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Best 30 Fun Things to Do & See in Key West, FL – Activities & Attractions

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The Florida Keys are a long island chain stretching southwestward from mainland Florida, toward Cuba and the open waters of the Gulf of Mexico. They’re low, scrubby, and ringed by stunning marine environments. Numerous settlements dot the Keys, as do several incorporated cities: Key Largo, Marathon, and Islamorada.

The Keys’ biggest town, and main draw for visitors seeking history and nightlife in equal measure, is Key West, with a population 25,000, give or take. Key West also happens to be the Keys’ southernmost populated island, and the southernmost populated place in the entire continental United States – closer to Havana, Cuba, than to Miami. It’s literally the end of the road for U.S. Highway 1 (the Overseas Highway), the only thoroughfare connecting the Keys with the mainland. And it has a truly unique culture that’s hard to put into words – like a miniature New Orleans, crossed with a progressive college town, splashed against a sunny Caribbean backdrop.

To get to the Keys, you can either fly into Miami International Airport and drive a rented car down U.S. Route 1, or fly into Key West International Airport, which has regular service to Miami, Charlotte, and other select U.S. destinations. Your point of origin, itinerary, and planned stay length (and, therefore, potential rental car cost) determine which option makes better financial sense.

Here’s a look at the top fun and cheap (or free) things to do and see in Key West and the Florida Keys.

Historical Sights

Key West is among Florida’s oldest continually inhabited communities. For a brief period, it was actually the state’s largest city.

Early Key West was a checkered place, home to shady shipwreck salvagers, salt miners, and U.S. military personnel manning the island’s strategically critical fort. Many 19th-century structures – and countless stories – survive in Old Town Key West, the historic district on the western half of the island of Key West. Other parts of the Keys have a smattering of surviving historical points of interest too. Notable attractions include the following.

1. Ernest Hemingway Home & Museum

ernest hemingway home key west florida
Ernest Hemingway’s home in Key West, photo by Joseph Sohm

  • Adult admission: $14 (cash only; includes 30-minute tour)
  • Hours: Daily, 9am to 5pm

The Ernest Hemingway Home & Museum, or Hemingway House, is a stately old mansion on Whitehead Street in Old Town. Built by a maritime magnate in 1851, the house was purchased by Hemingway and his second wife Pauline in 1931. The Hemingways undertook a massive renovation and expansion that included the addition of an in-ground pool (then the only such pool in Key West) at a staggering cost of $20,000.

Cat lovers, take note: The property is home to more than 50 cats descended from Hemingway’s six-toed tomcat, and approximately half share their forebear’s unusual morphology.

2. Harry S. Truman Little White House

  • Adult admission: $17.20 ($16 when you buy online) 
  • Hours: Daily, 9am to 4:30pm

A Missourian with no real ties to Florida, President Harry S. Truman loved Key West all the same. Who can blame him? The 33rd U.S. President visited the island a total of 11 times, using the Little White House (originally a naval outpost) as his winter home away from home.

Today, the building is owned by the State of Florida and managed by a nonprofit institution, which keeps its historic artifacts in good condition and provides interpretive content. Check the website for special events – the property hosts an eclectic mix of educational and community-oriented events, most free with the price of admission.

3. Audubon House and Tropical Gardens

  • Adult admission: $14 ($1 discount when you mention “Save a Tree”) 
  • Hours: Daily, 9am to 4:15pm (periodic tours included with admission)

Built by a wealthy sea captain in the 1840s, Audubon House is one of Key West’s oldest surviving structures. It remains in excellent condition, its interior a tour de force of 19th-century furnishings and art. Audubon House also features a solid bench of interpretive content about the shipwreck salvage industry that, in part, built Key West.

Outside, the well-kept Tropical Gardens contain more than 200 orchids and a colony of beautiful, delicate butterflies. Don’t miss the reconstructed Cook House, named not for an infamous maritime explorer but for the literal act of cooking – back in the 19th century, affluent families used outdoor kitchens to keep dangerous cooking flames out of the main house, lest the whole property go inferno.

4. Henry Flagler’s Overseas Railroad

  • Adult admission: Free 
  • Hours: 24/7 (best viewed during daylight hours)

As you drive along the Overseas Highway in the Middle and Lower Keys – particularly near Bahia Honda State Park and the Seven Mile Bridge – you’re likely to notice old, decrepit railroad bridge segments paralleling the roadway. That’s what remains of an old route that railroad magnate Henry Flagler (who contributed more than any other individual to South Florida’s growth in the early 20th century) built from Miami to the Lower Keys – known formally as the Key West Extension of the Florida East Coast Railway, or simply, the Overseas Railway.

The concept was breathtaking, especially relative to the technology available at the time: an overseas railroad bridge, stretching more than 100 miles, and built (quite literally) on shifting sands. Completed in the 1910s, it was abandoned in the 1930s after a powerful hurricane damaged it beyond repair. Still, parts of it stand as testaments to Mother Nature’s capriciousness. There is no admission charge – you simply see it from the Overseas Highway.

5. Fort Zachary Taylor Historic State Park

fort zachary taylor key west florida
Fort Zachary Taylor Historic State Park in Key West

  • Adult admission: $8 per vehicle; $2 per pedestrian
  • Hours: 8am to sundown (generally 5:30pm to 7pm, depending on season)

Fort Zachary Taylor Historic State Park occupies the westernmost portion of Key West. It includes a well-kept old fort that played a critical role (and remained in Union hands, unlike the rest of Florida) during the Civil War, as well as extensive natural areas and a natural sand beach that’s perfect for swimming and snorkeling. Guided fort tours are available – check the park website for up-to-date details and reservation information.

6. Key West Garden Club

  • Adult admission: Free 
  • Hours: Daily, 9:30am to 5pm

The Key West Garden Club is a nonprofit, volunteer-run oasis that bills itself as “one of the last free tourist attractions in Key West.” The Club is dedicated to the art and science of tropical gardening, which is actually harder than it sounds.

Come for the amazing variety of tropical plants and trees, including some exceedingly rare varieties. Also of note is the impressive stone West Martello Towers, part of a larger planned (but never completed) naval battery.

7. Basilica of Saint Mary Star of the Sea

  • Adult admission: Free 
  • Hours: 24/7

Located on Truman Street in Old Town, the Basilica of Saint Mary Star of the Sea is an impressive Catholic cathedral with a stunning, stately interior with a distinctively maritime flair, along with immaculately landscaped grounds. Even if you’re not Catholic (or at all religious), it’s worth poking your head in here for a few minutes and setting aside a few more to roam the oasis-like grounds. It’s free, after all. And you’re almost guaranteed to see a stray cat and/or roaming chicken, hopefully not locked in battle.

8. Roaming Chickens

Key West is full of historical oddities, perhaps none stranger (nor more amusing) than its endemic chicken population. Old Town crawls with feral fowl – it’s uncommon to walk more than a few blocks and not see a stray hen (sometimes with chicks in orbit) or hear a rooster’s distinctive crow. Descended from captive chickens brought by settlers in the 19th and 20th centuries, the birds have flourished thanks to Key West’s mild weather and low predator population. However, don’t get any ideas – these chickens are tough and bony, so you won’t find them on the menu in local restaurants.

9. Mile Marker 0

Mile Marker 0 marks the official end (or beginning) of U.S. Highway 1. Located at the intersection of Fleming Street and Whitehead Street, it’s a free photo op for visitors who wish to prove that they’ve been to one of the extreme points of the United States. Don’t confuse it with the gaudy tourist trap on nearby Duval Street, which mainly exists to sell hats and bumper stickers.

10. Bahama Village

bahama village old town key west
Bahama Village in Key West, photo by Chuck Wagner

Bahama Village is a sub-neighborhood of Old Town, covering roughly 16 blocks. Originally a landing spot for recently arrived Bahamian workers, who were often mistreated and taken advantage of by Key West’s Anglo-American elites, it contains a higher than average (even by Old Town standards) concentration of 19th-century structures.

Spend some time wandering the narrow streets, then take a load off at one of the many corner cafes. If you’re not up for a dip in the ocean, you can find Key West’s public swimming pool here too.

11. Pigeon Key Historic District

Pigeon Key Historic District is a tiny but fascinating slice of the Keys. Located on minuscule Pigeon Key, underneath the Overseas Highway’s Seven Mile Bridge, it’s accessible only by ferry ($12, which includes admission to the museum) or private watercraft (though plans exist to build a highway off-ramp in the near future).

The district contains several old buildings that once comprised a much larger community of workers (up to 400 at a time) enlisted to construct Henry Flagler’s Overseas Railroad. It’s now abandoned, save for a small museum.

Arts, Culture, and Entertainment

The Florida Keys have arts, culture, and entertainment in spades – much of it free, and much of it concentrated in Key West. Keep in mind that, with rare exceptions, cultural opportunities here tend to be offbeat (and sometimes downright rowdy).

Don’t be afraid to ask locals for their honest recommendations about where to go and what to do, based on your personal tastes (and tolerance for crowds). And, if you’re looking for traditional high culture, it’s best to head north to Miami.

12. Duval Street

Duval Street is Key West’s answer to New Orleans’s Bourbon Street. During the high season, Duval Street’s countless bars and music venues spill rowdy crowds out into the streets until the early hours of the morning. The party atmosphere is heightened by Key West’s laxly enforced open container laws – the city permits, or at least tolerates, the numerous sidewalk stands selling alcoholic beverages for streetside consumption.

The best way to experience Duval Street is simply to walk on it for a few blocks – or, if you’re able, to grab a prime people-watching seat at one of its outdoor lounges.

13. Mallory Square

Located near the “top” (northernmost end) of Duval Street, Mallory Square is a lively collection of shops, restaurants, and outdoor vendors housed in historic surroundings. In late afternoon, the area comes alive with street performers, hawkers, and curious wanderers. Be warned – with so many souvenirs on display, it’s all too easy to part with your money here.

14. Dolphin Research Center

Located on Grassy Key, about halfway down the Keys, Dolphin Research Center is an open-to-the-public facility that houses dolphins and sea lions in humane environments. It’s open year-round, though hours and programming may vary based on the animals’ needs.

The $28 adult admission and $23 child (under 12) admission gets you in the door and in view of the animals, but contact in hands-on settings costs much more – at least $60 per session.

15. Sloppy Joe’s Bar

sloppy joe's bar key west florida
Sloppy Joe’s in Key West, photo by Daniel Korzeniewski

Key West has a number of historic bars. Sloppy Joe’s, an old Hemingway haunt, is one of the most famous. The brick building in which it’s housed is historically significant, and the lively taproom (complete with countless wall plaques) is engaging to explore. Come during off hours, when crowds are manageable, and don’t linger – prices are higher than average.

16. Sunset Pier

Located on the grounds of Ocean Key Resort & Spa, Sunset Pier is a trendy bar and eatery that’s arguably Key West’s best place for sunset viewing. You need to spend some money to get a seat here, but a shared drink or appetizer plate shouldn’t set you back more than $10 or $15.

Parks and Beaches

Municipal and state parks, along with sandy public beaches, are found throughout the Florida Keys. Some are free and accessible throughout the year, while others come with fees or restrictions that necessitate advance planning. Check Key West’s city website for park hours and use caution at night.

17. Southernmost Point

Located at the end of Whitehead Street, this is supposedly the southernmost point on the continental U.S. Except it isn’t – the actual southernmost point is clearly visible a few hundred yards southwest, on a restricted-access U.S. Navy facility. Still, it doesn’t cost anything to pose in front of the big stone marker denoting this landmark.

18. Higgs Beach

Officially known as Clarence Higgs Beach Park, this moderately sized parcel is adjacent to the grounds of the luxurious Waldorf Astoria Casa Marina Resort. Its claim to fame is that it’s the gateway to the only “shore-accessible underwater marine park” in the United States, and is thus a top destination for Key West snorkelers. Also of note is the African Burial Ground at Higgs Beach, a sobering reminder of the ravages of the transatlantic slave trade. It is free to visit.

19. Simonton Street Beach

Located at the end of Simonton Street, on the edge of Old Town, this modest beach is wedged between a small jetty and some boat piers. Despite its modest size, it’s a great place to soak up rays away from the crowds. Admission is free.

20. Smathers Beach

smathers beach key west
Smathers Beach walkway

Smathers Beach is a large (by Key West standards) stretch of sand near Key West International Airport. Though it’s the busiest of the city’s beaches, it’s usually possible to find some uncrowded sand and stretch out here.

If you’re traveling with a group, consider snagging one of the volleyball courts for a friendly round or two. Admission is free, and there’s ample parking.

21. South Beach

Located at the southern end of Duval Street, near the Southernmost Point, South Beach is a popular spot for wading, and is probably the easiest Key West beach to access on foot. Free to visit.

22. Bayview Park

Bayview Park is a free, family-friendly spot with a picnic area, pavilion, tennis facilities, and a host of other recreational amenities. It’s a great place for kids (and adults) to blow off some steam. It’s also conveniently located between Old Town and New Town, making it an ideal waypoint for visitors heading from hotels in New Town to tourist spots in Old Town.

23. Overseas Highways Parking Areas

The Overseas Highway has lots of pullouts and parking areas, some of which afford incredible views of the smaller islands, marshy transitional zones, and open waters around the main body of the keys. Most have picnic benches, walking trails, and historic or nature plaques.

Depending on when you’re driving, these parking areas are great places to watch sunrises and sunsets. Shorebirds frequent these spots, no doubt looking for human food scraps, so they’re great for wildlife viewing too. And, best of all, they’re free to enter and enjoy.

Natural Areas and Marine Attractions

Despite the region’s limited landmass, humans haven’t completely overtaken the Florida Keys. Whole islands remain uninhabited, either because they’re unsuitable for building or because they’re off-limits to development. Many of the Keys’ uninhabited land areas are formally designated as natural parks or reserves. Offshore, many reefs and lagoons are protected as well.

25. Dry Tortugas National Park

dry tortugas fort jefferson aerial view
Fort Jefferson at Dry Tortugas National Park

Dry Tortugas National Park is an otherworldly realm in the open Gulf of Mexico, approximately 70 miles west of Key West. Most of the park is underwater – only a handful of sandy islands (with no natural fresh water, hence the “dry” in Dry Tortugas) poke above the waves, welcoming seabirds and turtles by the thousands. The rest of the park consists of submerged coral reefs that teem with aquatic life: sponges, anemones, colorful feeder fish, small sharks, and huge predatory fish (including terrifying-looking barracudas). These reefs are world-renowned scuba destinations.

The largest island, Garden Key, contains Fort Jefferson, a massive 19th-century fortification that was built over the course of three decades, abandoned, damaged in successive hurricanes, and finally rescued and restored by the National Park Service. Walking through the overgrown grounds (and along the towering parapets) is like walking back in time, and the exhibits on military and natural history are first class. Just offshore, shallow reefs make for excellent snorkeling.

Unfortunately, getting to Dry Tortugas National Park is very expensive. A day trip on the Yankee Freedom III, a Key West-based ferry service, sets you back $175 per adult. An overnight stay on Garden Key costs $20 more. Both fares include park admission. On the bright side, the Yankee Freedom package includes a free snorkeling excursion (with gear). And, on the trip to and from, it’s not uncommon to see dolphins frolicking alongside the coast.

26. Bahia Honda State Park

Located in the Lower Keys, about 35 miles outside Key West (mile marker 37), Bahia Honda State Park is a must-visit destination for people who love water sports. Its sublime beach is ideal for swimming and sunset viewing, and campsites start at $36. The park admission fee is $8 per vehicle or $2 per pedestrian.

If you want to linger and pay a bit more, consider kayaking or snorkeling. Kayak rental rates start at $12 per hour for singles and $18 per hour for doubles, or $36 per half-day for singles and $54 per half-day for doubles. Snorkeling tours to nearby Looe Key National Marine Sanctuary, a popular destination for snorkeling enthusiasts, cost approximately $30 for adults (equipment $8 extra per person).

27. National Key Deer Wildlife Refuge

In many parts of the United States, deer are nuisance animals. Not so in the Florida Keys, where a distinct sub-population is severely threatened by habitat loss – and, unfortunately, speeding cars. Situated on about 9,200 acres on Big Pine Key, the Key Deer Wildlife Refuge is a critical habitat for these unique creatures, as well as other flora and fauna native to the Keys. It is free to visit.

28. Curry Hammock State Park

A haven for windsurfers, kitesurfers, and traditional boaters, Curry Hammock State Park protects a sizable stretch of coastline between Marathon and Big Pine Key. Natural habitats include teeming lagoons and sultry mangrove swamps.

There’s a 28-site campground here, with tent sites starting at $36. Park admission is $5 per vehicle and $2 per pedestrian.

29. Crocodile Lake National Wildlife Refuge

If you spend enough time in rural Florida, you’re eventually going to encounter an alligator. Crocodiles, however, are much less common.

Located north of Key Largo, off Card Sound Road, Crocodile Lake National Wildlife Refuge is one of the best places in the state to see the threatened American crocodile in its natural habitat. Just don’t get too close – these beasts can grow longer than 10 feet. It is free to visit.

30. Long Key State Park and State Recreation Area

long key state park recreation area florida keys
Low tide at Long Key

Long Key State Park is a popular fishing and bird-watching spot smack in the middle of the Keys. Once the sight of a luxurious private fishing camp, the area was ravaged by a 1935 hurricane and returned to a natural state. It’s now arguably the best-known campground in the Keys, though (as at Curry Hammock and Bahia Honda) sites are pricey – $36 and up for oceanfront tent sites.

Pro Tip: Before you drive out to Key West, check in with two popular social coupon providers: Groupon and Living Social. Both can point you to last-minute package deals, discounts, and other opportunities to save on activities, services, and goods you’d purchase anyway (or were thinking about purchasing) in and around Key West.

In fact, businesses that use social coupons for promotional purposes are more likely to be small, independently owned entities about which the average tourist might not be aware. That’s great news for travelers who want to support local businesses in another part of the country or world.

There’s no cost to download the Groupon or Living Social apps, so there’s no real downside (and plenty of upside) to taking the leap. I personally prefer Groupon, as it’s been much more relevant to my everyday experience and much more prolific in its deal-brokering, but both are worth a look.

Also, if you haven’t already signed up for push notifications from Groupon or Living Social, and you don’t mind receiving prompts on your phone at random times, I’d recommend doing so before your trip. Over the years, social coupon notifications have saved me hundreds of dollars on things for which I’d have happily paid full price. In unfamiliar cities, they’re also extremely useful for plugging gaps in travel itineraries, and for pouncing on costlier activities that might otherwise remain out of comfortable budgetary reach.

When to Visit and What to Bring

The Florida Keys region has a tropical climate with distinct wet and dry seasons. Humidity is a near-constant, particularly outside the winter months, and temperatures vary little from month to month. The dry season, which runs from late fall through mid-spring, brings long stretches of sunny weather punctuated by occasional showers and thunderstorms. The wet season runs from mid-spring through late fall and brings steadier, more consistent rains – in some years, for at least a portion of nearly every day.

Hurricane season roughly coincides with the wet season and peaks in August and September. Hurricanes and tropical storms rarely strike the Keys directly, but their power must nevertheless be taken seriously. If you want to avoid even the outside chance of travel disruption (and danger to life and limb) due to severe weather, plan your visit for winter or early spring, when the statistical chance of tropical weather activity is near zero.

Compared with northern cities such as Boston, Chicago, and Minneapolis-St. Paul, Key West’s temperatures show remarkably little month-to-month variation. That said, winter is noticeably milder, with manageable humidity and high temperatures in the 60s and 70s. Accordingly, the winter and early spring months (particularly around spring break), comprise the high season. Crowds are larger and prices higher during this period.

By contrast, summer is less comfortable, with highs routinely reaching into the 80s and low 90s, and humidity persistently high. However, thanks to moderating ocean breezes, high temperatures well into the 90s are exceedingly rare. Notably, freezing temperatures have never been recorded in Key West, and locals consider temperatures below 65 degrees to be uncomfortably cool.

Here’s a basic packing guide for your affordable Florida Keys vacation:

  • Light, Breathable Clothing. It’s rarely scorchingly hot in Key West and the Florida Keys. On the other hand, it’s rarely jacket weather. Light, well ventilated clothing, such as cotton shirts and dresses, canvas shorts and pants, and sandals or flip-flops all work well here.
  • Sun and Rain Protection. The sun is strong year-round in the Keys. If you’re susceptible to sunburn, bring a brimmed hat (such as a baseball cap), along with plenty of sunblock (at least SPF 30). If you’re swimming or engaged in strenuous activity, you’ll need to reapply often. Also, don’t forget a lightweight raincoat or poncho (and possibly an umbrella), even during the dry season.
  • Swimwear. Key West isn’t really known as a beach town, but it is surrounded by water, and many hotels and inns here have swimming pools, so don’t forget your swimsuit. If you plan to snorkel, consider bringing your own equipment, both for comfort and to save on potential rental costs.
  • Hydration Gear. If you plan to spend any length of time outside in the Keys (and why else would you be here?), bring a refillable water bottle or pack hydration system (such as a Camelbak). Remember to drink plenty of water during exercise, even when you don’t feel thirsty.

key west southernmost point
Southernmost point in the continental United States in Key West, Florida

Getting to Key West

Most Key West visitors arrive on the island by air or private vehicle. My wife and I rented a car in Miami and drove down along the Overseas Highway, a lovely experience that I’d like to repeat soon. It’s about three and a half hours from Miami on a good traffic day, but driving time can vary quite a bit depending on the time of day, season, and stopping patterns. My wife and I took our time, stopping at several parking areas to snap pictures of the stunning scenery and once to eat lunch.

If you’re in a hurry, you can also fly into Key West International Airport (EYW). Four airlines have regularly scheduled service to EYW: Delta, United, American, and Silver Airways, a budget airline that chiefly serves Florida and the Bahamas. Destination cities include Miami, Tampa, Orlando, Chicago, Atlanta, Charlotte, and Newark. Fares are generally higher to EYW than to Miami International Airport – anywhere from 50% to 100%, depending on the season. But, when time is money on a quick-and-dirty weekend getaway, the convenience of flying direct to your final destination can well be worth the cost.

How to Get Around Key West and the Keys

How you get around in the Keys depends on how you arrive, where you plan to stay, and what you plan to see. The typical trip involves a mix of transportation options, including walking and biking – especially in Key West.

Personal Vehicles

If you plan to explore beyond Key West, it’s a good idea to rent a car (or, if your Keys vacation is part of a longer road trip, use your own car). Though taxis do serve the length of the Keys, long trips between islands can be expensive. Likewise, biking is time-consuming.

Parking is free throughout most of the Keys, including Key West. However, finding a parking space in Old Town Key West is not always easy. Once you arrive in Key West, scope out the parking situation around where you’re staying and find a good spot. In most places, there aren’t any timing restrictions on parking, and it’s permissable to leave your car on the street overnight.

Try to avoid driving locally in Key West, as you’re not guaranteed to find a parking space where you’re going (or when you return to your home base). Some hotels have small, self-serve, guest-only lots that charge for overnight parking ($10 to $20 is typical). There is also a centrally located municipal garage, called Old Town Garage, which charges $3 per hour and $18 maximum per day.

Public Transportation

Though Key West isn’t a metropolis by any stretch, it has a decent bus system operated by Key West Transit. Several local bus routes serve major streets in Old Town and New Town, often at frequencies of 15 minutes or less. If you’re staying in New Town (where accommodations are often significantly cheaper) and want to visit Old Town without hopping on a bike or committing to a long walk, these buses are very helpful. There is also a longer-distance shuttle service that connects Key West with the rest of the Lower Keys.

Single bus fares are $2 in Key West and $4 in the Lower Keys. If you plan to take multiple trips, get a one-day ($4 in Key West, $8 in the Lower Keys) or seven-day ($8 in Key West, $25 in the Lower Keys) bus pass. Both options allow unlimited rides.

Biking

The Florida Keys have virtually no natural topography – the highest point on Key West, a graveyard, is less than 20 feet above sea level. As such, the region is great for short- and long-distance biking. Plus, biking is an efficient way to sight-see – it’s faster than walking, and more flexible than driving or taking the bus.

Key West has a bikesharing program called Instabike. However, it’s somewhat pricey: $8 per hour, roughly double what big-city bikesharing systems charge, or $25 per day. After a slow but steady expansion effort, Instabike covers the entire island.

If you want access to all of Key West and beyond, or want to ride for the whole day, consider a daily bike rental from one of the many bike shops in town. Rentals usually aren’t geographically limited, and rates are reasonable – for instance, WeCycle offers basic cruisers (with locks) for $10 to $15 per day.

Taxis and Rideshares

Taxis are plentiful in Key West and parts of the Lower Keys, though it can cost well over $30 one way to get from Old Town Key West to some of the outlying islands. That said, since several taxi companies operate in the area, pricing is competitive – at $2.95 for the first one-fifth mile and $0.70 per one-fifth mile thereafter, Key West Taxi’s rates are representative. Bear in mind that rates are subject to change, however.

After a mighty struggle against the ubiquitous rideshare services, Key West’s city government finally acquiesced in July 2017 and admitted Uber and Lyft drivers into the Southernmost City for the first time since early 2015. Independent contractors who drive for ridesharing apps can now do so without formal approval from the city, a cumbersome process that effectively banished the apps from the island. If you plan to visit other islands in the archipelago, no worries: rideshares are plentiful in Marathon, Key Largo, and smaller Keys communities too.

pink taxi key west florida
A pink taxi cab in Key West, photo by Joseph Sohm

Where to Stay on Key West

On Key West proper, you’re never far from the action. Still, the island is large enough to have distinct neighborhoods and districts.

  • Old Town, Truman Avenue: The blocks between Key West Cemetery and Whitehead Street are relatively tranquil by Key West standards. They’re also slightly cheaper than the local hospitality industry’s center of gravity, along Eaton Street and the northwest waterfront. Still, you should expect to pay at least $250 per night for a roomy B&B here during the high season.
  • Old Town, Eaton Street: Eaton Street has even more selection – close to two dozen hotels in the 10-block stretch before Whitehead Street. Prices are roughly comparable: $250 and up per night for high-season B&Bs, and more like $400 for four- and five-star resorts. With plenty of historic architecture on this stretch, it’s no problem to find authentic digs like the Marquesa Hotel, a well-preserved inn dating to the 1880s. Most hotels in this area have pools.
  • Old Town, Waterfront: This is a party-hardy resort district with well-known (some would say notorious) nightlife. If you’re into the all-inclusive thing, you’ll find what you’re looking for here. Upscale properties like the Ocean Key Resort & Spa are popular honeymoon destinations.
  • Airport Area: Key West’s airport is close and uncrowded enough that there’s really no reason to stay nearby, but the hotel cluster along the facility’s southern and western edges is worth noting. Expect to pay at least $200 per night here – not exactly a bargain next to bigger airport hotel districts.
  • Causeway Area: This is the first neighborhood you enter as you cross onto Key West on Route 1. The Key West Beachside Marriott Hotel is the highlight here, but you’ll find a handful of local and name-brand resorts to suit your fancy too. Road trippers, take note: Parking and driving are easier on this side of the island.

Final Word

It’s not just Uber and Lyft – Key West has an uneasy relationship with the entire sharing economy. The city has cracked down on vacation rental owners, including Airbnb hosts, who don’t follow its hospitality regulations precisely and pay their fair share of hotel taxes, which account for a huge chunk of Key West’s municipal operating budget.

If you plan to stay in Key West on your Florida Keys trip, keep in mind that you’re probably going to end up in a traditional hotel or inn (or, alternatively, a budget-friendly campsite outside the city), and that you won’t be able to pull out your phone and call a car on demand. Look at it this way: The sharing economy’s near-absence from the Southernmost City is just one more example of this quirky, laid-back island’s nostalgic embrace of the past.

Have you ever been to the Florida Keys? What activities would you recommend?

Brian Martucci
Brian Martucci writes about frugal living, entrepreneurship, and innovative ideas. When he’s not interviewing small business owners or investigating time- and money-saving strategies for Money Crashers readers, he’s probably out exploring a new trail or sampling a novel cuisine. Find him on Twitter @Brian_Martucci.

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Buying an expensive sports car, getting some fancy bling, and getting Botox injections: What do these three behaviors have in common?They may be signs...
club store, photo by Alastair Wallace

Is a Warehouse Store (Costco, Sam’s Club, BJ’s) Membership Worth It? – Costs, Pros...

Smart-shopping blogs and magazines are teeming with stories about the great deals you can get on nearly everything - groceries, tires, vacations - at warehouse...

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