We are flying from South Africa for our first trip to Italy. We have been to other places in Europe and like food, strolling around, people watching and a glass of wine. We don't rush things.

We will be travelling via train and buses, I don't want to drive.

I won't have jet lag as we are in the same time zone.

I studied law and part of our studies were Latin and Roman Law so we did a lot of Roman history.

I am turning 50 on 12 October but don't want to really plan my vacation around the day, I see the whole holiday as my holiday celebrations. I am turning 50 in Cinque Terre with my current plan and that seems great to me.

Our rough itinerary is:

3-Oct-09 Leave Cape Town
4-Oct-09 (Land 6:00AM) Milan (Full day)
5-Oct-09 Milan to Venice
6-Oct-09 Venice
7-Oct-09 Venice to Florence
8-Oct-09 Florence
9-Oct-09 Florence
10-Oct-09 Florence to Cinque Terre
11-Oct-09 Cinque Terre
12-Oct-09 Cinque Terre to San Gimignano
13-Oct-09 San Gimignano to Siena
14-Oct-09 Siena
15-Oct-09 Siena to Positano
16-Oct-09 Positano
17-Oct-09 Positano
18-Oct-09 Positano to Rome
19-Oct-09 Rome
20-Oct-09 Rome
21-Oct-09 Rome Fly 23:50 from Rome
22-Oct-09 Cape Town

Any suggestions or ideas.? Longer in Venice? Cut a place at the coast or do other places in Tuscany? Weather wise I am not sure what to expect at the Amalfi Coast in mid-October.

Great plan! Weather deteriorating in late October so could be wet but not cold - walking trails could be muddy. Trains are great - and buying long-distance trains early could mean a sweet discounted fare as opposed to full fare. www.trenitalia.com and www.italotreno.com - 2 competing rail systems usin same trcks and stations. Check both and www.seat61.com has sage tips on helping you book your own discounted tickets online - general info - BETS-European Rail Experts and www.ricksteves.com.

I would suggest cutting 5 Terre and putting those days in Rome, which with your penchant for Roman history should have 4 days IMO.

Siena to Positano - probably quicker to go via Florence to Naples and then by private car or train and bus to Positano - but a long haul if all by public transports. Pomeii is on the way - maybe stop off on way back - luggage storage at entrance to ruins or if private car just have em wait or just take train to Naples from the ruins station Pomeii-Scavi station.

though Venice to CT is an hour q

Although Venice - Florence - La Spezia - CT is about an hour faster than going via Milan, the Milan to CT coastal route, despite many tunnels, is still far more scenic than the drab high-speed route to Florence.

You know what you mean by "We don't rush things." But for me this would be, perhaps not "rushed" but, covering too much. Eight hotels, very little time for Venice, and possibly a tad late for Positano when relying entirely on public transportation. The weather on the AC probably won't be a problem (no guarantees), but you should check when the bus and ferry schedules go off their summer frequency which could be Oct. 15th. There will still be service, but it may be less convenient getting around.

I'm not the biggest fan of Venice, but I wouldn't spend less than 4 nights there on a first visit. The Cinque Terre in recent years has become so insanely crowded, even in October, that I would be ambivalent about including it on this trip. If it's where you want to be on your birthday, then go, but expect crowds.

I would add at least a day for Tuscany and take a guided tour (or even better, hire a driver) to see other towns in the region. Perhaps a day in Chianti (easy from Florence) or a swing through the Val d'Orcia (better from Siena).

Considering your knowledge of Roman history, I'm surprised you're not spending more time in Rome. Since one of your days there is a Sunday, check your sightseeing plans to be sure you can do/see everything in the time you have.

We did two weeks in Italy last October, starting and ending in Milan. We had perfect weather and wished we had more time in Cinque Terre and probably could have dropped a day from Florence.

This is our full itinerary, feel free to ask me any questions.
​​​​​Two Week Italy Itinerary flying in and out of Milan - Strolling Adventures

Thanks for the replies.

I am considering cutting the AC.part and adding a night to Venice and another two to the Tuscany area using Florence as a base. The Siena to Positano trip does seem like a long day of traveling

I think three nights in Rome should be fine, we are only flying out at 23:50 and I will be booking that night too so we can go out the whole day and return to a room. My wife is not big into museums so we must both compromise.

My biggest concern in Tuscany is the getting around part, I would prefer to sleep over in the small towns that I visit. Somewhere like Montepulciano does look like a place we will enjoy.

It's hard to have both... stay in a small Tuscan town and only use public transportation. You should research the bus timetables and see for yourself.

https://www.discovertuscany.com/movi...ny/by-bus.html

Florence is a great base for exploring some parts of Tuscany (plus Bologna). Consider both buses (above info) and trains.

https://www.trenitalia.com/en.html
[Use Italian spellings... i.e., Firenze, Venezia, Roma.]

IMO, Rome is less about museums and more about "sights."

Okay, I have decided to cut the Amalfi Coast and stick to a mixture of small towns and big cities.

I think I will keep Cinque Terre on the itinerary to see the Italian coast.

My trips between these places will be relatively easy with trains and buses.

Our main objective is to relax, we are not "plan your whole day" travelers, if it was not for the Schengen requirement for a whole itinerary then I would have made no bookings. We also take days off just to sleep late and do absolutely nothing.

So my new plans are as follow:
3-Oct-19 Cape Town
4-Oct-19 Land 6AM Milan
5-Oct-19 Milan / Venice
6-Oct-19 Venice
7-Oct-19 Venice
8-Oct-19 Venice / Florence
9-Oct-19 Florence
10-Oct-19 Florence
11-Oct-19 Florence / Cinque Terre
12-Oct-19 Cinque Terre
13-Oct-19 Cinque Terre / San Gimignano
14-Oct-19 San Gimignano / Siena
15-Oct-19 Siena
16-Oct-19 Siena / Montepulciano
17-Oct-19 Montepulciano
18-Oct-19 Montepulciano / Rome
19-Oct-19 Rome
20-Oct-19 Rome
21-Oct-19 Rome Fly 23:50PM
22-Oct-19 Cape Town

Does these plans seem better? Or must I cut a night in Montepulciano and add it to Rome?

That last itinerary looks good. Glad you bagged the Amalfi. Have fun!

Or must I cut a night in Montepulciano and add it to Rome?>

Yes, if never been to Rome - you will wish you had a day more there when you're there.

I think the updated itinerary looks more sensible. As for adding another day in Rome, it depends on how much you want to see. The city is full of ancient sights. We didn't visit the Vatican and spent two full days seeing the main sights and walking around different areas.