Pisa Departure 1:15pm .... Can I make it from CT??
 

Below is my tentative plan for our September 2015 trip. It looks like my flight out of Pisa will be 1:15ish. Could we plan to just leave Rioggomore in the morning to make this flight or should we head to Pisa or Lucca the day prior to departure? I understand strikes, etc cannot be predicted, but wondering if this is doable given nothing out of the extreme ordinary happens.

I would prefer NOT to move locations just for 1 night if possible, but not at the risk of most likely missing a flight. Thanks for your help!!

Tentative Itinerary:

Day 1 : Fly into FCO from DFW; arrive 7:30 am; rent car and head to Montepulciano
Day 2-5: Montepulciano
Day 6-9: Siena
Day 10-14: return car then train to Rioggomore
Day 15: Fly out of PSA to DFW (flight at 1:15ish)

You should be able to take an early train. Have a plan B in case there is a strike, but strikes in Italy are pretty much scheduled in advance so you should know in time to make other arrangements if need be. The connection between Pisa Centrale and the airport (they are only 5 minutes apart) is under construction to improve transport. Might be finished by the time you visit, but currently is being served by bus instead of train.

I wouldn't stay that many days in Riomaggiore.

The train takes about two hours, with two changes of train, so you shouldn't have a problem.

I agree with kybourbon; I also wouldn't spend that much time there. You might want to spend the last few days closer to Pisa. Lucca might be a good choice.

Thanks for the info. How many days would you recommend for Riomaggiore? Currently I have 4 full days; 1 of the days I was hoping to do a day trip to Portovenere or somewhere.

Where would you suggest I add a day if I were to take it from CT?

I really want to see Orvieto this trip so currently planning it as a day trip from Montepulciano. On my first draft I had 2 nights in Orvieto but logistically it didn't seem to make the most sense.

Please share your feedback ... I want to maximize my time. Thanks!

You could spend a night in Lucca or Pisa. Then you could eliminate the worry abut the train connection the last day.

With only four nights in Montepulciano, I would add one or two nights there. You won't regret it.

Why not stop in Orvieto on your way to Montepulciano? It's on the way and you could have lunch and spend the afternoon exploring the town. If you want you can take the SR2 from Orvieto to Montepulciano, which is a prettier drive than the A1.

While Orvieto is on your way to Montepulciano, I don't think a few hours jet-lagged visit would be very enjoyable. It deserves an overnight (or two).

For your time in Siena, are you planning to stay there or do day trips?

If it were my trip (and assuming Day 2 is not a Sunday), this is what I would do:

Day 1. Fly to FCO, train to Orvieto, explore the town and spend the night.

Day 2. Pick up rental car and drive to Montepulciano via SP51 (not A1). Stop at Abbaye de Sant'Antimo along the way; have lunch in Montalcino. Wander Montalcino and then head to Montepulciano.

Day 3. Explore Montepulciano area.
Day 4. Explore Montepulciano area.
Day 5. Explore Montepulciano area.

Day 6. Drive to Siena. Stop at Abbazia di Monte Oliveto Maggiore along the way. (The Abbey is closed from noon to 3:00p, so arrive by perhaps 10:00a at the latest or 9:30a if this sort of place really interests you.) Depending on the time when leaving, perhaps have lunch at the ristorante located at the main entrance to the abbey. Closed Tuesdays. Continue on to Siena.

Day 7. Explore Siena area.
Day 8. Explore Siena area.
Day 9. Explore Siena area.
Day 10. Explore Siena area.


Day 11. Drive to La Spezia. Stop in Volterra along the way. After lunch, continue to La Spezia, arriving in time to return the rental car. Train to Riomaggiore.

Day 12. Explore Cinque Terre.
Day 13. Explore Cinque Terre.

Day 14. Train to Pisa and/or Lucca. Explore the town. Spend the night.

Day 15. Fly home.

Thanks for all of the ideas!

In Siena, I was thinking 2 full days in Siena then 1 day doing a Chianti day trip.

In Montepulciano, I was thinking 1 full day there then the rest day trips.

Is 2 full days too much in Siena? I don't want to be driving every day though. Some days we just want to "be"...

"Is 2 full days too much in Siena?"

No idea of your interests, but I would say 2 days in Siena is not too much. If anything, I would say 3 days in the area is not enough.

Just FYI, Siena will be very crowded in the main/central tourist area.