The Complete Guide – Key West Travel Tips & Things to Do

Your Ultimate Guide to Key West for First-Timers  

Thinking about planning a trip to Key West? Great choice! This tropical island gem, nestled at the southernmost point of the Continental United States, is packed with vibrant charm, mouthwatering food, fascinating history, and unforgettable sunsets. Whether you’re a first-timer or someone who just wants to make the most of their trip, we’ve got you covered with travel tips, must-visit spots, and insider advice to make your Key West vacation an experience you’ll talk about for years to come.  

The Best Ways to Get to Key West  

Fly Right In  

The easiest (and fastest) way to arrive is by hopping on a direct flight to the Key West International Airport (EYW). Multiple airlines offer flights from major South Florida hubs such as Miami and Fort Lauderdale. Pro-tip? Sit by the window—it’s the perfect place to spot stunning views as you descend over the turquoise waters of this tropical island.  

The Scenic Drive  

For those feeling adventurous (and patient), driving down the Overseas Highway is an unforgettable experience. This 113-mile stretch of road winds through the Florida Keys, offering breathtaking clear-water views and plenty of spots to stop for conch fritters or a quick snorkel. Fair warning, though—there’s only one lane in each direction, so buckle up and enjoy the ride, traffic jams and all.  

When’s the Best Time to Visit?  

Key West is a popular destination year-round, but the best time to visit depends on your preferences:

  • Winter (December to February): Avoid the humidity while enjoying mild weather.  
  • Summer (June to August): Expect fewer crowds but be wary of hurricane season. Don’t stress too much though—locals are pros at handling storms.  
  • Fantasy Fest (October): For those who love bold costumes and a good time, this wild week-long celebration is Key West at its party-animal best.  

If you’re here to take in scenic sunsets, you really can’t go wrong with any time of year.  

Must-Visit Spots in Key West  

The Famous Southernmost Point Buoy  

You can’t say you’ve visited Key West without snapping a (probably sun-drenched) picture by the iconic Southernmost Point Buoy. It’s one of the most popular things to do in the southernmost city—be prepared to line up, but the bragging rights are worth it.  

Ernest Hemingway Home and Museum  

Calling all bookworms and history buffs! Head to the Hemingway House, where the famed author wrote some of his best work. Bonus? Say hello to the six-toed cats, descendants of Hemingway’s beloved feline friends. Don’t forget to check out the story behind the “penny in the pool” while you’re there!  

Mallory Square Sunset Celebration  

Nothing says “Key West” like the nightly Sunset Celebration at Mallory Square. This is less a sunset-watching situation and more of a mini festival, complete with street performers, artisans, Cuban-influenced food stands, and live music. Fun tip for photographers—stick around after the sun hits the water; the afterglow colors are breathtaking and the crowds thin out.  

Dry Tortugas National Park  

If you’re feeling adventurous, make time for the Dry Tortugas National Park, a small slice of paradise 70 miles off the coast. You’ll need to book your spot on the Yankee Freedom Ferry months in advance—trust us, this remote gem is worth the planning. Think pristine beaches, snorkeling, and a historic fort all nestled in the middle of the Gulf of Mexico.  

Tastes of Key West  

Key Lime Pie Tour  

Who’s up for a Key Lime Pie taste test? Slathered in meringue, whipped cream, or none at all, this local delicacy is a must-try. From Blue Heaven to Kermit’s, hop around the island in pursuit of your favorite slice.  

El Meson de Pepe & El Siboney  

For authentic Cuban food, these family-owned gems are all you need. Picture juicy ropa vieja, flavorful rice, and fried plantains, all served with a side of sunshine.  

Blue Heaven  

This historic landmark-turned-restaurant is a local institution. Yes, you’ll wait in line, and yes, it’ll be worth it. Grab a cocktail, soak in the live music, and soak up the quirky vibes at this great spot.  

Schooner Wharf Bar & Green Parrot Bar  

Drink like a local with happy hour deals at favorite watering holes. The Schooner Wharf Bar even has two happy hours—one in the morning, one in the afternoon. After all, it’s always five o’clock somewhere in the Conch Republic.  

Grab our Happy Hour list here!

Things to Do for First-Timers  

Water Activities  

Key West’s clear water is made for exploration. Whether you’re snorkeling vibrant coral reefs, taking a glass-bottom boat tour, or spotting marine life on a dolphin cruise, the natural beauty here will leave you stunned.  

Sunset Cruise  

From romantic sailboats to lively party boats with live music, a sunset cruise is the great way to soak in those magical breathtaking sunsets. Pro-tip? Try them all and figure out your favorite vibe.  

Check out our favorites here!

Old Town Key West  

Staying in Old Town Key West means you’re in the heart of the action. Step outside your boutique hotel or cozy bed-and-breakfast and you’ll find live music, pastel conch-style homes, and plenty of surprises at every turn.  

Drag Shows and Nightlife  

Key West’s nightlife scene isn’t complete without checking out a drag show. Just bring some tip money, an open mind, and a good sense of humor—these talented performers know how to show you an unforgettable time.  

Where to Stay in Key West  

Where you stay can enhance the overall vibe of your trip. For first-timers, consider:

  • Boutique Hotels: Unique and full of charm, these converted historic homes are full of character.  
  • Bed and Breakfasts: Get personal attention and a taste of the island’s history. Many locals converted these homes to B&Bs to preserve Key West’s cultural heritage.  

If beachfront is your thing, head to Smathers Beach or splurge on a private spot at Sunset Key for the ultimate luxury experience.  

Travel Tips for Enjoying Key West  

  • Book Activities Early – Big-ticket items like the Dry Tortugas Ferry or charter fishing trips sell out fast.  
  • Stay Hydrated – This sunny island gets hot, so pack water and sunscreen.  
  • Pack Light – The island’s laid-back vibe means casual clothes and flip-flops are always in style.  
  • Explore Beyond Duval Street – While Duval Street is iconic, don’t forget to explore off-the-beaten-path neighborhoods for a more local feel.  

It’s Time to Start Planning Your Key West Vacation  

From the southernmost point buoy to the best restaurants to breathtaking sunsets, Key West has something for everyone. Whether you’re sipping on a Cuban Coffee Queen latte, hunting for the best key lime pie, or enjoying the quirky charm of the Conch Republic, this great place never disappoints.  

Start planning your Key West getaway now—and don’t forget to take your time and just enjoy the island vibes. Life’s too short for anything else.  

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