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First Time Visitors Guide

First Time Visitors Guide

First-time trips to Key West are always an unforgettable experience. It’s no wonder this Florida haven makes its way onto many travelers’ bucket lists. Now that it’s on yours, you’re ready to start planning the trip of a lifetime. And Old Town Trolley – Key West is prepared to help.

Key West is one of the most popular vacation spots in the state, boasting panoramic views, luxurious resort spas and breathtaking shorelines. Get ready to pair yourself with paradise on Florida’s southernmost coast.

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Old Town Trolley - Key WestWhy You Need This Key West Travel Guide

Whether you’re in town for a family getaway or celebrating an anniversary with the one you love, you’ll find an experience made just for you within this first-time visitor’s guide. You’ll feel far from a first-timer and more like a local when you’re taking your tips from the Old Town Trolley – Key West team.

Key West AttractionsMust-See Attractions in Key West

Our first-time visitor’s guide introduces travelers who are new to the island to some of the most popular must-sees in Key West. From activities that get you in, on and around the water to cocktail experiences and tours of the city, there’s always something to see and do on the island. And it doesn’t hurt that almost everywhere you go in the city has an amazing view.

Keep a pen nearby because you’ll want to remember these Key West attractions as you plan your trip.

Exploring Key West Attractions

Key West Sails to Rails Museum frontSails to Rails Museum

Embark on a journey through Key West’s maritime past at the captivating Sails to Rails Museum. Discover the remarkable transition from sailboats to steamships and railways that shaped the island’s history. Explore meticulously preserved artifacts and interactive exhibits, including the opportunity to lift a real silver bar and delve into maritime tales. Immerse yourself in the sights and sounds of Key West’s rich heritage with a Fort Jefferson diorama, offering a glimpse into the island’s strategic importance.

first trip to Florida Drink Your Way Through the Duval Crawl

There’s no better way to toast to one of your first trips to Key West than the Duval Crawl. To complete the crawl, you’ll have to down a tall order of 43 cocktails. Even if you tap out, you can say you’ve sipped on one of the most popular Key West attractions.

a must-see in key westStroll the Waterfront

There’s no shortage of scenic views of the water from every side of the island. In fact, the views and ocean currents tend to be dramatically different depending on whether you’re strolling the Gulf side or the Atlantic side of Key West. On the Gulf, walking the Historic Seaport and Mallory Square are great ways to experience the waterfront and mix in some shopping along the way. While on the Atlantic side, you’ll want to take your beach gear and have a relaxing stroll along Smathers Beach.

trips to key westHop On-Hop Off Key West Tours

The historic charm and quaint vibes are sure to inspire you to hop off at a few Key West attractions. Trips to Key West often include a visit to the Truman Little White House, Angela Street Depot and Bahama Village Market, and with Old Town Trolley – Key West, they’re all just a stop or two away.

Key West AttractionsWater Adventures

Key West attractions on the water are a must-do on our first-time visitor’s guide. With Fury Water Adventures Key West, you can snorkel to look beneath the surface, rip and ride on a jet ski or end the day aboard a stunning sunset cruise.

Southern Most Point Take a Picture at the Southernmost Point

A unique addition to our first-time visitor’s guide, the southernmost point of the continental US is, of course, only found in the Keys. Head down south for unforgettable views and photos you’ll be showing off for years to come, along with your other shots from picturesque Key West attractions.

Higgs Beach Hang Out on Higgs Beach

Trips to Key West are best spent beach bound. There’s a reason beaches are among the most frequented Key West attractions. Higgs Memorial Beach Park is one of the most highly rated experiences on our first-time visitor’s guide to Key West. Stroll the pier, build sandcastles, start a beach volleyball match or simply soak up the sun.

Mallory Square Key West Mallory Square Sunset Celebration

Mallory Square is a quintessential Key West attraction that includes a little bit of everything – Shops, restaurants, and of course, the world-famous nightly sunset celebration. Fun times await at the waterfront plaza that will keep you coming back, whether it’s your first time in Florida or one of your latest summer road trips to Key West.

Pepe’s CafeEat Breakfast at Pepe’s Cafe, the Oldest Joint in Key West

A historic addition to our first-time visitor’s guide, Pepe’s Cafe is the oldest eatery in the Keys and the second oldest in the state of Florida. Trips to Key West aren’t complete without grabbing a bite at one of the most seasoned and delicious Key West attractions.

Ghosts and Gravestones KeyWest tourGhost Tours

We bet you didn’t expect that trips to Key West could explore the supernatural. Brave one of the spookily spine-tingling Key West attractions on a ghost tour that introduces you to the Keys’ dark past. See the strange, confront the creepy and unearth eerie tales with the Ghost & Gravestones’ crew.

Best Places to Stay in Key West

The Orchid Key Inn is exclusively adult-only, the perfect oasis on the island for first-time travelers hoping for a peaceful experience.

You’ll be dreaming about your next of many trips to Key West as you unwind by the rooftop pool at H2O Suites Hotel. Book a scenic stay at the luxury resort.

Stay in the heart of Key West at the Conch House Heritage Inn. With the charming abode just a block from Duval Street, some of the best Key West attractions are within walking distance.

Pier House Resort & Spa is the beachside escape you’ve been looking for. Enjoy the resort’s private sands, top-tier dining, soothing spa treatments and more during one of your first trips to Key West.

Plan Your Trip to Key West – Know Before You Go FAQs

Old Town Trolley – Key West is one of the best ways to truly experience first-time trips to Key West. Our route covers some of the most incredible parts of the island. Because we know our way around town, our first-time visitor’s guide has a few more tips on what you need to know before you head south.

Planning for parking? If you’re driving down to Key West, expect city-owned paid lots and garages, parallel street parking and metered spaces. But keep in mind that many travelers prefer to leave their car parked in the driveway back home when they visit Key West to take advantage of this scenic walkable beach town.

But what about packing? When you’re making your Key West packing list, be sure to jot down sunglasses and sunscreen for your much-needed beach day. Exploring the city on foot? Bring your best walking shoes. And for nights out on the town, many tourists and locals alike like to dress casually, so no need to pack your Sunday best.

So, what’s the best time of year to visit? Well if you’re like us, every day in Key West is a beauty. While you’ll likely never be disappointed during your first trip to Florida, the most popular months to visit Key West are March, April and May.

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