Initial Itinerary to Milan, Siena and the Amalfi Coast for September 2025.

I cannot help with your decision on the Amalfi Coast, as we have never been there, although we have visited Italy 6 times over the past 15 years. From what I have read of the crowds there, it just does not appeal at all. We did, on the other hand, visit Puglia recently, and were thoroughly charmed by the coastal towns.

I hope someone who has actually been to the AC can help you. But I am guessing that one thing they will say is you definitely not want to be driving a large van there. Some I have read say do not try to drive there at all.

As for the van itself, you need to consider the pros and cons very carefully—-especially the cons, such as parking, ZTL restrictions, route-finding, stress on the driver, etc. But first of all, look into the licensing requirements for driving a van of that size in Italy. From what I have read, one needs a Class C license to drive a vehicle over 3500 pounds GVW. That will include many passenger vans carrying 8-10 people.

Speaking of stress, as travel planner for groups of 8-10 family members, I will just say I have been extremely lucky. Our family members have been content to let me do all the planning for our trips to Switzerland, Italy, and the UK, and it has always gone well because we are very compatible, and also like-minded in our travel goals. I do include special requests whenever possible, such as my daughter-in-law’s wish to show Venice to her kids (our grandchildren). But with a diverse group of friends, it might not be so easy. Do make sure that people are in agreement on costs and how to handle them. And I hope everyone will get travel insurance for the non-refundable costs.

One more comment for now—I do not think “basing” in Milan ito see the Italian Lakes is a good ide? If you want to see the lakes (which you should), then go to one and visit nearby towns and islands by ferry. Far more pleasant and less stressful that traveling back and forth by van or train. If you are flying into Milan, you can go directly to one of the nearby towns on Lago Maggiore by shuttle. I suggest Stresa or Baveno. Here is the shuttle schedule:

https://www.safduemila.com/linee/alibus-malpensa-lago-maggiore/

These towns are also served by train, so you can go to Milano Centrale and onward to Siena. People could also visit Milan for a day by train, around an hour from Stresa.

Taking on this planning project will be challenging- (but fun if you like to plan as I do).
You will need to communicate well with all parties so everyone is on same page as far as travel modes, budget, expectations…

My thoughts:

I think renting a car- which would need to be a very large commercial van- is a bad idea. Train travel is so much easier, faster, cheaper. Everyone should be encouraged to travel light, they have to be able to handle their own luggage no matter which transportation mode you choose.

I agree with Lola that 5 nights in Milan with Lake day trips is not the best plan. I know you don’t want to change locations too much but I would suggest going straight to Stresa on arrival to MXP- 3 nights. So easy to get there. Stresa is lovely and flat. We were there in Sept 2022 and it was not overly crowded with very few English speaking tourists.
Spend a day visiting the islands by ferry. Spend a day taking the narrow gauge train ride into Switzerland. Get over jet lag.

Then move to Milan- easy 1 hour train ride. Stay in Milan for 2 nights- that is enough to see Last Super and visit the Duomo- those that want to visit the roof terraces can while others can shop or visit nearby museums.
Milan is a big bustling noisy city with tram lines everywhere. We didn’t care much for it but were very glad we did LS and Duomo. I was having some mobility issues at that point— end of a 3 week trip- so we did the Hop On Hop Off bus and that was actually fine- we saw all of the outlying sites that way.
By moving from Stresa to Milan you eliminate a train change if you were to spend all 5 nights in Stresa then train to Siena. It’s just a small thing but it can make al the difference.
(As we’ve aged we make sure our transits are as simple as possible and we have no problem spending for transportation now- private drivers when needed taxis, etc.)

From Milan- train to Siena- you will have to change in Florence- then take a taxi from Siena station up into town. Siena is very hilly, so choose your lodgings with that in mind. Use Google maps to “walk” the area- it will indicate how steep your climbs are. I would give Siena 3 nights since it will takes time to get there. A 3 night stay is only 2.5 days of sightseeing. Spend 1.5 days exploring Siena then book a guided tour to some other Tuscan hill towns.
www.toursbyroberto.com operates out of Siena- he gets excellent reviews but you must book early!

From Siena- train back to Florence to change to a direct train to Naples (3.5-4 hours). Take a picnic lunch along with you - this will be a few hours rest as well. Everybody enjoys the train ride while if you choose to drive in a large van at least 2 people are stressed driving/navigating.

From Naples I would hire a driver to Sorrento. Splitting the cost 4-5 ways makes it very reasonable.
We used this company
www.topexcursionsorrento.com

Stay in Sorrento for 5 nights.
There is a reason people like Sorrento. It is flat. It’s a fun walking around, shopping, eating, passegiatta kind of town with the best transportation links to all of the AC, Capri, Pompeii, Naples, etc. You’ll have more choices for exploring the region from here than you would from Ravello. Everybody can explore together or they can go their own way, Lots of great hotels to suit all budgets.

As far as lodging I think you will find that finding an apartment or villa that accommodates a group of your size is difficult. You will want 4-5 bedrooms with real beds- no sofa beds or futons, and I would think at least 3 bathrooms. I recommend you budget for hotel rooms for all if possible. That way everybody has their own space and bathroom. Find a hotel that has a nice pool or courtyard where you can all gather- lots of those in Sorrento. Pick one with a good breakfast.

cont...

IMO Ravello is not a good choice. There is little going on there, accommodation choices are limited, yes the views are fantastic but getting anywhere from Ravello requires a bus to Amalfi then change to ferry or bus or a private driver or 2. That could add up!

From Sorrento consider Mondo Guides Shared Tours- we did the Pompeii and Capri tours with them and were very pleased- especially the Capri day. They also have an AC road trip tour that is very affordable.
www.sharedtours.com

The views of the AC towns are actually best from the water. Positano is extra steep- nothing but steps and nothing much there other than high end shopping. Amalfi is worth a look around, Duomo and cloister are interesting. You might want to spend most of your AC time in Ravello to walk out to Villa Cimbrone- gorgeous views.

If your departing flight from Naples is very late am/early afternoon you can stay in Sorrento for your last night. Hire a driver to the airport.
Otherwise you will need to stay in Naples- take taxis to airport- quick 15-20 min ride.
(If you base in Ravello you MUST stay in Naples for last night)

Trenitalia
https://www.trenitalia.com/content/tcom/en.html

Station Names:
Stresa
Milano Centrale
Firenze SM Novella
Sean
Napoli Centrale

Hi! Congratulations on your trip! I'm looking to plan a trip for my family in September 2025, but I can't access any booking that far in advance. May I ask/would, or anyone on this thread, you be willing to share your planning resources? I'm more interested in booking flights, first. Likely, DFW to Rome. Thank you!