1. Old Town Trolley Tours – 1-Day Key West Tour
Skip the hassle of parking a car and hop on this local narrated bus tour that includes thirteen stops at Key West landmarks. The visitors have the ability to “Hop on Hop Off” trolleys to explore the area or return to their hotel and finish the tour later in the day.
Guided Trolley Tours in Key West
This 90 minute tour will find you riding high above the streets while the driver-guide tells the unique history of Key West and points out some cool spots to check out. I really love these sightseeing tours because it serves as a great form of transportation to get around the island too.
The Old Town Trolley Tours start running at 10am and stop at 4:30pm every day which gives you plenty of time to check out local restaurants, museums, bars, and shopping along the way. The One-Day trolley ticket costs $55.60 for adults, $20.95 for children ages 4-12 and children under 4 ride for free.
2. Key West Extreme Adventures – Shark and Wildlife Tours
The two-hour catamaran trip aboard “Tiger Cat” at Key West Extreme Adventures is ideal for anyone wanting to see sharks in their natural habitat. You will cruise about 2 miles through the calm waters of Key West into the back country looking for sharks and other wildlife.
Once at the spot the crew starts dropping bait into the waters to lure lemon and nurse sharks to the boat. I don’t know what they are using for bait but let me tell you… it works. Within a few minutes there are tons of sharks circling around the boat.
This wildlife boat tour starts at 10am and 1pm daily in season. Tickets are $89 for adults and $49 for children 6-16 and kids under 6 are free.
3. Key West Food Tours – Southernmost Food Tasting & Cultural Walking Tour
Visitors say the cuisine sampled during a visit to Key West is unforgettable. This 3-hour walking tour focuses upon the impact Cuban and Caribbean cultures have on local cuisine and culture.
Starting with El Siboney, a Cuban restaurant, on Catherine Street and throughout this five stop tour you will find yourself immersed in the flavors of the island. Samples might include fish tacos and Cuban Roast Pork, Conch Fritters, along with rum cocktails and Key Lime Pie.
Explore a unique island cuisine
Your tour guide will cover local history and interesting facts about Key West along the way to The Speakeasy Inn & Rum Bar. The tour will take you off the beaten path and deep in the neighborhoods of Old Town Key West to give you a good feel for the culture that inspired our unique island cuisine.
One great stop on this Key West tour is Mangoes, who’s Caribbean inspired cuisine will leave you wanting more. Kaya Island Eats opened just last year and has quickly become a favorite among the locals. The introduction to flavors of Key West could be complete without the final stop at Cuban Coffee Queen to sample a Cafe’ con leche.
Rates are $79 for adults and $49 for children ages twelve and younger.
4. Lazy Dog Adventures – Key West Kayak Eco-Tour
Lazy Dog Adventures Mangroves tour starts from the Cow Key Channel about 4 miles east of Duval Street and the hustle and bustle of Old Town Key West. This slow-paced excursion is perfect for beginners or paddlers of varying abilities and is even dog friendly!
Kayaking through the mangroves
During this two-hour kayak tour guides will lead you through the calm mangrove channels at a leisurely pace. Most of the channels are mere inches deep and the crystal clear water allows you to spot loads of marine life and tropical fish. The guides share knowledge of this mangrove habitat in the Florida Keys.
What I love about this tour is how informal it is. The tour guides really let you go at your own pace and make sure that you find what you want to see even if its hidden in the mangroves.
Lazy Dog offers single and double kayaks in case you wanted to paddle with a friend! Adults Tickets are $55, Children are $40.
5. All Aboard the Conch Tour Train!
This three stop – 75-minute narrated tour takes you on a loop through the streets of Old Town Key West. This is the perfect tour if you are looking to save some steps getting around Old Town and cover some real ground in a day. Guests can feel free to hop on or off at any of the three stations throughout the city. The Drivers are a wealth of knowledge about Key West and are sure to entertain.
Stop One – Station Depot
At the corner of Front Street and Duval Street is Station Depot. Here you might want to hop off for a bit and explore the area. A few spots I suggest while you are here are The Truman Little White House, Key West Aquarium, Mallory Square, Key West Shipwreck Treasure Museum, The Customs House, and of course a refreshment at Sloppy Joes Bar.
Stop Two- Truval Village
Truval Village is on the corner of Duval Street and Truman Avenue. This Conch Tour Train stop in the heart of the city is just steps away from The Ernest Hemmingway Home and Museum, Key West Lighthouse, Key West Butterfly & Natural Conservatory, and Southernmost Point.
Stop Three- Sails to Rails Museum
Sails to Rails Museum at Flagler Station is the original Train Station for Henry Flagler’s 1912 railway. At this Historic Seaport location you can grab a beer at the ever exciting Schooner Wharf Bar or Enjoy a meal at the oldest restaurant in town, Pepe’s Cafe. Go wander the docks and be sure to check out the Tarpon feeding in front of A&B Lobster House.
The First Conch Tour Train of the day leaves at 10:15 am and the last tour at 4:15. The one day ticket costs $47.20 for adults, and $20.95 for children ages 4-12.
6. Key West Ghost & Mysteries Tour
It’s not unusual to find ghosts lurking on Key West streets after dark. This spooky 90-minute stroll departs daily from the Porter Mansion on Caroline Street and will take you through haunted areas in the town which most visitors will never get to see.
One of Key West’s most historic graveyards is one stop on this bone chilling tour. The Artists House which was the long time prowl of Robert the Doll is guaranteed to make the hari on your neck stand. Other Stops include Casa Antigua, The former Club Chameleon, and a stroll through the former home of a well-to-do Key West family that is now the Hard Rock Cafe.
Tours are daily and Prices start at $23 for adults and $15 for children. Discounts are available for military personnel.
7. Private Sandbar Charter with Casual Monday Charters
One of the most under rated Key West excursions is hopping on a boat and taking the trip out to the sandbars with Casual Monday Charters. These hidden gems of sand lie just offshore in only a few feet of water and sometimes no water at all depending on the tides. At low tide the exposed sand leads to a once in a lifetime Key West experience to complete your Key West island adventure.
This tour departs from Hurricane Hole Marina where you and up to 5 friends board the boat bound for the shallows to the north. This tour is BYOB so I recommend packing your own alcoholic drinks for the trip.
Once aboard the Captain will be happy to share fun facts about the area and point out all sorts of local marine life along the way. The sandbars are a peaceful and tranquil place to relax and enjoy the day while wading in the warm water of the Florida Keys Marine Sanctuary. Crack a beer and float, enjoy the sun, listen to the sound of nature or the boats killer stereo. This is by far one of my favorite sandbar tours in Key West and is not to be skipped!
This private 4 hour excursion is $650.00 for up to 6 guests. For another $50.00 they let you combine this tour with the snorkel tour for a complete Key West experience.
8. Sunset Watersports – Key West Rise and Reef Morning Snorkel
This morning snorkel trip begins with a seven-mile boat journey to Florida Reef, the third largest coral reef on the planet. The 3-hour tour starts at 9am each day and includes snorkeling equipment and instruction. Relax with a warm sea breeze on your face as you cruise out to the reef aboard the company’s newest and fastest 65 foot catamaran.
Once you arrive and instruction is given you can hop into the water where you can see tropical fish, turtles, and lobster while you enjoy snorkeling in the clear turquoise waters of Key West. The 358 Mile long living coral barrier reef is a known habitat for Sea Turtles, Tangs, Parrot Fish, Rays, Corals, and Sponges. Guests praise their catamaran’s excellent service and knowledgeable staff.
After snorkeling all morning guests can hop back aboard and enjoy complimentary Fruit, Cereal, Muffins, and Juices and soft drinks. Unlimited beer and wine are available after snorkeling and on the ride back to the harbor. Tickets are $40.95 for adults, $22.95 for children ages 6-15 years, and 5 and under are FREE. If you haven’t had enough vitamin sea by the end of the day check out their Sunset Sail.
9. Truman’s Little White House
If you are visiting Key West you may not be aware of this incredible home located in the Truman Annex on the western edge of Key West harbor. This hidden gem is one of the most overlooked Key West tours.
Come see where the 33rd US President Harry S. Trumann came to rest and relax at his “Camp David”. On this one hour guided tour of the property one of the extremely knowledgeable historians on site will walk you through the house and grounds. Come hear about the notable residents and guests of the Truman Little White House such as William Howard Taft, Dwight D. Eisenhower, John F. Kennedy, Jimmy Carter, Bill Clinton and Thomas Edison.
Explore the living spaces and bedrooms of the home while seeing it in its preserved state. If you’re interested in history this is one of the best Key West tours around. The home is an immaculate time capsule that was sealed the day that Truman left.
White Glove VIP Tours
If you are looking for a tour that is a bit over the top the White Glove VIP Tour is not to be missed. Along with getting to sit at Harry’s custom poker table for a rare photo op, you will be able to enjoy an alcoholic beverage from his personal bar. Topping this tour off is a tour of the Truman Waterfront in his ultra rare 1950 Lincoln Cosmopolitan Limousine. I mean how many chances do you get in life to ride in a presidential limousine?
Tickets are $24.67 for adults, $10.75 for children 4-12, and under 4 is free.
10. Danger Charters – Wind & Wine Sunset Sail
Take a ride on Danger Charters’ 65-foot sailing yacht on their two hour Wind & Wine Sunset Sail. This sunset excursion offers a breathtaking view of the Key West sunset as it falls below the horizon. This Sunset sail is the perfect way to end an incredible day in Key West.
Once aboard a wide variety of appetizers are available like Havarti Dill, Smoked Gouda, Brie, and Summer Sausage but the real winner is the wine. Can you really call this a wine tasting cruise if you don’t taste all 8 wines from around the world? If the wine does not interest you, no worries there are plenty of beer options available too.
One thing I love about Danger Charters sunset sail is that they keep it small when compared to other sunset cruises. Their boats are limited to 25 passengers which is nice if you’re avoiding the crowds. Guests can experience an unobstructed sunset while enjoying a nice glass of wine without feeling too cramped.
f your looking for the best sunset cruise in Key West you don’t have to look any further, these guys are it. One thing to note is that I would recommend bringing a light jacket along, after sunset it gets a bit chilly at times. Adult tickets are $109.00 each and this tour runs all year long.