Southernmost Key West History and Culture Small-Group Walking Tour
Meet The Locals, On Foot, At Eye Level
If you’re like us, you think of travel as more than just “going places.” You crave experience and discovery, not just monuments and museums. You want to understand what’s behind the touristic façade that most people never penetrate. That’s why the Southernmost Walking Tour is the best way to immerse you into the history and culture of Key West! When you’re on foot, the world can’t slide past you faster than you can absorb it. You’ll have time – and proximity – to get up close to the region’s culture and natural history.
Start your tour at the famous Cuban sandal factory - Kino Sandals before heading off toward the Southernmost Point of the continental United States. Along the way, our incredibly knowledgeable and well-connected local guides will show you the most popular landmarks and introduce you to local culture. By the time you’re finished, you’ll have a uniquely fun perspective of our tiny island!
Private Fishing Charter from Ramrod Key
you'll be able to fish the Atlantic side of the Florida Keys and the Gulf side in the same outing if you so desire.
Key West: Sunset Sail + Reef Snorkel & Sandbar
Reef Snorkel + Sandbar & Sunset Sail
• Summer Only with Small Groups on an Honest Eco Tour.
What Makes this Eco Tour different?
• Guided Snorkeling
Your mate hops in the water with you and points out animals and shows you the best spots, ensuring you and your loved ones get the best experience on your tour.
• Small Groups
With a max group size of 24 guests and the warm calm weather of summer, you will see what makes an Honest Eco tour great for your group.
Who is this trip for?
We are a small family owned business, started by a biologist to offer authentic experiences that we would want to book.
• We cater to Couples and Families who want a nature experience and would prefer to avoid the packed party boats.
What is the Boat?
The boat is a wide open 42' sailing catamaran that immerses you in the nature experience. It has a head on board, and we offer Fresh Organic Fruit and Filtered Water, Safety equipment and really good snorkeling gear.
Private Looe Key Snorkel from Big Pine Key
Looe Key Marine Sanctuary is part of the Great Florida Reef, the only coral reef in the continental USA, and the third largest barrier reef system after the Great Barrier Reef in Australia, and the Palancar Reef in Mexico and Belize. It is a special place for snorkeling.
Key West Sunset Sail Aboard Legendary Schooner Appledore
Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th century, while enjoying the luxurious state-of-the-art accommodations of a modern passenger schooner. Her decks are spacious and comfortable. We limit passengers to just 36, guaranteeing you'll have room to move about and have an intimate evening experience. Feel the sense of adventure as the crew hoists the sails. Participate in this age-old tradition by helping raise the sails. Take a turn at the wheel and feel the exhilaration of captaining a traditional tall ship.
With the painted sky as an exquisite backdrop, your sunset sail takes you past Key West’s Historic Seaport, Mallory Square’s Sunset Celebration, the Navy Mole where the big ships dock and the civil war era Fort Zachary Taylor. Soak in these sights while enjoying a glass of premium wine, an icy cold premium beer, full cocktail bar or soft drinks.
Sunset Cruise
Come see for yourself why Marathon Mermaid is voted the #1 thing to do in Marathon! Watching the sunset by water is a must-do when visiting the Keys!
Private Boat Charter Key West, Dolphin Tour, Snorkeling & Sandbar
Escape the crowds and discover hidden sandbars on a private eco tour through Key West’s backcountry waters. Swim, snorkel, or simply relax on pristine beaches only accessible by boat, with a flexible itinerary customized just for you.
• Watch wild dolphins in their natural habitat
• Private eco-friendly tour, just for your group
• Cruise Key West’s beautiful backcountry waters
• Flexible departure times to fit your schedule
• Learn about marine life from a local guide
Marathon to Key West Private Tour of Florida Keys
Visit the one-and-only island city of KEY WEST!
Enjoy a narrated tour on the way down, and island music on the way back.
HIGHLIGHTS
• See the sights in Key West
• Stay for the Key West sunset
• Plenty of Free Time
• Designated Driver
• Narrated Tour
Do what you want in Key West! We're doing the driving!
Sightsee, enjoy a happy hour, eat a nice dinner, check out Mallory Square at sunset, take a sunset sail, and more!
Sit back & enjoy the scenery as we drive down to Key West. Learn the history, culture, and ecology of the Florida Keys & Key West from your friendly local guide.
See the Southernmost Point, Hemingway's House, Mile Marker Zero, Sloppy Joe's, and Mallory Square
It's more like a road trip than a tour - ask questions, point out wildlife, make new friends.
Kayak + Guided Snorkel & Morning Sail hosted by Honest Eco
I founded and own HONEST ECO. With Kentucky bluegrass roots and a B.S. in Biology, I found a world with a blue sea too alluring to ignore. I arrived to Key West in 2005. Now I have 10+ years of experience studying Biology and being on the water in Key West. I now own a small business with my wife and 2 young kids. We are trying to make a big impact by educating and leading by example. I'm very passionate about being respectful to the wildlife and the environment
Private Sunset Cruise around Key West
*Visit Stockislandboatcharters.com for alternate availabilities and pricing.*
Embark on a tour around the island of Key West on our 20 foot pioneer center console. Your guide will be talking you through many points of interest around the island. Make sure to keep an eye out for wildlife throughout the tour. About 20 minutes before the sunset, your captain will find a quiet and private spot to watch the sun drop into the water uninterrupted by other boats, people, or land!
Marathon FL Sandbar Cruise & Sightseeing Adventure
Discover the charm of Marathon, FL, with a delightful Sandbar Experience and Sightseeing Cruise. Enjoy a 4-hour adventure exploring the local scenery on a comfortable boat, complete with unique views of the island. Spend a relaxing day at the sandbar, where you can swim in the crystal-clear waters, or opt for kayaking and paddleboarding to enhance your aquatic adventure. Light snacks, drinks, and friendly crew members ensure a fun-filled day for all ages.
- 4-hour tour ideal for families and all ages
- Scenic boat ride to the sandbar with opportunities for swimming and water sports
- Light snacks and drinks provided; guests can bring their own food (no glass or hard alcohol)
- Relaxed atmosphere with ample time to enjoy the beautiful waters and surroundings
Key West Historic Bahama Village & Hemingway Heritage
Experience Historic Key West With A Small-Group Walking Tour
Ever wondered how the island of Key West was discovered and became so rich? Explore Key West’s history, lore, and legends from the ground up with an intimate walking tour. Whether you want to learn more about the island’s first industries such as shipwrecking and cigarmaking, are curious about local history, or are looking for a fun-filled walk, Key West’s Historic Districts are waiting for you!
This small-group walking tour offers both an educational experience and unparalleled delight for the lovers of history and culture. Our experienced local tour guides will lead you on an impressive stroll through the scenic streets of the Old Town where you can connect with the culture of a historic city. This unique experience is enjoyed by visitors from across the world and is a must-do while in Key West!
What to bring and to wear:
Comfortable clothing and shoes, sunscreen, hat, sunglasses, water.
Shark and Wildlife Viewing Adventure in Key West
This is the only shark tour in the USA and to our knowledge the only tour where guests do not get in the water to view the sharks. Delight in close-up views of sharks and a variety of other marine life. In this eco-friendly catamaran, travel through shallow waters to a location a few miles from shore, observing dolphins, stingrays, barracudas and native birds along the way. Bait is used to attract lemon, nurse and other types of sharks to the side of the boat. Learn all about Key West wildlife and enjoy complimentary soda, juice and chips throughout this family-friendly tour.
Guided Bike Tour of Old Town Key West
Ride with Key Lime Bike Tours for a truly unique and unforgettable Key West experience! See the islands top attractions with your own friendly knowledgable guide! Cruise Old Town, visit iconic landmarks, and hear stories about some of the colorful characters that have called Key West home. You will get the best Key West photos and see more in two hours then most visitors see their entire trip to Key West. Ride a bike from the Gulf to the Atlantic and see the Southernmost from Coast to Coast!
Voted Key Wests #1 Land Excursion 10 years in a row!
ALL OF OUR AMAZING RIDERS ALSO RECEIVE DISCOUNTS ON BIKE RENTALS AND OUR AWESOME MERCH!
Cold bottled water and Key Lime pie included!
Key West Jet Ski Tour: The Only 2-Hour Island Lap.
It's the only full 2-hour jet ski tour in Key West — a longer, more complete ride than the 60–90-minute harbor loops other operators run.
✅ A full 2 hours and a 28-mile loop all the way around the island
✅ Yamaha WaveRunner VX skis — fast, stable, and comfortable
✅ 5–6 scenic stops, from the Southernmost Point to sandbars and wildlife areas
✅ Small-group or fully private options
✅ Local guides who share island history and insider tips
Island Sunset Cruise 2 Hour Catamaran Tour in Marathon Florida
Cruise into a stunning Florida Keys sunset aboard a comfortable 53’ catamaran. Your crew will guide you through the waters surrounding Marathon, passing local landmarks such as Boot Key Harbor, the Atlantic Ocean, and the historic Seven Mile Bridge.
Relax on deck and enjoy the changing colors of the sky while sipping a complimentary champagne toast. The catamaran offers plenty of seating, shaded areas, an onboard restroom, and a cooler stocked with ice, water, and soda.
This tour provides a laid-back and memorable way to experience the Keys at golden hour—perfect for couples, families, and anyone who wants to unwind on the water.
Sunset Sail Cruise in Key West
Sailing on the Rover is an exciting, traditional sailing experience with a Hint of Piracy! Yes - We have cannons! Come sail on Key West's most photographed ship! The Schooner Jolly II Rover is the only squared rigged, topsail schooner in the Historic Seaport! It is Key West's famous "Red Sails in the Sunset" Tall Ship! There is no band playing or loud music. We go sailing! Plenty of room to get up and mingle with other guests. Help raise the sails! Steer the ship! Shoot the cannons! Or just sit back and relax!
Key Lime Pie Walking Tour of Key West Historic Seaport
Taste the sweetest adventure in Key West—sunshine, stories, and the island’s most iconic dessert. Led by a Key West expert who’s part historian, part foodie, and fully obsessed with the island’s iconic slice, this small-group tour is a feast for all your senses. Wander the Historic Seaport while savoring three decadent Key Lime Pie tastings, each with its own tropical twist, and sip a refreshing Key Lime cocktail. Along the way, your guide shares insider tales, quirky legends, and secret local spots you won’t find in any guidebook. Fun, flavorful, and unforgettable—this is the Key West experience you’ll be raving about long after the crumbs are gone.
The Original Key West Island Jet Ski Tour from Barefoot Billy's
Billy started his Island Jet Ski Tour in 1992. There are many imitators, but only one Original Island Jet Ski tour! Our guides are licensed and local, so they know the waters surrounding our island like their backyard - because it is!
Full Island Loop: You completely circle Key West, a trek that is impossible for most larger boats due to shallow backcountry waters.
Sightseeing from the Water: You get unique vantage points of famous landmarks, including the Southernmost Point buoy, Mallory Square, and Sunset Key.
Marine Life: The route passes through the Key West backcountry (mangroves), where it's common to spot dolphins, sea turtles, rays, and tropical birds.
Freestyle "Play" Time: Unlike strictly regimented tours, this includes a dedicated "free play" segment where you can go full throttle, practice carves, or jump wakes in a safe, open-water zone.
Key West Wreckers Race Aboard Schooner America 2.0
Join in on the annual Wreckers Race and take part in a fast pace race toward Sand Key Lighthouse aboard Schooner America 2.0! Back in the day, pirate ships from afar often ran aground on Sand Key Reef, nine miles off the southern coast of Key West. When all the sailors in Key West heard there was booty to be had, they'd get in their boats and race each other out to the reef. The first one there could claim the ship's cargo. Today, we celebrate it with the firing of the canon to start the race, and all of the schooners of Key West are on their way in a one-way race to Sand Key Lighthouse! The boat that gets there first, "wins"!
Key West USCGC INGHAM Maritime Museum
The USCGC INGHAM was the longest continually serving, most decorated ship in Coast Guard History.
Serving in active duty from 1936 to 1988. Only remaining American ship afloat to have fought in the Battle of the Atlantic. Command ship for several Philippines landings including General Douglas MacArthur's return to Corrigedor, he was aboard during this action. First allied vessel into Chinese waters at wars end. Two Presidential Unit Citations for support missions in Viet Nam. Also part of the Mariel Boatlift, when tens of thousands of Cuban refugees left their island home seeking refuge in the U.S.
Now a National Historic Landmark and Coast Guard National Memorial to Guardsmen that have lost their lives in World War Two and Viet Nam.
The Ingham also offers one of the best sunset views in Key West.
Private Key West Sandbar and Paddle by Boat
Enjoy a private half day adventure for up to 6 guests aboard our late model pontoon boat. Guests may discover and observe diverse marine habitats and wildlife refuges as well as spot an abundance of marine birds and sea life. Paddle on your own via kayak or paddleboard through natural, winding, mangrove lined tidal creeks and then relax on a sandbar or island on one of our floats. Bring your own snacks and drinks and your dog!
Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres
The Wind & Wine Sunset Sail offers a boutique experience unlike any other in Key West! This isn’t your typical party boat—it’s a calm, uncrowded sail aboard a historic schooner with an intimate, relaxed vibe. You’ll enjoy a guided tasting of fine wines from around the world, along with a selection of craft and domestic beers and light hors d'oeuvres including crudites, meats, cheeses, crackers, fruit, and chocolate.
With small group sizes, there’s plenty of space to move around and enjoy the view without the crowds. It’s perfect for a romantic date or a fun evening with friends—upscale, but never uptight.
What really sets this trip apart is the crew. They’re fun, welcoming, and passionate about what they do—ready to pour your next glass, share a story, or make sure you’re having a great time. Add in a Key West sunset, and you’ve got one of the most unique and enjoyable evenings on the water!
Classic Key West Schooner Sunset Sail with Full Open Bar
There's no better way to savor the magic of a Key West sunset than aboard a majestic schooner, complete with a full open bar. This enchanting journey blends the timeless elegance of traditional sailing with the lively spirit of Key West, promising an unforgettable experience for all.
As you sail further into the sunset, the full open bar comes to life, offering an enticing array of cocktails, wines, and spirits to complement the evening's splendor. Sip on our signature Schooner Bloody Mary or Dark & Stormy as you watch the sky ignite with color. The skilled bartenders are on hand to craft your favorite drinks, ensuring that your glass is never empty as you drink in the sights and sounds of the sea.
As the schooner begins its journey back to Key West, you find yourself lost in the timeless rhythm of the sea, grateful for the opportunity to witness the beauty of a Key West sunset from the deck of a historic schooner.