We booked this tour online through Green Zone Tours. It looked far more interesting than anything our cruise ship was offering, it would just be the two of us and we could escape our fellow passengers for a few hours.
We were met by Filipe as planned at the Cruise Ship Terminal and off we went in his four wheel drive. Through the winding streets of Ponta Delgada along the coast road to a spectacular outlook over the Monastery Rock, sea and countryside. Next stop was the little town of Sete Cidades at the base of the crater. From there it was a minute or so to the two lakes that dominate the landscape and an explanation of the mythology surrounding them.
Then the real fun began as Filipe and the 4WD earnt their money climbing to the top of the crater's rim. It was a narrow dirt track with the occasional hazard of a farmer's tractor coming the other way. At each stop to admire the view the thought was "how much higher can we possibly go?" The answer was: right to the top at a knee trembling, wind howling 850 metres.
The views were worth the climb but with sheer drops either side of the track for most of the way there was relief that the return trip was in another direction with a more gentle decline. The final bonus was a detour around a huge mist enshrouded lake edged with azaleas before a rural drive back to town.
This was one of those occasions where reality far exceeded advertising hype. A glorious route through one of the most beautiful landscapes on the planet was enhanced even more by Filipe. He was a charming, knowledgeable and erudite guide and fortunately a very skilful driver. He explained at the beginning that he didn't prattle non-stop like some but would point out everything that mattered and we should ask whatever we wanted. It worked a treat.
This was an outstanding 3.5 hour trip, great value and highly recommended. I don't know whether you can ask for Filipe but I'd give it a go.