I selected this tour operator based on feedback from my mother who used his tour services a few years ago when visiting the island... my parents are originally from this island and left ~50 years ago. The recommendation came with the claim that my parents were shown aspects and locations of the island they were not even aware of, even having spent their entire early lives there.
Gary the tour operator/owner booked the 2 tour dates (east and west tours... I forget the numbers) and I am glad it ended up being very early in our trip. Email communication prior to the trip was efficient and prompt. I'm now convinced that even phone communication would have been perfect, as his English is absolutely flawless. The day after our arrival, we were scheduled for the West end tour (Sete Cidades etc.) but when he arrived at our hotel he informed us he was switching them around due to poor weather conditions that morning (poor meaning thick cloud cover). We did the east tour first. The information was great and I learned a tremendous amount about the locations we visited. We visited some spots I was not expecting to see (some gorgeous waterfalls!) and even in cases where I had seen photos prior to the trip, they did not do the experience justice because in person it was quite extraordinary. Gary handled the lunch plans at Furnas which was great because I did not realize one had to reserve early. I had visited a fraction of these sites back in 1985 during my first visit but with the additional information even these all seemed brand new (I mean, it was nonetheless 32 years ago!). Yes you can find some of these spots on your own with a map, but the whole point of a guided tour is the "guided" part and being free to look around and shoot photos without having to stress over driving and maps, etc. not to mention the benefit of background information. On that topic, Gary not only researches the locations in a thorough fashion but he also incorporates stories and info gathered from prior residents who return to visit many years later (as with my parents). It also helps that he's a pretty pleasant guy to be around.
The greatest thing about doing such a tour early on in a visit, is that one is then free to rent a car and revisit some of the places that one finds most interesting, or even explore a bit now that one has an idea of the area. This is what we did on our "day off".
The second tour day covered the western portion. Gary is prompt in his start times, and I have to mention that he did not give the impression of "counting the minutes"... there were times I was concerned I was abusing his allotted tour time and things were getting late in the day (I don't recall an exact tour end time, I'll be honest). He appears fairly flexible... at the Sete Cidades visit we ended up exploring the abandoned hotel which turned out to be quite the fascinating aspect of our tour... quite unexpected. A visit to a tea house operated by a relative for a mid-trip break was the sort of stuff you won't get on a big-bus-style company tour.
By this point the weather was outstanding so Gary made the right decision in swapping tours because both days ended up absolutely gorgeous and I had the tan to prove it. After stopping at some lookouts along the north shore (which gave us ideas for further visits in the coming days) we visited a few more waterfalls and managed to get a fantastic view up at Lagoa do Fogo. Again, Gary is quite flexible and granted me the ability to shoot photos from the antenna lookout, which allows one to photograph both sides of the island simultaneously it's that high.
Furthermore there are practically no moments of silence in Gary's presence. Do not expect long awkward stretches of silence between stops, like on big-bus tours when the guide switches off the microphone. There is always information being delivered in some way.
The equipment itself seemed in perfect shape. Being a car guy I was hoping for the Mercedes sedan (because it looked good on photos) but I'm glad he brought a van because not only did it make it easy to see out of during the driving portions but it also made entry and exit much easier for a family of 4. It also made it easier for me to manipulate my camera bag... being in a car would have been too cramped.
Gary is also quite good at parking in tight spots. :)
In summary, I had no doubt about getting my money's worth on both tours and no reservation about the tip I gave him at the end nor about buying him lunch both times. The timing was right, we learned more than enough about the island both tours early on and this allowed the rest of the vacation to be out of this world with all the additional driving we did on our own. Without these tours so early on in our stay, it would not have been anywhere near the outstanding vacation we ended up having.
A note to potential visitors about the weather: as has been mentioned in other reviews, Gary nor anyone else cannot control the weather. However, as a visitor I *CAN* control when I schedule my visit to the island. I spent a LOT of time researching the weather cycles before choosing my visit dates. I was aware of the rainy season and the days where temperatures are very hot and humid. I also chose my length of stay to allow for the potential of a few rain days so that we had some wiggle room in our sight-seeing activities (which turned out not to be the case so instead we ended up with 9 straight gorgeous days). This was an expensive (for us) trip and I made the effort to set it up such as to minimize the chances of it going to waste. While not everyone has that luxury, it is something to keep in mind. (it's really not much different than when someone books a Florida vacation during hurricane season, and complains that it rained too often).
Wishing Gary all the best and for continued growth of his business and good health to his family.