organized tours or self exploration

This is such a personal decision. Both methods of travel have their pros and cons. It really depends on what are your priorities. The truth is you can have great experiences either way.

Group travel has pros of much of the logistics taken care of including in country transportation, and a knowledgeable guide to teach and build background for the sites that you see. With Rick Steves Tours there are often unique experiences you probably would not be able to replicate independently and a group of congenial people to travel with. The key con can be be lack of flexibility and an itinerary that may not match with all your priority “must sees.” The original “sticker” price can seem higher than independent travel so it is important to see what all is included in the tour in terms of meals, admissions, etc.

Independent travel has pros of flexibility in terms of itinerary and more room to adjust budget. You only do the activities that you are interested in, when you are interested in. Cons: The responsibility for planning lodging, transport, itinerary, meals is entirely on you as is the need to research in advance about what you will be seeing. This isn’t necessarily a con if either of you are big planners and like the research process.

It really just gets down to the type of experience you would like. Some forum members combine both travel methods. They will travel independently before or after a tour.

Remember, there is no wrong answer here. Choose what seems to fit your needs, not the opinions of a bunch of strangers and their travel styles.

PS: I just realized you appear to be talking this October. I think that independent travel will probably be your most likely choice for a few months from now.

You could have the best of both worlds by adding a few days on your own before and/or after the tour. The time before would help with adjusting and overcoming jet lag, and the time after would let you cover things that the tour didn’t.

Carol is right about pros and cons.

I will add another observation as I end 2 weeks in Greece tomorrow. I am 65 and unfortunately needed to travel in July - which means HEAT. However, my friend and I conquered that by traveling at our own speed. We see things (and walk) in the mornings, take a break for heat in the afternoon, then go back out late afternoon and evening. A package tour might not have given us that flex. In Oct., that might not be an issue - but there is still a lot of walking.

That being said, a good guide is very helpful in some places.

We rented a car in Athens and drove Nafplio, Delphi, Meteora, and back to the airport. Driving freeways and main roads was great. But getting to and around some of our destinations required small roads, and some curvy mountain roads. I drove and my friend was a great navigator, so we did fine. But how that goes will depend on your comfort and skill level. One poster here recommended Athens Car Rental and I would certainly second that.

As stated by previous posters, this is such a personal decision after considering your travel style. We prefer to explore on our own and not be tied down to a preset schedule. With that flexibility we have been able to stop along the way if we see something unexpected that is of interest to us. However we have also had great luck in hiring private guides for areas where we feel that a local's expertise will enhance our travel experience. For example, we did not have a car on Naxos and so we spent the day with a local guide discovering things we never would have seen on our own.

Of course much depends on where you are going, but we found the driving quite easy in the Peloponnese.
As for a tour or not, that would also depend on what you want to see and whether a tour facilitates that or not. The biggest challenge I found when planning a trip to Greece was the sheer number of options. Once I settled on a region to focus on, it became easier.

PM and I will give you contact info for a good guide. Talk to her and see if it works for you.

Thanks all for your advice. I now have another question. Are the flights to and from Cypress from Athens reliably on time? We want to fly back from Cypress to Athens and leave on our flight home 2 hours later in order to avoid another night at an Athens hotel.

Just like here in the States, flights are on time....until they are not. Too many things can go wrong to book a connection like that. I would stay in Athens the night before and avoid the stress.