Add dates

Key West Neighborhood tours

Our most recommended Key West Neighborhood tours

Key West: Old Town Trolley 12-Stop Hop-On Hop-Off Tour

1. Key West: Old Town Trolley 12-Stop Hop-On Hop-Off Tour

Enjoy the sun, charming setting, and clear waters of Key West on this Old Town Trolley Hop-On Hop-Off Tour. This tour covers the entire city. You can avoid the trouble of driving and parking in a new place. The trolley tour is also designed so that you can hop-on and off and explore on your own, on any of the 12 stops. Your ticket is valid for all day, so you can tour at your own speed. There are frequent pick-ups at all of the 12 stops so you’ll never have far to walk. And our Old Town Trolley conductors will be there to guide you through this tropical paradise on one of the distinctive orange and green trolleys. There are 13 Stops conveniently located close to many places of interest in Key West: 1) 400 Wall St: Mallory Square1a) Whitehead/Caroline St: Presidential Gates2) 280 Margaret St: Mac’s Sea Garden3) Corner of Greene/Simonton St: Simonton Row4) 430 Duval St: La Concha Hotel5) Whitehead/Petronia: Bahama Village6) 2400 N. Roosevelt Blvd: Fairfield Inn7) 3840 N. Roosevelt Blvd: Roosevelt Station8) 3755 S. Roosevelt Blvd: Hampton Inn9) 3501 S. Roosevelt Blvd: East Martello10) 1500 Reynolds St: Casa Marina11) South/Simonton St: Southernmost Trolley Stop12) Corner of Truman/Duval St: Truval Village13) Corner of Angela/Duval St: Angela Street Depot

Key West: Old Town Secret Food Tour

2. Key West: Old Town Secret Food Tour

On our Secret Food Tour: Old Town Key West, we'll walk far from the tourist traps of Duval Street to show you the real city and its best food. After our two first delicious bites we take a leisurely walk and explore the history and culture of the city. You'll learn the stories of Key West's luck with affluence and how treasure ignited this tiny island into a global destination. Enjoy tropical soups, mouth-watering appetizers, gourmet tacos, exclusive island sweet treats and lots more. Plus there’s our amazing Secret Dish that you can only find about it on the day!

Key West: Southernmost Food and Cultural Walking Tour

3. Key West: Southernmost Food and Cultural Walking Tour

Celebrating the Cuban and Caribbean influences on both food and culture, enjoy a 3-hour guided small group experience. Visit 5 different locations, carefully chosen to help you check off those "must try" dishes that Key West is known for. Enough for a hearty lunch, tastings are served from locally adored eateries, unique "hole in the walls", and family-owned ethnic restaurants. Discover the spots that the locals frequent to eat, drink and discover the island. Between tastings, explore the island’s different cultural neighborhoods and rich history through the generations. Your knowledgable local guide will share stories of the local industry, Key West's colorful past, and historical landmarks. After the tour, explore Old Town with confidence and take advantage of recommendations on restaurants, attractions, entertainment, and cultural offerings. You'll also receive a collection of exclusive recipes, ensuring that you can enjoy memories from this tour for many years to come.

Key West: Hemingway's Life and Local Food Walking Tour

4. Key West: Hemingway's Life and Local Food Walking Tour

Discover the life of Ernest Hemingway while he lived in Key West on this guided walking tour. Uncover where the author lived, worked, and played. Stop to try three different samples of Key West cuisine as you walk.  Meet your guide at the front gate of the elegant residence where the author lived during the 1930s, Hemingway House. Make your way to get some local treats to help energize you for your walking tour. Try some delectable food like grilled chicken street tacos, conch fritters, and key lime pie. Find out where he watched and refereed boxing matches. See where he kept his boat the Pilar. Capture pictures of the bookstore where his books were sold. Stroll by his first apartment in Key West where he finished writing “A Farewell to Arms.” Make another stop to for some food before visiting where the author used to catch the train. Observe where he used to fish and charter boats. Finally, head to Sloppy Joes which was a favorite watering hole for the writer. 

Key West: Food Tasting and Cultural Walking Tour

5. Key West: Food Tasting and Cultural Walking Tour

Celebrate Key West's diverse and abundant local fruits of the sea. This 3-hour guided small-group experience stops at 6 tasting locations, each carefully chosen to give you an eclectic view of Key West's best restaurants along the historic seaport. Enough for a hearty lunch, tastings are served from adored local eateries, tucked-away hidden gems, and a fisherman-owned seafood market. This tour will allow you to bypass the Duval Street tourist traps and go straight to the spots that the locals frequent to eat, drink, and discover the island. As you stroll the charming side streets and docks, you will experience the island’s seaport, as well as the rich industrial history which has transformed through the generations. Your friendly and knowledgable local guides will share stories of local industry, including the colorful past and historical landmarks. Following the tour, you can explore Old Town with confidence and take advantage of recommendations on restaurants, attractions, entertainment, and cultural offerings. You'll also receive a collection of exclusive recipes, ensuring that you can enjoy memories from this tour for many years to come.

Key West: Off-Duval Cocktail Crawl

6. Key West: Off-Duval Cocktail Crawl

This craft cocktail crawl leads you through the side streets of Key West visiting a fun variety of locally-loved watering holes. Sample fun craft cocktails and tasty gourmet bites on this 3-hour upscale pub crawl. Visit over 5 establishments, ranging from a sleek bar within a historic hospital, a microbrewery inside the birthplace of PanAm, a tiki bar, and more. This tour veers vacationing drinkers off the infamous Duval Street into some of the city’s best and most locally-loved bars to sample fresh spins on old classics. Discover the iconic stories behind Key West’s signature drinks, like the Hemingway Daiquiri, and explore the sights, sounds, and “intoxicating” flavors of the tiki era. This bar hop is about getting off the touristy Duval Street and into more local lounges. Between tastings, you will stroll the charming side streets alongside Duval with protected, wild chickens. Your fun and friendly local guides will share bits of the town's colorful past and historical landmarks. Explore Old Town with recommendations on restaurants, attractions, and entertainment. Return home with exclusive recipes, ensuring that you can enjoy memories from this tour for many years to come.

Key West: History and Culture Southernmost Walking Tour

7. Key West: History and Culture Southernmost Walking Tour

Start your journey at the famous Kino Sandals Plaza, where you will meet with your local guide. On your walk listen to stories about how Key West became one of the wealthiest cities in the mid-1800s. Learn about the island’s shipwrecking industry, sponge harvesting, and cigar manufacturing.  The end of the tour will end at a buoy showing the Southernmost Point of the continental U.S. Here, your guide will give you free maps so that you can continue to explore the various shops,  museums, and other points of interest along this section of the island.

Frequently asked questions about Key West

What top attractions are a must-see in Key West?

What are the most popular museums and exhibitions in Key West?

Other Sightseeing Options in Key West

Want to discover all there is to do in Key West? Click here for a full list.

What people are saying about Key West

Overall rating

2.5 / 5

based on 2 reviews

This tour with Marjorie was our TOP 2 or even one for all of my friends who went. Marjorie was super knowledgeable, friendly, and could tell loved and takes pride in what she does. The food was delicious!! My friend has been to Key West at least 20 times, but did this for the first time. We highly recommend it!! We added the $17 alcohol drink package---of course & well worth it.

Very personable and knowledgeable guide - Chris. Excellent choice of restaurants; delicious food. Great hospitality and service. Only suggestion: End the tour in an air conditioned location that participants can cool off and chill out after the tour is over.

Really loved this food tour. We got to try restate hadn't tried before, and learned a lot of Key West history we didn't know. Our tour guide Sarah was great also! So glad we did it. Highly recommend it!

I don't want to give away the details, but it's well worth the time and fee. The food and drink tastings were excellent. We had a great time!

The experience was awesome. Maxwell knowledge and personal experiences with the various sites made for a most interesting day.