Slovenia and Italy

I was there 2 months ago.

We really enjoy Merano and Bolzano. We did a day trip to Ortisei and spent the day hiking in the most famous of the Dolomite mountains. The Dolomites could be a week adventure in themselves - there are numerous jumping off points, and plenty of world class hikes in that area.

Then we went to Verona which has a roman coliseum and the house of Juliette (of Romeo and Juliet fame), then Venice (which is overrun with tourists and too expensive) then Trieste (don't bother), then Ljubljana which is nice, the Lake Bled which is very nice too. Then up to Klagenfurt and Graz Austria and Vienna. You could cut back toward Salzburg and see some of the Austrian alps and then drop back down to Bolzano from Innsbruck.

Cinque Terra is not really worth the time and effort in my view - been there three times. nothing much to do but take the same photos from the same exact places as everyone else. not many restaurants. You can also go to Positano in that area. The real place to go is Sorrento and Positano if you want to take the high speed train down to Naples and go from there - surprisingly, its almost as long on the train to go to Cinque Terra as Sorrento despite the distance being 10 times as much because of efficient high speed trains versus slow trains with a lot of stops.

Rome - plenty of criminals.

Tuscany and Umbria - very nice - but you need a car. But it's easy - just like driving in the countryside in the US.

Some other ideas are Turin which is quite nice and the Aosta valley to its north and the Barrolo wine area to its south (also the scenes of some of Napoleons early battles against the Austrians).

https://www.slovenia.info/uploads/publikacije/pohodnistvo/hiking-slovenia-en.pdf

http://www.vogel.si/summer/vogel/hiking-trails/

Slovenia is one of my favorite countries... a great place for history and outdoor activities. Can you tell us more about your interest in the country? Family roots there? Do you have a place in particular you want to visit? Knowing those things helps us give better advice.

Here is what I did with 25 days in Slovenia... https://community.ricksteves.com/travel-forum/trip-reports/25-days-in-slovenia

The Slovenia page of a travel blogging mother that features activities her outdoorsy family did there... https://www.earthtrekkers.com/destination-slovenia/

Some thought about logistics:

• International train connections between Italy and Slovenia are very limited.
• Multi-country one-way fees for rental cars are huge (or not even possible).
• With your outdoors focus I would recommend to rent a car in Slovenia once you leave Ljubljana. The drives over Vršič pass or up to Mangart saddle are stunning (as long as you feel well driving narrow and winding mountain roads).

How you could deal with it?
Scenario 1 – fly to Ljubljana, rent a car once leaving Ljubljana, visit the lakes, caves, castles, mountains and hikes you prefer and return the car in Nova Gorica. Transfer to Gorizia Centrale, Italy and train to Florence.
Remark: Nova Gorica, Slovenia and Gorizia, Italy are more or less one town separated by the border.

Scenario 2 – fly to Venice and take train to Udinese. Rent a car there and do your loop through Slovenia (and consider high parking costs in Lubljana). Return car in Udinese or Trieste (in case plan to visit Slovenia’s Adriatic coast) and take train to Florence.

Florence would be the best location to explore Toscana by public transport and you would need to consider one night in La Spezia to visit Cinque Terre.
Alternatively take a rental car in Florence, find your lonely hilltop villa somewhere in rural Toscana and enjoy life for a couple of days.

Finally take the train to Rome and stay there at least 3 days before flying home.

It's already a lot for 14 days, thus you might need to consider to skip one or the other location.