Walking tours dominate Key West’s historical scene, each offering distinct perspectives on this fascinating island. The Historic Seaport Food & Walking Tour stands out by combining local flavors with maritime stories – it’s especially good in the early evening when temperatures cool. For industrial heritage buffs, the Southernmost Walking Tour delivers compelling tales of shipwrecks and the once-booming cigar trade. Architecture enthusiasts will appreciate the Historic Homes tour, which showcases preserved 19th-century buildings while explaining their significance to Key West’s development. The Florida Keys Nature & History Tour effectively connects human history with the island’s unique ecosystem. For an extraordinary perspective, parasailing tours provide stunning aerial views of the historic seaport. Let’s explore the best historical tours Key West has to offer…
Key Points
- The Key West Historic Homes and Island History Tour offers a 99% recommendation rate, exploring historic buildings with engaging storytelling.
- The Southernmost Key West History and Culture Tour provides a 5-star rated, intimate experience covering significant landmarks like the Hemingway Home.
- The Southernmost Walking Tour is a 1.5-hour guided tour with a 4.9/5 rating, covering shipwrecking, sponge harvesting, and cigar manufacturing.
- The Key West Conch Train Tour showcases top sights, including admission to the Sails to Rails Museum, with live commentary on pirates and famous residents.
- The Key West Historic District Small-Group Tour has a 5.0 rating, covering 1.4-1.8 miles and providing stories, photos, and historical documents.
Historic Seaport Food & Walking Tour by Key West Food Tours
The Key West Historic Seaport Food & Walking Tour by Key West Food Tours offers a gourmet walking experience through the vibrant neighborhoods of downtown Key West.
Led by a knowledgeable local guide, the tour explores the area’s history and culture while treating guests to a variety of locally caught seafood and other culinary delights.
With 549 reviews and a 98% traveler recommendation, this tour comes with a Badge of Excellence.
The 5-hour experience includes food and drink tastings at 5 locations, as well as exclusive coupons and recipes.
Although not suitable for vegetarians or vegans, the tour can accommodate various dietary requirements with advance notice.
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Key West: History and Culture Southernmost Walking Tour
Enjoy the rich history and captivating culture of Key West on the Southernmost Walking Tour. This 1.5-hour guided experience takes you through the island’s past, from its shipwrecking and sponge harvesting industries to its cigar manufacturing legacy.
Along the way, you’ll visit the Southernmost Point of the continental U.S. and receive maps for exploring shops, museums, and other attractions at your leisure.
Suitable for most travelers, the tour operates rain or shine, covering 1.4 to 1.8 miles in warm weather.
With a 4.9/5 rating from 10 reviews, this tour provides an engaging and informative introduction to Key West’s vibrant history and culture.
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Parasailing Over the Historic Key West Seaport
Parasailing over the historic Key West Seaport offers an exhilarating adventure for thrill-seekers. Available for singles, doubles, and triples, the activity is perfect for friends and families.
Departing from the Sunset Watersports booth, the tour includes a parasail ride, gratuities, and an optional photo package. While not wheelchair accessible, most travelers can participate, with a maximum of 12 per tour.
Priced from $74.95 per person, the experience earns 4.5 stars from 170 reviews, which highlight the friendly crew and breathtaking views. However, some mention issues with professionalism and service duration, suggesting room for improvement.
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Key West Historic Homes and Island History – Small Group Walking Tour
Guests can explore Key West’s rich history and iconic architecture on the Key West Historic Homes and Island History – Small Group Walking Tour.
With 373 reviews and a 99% recommendation rate, this small-group tour takes visitors on a journey through historic buildings like Casa Antigua, Curry Mansion Inn, and Truman Annex Park.
Led by professional, friendly, and knowledgeable local guides, the tour provides a personalized experience for up to 12 people. Guests can expect engaging storytelling and insights that enhance their appreciation for Key West’s past.
Convenient amenities, such as rain ponchos and bottled water, are included. The tour is accessible for strollers and wheelchairs, making it suitable for travelers of varying fitness levels.
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Florida Keys Nature & History Tour From Key West
This tour provides travelers with a captivating exploration of the natural wonders and historic sites scattered across the Florida Keys.
Riding along the Overseas Highway and over 20 bridges, guests visit Bahia Honda State Park, the National Key Deer Refuge, and the Blue Hole.
They’ll walk on the Old Bahia Honda Bridge, taking in views of famous beaches. Wildlife sightings may include key deer, alligators, turtles, and rare birds.
The tour includes hotel pickup, snacks, and entry fees, with a knowledgeable local guide providing live commentary.
Rated 4.9 with a 97% recommendation rate, this half-day adventure offers an immersive experience of the Keys’ natural and historical treasures.
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Sunset Sail on Historic Schooner in Key West
For a captivating sunset sail on the historic schooner “When And If!” in Key West, visitors can embark on a memorable journey.
The schooner, built for General Patton in the 1930s, offers a family-friendly experience with a 4.8-star rating and a Badge of Excellence.
The evening cruise features complimentary cheese boards, the opportunity to take the helm, and potential wildlife sightings.
Travelers can enjoy included wine tasting, select beer and wine, and a champagne upgrade.
With ample free parking and a maximum of 28 guests, this sunset sail provides a scenic ocean escape from the tourist crowds.
Reviews highlight the knowledgeable crew and the historical significance of the vessel.
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Southernmost Key West History and Culture Small-Group Walking Tour
Visitors to Key West can explore the island’s rich history and vibrant culture on the Southernmost Key West History and Culture Small-Group Walking Tour.
This 5-star rated tour takes guests through Old Town Key West, including stops at the Ernest Hemingway Home and Museum, the Southernmost Point, and the Audubon House & Tropical Gardens.
Along the way, the knowledgeable guides share insights into Key West’s shipwrecks, cigar manufacturing, and treasure hunting history.
The tour is suitable for moderate fitness levels, covering 1.4-1.8 miles at a moderate pace.
With a maximum group size of 10, the tour provides an intimate and personalized experience.
Visitors can expect an informative and enjoyable excursion, perfect for first-time visitors to the island.
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Key West Conch Train Tour: Explore Iconic Sights and History
The Key West Conch Train Tour offers visitors a captivating and informative sightseeing experience that explores the iconic attractions and rich history of this vibrant island.
Operating for over 50 years, the 1-hour 30-minute tour departs from Front Street Depot and concludes at Mallory Square, showcasing Key West’s top sights, including the Southernmost Point and the Key West Aquarium.
Knowledgeable guides provide live commentary, sharing stories of pirates, Native Americans, and famous residents like Ernest Hemingway and Harry Truman.
The tour includes admission to the Sails to Rails Museum, free walking tours, and various discounts, making it an accessible and value-packed experience for travelers.
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Key West Historic District Small-Group Walking Tour
Enjoy the captivating history of Key West’s Historic District on this small-group walking tour. Rated 5.0 with 234 reviews, this 2-hour tour covers 1.4 to 1.8 miles and showcases the island’s rich history, lore, and legends.
Led by knowledgeable local guides, you’ll visit famed landmarks and hidden gems, learning about the area’s architecture, cultural influences, and historical events. The small-group experience ensures personalized attention, and includes stories, photos, and historical documents for enhanced learning.
With moderate physical fitness required and accessibility for service animals and strollers, this tour provides an authentic Key West experience that’s highly recommended by 99% of travelers.
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Key West Art History Private Tour
This private Key West Art History Tour offers travelers a unique opportunity to explore the island’s vibrant art scene.
With a 100% recommendation rate from previous guests, the tour takes participants on a curated path through various art exhibitions, culminating at the renowned Studios of Key West.
Along the way, guests can engage with local artists and gain insider perspectives on the community.
The tour is wheelchair accessible and suitable for most travelers, though not recommended for those with specific medical conditions.
Reviewers praise the knowledgeable guides, Lindsey and Ryan, for their enthusiasm and expertise in bringing Key West’s artistic legacy to life.
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Sum Up
Key West’s historical tours offer an immersive experience, allowing visitors to discover the island’s rich past. From walking tours that highlight its architecture and culture to boat excursions showcasing the scenic coastline, there’s something for every interest. These tours provide an engaging and informative way to explore the Southernmost city’s unique heritage and captivating stories.