Know Before You Go

A Guide to Key West Neighborhoods

Welcome to the vibrant neighborhoods of Key West, a paradise tucked away at the southernmost tip of the U.S. Our guide will take you through the unique character and charm of each neighborhood, immersing you in the rich culture, stunning architecture, and lush tropical allure that make Key West an unforgettable destination. Discover hidden gems, iconic landmarks, and local favorites as we embark on this journey through the enchanting neighborhoods of Key West.

Truman Little White House White Glove Tour

Take a step back in time to tour the Harry S. Truman Little White House with an expert tour guide and experience our White Glove Lounge.

1-Day Conch Tour Train

Hop aboard the 1-Day Conch Tour Train and discover Key West’s iconic landmarks, including Mallory Square and Duval Street.

2-Day Old Town Trolley Tour

Buy discount tickets online for the 2 Day Old Town Trolley Key West Tour. See the best first and learn about all the famous sites with our sightseeing tour.

1 Day Key West Tour With Old Town Trolley

Buy discount tickets online for the 1 Day Old Town Trolley Key West Tour. See the best first and learn about all the famous sites with our sightseeing tour.

Ultimate Key West 3-Day Weekend Itinerary

Nothing is more thrilling than the prospect of a long weekend around the corner. Since the two most prominent holidays that feature that most welcome Monday off, Labor Day and Memorial Day, occur in the warmer months, visions of outdoor grills, swimming pools, and chilling hard on the old Barcalounger are among the most desirable. However, if you decide you want to level up from the common ‘staycation’, there’s an island situated in the southernmost reaches of the Sunshine State that has been delighting visitors for decades. With its pioneer spirit, off-the-grid appeal and beach town charm, Key West is your ticket to adventure!

Holiday Light Contest

Historic Tours of America invites home owners to enter into our friendly competition for the most beautiful house on the block! People of all ages will delight as Key West homes dazzle with their holiday lights adorning every corner of the island. And our sleighs for the night will take guests to some of the most resplendent island homes. This is your opportunity to shine and have the chance to win one of our three cash prices!

The Best Shopping in Key West

In the land of key limes, errant roosters, partying and sunsets, every day is never the same as the one before. With its turquoise waters and hang-loose state of mind, time moves differently here in paradise and that is a very good thing. It’s an easy place to visit but is it ever tough to leave. You forget about the rest of the world here, but you are reminded of it just enough. If you plan on visiting the Conch Republic and want to drop some coin on a bit of a shopping spree, this tiny island is big on options.

Key West For The Holidays

Much in the same way Harry S. Truman retreated to his Little White House when things got a little too cool for comfort up in DC, Key West is where Santa comes to spread cheer and hang out in his Christmas-themed board shorts. This is one of the best places on Earth to celebrate the holiday season, just ask Conchy The Sandman and Rudy The Bottle-nosed Dolphin!

Key West Holiday Tours

No need to gas-up the snowblower this year if you’re planning a holiday escape to the Conch Republic! Here, ‘Christmas chill’ means rockin’ your flops and kicking back island-style and one of the best ways to do that is hopping a ride on Old Town Trolley’s Holiday Lights & Sights Tour! The Southernmost City is all a twinkle, as the locals decorate their historic Key West homes in a splendid cascade of lights and other decorative touches to see who can outdo the other in a friendly, holiday-inspired competition.

Romantic Things To Do in Key West

Spectacular sunsets, warm ocean breezes and a laid-back island atmosphere create the perfect setting for a budding romance or rekindling a long-term relationship. These are some of the enduring images and themes featured in many of Hollywood’s most romantic movies. Key West offers this and more. A favorite destination for royalty, political leaders and literary legends, this tropical oasis is an idyllic backdrop for a first date or special getaway celebrating a long-term relationship. Take that special someone on a romantic, unforgettable trip to experience attractions that allow couples to enjoy the sights while spending quality time together. 

Perfect Girls Weekend Key West

Planning a girls weekend in Key West? We’ve got you covered with everything from where to stay, what to eat, the hottest bars and the best activities on the island.

The 6 Best Beaches in Key West – The. Best. Escape. Anyone. Can. Have.

If you are planning a Key West vacation, spending some quality time at the beach is a top priority on your travel itinerary. Boasting temperate waters and more than 3,400 hours of annual sunshine, the beaches of Key West are some of the most popular destinations on this tropical island paradise. You can enjoy the sun, sand and warm water as well as a variety of activities like swimming, snorkeling and fishing.

Things To Do Near The Southernmost Point

Key West is famous for being the southernmost city in the continental United States. When you visit, it’s essential that you make it to the southernmost point on the island, found at the intersection of Whitehead Street and South Street. Here, you’ll see the landmark Southernmost Buoy (a required photo opp) and a whole host of other “southernmost” attractions that make for a fun Key West afternoon.

Hidden Gems In Key West

An island of only five square miles, Key West is a pretty easy place to navigate. It’s also filled with hidden gems ripe for discovery.

To paraphrase former Key West resident and famed poet Robert Frost, the road less traveled in Key West can make all the difference. And that’s exactly what you get when you hop aboard Old Town Trolley – the road less traveled far beyond Duval Street.

Casa Marina Resort Guide

The Casa Marina was built by Henry Flagler for his passengers on the overseas rail road in 1920 and exudes splendid Mediterranean charm. Sophistication and luxury mesh beautifully with this ideal Key West locale offering visitors a heavenly retreat in the midst of historic sites, natural beauty and enticing attractions. Ocean view rooms, an expansive private beach and a gorgeous swimming pool make it easy for guests to relax and appreciate every moment of their stay. The Casa Marina recently emerged anew, even grander, after a magnificent renovation of the guest rooms, pool and other areas and is now part of the Waldorf Astoria collection of hotels.

Ultimate Guide To Duval Street Key West

Perhaps one of the most popular destinations on the island of Key West, Duval Street is the main drag of downtown, running north and south from the Gulf of Mexico to the Atlantic Ocean. Although it is not much more than a mile in length – this is where the heartbeat of the city comes to life with a diverse array of restaurants, shops, world famous pubs and attractions.

Know Before You Go

Things To Do In Key West On Vacation

Some of the most popular Things To Do In Key West include touring the historic museums, relaxing on the beach, and watching the sunset at Mallory Square.

Mallory Square Sunset Celebration

Located at the center of the historic Key West waterfront, Mallory Square Things to do is filled with attractions, unparalleled shopping, fabulous restaurants and the world famous sunset celebration. You haven’t visited Key West until you’ve experienced Mallory Square.

Key West Restaurant Guide

Read the Old Town Trolley guide for foodies to top-rated Key West restaurants. Learn about local dives and popular places to eat for tourists.

Hometown Pass

Introducing the Old Town Trolley Hometown Pass Program. Residents of Key West and Monroe county can take advantage of our tour for FREE when accompanied by an adult paid guest.* It’s free to join and easy to use.

Key West Wedding Transportation & Group Trolley Rental

Old Town Trolley Tours offers discounted rates for charters, group ticket sales and special events. All of our Key West trolley rentals can be custom designed to meet your group’s specific transportation needs.

Getting Around Key West On Vacation

A visit to Key West is always an adventure and if you’re heading that way, you’re in for great time. The Southernmost City offers a host of interesting things to see and do, fascinating history and gorgeous natural scenery. When you begin your planning, make sure to plan how you’re going to get from one place to another. Here are some of the best ways to get around Key West.

Fun Facts About Key West

To most, Key West is thought of as a beach town with great parties, endless sandy coastline and year-round sunshine. But did you know its history stretches much farther than its shoreline? Read on for some of the best fun facts about this island oasis.

Reasons To Visit Key West

The Southernmost City in the USA, Key West is an oasis surrounded by gorgeous crystal waters. It’s here that you’re invited to come as you are, kick back and let go of all the stresses of hectic day-to-day life. Learn some of the top reasons to visit Key West.

Key West Cruise Excursions

Welcome to Key West

Key West is a beautifully historic town filled with impressive attractions and sites. Maximize your time for sightseeing by taking Key West shore excursions from Old Town Trolley. Whether you take the tour purchased from your cruise excursions desk, or take the tour with on-and-off privileges purchased from Old Town Trolley directly, you will have time to shop, visit attractions, and find your way to some of our most famous landmarks.

Labor Day Events

Old Town Trolley Tours of Key West has provided vacation guests and locals with more than 30 years of historic tours, news, and events. Each month the Trolley Team publishes upcoming events in Key West for visitors and residents to enjoy.

How To See Key West in 2 Days

Planning a two-day trip to Key West?

Follow this guide to get the most out of your time on the island.

How to See Key West in 1 Day

So, you’re heading to the southernmost city in the USA? Lucky you! There is so much to do and see in this island paradise, from intriguing attractions and historical sights to water sports, entertainment and world-famous points of interest. If you want to see the best of Key West in one day, hop aboard Old Town Trolley.

Bahama Village

Get MORE out of your summer in Key West aboard the iconic Old Town Trolley and see the best first!

Get a taste for the Caribbean heritage that is so much a part of Key West. In Bahama Village, which is a 12-block area between Whitehead and Fort and Angela and Catherine Streets, you’ll be able to see the original area in which the first black Bahamian settlers arrived in the 19th century. Sample true Bahamian culinary recipes in a variety of restaurants, stop in for a refreshment in one of the bars and shop in the Bahama Market. All the flavors, culture and traditions that this historic neighborhood represents come alive through the many streets.