I booked trip via Air Key West (AKW) to Havana, Cuba for guided day tour on 2/27/26. At AKW, the lady issuing our visas (after asking each of us if we "were scared," told us we should've come a week later after Trump had invaded, (according to her, the island would no longer be communist & the embargo lifted, allowing us to buy rum and cigars). She also told us that it would be "no problem" to get passports stamped in Havana, or if they wouldn't, we could request it on a piece of paper. Upon arrival I asked our liaison if I could get a stamp. He said it was no problem, & to follow him. He had a word with our pilot (in Spanish) who shook his head disgustedly. The Liaison then turned around and said it was "impossible". So some pilot with no standing in Cuba, basically tanked that for us, (though one guy in our group actually got his stamped, so it's not like it was a regulation or anything). According to the itinerary from AKW, the tour would go from the Airport to the Hemingway Home. We'd then go to Cojimar (village where Hemingway launched his boat & fictional home of the "old man" in Old Man and the Sea) followed by a few hours in Havana Vieja where we'd lunch & visit Hemingway haunts like Bodeguita Del Medio, El Floridita, and Ambos Mundo Hotel. After leaving the Hemingway Home, I asked the guide when we'd be going to Cojimar. He said that wasn't/never had been part of tour. When I mentioned it being on Itinerary, he said it never had been. Due to huge data rates on Cuba, I couldn't pull up/show him the online itinerary, which the owner (Rob) acknowledges is still on the website and "probably needs to be changed". We went to Havana Vieja, walked around, & while the guide pointed out the Ambos Mundo hotel, we just kept walking. When I spoke to Rob 2 weeks ago, he said Cojimar was taken off tour when the restaurant closed... during covid. Yet, Cojimar is still on the itinerary while lunch is listed on the itinerary as being at Paladar in Havana. If the lunch location was edited on itinerary because Cojimar could no longer play host, & that resulted in no longer visiting the village,, why not remove Cojimar from the itinerary at same time... I mean, the restaurant closed 6 years ago!!! In conversations with Rob, he kept reiterating changes in tour can be made WITH SUBSTITUTIONS by guides at their discretion in case of events like a power outage. There was no power outage (and why would that matter in a fishing village anyway) and no substitutions were made. The trip was $1,342. I requested $250-$300 refund. Rob denied it, saying, "Even when we went to Cojimar, we only stayed for about 5 minutes & it's very run down, now". I feel that between omitting Cojimar & just pointing out Ambos Mundo hotel (not going into museum on the 5th floor, explicitly mentioned in itinerary & for which admission-while small- was paid as part of trip cost) I deserve at least a partial refund. The fact it's taken over 3 weeks to even get a response is equally ridiculous. The buckpassing at AKW is extraordinary. Everything from the guide supposedly "not knowing they once went to Cojimar because "he must be new"" to "it's at their discretion" to my personal favorite, "that's just how things go in Cuba." I feel like AKW thought they could just throw whatever on the tour and people would be fine. I came to see the Hemingway haunts in an exotic locale. I also thought (with Cojimar) that I'd get a small taste of what "real Cuba" was like. But no, we were taken to the Hemingway home & while we can't go in, we were told we could get pics. We were also told by our guide that we were expected to pay workers to take pics of the inside for us (again we'd already paid admission via our trip cost) It was very disappointing given that I'd wanted to make this trip for literally over 2 decades, and even more frustrating to be told "that's just Cuba" read more

Air Key West - AKW Mgmt says trip to Cojimar ended 6 yrs ago; Yet that & stop at Ambos Mundo both on itenerary. - Private Jet Charter Near Me - Key West, Florida

Several months ago I was referred to AKW by a local friend who is a private pilot based here out of Key West. Didn't think we would actually use them because flights on commercial airlines here are so easy..... until they aren't! We were beyond thrilled with how easy it was to work with AKW! Our Silver flight to Tampa for the Bucs playoff game was delayed, then moments later cancelled. Standing in the airport wracking our brains on how to get to the game, I remembered the referral and gave AKW a call. Literally within moments we were walking to the Signature facility next door and within 45 minutes we were airborne on our way to Tampa! Pilots Jonathan and Raul (??? Sorry!) were so friendly and helpful! Excellent flight! We considered asking them to stay and take us back to Key West it was so convenient and perfect a trip! Highly HIGHLY recommend this company! We can't wait to fly with them again! read more

Air Key West - Private Jet Charter Near Me - Key West, Florida

We chartered a flight to Havana from Key West on 5/23/25. Everything was beyond our expectations and truly exceptional. They take care of all the paperwork and provide the highest quality service throughout the trip. We are experienced travelers, so we chose not to partake in the guided day-long tour, so I can't speak to that experience. However, the 7 other passengers spoke very highly of it. I would recommend the tour for anyone that is not a highly experienced traveler. With that said, there is plenty to do and many cultural experiences you will miss in the group setting. I easily put together an itinerary that was quite easy to follow in the Old Town area - starting at the cathedral and finishing at the Hotel Nacional. I would enthusiastically recommend Air Key West. Again, the service was top notch, and they went above and beyond any and all expectations we had. read more

It was in and out with no delays! Love the simplicity and convenience of flying into key west without the hassle. Thanks you! We will be back soon! read more

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Office staff was pleasant to get our flight reserved. Our pilot Jonathan was great and the smooth flight and views were a pleasure!

Used them for a quick business flight from Venice to Key West and back in the same day. They worked around my schedule to accommodate. Got us there on time and the flight was smoother than a commercial flight. Extremely professional and felt very safe. There were no commercial flights that fit my schedule. Even if one did, I would have to drive an hour north to TPA to catch it and go through TSA. Or I could drive 6 hours each way for a total of 12 hours in the car... Using Air Key West to get me there in a little over an hour on my schedule from my small airport next to my house totally spoils me. Arrived at Venice Airport (5 min from my house) at 7:35 a.m and was on the ground renting a car in Key West at 9:03 am. Will definitely use them again. Thank you! read more

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Amazing professionalism and response. We have flown Air KeyWest numerous times and are always happy because of the on-time service and well maintained aircraft. read more

we have flown with them a half dozen times, and every pilot has been professional and highly competent. They are responsive, always on time, and have well-maintained planes. Highly recommend. read more

We had a great time on the Havana excursion. The day was filled with visits and experiences-much more than expected. The tour guide and the bus driver were excellent. The pilot was very professional (read his online bio to build your confidence). Remember that you are flying to a communist country that has limited relations with the US. Rules, relationships, and laws are ever changing. Expect the unexpected and possible delays. This is not a day trip to the Bahamas. Best left to the adventurers and well travelled. read more

We decided that the 3 hour boat ride back to Marco Island in rough seas wouldn't be a good idea. So, I found Air Key West and had an amazing experience getting back from Key West to Naples airport in only 40 minutes. I highly recommend! read more

We have used them twice and will do so again. Professional , no hassle, on time , flexible safe charter. Whist the big boys wish they could do. Customer service like you've never had before read more

Excellent service and scenic enjoyable flight. Convenient and allows you to avoid normal hassles of flying commercial

Used Air Key West for round trip from Marco Island, FL. Great flights. Friendly, punctual, and professional service. Highly recommend them.

We used Air Key West for our day trip to Havana with Julio as our pilot. The flights were both under an hour. Julio was with us guiding the way until we crossed thru customs. It was great to have someone showing us the way. He was waiting for us when we got back from our tour. Very reassuring. Great guy. A couple of things. Please tell passengers that the planes are small. Might be off-putting to someone that's not comfortable with that. Prepare guests for actual situations. This is not a comfortable/clean resort type tour. In particular, the restrooms. Our tour guide was very nice but quite difficult to understand. That proved to be somewhat frustrating. All in all, quite an experience. read more

DO NOT TRUST THIS COMPANY. THEY´RE SCAMMERS. We booked a flight with them 2 months ago. Everything seemed perfect and we were so excited to fly from Key West to Cuba. We had everything booked: flights, hotels, etc. Surprisingly, 10 days before our trip they told us that they didn´t have permission to fly to Cuba anymore and that they could not take us there when we had already paid extra cost for our VISA. (weird that they are submitting VISAS if they don´t have a permit to fly...) We had to assume the extra cost of $1500 in order to get new flights and we lost 2 nights of hotel (+$400). And guess what? After 2 days of back and forth calls and emails, employees blaming manager, manager blaming employees, THEY WILL NOT COMPENSATE US and will take from 30 to 50 days to refund us the $1.200 we had already paid. Due to their lack of commitment, management inefficiency and rudeness, I will NEVER recommend this airline. read more

Do not trust this airline, it is completely unreliable. I booked my flight from Key West to Havana for the holidays two months in advanced. Two weeks before the flight they cancelled my flight because one of their employees made a mistake and should have never booked the flight. I talked to Robert Valle, the boss of this unreliable airline, and asked if they could cover the extra expenses for the new flight and said all he would do is refund me my money, and then tried to sell me a private charter that would be much more expensive. Now I will have to fly put of Miami and pay twice as much because the trip is only two weeks away. See other reviews, I am not the first one. They will be hearing from my lawyer. read more

Great tour. Our guide was very knowledgeable. Only one problem: since my wife was born in Cuba ( place of birth is on your passport) she needs a different visa or some kind of paperwork than I do. Apparently Air Key West , who gets the visa for you, was not aware of this. They got her the same visa as mine and the Cuban authorities held her for a half hour resolving this. read more

The flight to Cuba was great! We were quite impressed with the thoroughness of the pilot and felt quite safe and comfortable. Once in Cuba things moved smoothly. I wish we had been able to explore a bit more but over all our guide Lazaro was super informative. Lunch was more lengthy than I cared for also. No need to get pesos, American currency was accepted. Hemingway house and places he frequented were fun to experience. Overall an exceptional experience. read more

Flawless. Smooth, fast, and so easy. Our Pilot took excellent care of us. Every flight was absolutely on time. We saved about ten hours of drive time by flying to Key West instead of driving. And Air Key West was the perfect connection to do this. Thank you Gentlemen!! You made our travel just that more safe and enjoyable. Beautiful! read more

This was the nicest and most scenic flight I've ever been on. It was smoother than commercial airlines and landing was nice and easy. The trip was very well organized and our tour guide was amazing! Very informational and intelligent! I will definitely be recommending this company and the day trip to Havana to all my friends and family that visit the Keys! Thank you to all and I will more than certainly be going again! read more

I took a Hemingway - Havana Day Trip out of Key West on 27 July 2018. What a unique experience! The Air Key West charter air service was outstanding. Our pilot, Rob Valle, arrived early and took time to brief us on the details of the flight and the tour. His passenger briefing in the aircraft was professional, complete and delivered in a comfortable manner that showed he had done this hundreds of times before. The flight was less than an hour. There were rain showers in the Havana area and he advised us there might be some light turbulence. But with a few gentle turns to avoid them, we never hit a bump. The Hemingway tour was a full day of everything Hemingway. His Cuban home, the little fishing village where he kept his boat, some plazas in Old Havana and a couple of bars where Hemingway held court in his day. The return flight to Key West was as smooth as the trip over. Customs in Havana and Key West were no hassle and everybody was professional and welcoming. read more

I took myself and family out of Punta Gorda to Key West. I looked at flying commercial and besides being inconvenient, it was expensive for a 1 hour flight out of Ft. Myers. I decided to try a private plane. I couldn't be happier. The plane was great...the service was remarkable and there was NO wait. Anytime I fly to the Keys or anywhere else these guys fly, I will using them exclusively. 5 stars all the way! read more

We used Air Key West for the Hemingway Havana Day Trip and was very, very pleased. The trip was extremely well organized from booking through return through Customs in Key West. Everyone we came in contact with was very professional and our guide in Havana was fantastic. I would definitely recommend this service. I would note that the plane used (we had 9 people total, four in my group) was quite small so be prepared for that if you go on the 50 minute flight. A larger plane would have been better. read more

Do not trust them. On 9/24 I booked a flight from Key West to Havana for a day trip. On 10/10 they cancelled the flight. On 10/14 they said that the flight was back on, and my credit card was charged for the full amount for a flight on 11/5. Per instructions, we arrived at the airport at 7:15 am for the flight, and there was no flight. The private air terminal agent said that they called Air Key West and that AKW would call right back. I never received a phone call, and messages that I left on their answering machine were never returned. The booking agent, Our Key West, was very sympathetic, and said that no one put us on the manifest after being charged. I still have not heard from Air Key West. read more

I needed to get to Naples from Key West for a business meeting with my partner. Time was of the essence and I had a few options for travel all very inconvenient to expensive. One would be to rent a car for at least a 12 hour round trip; fly back to Miami via AA then to Fort Myers; or call for a private flight service. My trusted assistant started Googling private charters and near the top of the list was Air Key West. The web site showed perfectly fine planes, twin engine and Italian in design, 8 seats and rates, flight times and requirements. We signed up and also found out that the flight was probably one of the cheapest charters I could get. Tuesday arrives; ferry off Sunset Key; cab with Randy the cabby to Key West Airport and the private terminal and we meet Robert "Rob" for our flight. Deduct one star for sticking the two of us in to back; quick intro to safety rules; Rob climbs aboard snakes his way to the pilot's seat (cramped); a little claustrophobia setting in; a/c comes on; direct blower in my face; and I am fine. Take a peak at Rob's card and realize we are flying with an F16 freaking pilot in the Guard. Ok the expected clouds and low ceiling occasional thunderstorms and black sky off the coast are all countered by the F16 freaking resume. Quick take off, cell phone still works but conks out off shore; some great shots of the Keys with camera phone and we are in Naples in 40 minutes. Super clean airport; pick up by partner and off we go to meeting. Rob waits for you and you are charged $50.00 per hour for the wait. Fair! Cheap! Back to KW 3 hours later perfect landing; perfect flight; sunny skies; even better photos and we are done! There's good old Randy in his rickety yellow cab; more stories and back to Sunset Key all in 4 hours! Total charge $1050. Not bad at all for these very important people with some partying ahead of them. Add back star for perfect flight and professional treatment. 5 stars! read more