Logistics for Milan to Siena to coast and back to airport

One more bit of info: We probably have flexibility for 2 nights on the front end prior to arriving in Siena, and up to 3-4 nights on the end of the trip after leaving the coast.

I always like to get rental cars at the airport. Perhaps more expensive but a lot easier than trying to handle in town driving. It is 260 miles between Malspensa and Siena (I assume you are going into Malpensa and not Linate). If you take the train somewhere then you deal with the down time of train schedules and off/on loading and unloading. If you are going straight to the agriturismo perhaps a train would be better and pick up a car in Siena (stazione). If you have a day or two you might consider staying somewhere on the way. Maybe Parma, a great town, or Modena, of even Bologna, but that is a bit further.

I like Portovenere near La Spezia. No trains there but you can drive. You can take the boat to 5 Terre if your intention is to go to 5 Terre (I assume it is). While driving be sure wherever you stay you have parking. Sometimes that can be a problem.

Since you are basically in Tuscany, you do have Pisa, Florence, and Genoa as airport options that are closer to your final destinations. Certainly consider Rome. You are only 160 miles from Sienna, much closer than Malpensa (Milan). Rome is easy to get in and out of with a rental car and has great access to autostrade and even the highway up the coast. A day on the front end here could be enjoyable, Ostia Antica, Civitavecchia, Argnetario, Maremma, or somewhere like that for a night.

You have 13 nights apparently (2 weeks) and you have only used 5,3, and 1. That leaves 4 nights left to plan. Now you have to consider Milan, Florence, Rome, etc, if you haven't been there.

Thanks for the feedback - exactly the kind of input I was looking for. I started out looking at flying in/out of Milan since there are non-stop flights from MIA but just noticed there also are non-stops to Rome. I would actually prefer flying out of PBI or even FLL since they are closer to home, but not if it means making more connections. For instance, PBI to Florence would require two stops and Rome one, with both requiring a stop stateside (which I try to avoid - especially if it means stopping in Newark or Atlanta). I suppose also that we could fly into one airport and out of another if that were much more convenient and not too pricey. I still have another couple of months before flights open up for our dates so I'll play around with different options in the meantime.

We will have some time when we first arrive, so it may be best to rent a car on arrival so we have flexibility to stop along the way. I'll take a look at Parma and Modena, and also the other options you mention if we fly into Rome. We are looking at Tellaro for the 3 nights after the agriturismo, since it sounds lovely from everything I've heard. I will look at Portovenere as well. It looks like they are pretty much across the bay from each other so I am sure we will visit both in any event! After that, we do have several days to plan for.

This is actually our first trip to Italy, and we wanted to make sure we didn't overload it with trying to do too much or moving every two days. We want it to be pretty slow paced, focusing on food, wine and the scenery, and skipping many of the typical tourist locations. From this standpoint, I'd appreciate any thoughts on how to spend the latter part of the trip.

Thanks again!

I would definitely look at flying open jaw (into Milan or Rome and out of the other one). This maximizes your time "on the ground" because you are not backtracking, and not only is usually not more expensive than round-trip, it's often less.

As someone experienced in traveling many time zones, I strongly recommend not renting a car your first day (or even your second, if possible) unless there is a compelling need. You will be tired and disoriented and taking a train or even a private driver will provide you with opportunity to not only relax, but also to see the countryside you are passing through. I have driven a lot in Europe and many miles in other countries, too, and am hesitant to drive in Italy, at least in the cities/larger towns, due to ZTLs and what is often described as a careless or reckless driving style seemingly shared by many Italian drivers.

I think we'd probably opt to stay someplace relatively close to the airport for at least the first night if we rent a car immediately upon landing. There certainly is an appealing side to traveling via train and not having to worry about driving and navigating.

In playing around with flights, it's interesting to see that flying into Florence with a (very) long layover in London is an option that is significantly less expensive than everything else I've looked at. I'll have to ponder whether we might want to spend some time in London on our way ...

Layni makes a good point about the first day after a long flight with a 6 hours time change. Take it easy that fist day. So, you lots of options. Ostia Antica is very close to the Rome airport, you could get an airport hotel, see Ostia and then hit the road. Argentario is pretty cool too if you go up the coast.

If you fly to Rome instead of Milan I think you will have better front end. You can always fly out of Milan. Malpensa is not very close to the Milan, it is a ways out, so I would recommend getting an airport hotel the night before departure. Think about The Last Supper if in Milan, you need advance reservations.

I haven't been to Tellaro but it looks lovely. I don't know if you can get to 5 Terre by boat from there. The La Spezia train station has a great parking lot underground. Very easy to park there and jump a train to any of the 5 towns if that is something you want to do.

Good plan to not put too much into your first trip. It sounds like you re more interested in the country side rather than cities. Picking a base and doing day trips has always worked well for us. We usually spend a week somewhere and travel out every day. It is surprising how close everything is in Italy. It is different than the US.

Have a great trip and start planning your return after this one. If you have a specific question just drop me a message. I will try my best to answer it.

Our interest is definitely in seeing more of the countryside than cities, and we are planning to do a lot of day trips to explore. Having some specific places to look at as options along the way helps a lot. I'm sure I'll be back with more questions as we get further into the planning.

Thanks again!