. Day
February (third Monday): Presidents Day
March/April: Good Friday (two days before Easter Sunday)
May (last Monday): Memorial Day
July 4: Independence Day
September (first Monday): Labor Day
October (second Monday): Columbus Day
November 11: Veterans Day
November (fourth Thursday): Thanksgiving Day
December 25: Christmas

Time Zone

The Florida Keys are in the Eastern Time Zone.

To check the local time in the Florida Keys now, see the World Time Server.

Daylight Savings Time (DST) begins in spring on the second Sunday in March, when clocks are advanced one hour. In the fall on the first Sunday of November, clocks shift back one hour to standard time. With few exceptions, the entire country (including Florida) participates in this ritual of “springing forward” and “falling back.”

What To Pack and Wear

Florida is extremely casual, and in general, quite warm. Shorts and lightweight tops are perfect for the ladies, and the fellows will always look sharp and stay dry in lightweight fishing shirts paired with nylon pants.  Much of the state is perpetually in t-shirts, shorts, and flip-flops, but if you’re staying at a luxury resort, bring resort casual wear. And don’t forget your swimsuit!

It’s also always smart to stash an extra layer – a sweater or overshirt – in your luggage to combat the perpetual chill of air conditioning found in the common areas of most resort hotels and restaurants.

Planning any outdoor adventures? Bring quick-dry nylon pants and shorts and lightweight tops. Wear Crocs or sandals for water sports, and use trail runners for hiking, as they dry most quickly.

Other

Insects

While mosquito control spraying does occur along US 1, there are times when the mosquitoes can be intense, especially in salt marsh areas. Salt marsh mosquitoes do not carry the diseases that fresh water mosquitoes do, but they can still swarm you, especially at dawn and dusk. Midges and gnats can also swarm and just generally be annoying. If you plan to play in the outdoors, packing a headnet and carrying some insect repellant would be prudent.

Poisonous Plants

Natural areas in the Florida Keys are dense with Caribbean shrubs and trees, which are also native to these islands. Among these, there are two extremely toxic trees here you should never lean against, sit under, touch, or eat the fruit of, since the poisonous fruits are fatal: the manchineel (which isn’t common) and the poisonwood (which is VERY common). Once you know how to spot them, you will notice thousands of poisonwood trees in the tropical hammocks. Both contain massive amounts of urushiol, the active toxin in poison ivy, than is found in other plants. Manchineel grows in the Everglades and Florida Keys; poisonwood grows from Key West north towards West Palm Beach in tropical forests. Both trees have oozing black splotches on their bark.

Wildlife

The Florida Keys are one of the few places you may see an endangered American crocodile. Alligators are common in canals and can be seen in any waterway, including on beaches. As you walk along the historic bridges, watch for manatees and dolphins in the water. Birders will appreciate the broad variety of species seen along the route, ranging from colorful roseate spoonbills to the rare mangrove cuckoo. You will see also many iguanas in the Keys. They are not native, but they’ve adapted well. They like to bask in the heat of the pavement on bike paths and on driveways.

What it Costs

There has always been a certain air of exclusivity of travel to the Keys, particularly in the early days, before the Overseas Highway existed. Most of the visitors then were here for the fishing. Over the course of my lifetime, the pendulum in the Keys has swung from “crash on the beach after a night at the tiki bar” to luxe accommodations with high price tags. And if you want to sleep under the stars, you can only do so at an established campground.

While you’ll find relative bargains at many of the old-school motels in the Middle and Lower Keys, expect to pay top dollar for oceanfront resorts, chain hotels, and campsites, some of the highest rates you’ll encounter in Florida. The same goes for fuel (it does have to be trucked in) and food, just as you would expect to find on most islands.

Abstract Pricing at a Glance

Prices often fluctuate dynamically depending on capacity, seasonality and deals. We don’t want to lead you astray by quoting exact prices that quickly become wrong. To give you a rough idea for budgetary planning purposes, though, we have indicated general price ranges for all points of interest.

Price ranges are quoted in $US.

See & Do
N/A => Not applicable
Free
$ => Tickets less than $10 per person
$$ => Tickets $11-25 per person
$$$ => Tickets $26 per person

Sleep
$ => Rooms less than $100 for a double
$$ => Rooms $200 for a double
$$$ => Rooms $300 for a double

Eat
$ => $1-15 per person for a meal (without alcohol, tax, tip)
$ => $16-40 per person for a meal (without alcohol, tax, tip)
$$$ => $41 per person for a meal (without alcohol, tax, tip)

Shop
N/A => Not applicable

Tours
$ => Tickets less than $10 per person
$$ => Tickets $11-25 per person
$$ => Tickets $26 per person

Airfare and Car Rental Prices

Flights to Key West International Airport (EYW) from Florida destinations can be several hundred dollars or more, despite the short length of the trip. Why? It’s a popular destination with a limited amount of service and seats. If you’re looking for a flight to Key West, visit the airline websites for American, Delta, Silver, and United, all of which work with codeshare partners to connect passengers to Key West. You may find some competitive pricing by checking a site like Momondo which displays prices for multiple airlines.

If you’re renting a car, you’ll probably do so elsewhere in Florida to get here. Keep in mind that airport rentals are generally much less expensive than renting a car at a hotel concierge desk. Companies like Expedia and Hotwire offer comparison price shopping for car rentals. Aggregators such as Priceline may be able to get you an excellent deal for a week’s rental.

Tipping and Costs That Add Up

Tipping is a cost you must build into the budget for any U.S. travel experience, whether urban or rural. Tipping is most relevant to dining out and hotel stays, but other costs should also be taken in to consideration. General guidelines include:

Restaurants

For excellent service, plan to tip 20% on the total bill, before taxes. For less-than-stellar service, 10-15% is customary, as an imperfect experience is often not solely the responsibility of the server. In many states, servers work for below minimum wage and live mostly on tips, so consider the ramifications of your tipping decisions.

Oh, and one more complication: Sometimes a tip is automatically included, usually for groups of six or more people. But at least it will be itemized in plain sight on the bill, if you look closely for it.

Hotels

Most bell staff receive $1 to $2 per bag they assist with; if someone carts all of your bags up to your room, expect to tip $5 to $10.

Tips for housekeeping are also good form. The rule of thumb is $2 to $3 per day and about $5 per day in higher-end properties.

At properties with concierge services, consider tipping concierge staff who assist you in planning activities, making reservations or acquiring tickets around $10 to $20 per day. Concierge staff do not normally expect a tip for simply orienting you with driving directions or public transportation info. Car valet staff expect $2 when returning your car. Spa employees (massage therapists, aestheticians, etc.) usually see 20% tips on their services, whether performed at the spa or in your room.

Other Costs
Invariably, there are incidental costs associated with being on the road. Make sure to budget between $10 and $40 per day for batteries, lost phone chargers, bug repellent, headache medicine, sunburn relief and other personal items you might have forgotten. If you’re traveling with kids, consider the snack budget. Local grocery and drug stores will be cheaper than tourist shops for all of the above.

Sales Taxes, Lodging Taxes & Resort Fees
In the Florida Keys, the sales tax rate is 7.5%. Taxes are not usually included in display prices, unless otherwise stated.

The lodging tax – which you pay no matter the quality of your accommodations, whether it’s for tent camping at a state park, a private vacation rental, or a penthouse suite at an oceanfront resort – tacks on an additional 12.5%.

That’s 20% on top of the stated rate. These taxes are rarely mentioned as a part of the advertised room rate.

Neither are the mandatory nightly “resort fees” that some resorts charge. Sometimes this fee covers internet access, parking, and a few incidentals, while at other times it’s merely a surcharge for amenities that should be free. Beware that third-party booking agents, especially online, often don’t include resort fees in their reservation charges, so you may be unhappily surprised by the final bill when you check out. Do ask when you’re booking if there is a resort fee, and if so, what it is. Check on any parking fees as well; these may apply in Key West.

Transportation

Drive, fly, or ride? Those are your options for travel to the Florida Keys, unless you’re a boater — in which case, you have multiple marinas to choose from on all of the major islands.

If you’re a driver who gets nervous about bridges, be aware that you’ll have to cross 43 of them to get to Key West, and then cross them again on the way back. The Seven Mile Bridge, above, is the longest span you’ll cross over the open ocean. It has broad shoulders on both sides of the two-lane highway and is an easy drive in good weather. If crosswinds pick up to dangerous levels, the bridge will be closed by the Florida Highway Patrol until bad weather passes.

US 1 is the only road running the length of the Florida Keys. It’s a very busy, mostly high-speed two-lane highway with some of the most aggressive drivers we’ve encountered in Florida. Traffic often piles up behind someone making a left turn. The heaviest traffic is on the weekends, sometimes coming to a standstill. Often.

By Car

Most visitors drive down to the Florida Keys, which is why you’ll find US 1 to be quite crowded at times, particularly on the weekends. Since it’s the only road connecting to Key West and is two lanes for most of its length, any left turn across traffic can be challenging – and creates traffic backups.

An important note for RV and camper drivers: Key West does not allow RVs or campers to park along their streets. Many of the streets are too narrow for large vehicles. You’ll need to get settled in one of the campgrounds on Stock Island and use your car, your feet, or public transportation to roam Key West.

By Air

If you’re flying into Miami or Fort Lauderdale and simply interested in getting to Key West, there are two shuttle services that can do the driving for you. The Florida Keys Shuttle Service picks up from Fort Lauderdale and Miami International Airports. The Keys Shuttle departs six times daily to and from Miami and Fort Lauderdale airports. Advance reservations required.

Flights into Key West International Airport (EYW) occur on a regular basis, with daily commuter service via American, Delta, and Silver Airways from Miami, Orlando, Tampa, Fort Lauderdale, Fort Myers, and Atlanta. There are car rentals and taxis at the airport.

By Bus

You can also use public transportation from Miami with a minimum of three bus transfers to get to Key West very economically. These buses stop at various points along the Overseas Highway, so they also provide a way to stay on the other islands, too. From the Miami International Airport (or other points in the Miami metro) take Miami-Dade Metrobus routes 34, 35, or 38 to connect to Florida City. In Florida City, switch over to Route 301, the Dade-Monroe Express, between Florida City and Marathon. There are a few scheduled stops along the route including Key Largo at MM 95, Tavernier at MM 90, and Islamorada at MM 74. The final stop is at Marathon at MM 50. To continue south on public transportation from Marathon, use the Key West Transit Lower Keys Shuttle, which has scheduled stops on each of the Lower Keys. Exact change is generally necessary on all bus routes.

By Ferry

Finally, for a different way to get to Key West, think about the Key West Express ferryboat. These high-speed ferries depart from Fort Myers and Marco Island daily and dock in the historic seaport at the Key West Bight Ferry Terminal. Since the ride is 3.5 to 4 hours each way, it’s best to plan a ferryboat ride as a way to spend a multi-day stay in Key West, rather than as a day trip.

Getting Around

Once you’re where you want to be, wandering around is best done on foot or by bicycle, particularly on Key West, where public parking can be very hard to find. Day-trippers to Key West can use the Key West Park N’ Ride at The Old Town Garage, corner of Grinnell and Caroline Streets. $2 per hour or $13 daily gives you on/off privileges on their shuttle bus.

In Key West, you’ll find many vendors with scooters, trikes, and bicycles for rent, if you’d rather roam on wheels. Be sure to lock up your means of transport if you rent one.

In the rest of the Keys, unless you settle down into a resort complex and don’t leave, you’ll find yourself hopping in the car to get between places, since everything is linear along US 1. Some parts of the Overseas Highway, particularly in the Lower Keys, have very few gas stations.  If you bring a bike, you can utilize the bike paths, especially the Overseas Heritage Trail, to get to restaurants and shops.

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