Key West Questions Answered: 30 Things First-Timers Always Ask

Spend an hour at the Mallory Square sunset and you will hear the same handful of questions asked over and over, in every accent in America. Is that Cuba out there? Where’s the buoy? Are those chickens anybody’s? Can I take my drink with me? None of them are silly questions. Key West is a small island with some genuinely odd rules, customs and logistics, and the travel brochures tend to skip the practical parts. This page collects the Key West travel questions first-timers ask most often and answers each one straight, including the ones where the honest answer is “it depends” or “not really worth it.”

The 30 questions are grouped by the stage of the trip they come up in: getting there, getting around, timing, money, the famous sights, local rules and culture, food, and the trips beyond the island. Each answer is short and links to the full guide when there is more to say. Prices and schedules were checked in October 2026 against the operators’ and agencies’ own sites; treat them as the right order of magnitude and confirm before you book, because fares and fees here change often.

§ 01

Key West costs at a glance

The questions people ask most about money come down to a few fixed prices. These are the figures published by the operators and parks themselves in October 2026.

§ 02

Getting to Key West

1. Do I need a passport to visit Key West?

No, not if you are a US citizen. Key West is in Florida, and getting there by car, by domestic flight or on the ferry from Fort Myers Beach is domestic travel. You will still need a government photo ID to fly, and the Key West Express ferry asks adults 18 and over for a driver’s license or passport when boarding. International visitors need the same documents they would need anywhere else in the United States. A passport only becomes relevant if you arrive on a cruise that visits foreign ports or take a separate trip out of the country, such as the excursions covered in our Key West to the Bahamas guide.

2. How far is Key West from Miami, and is the drive worth it?

Key West sits at the far end of the Overseas Highway, the stretch of US 1 that hops from island to island across the Florida Keys. The mile markers along it count down to zero in Key West, and the highway is the only road in or out. In a straight line Key West is about 130 miles from Miami, but by road it is considerably longer, and traffic in the Upper Keys can add a lot of time on weekends and holidays. Check a live route planner on the day rather than trusting a fixed figure.

Is it worth it? For most first-timers, yes, at least one way. The drive across the Seven Mile Bridge and the long causeways of the Lower Keys is one of the great road trips in the country, and it lets you stop in Key Largo, Islamorada and Marathon. The trade-off is time: with stops, it easily fills most of a day.

Two things surprise first-time drivers. The first is how much of the road is a single lane in each direction, so one slow truck or one accident can hold up everything behind it, and there is often no alternative route. The second is the speed limits through Big Pine Key, which drop at night to protect the endangered Key deer that wander onto the highway; slow down and watch the verges at dusk. Fill up before the long empty stretches, keep water in the car, and plan the drive so the last hour is in daylight if you can. Arriving in Key West just in time for sunset is a fine plan; arriving in the dark after six hours behind the wheel is a tiring one. Our guides to the Miami to Key West journey and driving to Key West cover the route, the stops and the timing.

3. Should I fly into Key West or into Miami?

Key West International Airport (EYW) is owned and run by Monroe County and sits on South Roosevelt Boulevard, a short taxi ride from Old Town. Flying straight in saves you the drive and puts you on the island within minutes of landing. The catch is choice and price: fewer routes serve Key West than Miami or Fort Lauderdale, and fares are often higher. Many visitors compare a direct flight to EYW with a cheaper flight to Miami plus a rental car, and choose the drive when there are two or more people to share the car. Check which airlines fly nonstop from your city on the airlines’ own sites; our Key West airport guide covers the terminal and the ride into town.

4. Can I get to Key West without a car?

Yes. Besides flying, the main car-free option is the Key West Express, a fast ferry from Fort Myers Beach on Florida’s Gulf coast. Boarding starts at 7 a.m., the boat leaves at 8 a.m., and the crossing takes about three and a half hours; the return leaves Key West at 6 p.m. A full-fare adult round trip is $194, or $170 Monday to Thursday and $180 Friday to Sunday if you book at least eight days ahead on the non-refundable fare. It lands at the Key West Bight, a short walk from Duval Street. Our Key West Express guide covers the details, and the getting to Key West guide compares every option.

5. Do I need a car once I’m in Key West?

Usually not, and many visitors wish they hadn’t brought one. The island is only about four miles long and a mile or so wide, Old Town is flat and compact, and parking is scarce and expensive. The city’s downtown garages listed rates of about $6 to $7 an hour and $48 for a full day for Fantasy Fest 2026; check the City of Key West for current rates. If you are staying in Old Town, walk, cycle or use Key West Transit, which runs bus routes and an on-demand ride service; check its pages for the routes running during your stay. If you are staying out on North Roosevelt Boulevard or Stock Island, a car or a bike becomes more useful. Our Key West parking guide and transportation guide go through the choices.

§ 03

Getting around

6. Is Key West walkable?

Old Town is very walkable. Duval Street, the main drag, runs about 1.1 miles and 14 blocks from the Gulf of Mexico at Mallory Square to the Atlantic on the south shore, and most of the famous sights sit within a few blocks of it. The island is flat, so the only real obstacles are heat and distance. In summer, walking a mile at midday is hard work; plan the long walks for the morning and the evening. Wear proper sandals or sneakers rather than flip-flops, because the sidewalks are uneven and tree roots lift the paving in places. Our Key West neighborhoods guide shows how the island fits together.

7. Should I rent a bike or a scooter?

A bike is the classic Key West way to get around, and the City runs a “Car Free Key West” program that promotes cycling, multi-use paths and bike safety. Rental shops are all over Old Town and many guesthouses lend or rent bikes. Ride with lights after dark and lock the bike every time. Scooters cover longer distances, such as a ride out to Smathers Beach or Stock Island, but they are less forgiving in traffic, and new riders on unfamiliar streets are a common sight in the emergency room. If you have not ridden one before, a bike is the safer choice. Our scooter rental guide covers the rules and the alternatives.

8. Where should I stay on a first trip?

For a first visit, stay in or near Old Town if your budget allows it. Being able to walk to dinner, the sunset and the bars, and back again without parking, is most of the appeal of the island. The quieter streets of the historic district, a few blocks off Duval, give you the location without the late-night noise. Hotels along North and South Roosevelt Boulevard cost less and often have more space and parking, but you will be riding or driving into town. Our neighborhoods guide compares the areas, and the vacation planning guide below has more on booking.

§ 04

When to go

9. When is the best time to visit Key West?

It depends on what you want to trade off. Winter, from December to April, brings dry, sunny weather and high prices, with the busiest weeks around the holidays and spring break. Late spring, especially May, combines warm water, longer days and fewer crowds. Summer is hot and humid with afternoon storms, and prices fall. Fall is the cheapest season but sits in the heart of hurricane season. If you want one recommendation for a first trip, aim for late April or May, or early December before the holiday rush. Our best time to visit Key West guide and the month-by-month guide go into each season.

10. When is hurricane season?

The Atlantic hurricane season runs from June 1 to November 30. According to the National Hurricane Center, the statistical peak is September 10, and most activity falls between mid-August and mid-October. That does not mean you should never visit in those months. Most weeks pass with no storm at all, and prices are at their lowest. It does mean booking refundable rooms, buying travel insurance that covers hurricanes, and watching the forecast for the week before you go. In an evacuation, visitors are ordered out first, and the only road out is US 1. Our Key West weather guide covers the seasons in detail.

11. How many days do I need?

Three full days covers the essentials: the Hemingway Home, Duval Street, a Mallory Square sunset, a reef snorkel trip and a beach afternoon. Four or five lets you add the Dry Tortugas and slow down, which is the point of Key West. If you are driving down from Miami, add at least a day for the journey and the Middle Keys. A week is a holiday rather than a sightseeing trip, and a good one. Our how many days in Key West guide has sample plans for each length.

12. Is the water warm enough to swim?

From May to October, comfortably: the sea averaged in the high 80s at NOAA’s Key West gauge in June to August from 2023 to 2025, touching 90 in July 2023. In winter it averages from about 70 to the mid 70s, which is refreshing rather than warm, and a cold front can push the water near shore into the 60s for a few days. Most visitors from the north swim happily in winter; snorkelers often want a thin wetsuit. Our Key West water temperature guide has the month-by-month figures.

13. What is Fantasy Fest, and should I avoid it?

Fantasy Fest is a ten-day costume and party festival held every October, first staged in 1979, which runs from October 16 to 25 in 2026 and ends with a big parade on the final Saturday. It is loud, crowded and very much adults-only in spirit, with a lot of body paint and not much clothing on Duval Street during the final weekend. If that sounds like fun, it is one of the country’s best-known parties. If you are coming with children or want a quiet week, avoid it, because hotel prices jump and the town is given over to the festival. Check the official Fantasy Fest site for future dates; our Fantasy Fest guide explains what happens when.

§ 05

Money

14. Is Key West expensive?

Yes, by Florida standards. Hotels are the big cost: winter rates in Old Town are high, and taxes and resort fees add a noticeable amount on top of the room rate. Food and drink cost about what you would pay in a big-city tourist district, and attractions and boat trips add up quickly. The good news is that many of the best things on the island are free or nearly free: the sunset at Mallory Square, walking Old Town, the beaches, the architecture. To control costs, travel in late spring or summer, stay a little outside Old Town, skip the car, and eat lunch as your main meal. Our Key West trip cost guide builds sample budgets, and Key West on a budget covers the savings.

15. How much do the main attractions cost?

The cost table at the top of this page has the main fixed prices. The Hemingway Home is $19 for adults, Fort Zachary Taylor is $6 per vehicle, and the Dry Tortugas ferry starts at $260 for the day, park entrance included. Boat trips, such as snorkel tours and sunset sails, vary widely by operator and season, so compare what is included before you choose. Discount passes and combination tickets are sold for many attractions, but they only pay back if you would really have visited everything on the list. Our things to do in Key West guide has the rest.

16. How much should I tip?

Key West follows normal American tipping customs, and much of the island runs on service-industry wages. In sit-down restaurants, 18 to 20 percent of the pre-tax bill is standard. In bars, a dollar or two a drink, or 18 to 20 percent of a tab. Tip boat crews and tour guides at the end of a trip, usually 15 to 20 percent of the fare, and housekeeping a few dollars a night. Check your bill before you add a tip: some restaurants add a service charge for large groups.

§ 06

The famous sights

17. Can you see Cuba from Key West?

No. At its closest, Cuba is about 95 statute miles from Key West, well beyond the horizon even from a high point. The famous buoy says “90 Miles to Cuba,” and the line has stuck, but the true figure is a little further. On a very clear evening, people at Mallory Square sometimes convince themselves they can see a smudge on the southern horizon; it is cloud. What you can feel is how close Cuba is in the island’s history, food and architecture, which our Key West history guide traces.

18. Where is the Southernmost Point buoy, and can I visit it?

The famous red, black and yellow concrete buoy at the corner of South and Whitehead streets is closed while the City carries out a roadway project at the street end. While the work goes on, a full-scale replica stands at a pedestrian plaza at 1400 Duval Street, and it draws the same photo queue as the original. The City’s own notice in September 2026 described a project of about 180 days, with road closures and detours around South, Duval, United and Whitehead streets, so check the City of Key West’s news page before you go if you want to see the original. Two other facts the buoy does not tell you: it was unveiled in 1983, and the true southernmost point of the island is on military land that is closed to the public.

19. What happens at the Mallory Square sunset?

Every evening, Mallory Square on the island’s northwest waterfront turns into a street festival around the sunset, with jugglers, magicians, musicians, tightrope walkers, food carts and craft stalls. It is free, it is a bit of a circus, and almost everyone goes at least once. Arrive about an hour before sunset to see the performers and get a spot on the waterfront; bring small bills to tip the acts you watch. If you want the sunset without the crowd, the piers and waterfront bars along the harbor have the same view. Our Mallory Square sunset guide has tips on timing and where to stand.

20. Are the Hemingway Home cats really six-toed?

Many of them are. The Ernest Hemingway Home and Museum says it is home to nearly 60 polydactyl cats, about half of which show the extra toes, and all of which carry the gene (see the museum’s own page on the cats). The museum traces them to a white cat named Snow White, said to have been given to Hemingway by a ship’s captain. The cats roam the house and gardens and are cared for by the museum staff. The house is open every day of the year from 9 a.m. to 5 p.m., with guided tours every 15 minutes; admission is $19 for adults. Our Hemingway House guide has more on the tour.

21. Why are there chickens everywhere?

Free-roaming chickens and roosters are one of the first things visitors notice in Key West. They wander through restaurant courtyards, cross Duval Street and crow at every hour of the night, not just at dawn. They are part of the island’s character, and the town has made a kind of mascot of them. For a light sleeper, they are also a good reason to pack earplugs and ask for a room away from the garden. The story of how they got here, and why nobody rounds them up, is worth reading before you go.

22. Does Key West have good beaches?

Good, but not great, and it helps to know that before you arrive. The reef offshore takes the force out of the waves, so Key West’s beaches are small, calm and shallow, with no surf and in some places more rock and seagrass than sand. They are lovely for a swim and a lazy afternoon, but they are not the long white beaches of Florida’s Gulf coast. Fort Zachary Taylor, inside a state park at $6 per vehicle, is the favorite for snorkeling off the beach and shade under the trees. Smathers Beach is a long stretch of sand, and Higgs Beach is popular with locals. For postcard beaches, head 37 miles up the highway to Bahia Honda. Our Key West beaches guide compares them all.

§ 07

Rules, culture and safety

23. Can I drink alcohol on the street?

Be careful with this one. Key West’s city code restricts open containers of alcohol in public places, and the rules on beaches and in parks are posted at each one. In practice, you will see people walking between Duval Street bars with drinks in plastic cups, but that is not the same as a license to drink anywhere, and glass is a bad idea on any street. If in doubt, finish your drink in the bar. The bar scene itself is one of the island’s great pleasures; our Key West travel tips cover the local etiquette.

24. Is Key West LGBTQ-friendly?

Very. Key West has been one of America’s best-known LGBTQ destinations for decades, and its official motto is “One Human Family.” Gay-owned guesthouses, bars and drag shows are part of the mainstream of the town rather than a separate scene, and the June Pride celebration and other festivals draw visitors from all over the country. Our Key West Pride guide covers the festival.

25. Is Key West good for kids?

More than its party reputation suggests. Children usually love the Hemingway cats, the aquarium, the Shipwreck Museum, the Conch Train, the butterfly conservatory, the fort and the beach at Fort Zachary Taylor, and a snorkel trip if they are confident swimmers. The thing to manage is the late-night Duval Street scene, which is not for children, and Fantasy Fest week, which is best avoided entirely with kids. Pick a family-friendly hotel with a pool, and plan the day so you are back before the bars get loud. Our Key West with kids guide has the details.

26. Is Key West safe?

Key West is generally a safe place to visit, and most visitors’ problems are the ordinary ones of any busy resort town: unlocked bikes stolen, valuables left on the beach, too many drinks on Duval Street. Lock your bike, keep your phone and wallet with you, use a taxi or rideshare after a late night out, and stay hydrated in the heat. The more serious risks are natural rather than criminal: sun, heat, rip currents on rare rough days, and hurricanes in the late summer and fall. Our travel tips guide covers the common-sense precautions.

27. What is a Conch, and what is the Conch Republic?

“Conch” (pronounced “konk”) is the local name for someone born in Key West, after the sea snail that has long been part of the island’s diet. People who have lived on the island for years but were born elsewhere are sometimes called “freshwater Conchs.” The Conch Republic is the island’s tongue-in-cheek independent nation: on April 23, 1982, Key West “seceded” from the United States in protest at a Border Patrol roadblock on US 1 that was choking traffic to the Keys. The secession is celebrated every April and the Conch Republic flag flies all over town. Our Conch Republic guide tells the full story.

§ 08

Food and drink

28. What should I eat in Key West?

Start with Key lime pie, which Florida made its official state pie in 2006; the debate over whether it should be topped with meringue or whipped cream is a local sport. Then try conch fritters, fresh-caught fish such as hogfish or mahi-mahi, Key West pink shrimp, and Cuban coffee and pressed sandwiches from a walk-up window. From mid-October to the start of May, Florida stone crab claws are in season and on menus across the island. Our Key lime pie guide rates the best slices, and the stone crab season guide covers the claws.

§ 09

Beyond the island

29. Is a trip to the Dry Tortugas worth it?

For most people who make it, yes. Dry Tortugas National Park is a group of small islands about 70 miles west of Key West, dominated by the vast brick Fort Jefferson, with clear water and good snorkeling around the fort’s moat wall. The Yankee Freedom ferry leaves Key West at 8 a.m. and is due back between about 5:15 and 5:30 p.m. (the operator gives both times on different pages); the day trip starts at $260 and includes the $15 park entrance fee, breakfast snacks, lunch, snorkel gear and a guided tour of the fort. It is a long, expensive day, and the crossing can be rough, so it suits people who like history, snorkeling or remote places more than those who get seasick. Book early in winter, when it sells out. Our Dry Tortugas day trip guide has the full picture.

30. Do cruise ships still stop in Key West?

Yes, but the picture has changed in recent years. In 2020 Key West voters approved limits on the size and number of cruise ships, the Florida Legislature overturned those limits in 2021, and the city then restricted docking at the two piers it controls. In 2026 the Navy ended the city’s lease on the Outer Mole pier, which took effect in August. Cruise ships continue to call at Pier B, the privately run pier next to the Truman Annex. If you are on a cruise, you will usually have a single day in port; the Key West cruise port guide shows how to use it well.

§ 10

A first-timer’s checklist before you book

Most of the answers above boil down to a short list of decisions. Settle these before you pay for anything and the rest of the trip tends to fall into place.

• Pick your dates against the calendar. Check whether your week overlaps Fantasy Fest, spring break, a holiday weekend or a big festival. Those weeks change the price, the crowds and the noise level more than the weather does.
• Decide on the car first. If you are driving down, choose a hotel with parking and check what it charges per night. If you are flying or taking the ferry, choose a hotel you can walk from, and budget for bikes or the occasional taxi instead.
• Book the things that sell out. The Dry Tortugas ferry, popular snorkel trips and good restaurants on Friday and Saturday nights fill up in winter. Book them as soon as your dates are fixed.
• Read the cancellation terms. Between June and November, book refundable rooms where you can and buy travel insurance that covers hurricanes. In winter, look for the resort fee and the minimum-stay rules before you compare prices.
• Pack for heat, sun and the occasional cold front. Light clothes, a hat, reef-safe sunscreen, a rash guard for snorkeling, and one warm layer for a windy winter evening on the water. Earplugs, for the roosters.
• Leave gaps in the plan. The best days in Key West are often the unplanned ones. Two fixed activities a day is plenty.

Our Key West packing list covers what to bring in each season, and the Key West events calendar shows what is on during your dates.

§ 11

Frequently Asked Questions

Related Key West Guides

• Key West Travel Tips
• Key West Vacation Planning Guide
• Getting to Key West
• Best Time to Visit Key West
• Key West Trip Cost
• Things to Do in Key West
• Key West Water Temperature by Month

§ 13

Photo Credits

Southernmost Point buoy: Florida Keys Scenic Highway – The Southernmost Point Marker – NARA – 7718454 by an unknown author (U.S. National Archives), Public domain, via Wikimedia Commons.

Tightrope walker at the Mallory Square sunset: Florida Keys Scenic Highway – Tightrope Walker at Sunset Celebration – NARA – 7718458 by an unknown author (U.S. National Archives), Public domain, via Wikimedia Commons.

Mallory Square from the water: Key West – Mallory Square (3886264276) by Roger W from Sarasota, Florida, U.S.A., CC BY-SA 2.0, via Wikimedia Commons.

Front and Duval streets (featured image): Buildings on the Corner of Front and Duval Street, Key West, Florida by Julian Lupyan, CC0, via Wikimedia Commons.