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Local’s Guide to Visiting Key West

First Time Locals Guide To Visiting Key West

The warm welcome of the Florida Keys will make anyone feel right at home. Still, if you’re new to exploring Key West, it doesn’t hurt to have a travel buddy who knows their way around the island — from the historic hidden gems to the best local spot for a Keys-style cocktail. At Old Town Trolley – Key West, we’ve been making our way around the Keys for years. Our Key West tours put you in the center of that laid-back lifestyle that you’ve been craving.

Locals and tourists alike board our trolleys to get to know Key West on a new level. With our seasoned conductors leading the way, you’ll learn more about this piece of Florida paradise than you ever imagined.

  • Admissions Admissions
  • Shopping Shopping
  • Dining Dining
  • Entertainment Entertainment

See the Best First

Old Town Trolley – Key West knows exactly where the hidden gems of the island are tucked away. You’ll see all the best local spots as you tour the island with our guides at the helm. Consider your time with our team as your look into an exclusive local’s guide of the area.

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.

Key west tourSee the Island from a Jet Ski

What better way to start our local’s guide to Key West than adventures on the water? You can hop off the trolley, then hop on a jet ski and see everything the Keys has to offer from a new point of view. Unleash your inner adrenaline junkie at any of the island’s local spots on the water.

key west visitors guideTour the Ernest Hemingway House

The Hemingway Home and Museum is open daily, giving visitors a glimpse into the life of the late writer Ernest Hemingway. Six-toed cats prowl the grounds at this local spot, making it one of the most unique attractions in Key West. Get closer to the stories of one of the greatest writers in American history and discover why he made Key West his home.

first time key west tourist informationSoak in a Sunset

With panoramic views, local spots in Key West offer some of the best sunset scenes anywhere in the world. With our local’s guide in hand, you’ll know exactly where to go to see the sun go down. Set sail on a sunset cruise for a scenic experience on the water or stay on land to take in the view as you stroll a pier at one of the many nearby beaches.

And for the ultimate good time with good views, visit Mallory Square for the Key West Sunset Celebration. This nightly event invites everyone on the island to the popular square to enjoy live music, shop with local vendors, be amazed by street performers, and of course, watch the sun disappear over the horizon before they do it all over again the next day.

Secret Garden of Martello TowerSee the Secret Garden at West Martello Tower

Hidden gems, such as the West Martello Tower (also known as the Key West Garden Club) are sure to help you make the most of your time in Key West. Visit the site to discover its interesting history that dates back to the Civil War era.

Key West beaches Relax at Fort Zachary Beach

Beach days at Fort Zachary Taylor Historic State Beach Park are one of the locals’ favorite places to be on a sunny afternoon. Once you spend some time soaking up the sun on the shore, you’ll feel as if you’ve called the island home for just as long as we have.

Historic SeaportStroll Along the Historic Seaport

There’s something for everyone to enjoy at Key West Historic Seaport. Hidden gems and water activities await around the boardwalk. Try sponging, shrimping, browsing the souvenir shops, or get a taste of Key West at a local spot in the area.

View Historic Homes by Bike

If you really want to navigate the Keys like a native, remember to pack your helmet so you can bike to the popular local spots. When you’re not exploring with Old Town Trolley – Key West, biking is a great way to experience some of the activities on our local’s guide.

Concerts at Coffee Butler Amphitheater

There are enough events at the Coffee Butler Amphitheater to fill your getaway from start to finish. See your favorite artist in concert at the amphitheater or head to Truman Waterfront Park just a few steps away for fun at the splash pad (a hidden gem for traveling families).

Things You Need to Know Before Visiting Key West

If you really want to live like a local during your stay in Key West, you’ll want to get to know the city as much as you can, even before you pack your bags. Since you found our local’s guide, you’re already on your way to an unforgettable vacation.

Now that we’ve introduced you to some of the natives’ favorites — from hidden gems to famous local spots — we’ll let you in on a few more of the beach town’s secrets. Between the gorgeous drive down, the scenic stops along the way and the island cuisine, our local’s guide isn’t done showing you the best of Key West yet.

1. There Are Amazing Places to Stay All Over the Island

If you take just one thing from our local’s guide, know that you and your travel crew have endless options for the perfect stay in Key West. Feeling coastal? Book an oceanside room for yourself and your friends. Celebrating an anniversary? Try a romantic luxury suite. Traveling with family? There’s plenty of fun in store at one of the many kid-friendly resorts.

2. Shoulder Season is the Best Season to Visit

If you’re planning your island getaway around shoulder season, you’ll want to visit Key West in March, April or May. During this time of year, you’ll experience optimal weather and less traffic at some of the hidden gems and at some of the activities mentioned in our local’s guide.

3. A Drive to Key West is a Drive Through Paradise

We know, sometimes adding a drive to your travel to-do list can be a pain. But something about driving through paradise seems to make all of those troubles disappear. With nothing but turquoise waters and clear skies, your scenic drive down south will be one of the highlights of your trip.

4. The Beaches Are Unforgettable

No matter how long we’ve been in the Keys, we’ll never get over its beaches. When you’re packing your bag for your stay, include plenty of sunscreen, a new pair of sunglasses and your favorite beach activity.

5. Some of Key West’s Best Views Are From the Water

Finding yourself in awe of the picturesque ocean views of Key West as you’re browsing the web planning your vacation? Just imagine its beauty in person. On the water, you’ll get an even deeper connection to the island and experience its magic from the waves.

6. Conch Fritters Are a Must-Have

Florida is famous for its fresh seafood, but nobody does seafood quite like Key West, a hidden gem for foodies. Conch fritters make a delicious addition to our local’s guide as one of the longtime favorites across the island.

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