Key Largo/Islamorada to Key West Private Day Tour Florida Keys
Description
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. This is way more than just a shuttle service. HIGHLIGHTS • See the sights in Key West • Stay for the Key West sunset • Plenty of Free Time • Stops of your choosing along the way • Designated Driver • Narrated Tour Do what you want in Key West! We're doing the driving! During your free time we recommend to sightsee, enjoy a happy hour, eat a nice dinner, check out Mallory Square at sunset, take a sunset sail. There's so much to do! 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. It's more like a road trip than a tour - ask questions, point out wildlife, stop to visit the Florida Keys landmarks of your choosing and more!
Tour Options
Itinerary
The Old Seven Mile Bridge in Marathon, Florida, is a historic landmark and engineering marvel. Originally part of Henry Flagler's Overseas Railroad, completed in 1912 which was the longest bridge in the world when it was built., it linked the Keys by rail. After hurricane damage, it was converted for automotive use. Now, a 2.2-mile section is a beloved pedestrian and cycling path, offering stunning ocean views and access to historic Pigeon Key, which once housed railroad workers. It's a testament to ingenuity and a popular spot for recreation and enjoying the Keys' natural beauty.
Experience the spectacular views along the Overseas Highway from the comfort of our customized touring van with panoramic windows.
Robbie's of Islamorada, located on the Overseas Highway, is a quintessential Florida Keys roadside attraction. Famous for its unique tarpon feeding experience, visitors can hand-feed massive "silver kings" right from the dock. Beyond this iconic activity, Robbie's is a bustling marina offering boat and kayak rentals, fishing charters, snorkeling trips, and jet ski adventures. It also features the Hungry Tarpon Restaurant, souvenir shops, and an open-air market, making it a lively, must-stop destination for families and adventurers exploring the Keys.
HIGHLIGHTS • Lots of free time in Key West • Designated driver • Narrated tour It's not an ordinary sightseeing tour. It's an extraordinary road trip of the Florida Keys! You depart in a comfortable 15-passenger, air-conditioned van, and you'll travel over 40+ bridges on the Overseas Highway. Your driver is also your friendly local tour guide that entertains you with interesting stories and fun facts with a headset microphone set to a comfortable audio level. You are encouraged to ask questions and make comments and observe the wildlife and interesting sightings along the way. Once in Key West, enjoy approximately 3 hours of free time to do whatever it is you want. Add a sunset sail, Key West attraction, or a dinner cruise to enhance your experience. We'll provide you with a list of suggested places to go and things to do. You'll be picked up at your accommodations or specified location of your choosing. You'll receive an email with your pick-up time the day before your tour.
HIGHLIGHTS • World-Famous Key West Sunset • See Key West's iconic attractions • Lots of free time in Key West During your free time we recommend you check out the Southernmost Point, Hemingway's House, Mile Marker Zero, Sloppy Joe's, Mallory Square, get lost in the island city of Key West! Ask us how to a sunset sail, Key West attraction, or a dinner cruise to enhance your experience. We'll provide you with a list of suggested places to go and things to do.
We'll drop you off at the Historic Seaport so you can enjoy your free time from a convenient location. Duval Street & Sloppy Joe's is only 2 blocks away!
Experience world-famous Duval Street during your free time in Key West! Enjoy the countless bars, restaurants, shopping, and world-class people-watching.
We'll drive by the Southernmost Point so you can see it & photograph it from the van. You'll have plenty of time to go on your own for more pictures.
Mallory Square in Key West is a captivating and fun destination, especially famous for its nightly Sunset Celebration. As dusk approaches, the waterfront transforms into a lively open-air festival. You'll find an eclectic mix of street performers – including jugglers, magicians, acrobats, and musicians – alongside local artisans, food vendors, and eager crowds. It's an energetic, quirky, and beloved Key West tradition offering spectacular views of the sunset over the Gulf of Mexico, making it a truly unique and memorable experience for all ages. Nearby shops, museums, and restaurants add to the appeal
Highlights
What's included
Pickup Locations & Times
Free Pick-up at your Hotel, Vacation Rental, Private Home, or any other requested location in Key Largo, Islamorada, or anywhere in between!
Traveller Ratings
Important Information
- Specialized infant seats are available
- Service animals allowed
- Public transportation options are available nearby
- Infants and small children can ride in a pram or stroller
- Suitable for all physical fitness levels
Reviews(10)
Troy was great! He showed the sights and provided a wealth of information about the Keys. He tailored the day to our requests, which worked out perfectly for our group. He advised us what to do and where to go. Our day was so fun! Lots of great memories. We loved that we didn’t have to drive and deal with parking as well. Thanks to Troy. Very personable and funny!
Thank you so much for this awesome review! It was a blast spending the day with your group and I’m really glad the mix of sightseeing, local tips, and not having to worry about driving or parking all hit the spot. Hearing that you made lots of great memories is exactly why I love doing these tours. Hope to see you back in the Keys for another adventure soon! Troy
We highly recommend this tour. Communication was excellent and easy pre tour and on the tour. When on the tour, Troy went out of his way to get to know us, and tailored the tour to cater to our interests, providing the best experience and enabling us to see things we would not have seen otherwise. We found the flexibility and tailored suggestions great - it was a unique and private experience with so much information provided - we learnt a lot about the area.
I am so glad you enjoyed your tour! My goal is to make your experience as enjoyable and memorable as possible. I’m glad to have met you two! Thank you Troy
Troy hospitality is the best. The charm of Key West was also doubled when Troy attended! They are flexible enough to adjust the time and change the location. I would recommend it to anyone who wants to visit Key West.
Thank you very much for the great review. You guys were an outstanding and fun group! I’m glad I was able to be part of it. Thank you Troy
I only have one word to describe this tour fantastic!!!! both Troy and Marianne were great tour guides, if you want to see the Keys in one day this is for you Duval street and Hemingway house is a must this is a real good touring company.
Thank you Augi. We had an amazing time with you! I sure am glad you enjoyed it. We’ll take up on your offer to show us around if we get up to your neck of the woods Troy n Marianne
Private tour to the Keys I can only recommend! Our guide Troy, who is also the owner, took excellent care of us. The tour can be customized, which makes it very varied and personal. We had a wonderful time, and the tour was definitely worth it. Thumbs up! I would book them again anytime. He also has tips on where to eat and offers a selection of attractions depending on what you are interested in. Overall very pleasant and entertaining design.
Thank you guys for the outstanding review. I really had a great time with you. I just wish we could’ve talked to girls into feeding the tarpon. 😜
Troy our guide was the most amazing tour guide I have ever had. He picked us up at our hotel and took us on a day tour of the Florida Keys. He had so much information on the area and he took us to some beautiful spots. We also went to key west for the day and got enjoy food drinks and sight seeing before he drove us back to our Hotel. He made the day so special for our Siblings trip we will definitely book again. Troy really goes the extra mile for his quest!!!
Thank you so much for the awesome review! I really enjoyed you guys! I still tell people about our tour together! Hopefully, I’ll see you next time! Troy
Troy was a very knowledgeable guide who provided some very interesting facts about the Keys. Great personality for a guide. Our day was very enjoyable. I would definitely use Troy again.
Thank for the great review! You guys were an awesome group. I’m looking forward to seeing you again. Keep in touch! Troy
We recently went to Islamorada for a family vacation and I had reached out to Up The Keys about a tour to Key West from our resort. Scott and Maddie were INCREDIBLE to work with. They were very responsive and thoughtful. Scott was our guide the day of and WOW did he know his Florida Keys facts! From Islamorada to Key West he educated us on everything from history to ecology. It was such a wonderful experience. Since this was a multi generational trip we went with my daughters, youngest 4, to my grandmother, in her 80's. He dropped us off door to door so my grandmother wouldn't have to walk. He gave advice on things to do that would be great for my kids while my family went to a few museums, he really thought of it all. I cannot express how excellent this tour was. I would HIGHLY recommend Up The Keys!
Thank you again for letting us show you around the keys, we're so glad you all enjoyed your day trip!! Thanks for sharing your thoughts, we appreciate it!
My family had an amazing time in Key Largo and Key West! Scott was an amazing Tour Guide! He was extremely friendly and cared a lot about our family experience. He was very knowledgeable about the Keys and we learned a lot of awesome information about Key Largo and Key West. My entire family said when we come back, we want Scott and his team!
We are so happy to hear you and your family enjoyed it so much! We would be honored to tour you around these beautiful Keys next time you're in the area! Til next time :)
We have always travelled a lot internationally in the past and just resumed it in full after the pandemic. It’s extremely rare to see such enthusiasm from people who do pretty much the same things every day, not to talk about the drive. Our guide for the day Scott made us feel super comfortable and special. No request is a problem to him and beyond that we felt like he was a long time friend of ours .. it did not take long for us to feel like he was an integrated part of our group and it was an absolute pleasure to spend time with him on the lunch and dinner breaks. We ended up having a couple of traffic delays on the way and returned to Miami a couple of hours later than agreed and expected. Despite being super tired and with us from 7.30 in the morning until beyond midnight, Scott was all along happy to be with us without putting any pressure to come back and still showing the same enthusiasm in his job. Hands up for this 6 star tour service!
It was a pleasure spending the day with you and your family, and being able to host you throughout the Keys! All the best - Scott
