Key West offers more than sun and beaches—it’s a culinary playground packed with flavors from the Caribbean, Cuba, and beyond. What sets Key West apart is its small, colorful neighborhoods where local eateries serve fresh seafood, tropical drinks, and Caribbean-inspired dishes, often with a side of fascinating stories. We especially like the Key West Historic Seaport Food & Walking Tour for its fresh pink shrimp, white wine, and history lessons, making it a perfect introduction for newcomers. Whether you’re into seafood, Cuban cuisine, or sunset drinks, these tours offer authentic bites and insider insights.
Below, you’ll find a curated list of the best food experiences in Key West, each with its own signature focus—some explore history while others highlight local seafood, Caribbean influences, or sunset sails with bites. From small-group walking adventures to private gourmet tours, there’s an option here to match your style and appetite.
1. Key West Historic Seaport Food & Walking Tour
At number 1 is the Key West Historic Seaport Food & Walking Tour, which has earned a perfect 5.0 rating from over 600 reviews. This 3-hour stroll takes you through Key West’s colorful Historic Seaport and nearby neighborhoods, where you’ll sample locally caught pink shrimp, spiny lobster, and other delicious options. The tour is led by a knowledgeable local guide who shares stories about the area’s maritime past and culture.
What makes this tour stand out is the combination of food and history, with stops at Garbo’s Grill, a seafood-focused American eatery, and the Eaton Street Seafood Market, where you enjoy Key West pink shrimp paired with white wine. The small group setting allows for personal interaction, making it ideal for travelers eager to learn about local food and customs. Many reviewers praise the guide’s friendliness and the quality of the food, with some mentioning they wish they’d started their trip here.
Bottom Line: Great for first-timers and seafood lovers wanting an engaging, relaxed introduction to Key West’s culinary scene.
2. Key West Walking Food Tour With Secret Food Tours
At number 2 comes the Key West Walking Food Tour With Secret Food Tours, which has a perfect 5.0 rating from 237 reviews. This 2.5-hour tour is designed for those who want a balanced mix of culture, history, and flavor. It offers a curated tasting experience that explores lesser-known eateries and neighborhoods off the usual tourist trail.
You’ll start at the Mel Fisher Maritime Museum, then move through charming streets, sampling local specialties like conch fritters and fish tacos. The tour also includes a rum tasting, giving you a taste of the Caribbean influence that runs deep in Key West. The guide does an excellent job of blending food with storytelling, making each stop both tasty and educational. Many walkers appreciate the intimate size of the group and the focus on authentic local cuisine.
Bottom Line: Perfect for foodies who want to see the city from a local perspective and enjoy diverse, well-curated tastings.
3. Key West: Schooner Sunset Sail with Food & Drinks
Number 3 is the Key West: Schooner Sunset Sail with Food & Drinks, rated 4.9 from over 300 reviews. For those wanting a relaxing evening, this 2-hour sail on a beautiful schooner offers a fantastic sunset experience with plenty of snacks and drinks. You’ll feel the wind in your hair as you cruise past Key West’s shoreline, watching dolphins and waterbirds.
The highlight is the Green Flash, a rare optical phenomenon that occurs right at sunset, and the chance to enjoy hors d’oeuvres and cocktails on deck. The relaxed atmosphere, combined with stunning views, makes this ideal for couples or anyone looking to unwind after a day of sightseeing. It’s less about eating a full meal and more about enjoying a special moment in style.
Bottom Line: A scenic, romantic way to end the day, with light bites and a good chance to see wildlife and the sunset.
4. Key West Signature Sunset Cruise with Open Bar, Food & Music
Number 4 on our list is the Key West Signature Sunset Cruise, rated 4.5 from hundreds of reviews. This 2-hour cruise features an open bar, appetizers, and lively music, making it a fun, social way to enjoy an evening. The boat is a comfortable catamaran that takes you along the coastline while you sip cocktails and nibble on tasty hors d’oeuvres.
The live music adds a festive touch, and the open bar means you can indulge in your favorite drinks as the sun dips below the horizon. This tour is excellent for groups wanting a lively, party-like atmosphere combined with beautiful scenery. It’s a good value for those who want a bit of everything—drinks, music, and sunset views.
Bottom Line: Perfect for those seeking a lively, all-in-one sunset experience with drinks and music included.
5. Key West: Cuban and Caribbean Food and Cultural Walking Tour
Coming in at number 5 is the Key West: Cuban and Caribbean Food and Cultural Walking Tour, with a high rating of 4.9 from 88 reviews. Over three hours, you’ll explore the influence of Caribbean and Cuban flavors on local cuisine through five generous tastings, including conch fritters, fish tacos, and key lime pie.
This tour shines with its focus on cultural storytelling—your guide shares insights into how these influences shaped the island’s food and traditions. It’s ideal for travelers who want more than just food, gaining a deeper understanding of the multicultural roots of Key West. The small group size ensures an intimate experience, and many reviewers mention how the guide’s insights added value.
Bottom Line: A flavorful, culturally rich experience perfect for those interested in the melting pot of Key West’s culinary scene.
6. Key West: Secret Walking Food Tour
Rated 4.9 from 22 reviews, the Key West: Secret Walking Food Tour is a three-hour journey into the city’s lesser-known culinary corners. It takes you far from the touristy spots into historic neighborhoods where authentic flavors thrive.
Led by a passionate guide, you’ll explore the cuisine and architecture of the Old Town district, tasting local delicacies, and learning fascinating stories along the way. The tour is designed for those who want to experience Key West as the locals do, with food included at every stop. Reviewers appreciate the authentic feel and the depth of local stories shared.
Bottom Line: A great choice for travelers who want a genuine, off-the-beaten-path taste of Key West’s food and culture.
7. Private Secret Food Tour of Key West
At number 7 is the Private Secret Food Tour of Key West, which provides a personalized experience with a dedicated guide. This 2.5-hour tour costs $370 per person and focuses on showing you the city’s most authentic flavors away from the crowds.
The tour hits spots like the Mel Fisher Maritime Museum and the Key West Aquarium, blending food with local history, culture, and stories. It’s perfect for travelers seeking an exclusive, tailored experience, with the guide sharing insights based on your interests. Although more expensive, many reviews highlight how this tour offers in-depth knowledge and a private, relaxed vibe.
Bottom Line: Best suited for food lovers wanting a private, customized tour with in-depth local stories.
8. Key West: Hemingway’s Life and Local Food Walking Tour
Number 8 is the Hemingway’s Life and Local Food Walking Tour, rated 5/5 from 3 reviews. Walking in Hemingway’s footsteps, this 2-hour tour explores the landmarks of his life and includes tastings of local specialties.
You’ll see where he lived, wrote, and fished, while learning fun facts about his time in Key West. The tour pairs literary history with culinary treats, making it ideal for fans of Hemingway or anyone wanting to combine culture with food. Reviewers mention how the guide makes the stories come alive, adding a personal touch to the experience.
Bottom Line: A unique mix of literary history and local cuisine, perfect for Hemingway fans or those seeking a cultural flavor.
9. Exploring and Walking Food Tour of Cayo Hueso
Rated 5/5 from just one review, this Exploring and Walking Food Tour of Cayo Hueso offers a 2.5-hour deep dive into local flavors. It begins at Doing Work Coffee, includes stops at Mallory Square, and ends at Bo’s Fish Wagon, with plenty of authentic tastings along the way.
This tour emphasizes local stories and secret spots, giving you a more personal look into the city’s culinary scene. It’s suited for travelers who want a small-group, relaxed experience that combines sightseeing with delicious bites. Reviewers praise the friendly guide and the chance to see parts of Key West many visitors miss.
Bottom Line: An intimate, flavorful adventure ideal for those wanting to explore Key West’s core neighborhoods with tasty stops.
$80.00 per person
10. Southernmost Food & Cultural Walking Tour by Key West Food Tours
This highly-rated tour, with over 1,490 reviews and a 5.0 rating, offers a comprehensive 3-hour culinary walk through Old Town. It includes tastings at local “mom and pop” eateries, featuring seafood, Cuban classics, and key lime pie. The guide provides insights into the city’s architecture, history, and food traditions, making it perfect for those wanting an all-encompassing local experience.
Participants love the relaxed pace and the variety of flavors, with many considering it a hearty lunch in itself. It’s especially suited for travelers interested in learning about Key West’s diverse culture while savoring authentic dishes. The small-group size ensures personalized attention and a detailed narrative.
Bottom Line: For the most complete taste of Key West’s culinary and cultural scene, this tour is a top pick.
$90.19 per person
11. Key West Street Food Private Local Guided Tour
Finally, the Key West Street Food Private Local Guided Tour offers a tailored experience focusing on street eats like shrimp and Key lime pie. Priced at $372.49 per person, this private tour lasts about 3 hours and highlights the city’s street food culture with a guide who shares behind-the-scenes stories.
The tour visits spots like Kermit’s Key Lime Shoppe and Sandy Bottoms Charter, combining food, local history, and scenic views. It’s ideal for travelers who prefer a personalized, flexible experience with a gastronomic focus. While pricier, reviews suggest it offers a deep dive into the city’s flavors while enjoying exclusive access and tailored attention.
Bottom Line: Best suited for foodies wanting a private, customizable tour with insider stories.
$372.49 per person
How to Choose the Best Food Tour in Key West
When selecting your ideal food experience, consider your interests and how much time you have. If you want a broad overview of local seafood and history, the Key West Historic Seaport Food & Walking Tour offers great value for three hours of walking and tasting. For those eager to explore Caribbean influences and cultural stories, the Cuban and Caribbean Food and Cultural Walking Tour provides a more in-depth cultural experience.
Budget-wise, the group tours like the Southernmost Food & Cultural Walking Tour strike a nice balance between cost and content, while the private tours suit travelers wanting exclusivity and personalized attention. Consider your physical activity level, as most tours involve walking, and book early during peak season to secure your spot.
Final Thoughts
Key West’s food scene offers a diverse array of flavors and stories, from historic seafood spots to Caribbean-infused dishes. For a relaxed introduction, the Key West Historic Seaport Food & Walking Tour is a personal favorite, combining history with fresh seafood in a charming setting. If you seek cultural depth, the Cuban and Caribbean Food and Cultural Walking Tour makes for an engaging, flavorful experience.
For sunset lovers, the Schooner Sunset Sail offers a peaceful way to unwind with snacks, wildlife, and spectacular views. Whether you’re after a lively party cruise or a private gourmet journey, booking in advance ensures you won’t miss out on these delicious adventures.