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Which way to order trip?

We plan to travel to Italy in May to celebrate our anniversary. We want to go to Lake Como, Tuscany, and the Amalfi Coast. What is the best way to lay this out? Should we fly into Milan and go straight to Como and then on to Tuscany and then fly out of the Amalfi Coast area back home?

What weather should I expect in May in these areas?

Any tips on romantic places/must see or romantic sites?

Thanks in advance for any advice/opinions you can offer.

Posted by
245 posts

We will be flying in to either Milan or an airport close to the Amalfi Coast and will have 14 days.

Posted by
5648 posts

Your proposed itinerary makes sense.
Having just booked an Italy trip for May 2025, I think airfare may guide your itinerary. For example, flying out of Rome, after touring the AC, may be much cheaper than flying out of Naples.
I found rates into/out of Milan to be least expensive in Italy. However, you'll want to fly open jaw, (multi-city ) to avoid backtracking. So fly into Milan and out of Rome, or reverse.
Set up alerts in Google Flights to track prices and research trends.

How long is this trip?Have you been to Italy before? Are you mobile? What are your interests?

Weather is increasing variable in recent years, so just be prepared with layers and rain gear. We had a very rainy Italy trip in 2023, with only three days out of 14 without rain.Hopefully that won't happen to you.

Have fun planning. Safe Travels!