Do Not Make These 14 Mistakes When Visiting Key West
THE TOP 14 MISTAKES VISITORS MAKE WHEN VISITING KEY WEST
A Local Insider’s Guide to Doing Key West the Right Way
Welcome to paradise! Whether this is your first visit or your tenth, Key West has a way of surprising people. It’s quirky, colorful, laid-back, and filled with natural beauty — but it also has a few hidden rules, local quirks, and insider secrets that can completely change your experience.
For more than 40 years, Sunset Watersports has helped visitors explore the island from every angle, jet skis, snorkel trips, sunset cruises, sandbar excursions, parasailing, dolphin tours, and more. During that time, we’ve seen travelers make the same mistakes over and over again, mistakes that can cost you time, money, and some of the best experiences Key West has to offer.
This guide fixes that.
Inside, you’ll find the 14 biggest mistakes people make when visiting Key West, and how to avoid them like a local, so you can get the most out of every moment.
1. DO NOT PAY FOR PARKING IF YOU DON’T HAVE TO
Parking downtown can quickly turn into a headache as it is filled with expensive lots and confusing signs. But here’s the insider trick: you rarely need to pay for parking in Key West. There are tons of free side-street spots throughout the island. Just avoid Residential Only parking spaces, which are clearly marked and enforced. Resident parking spaces will be marked with the word “RESIDENT” clearly marked on the actual parking space. There are no resident parking street signs but there are plenty of “Pay For Parking” street signs. If you see those you will need to find a parking kiosk and pay to park in that space. Additionally, during holidays or major events, free spots fill quickly, so arrive early or plan for a paid lot.
Local Tip: If you’re doing a Sunset Watersports tour, follow our parking instructions for smooth arrival. Here is an insider’s guide to parking in Key West
2. DO NOT RENT A CAR
A car becomes a burden in Key West or just ends up parked at your resort. The island is small, just 4 miles long, with most attractions in a 1 to 1.5-mile radius.
Parking is limited, sometimes expensive and often unnecessary.
Use instead:
• Uber/Lyft from the airport
• Your hotel’s shuttle
• Golf carts
• Bikes
• Mopeds
• Walking
A car cramps your style, rent a golf cart or bikes and travel island style.
3. DO NOT VISIT THE SOUTHERNMOST POINT AT PEAK HOURS
The Southernmost Point buoy can have wait times exceeding an hour, especially when cruise ships are in port.
Peak hours are 11 AM–4 PM.
Go early morning or at sunset for the best lighting and no crowds. Click here for a visitors guide to the southernmost point
4. DO NOT MISS OUT ON WATER ACTIVITIES
Key West’s magic isn’t just on land it’s surrounding the island. Snorkeling, parasailing, jet skiing, sandbar charters, dolphin watching… all are available year-round thanks to warm water temperatures rarely dipping below 70°F.
If the water feels cool, we provide wetsuits. Trust us, seeing Key West from the water is essential.
5. DO NOT MISS THE 3RD LARGEST LIVING CORAL REEF IN THE WORLD
Most visitors don’t realize that Key West sits just a short boat ride from the Florida Keys Reef Tract — the third-largest living coral reef system on the planet, and the only barrier reef in the continental USA.
This underwater wonder is home to:
• Colorful coral formations
• Hundreds of tropical fish species
• Sea turtles
• Rays
• Nurse sharks
• Clear Caribbean-blue water
And the best part? Daily reef trips start at just about $40. Reef snorkeling trips
Many travelers overlook this bucket-list experience entirely don’t be one of them.
Local Tip: Morning snorkeling tours usually offer the best visibility & are less expensive.
6. DO NOT OVERPAY FOR WATERFRONT HOTELS
You don’t need a waterfront room to enjoy waterfront amenities.
With ResortPass, you can access luxury pools and private beaches for $25–$75 per day.
Stay affordably — play luxuriously.
7. DO NOT OVERPAY FOR DRINKS
Drinks in Key West can get pricey — $12 beers and $15–$20 cocktails.
Use a Party Pass or similar discount program to unlock BOGO deals, free shots and drink specials at over 20 of the island’s top bars.
You’ll save money while still enjoying the nightlife. The Party Pass pays for itself the first time you use it.
8. DO NOT CHUG YOUR DRINKS
One of Key West’s unsung perks: you can walk between bars with your drink in many areas, as long as it’s in a plastic cup.
Sip slow. Stroll. Enjoy Duval Street at your own pace.
9. DO NOT ASSUME ALCOHOL IS ALLOWED ON ALL BEACHES
Beaches like Smathers Beach and Fort Zachary Taylor do not allow alcohol.
Police may give warnings, but tickets are possible.
If you want to enjoy drinks stress-free, try:
• Sandbar charters
• Sunset cruises with open bars
• Private boat rentals
10. DO NOT MISS THE FREE FISH FEEDING SHOW AT THE DOCKS
Every afternoon around 2:30 PM, fishing boats return and the filleting begins — and that means tarpon, sharks, and Goliath grouper gather in a wild feeding frenzy.
The best spot?
Foster & Foremost, where the Salty Goat returns.
It’s thrilling, totally free, and unforgettable.
11. DO NOT MISS THE MANATEES AT STOCK ROCK CAFÉ
Stock Rock Café at Cow Key Marina is a hidden local gem.
Manatees often swim up to the docks, especially late morning and early afternoon.
Pair that with cold drinks, waterfront seating, and true island vibes — this is Key West at its most authentic.
12. DO NOT BOOK AFTERNOON TOURS WITHOUT CHECKING EARLY BIRD SPECIALS
Morning tours often mean:
• Lower prices
• Fewer crowds
• Better visibility for snorkeling
• Cooler weather
• Calmer seas
Many include breakfast or open bar, better value + better conditions.
13. DO NOT SKIP SUNRISE AT WHITE STREET PIER
Sunset gets all the hype, but sunrise at White Street Pier is a peaceful, colorful, dolphin-friendly hidden gem.
Bring a coffee, breathe in the morning air, and enjoy the quietest, most beautiful part of the day.
14. DO NOT STRESS ABOUT RESTAURANT RESERVATIONS (EXCEPT THIS ONE)
Most restaurants in Key West are walk-in friendly or accept same-day reservations.
But there is one dining experience you should book early:
Key West’s Only Sunset Dinner Cruise
Featuring:
• Live music
• Tropical buffet
• Open bar
• 360° ocean sunset views
It’s the island’s most unique dining experience and the only true dinner cruise.
Reserve ahead of time here: Sunset Dinner Cruise Reservations
BONUS SECTION: QUICK LOCAL FAQ
1. Best time to visit?
November–April (cooler, calm seas) or summer for warm water.
2. Can you swim year-round?
Yes — water stays around 70–80°F.
3. Best way to get around?
Golf cart, bike, walking, or shuttle.
4. Should you bring sunscreen?
YES. Reef-safe and plenty of it.
5. What do most visitors miss?
• The reef
• Sunrise
• Stock Rock Café
• The fish feeding show
• Sandbar trips
Next Key West Tip: Happy Hour At The Sandbar In Key West
