Italy or Greece first?

Recommend you go in the Spring if possible (wonderful flowers etc.) or Fall (great Fall season foods) but avoid Summer. Way way to hot and humid. Presume you will be using the ferry system to get to the Greek isles. Plan on being flexible especially in Greece. Strikes, walk-outs are always simmering in the background these days and the future isn't looking to rosy there. Just have plan B and may C in your pocket. Everywhere you plan on going is great but I think you will have to put some real planning into the logistics/costs. Happy travels!

I personally would fly from Rome to Mykonos then to Santorini then back to Italy. The ferries take time and I am not sure how much of that you have with quite a few desinations listed.

Charlie, Whether to see Italy or Greece first is somewhat a matter of personal preference. I've taken a similar trip, and in my case I chose to see Greece and the islands first and then enjoy Italy at the end of my trip (I visited Naxos instead of Mykonos). What is the time frame for your trip and what time of year will you be travelling? You may find it helpful to have a look at Matt Barrett's Greece Travel website. I used it extensively when I was planning my trip. I used one of the Greek travel agencies recommended on his website to arrange my Hotels, transfers and other details, and that worked really well. You could consider something along these lines.... > Flight to Athens > Athens - 3 days (add a few days if you want to take side trips to Nafplion or Hydra) > Flight to Mykonos > Ferry to Santorini (taking a relaxing ocean voyage is a bit nicer than flying) > Flight to Milano via Athens > Cinque Terre > Montepulciano > Train to Rome, flight to Sicily (I use EasyJet on that route) > Flight back to Rome and then to the U.S. There are many ways this could be arranged, so this is just one suggestion. Happy travels!

Ken's plan above is exactly what I did years ago. The hydrofoil from Mykonos to Santorini was the most relaxing experience I've ever had. GREECE-ITALY (or viceversa) You seem to be interested in Tuscany (Cinque Terre is not technically Tuscany, but just passed the border) and Sicily. I wouldn't go to Milan, as Ken suggested, but rather would fly from Greece to either Tuscany or Sicily. Then I would fly between Tuscany and Sicily (or viceversa). GREECE TUSCANY Pisa is connected to Athens with AirOne (summer only); also with Kos, Chania and Rhodes, if you happen to go there. Bologna (not Tuscany, but just 37 min from Florence via train) is connected to Santorini and Mykonos with Meridiana Fly. There are also several charter flights from Bologna to Greece, including Mykonos (with Prima Aero). Florence FLR has no connections to Greece at the moment. GREECE-SICILY Catania CTA is connected to both Santorini and Mykonos with Blue Express (summer only) Palermo is connected to Santorini with Volotea (summer only) TUSCANY-SICILY
Various options connecting the Sicilian airports (Palermo PMO, Catania CTA, Trapani TPS) with the Tuscan Airports (Pisa PSA and Florence FLR) with Ryanair (Pisa-Trapani or Palermo), Volotea (Florence-Palermo or Catania), Alitalia (Florence-Catania), AirOne (Pisa-Catania). Sicily is too far from Tuscany (and Cinque Terre) to do in any other way but air.

We are planning this trip for early Sept 2014. Our plan is the go to the Cinque Terra again for 3 or 4 nights. We love this place. This will be our third time there. We want to do Montepulciano as a base for day trips to Tuscan areas. Figure about 6-7 days there. We will probably figure 3 nights each Greek Island. Sicily is a want more than a need. Is it worth it to see Sicily? Is so, what town or city would be best? So mainly, do we fly into Greece and out of Italy, or the opposite? We will probably do train and ferry systems rather than flying other than to and from the states. Where does the ferry stop in italy? Is is close to Sicily to make it worth going? Total trip will be about 4 weeks. Thank you all for all this great information. Even these planning stages get us excited about our trip.

First of all if you choose Montepulciano as a base for Tuscany I recommend that you rent a car (not sure if that was your intention). Sicily is consistently voted as the best region to visit by Italians, Tuscany is generally no. 2 in that ranking. Some might agree or disagree as to which of the two should be first or second, but very few will disagree that Sicily is an amazingly beautiful place to visit. In counterclockwise direction from Palermo these are the place to visit: Palermo and Monreale, Scopello and Zingaro Natural Reserve, Segesta temples, San Vito Lo Capo, Erice, Trapani and Egadi islands, Selinunte temples, Sciacca, Agrigento and Valley of the Temples, Piazza Armerina, Caltagirone, Ragusa, Noto, Syracuse, Catania, Taormina, Mt. Etna, Eolian Islands, Cefalu'. And I've mentioned only the most important ones. Going by ferry to Greece starting from Tuscany is a very long trek. First you need to travel to Brindisi (nowhere close to Sicily), in Apulia (the Boot's heel) approximately 500 miles southeast of Montepulciano, take a night long ferry ride, then travel from Patra in Greece to Athens (over 200 km). To the islands you then have the option to fly or take ferries or hydrofoils. Four weeks is a decent time to visit those places, however Tuscany, Sicily and Greece are far from one another. If you aren't willing to fly a lot of time will be wasted traveling to one another. It doesn't matter if you travel to Greece first or vice versa. Since you are going in September I would do the northernmost areas first then the southern ones. That's the migratory bird strategy of travel.

I did forget to mention that we did plan on renting a car while in Tuscany. I agree with you that starting north and following the warmth south. Sounds like Sicily is gong to be on the agenda. Looking at maps, I didn't realize just how far the greek islands are from Italy. Or even Santorini from Athens. Maybe some flying will be necessary. If we flew into Athens,is it better to fly to Mykonos or ferry? And then to Santorini? Best route back to Italy? Someone told us about a fast ferry. Where does that go from and to? Sorry for all the questions. I thought tghis was going to be simple. But I'm sure it will be worth it.

Yes you should fly from Italy to Greece. I gave you all flight options from Tuscany above, however most are summer only. In September you might be forced to go to Rome first. From Athens to Mykonos you have the option of flying or taking a boat. The flight is very short of course. With a high speed catamaran from the Pyreus (Athens' port town) you can be in Mykonos in just over 3 hours. From Mykonos to Santorini, further south, the catamaran is the best and maybe the only choice outside of summer. I did that years ago. 2 and 1/2 hours. Catamarans are smooth and comfortable, unless of course it's rough sea. In nice weather the Med is smoother than a lake of olive oil. When coming back from Santorini to Athens I would fly because otherwise it's a long journey to be done at once.

Charlie, If you're planning to rent a car in Italy, note that each driver must have the compulsory International Driver's Permit, which is used in conjunction with your home D.L. These are valid for one year, and can be obtained at any AAA office for a small fee. Failure to produce an I.D.P. if requested may result in fines on the spot! Note that I.D.P.'s are also compulsory in Greece (I know that, as I've been asked to produce one when renting cars). You may also want to have a look at some of the Posts in other sections of the HelpLine regarding fines for speeding or passing through limited traffic zones (which are common in Italy). There seems to be an increase in posts on that topic lately. Other commonly discussed "issues" for driving in Europe are high fuel costs, tolls, high CDW (insurance) costs and the fact that some automated fuel pumps will ONLY accept "Chip & PIN" credit cards. Cheers!

To add to what Ken said. You will definitely need a car for your Tuscany roaming around from Montepulciano. A car will not be needed at the Cinque terre, but if you have it already, you might as well keep it. You will also need a car in Sicily, or at least I recommend you get one. you won't need one in Palermo+Monreale (actually it's better you don't have one in the city because Palermo's traffic is ridiculous), but anywhere else it will be very helpful. You won't need a rental car at all in Greece if you go only to Athens, Mykonos and Santorini. You can use public transit or walk in all of those locations. There isn't a whole lot to do in the islands other than eat, drink Ouzo while watching the sunset and of course party at the many discos and bars (Mykonos is Europe's gay party capital).