Adventuregal

bvlenci would you be so kind as to suggest a 1-2 week itineraries for the different regions you’ve mentioned? I basically want to determine if there are any middle ground here (LOL) I will be traveling with my 14 year old as well so this would need to be interesting for him too.

Traveler_Nick

You don't have to take Greece off the table IMHO. You need to take the idea of doing the whole country off but you could fly to an island and spend a week easily enough. You just need to pick one .

In Tuscany with one week I'd suggest sticking to the areas that can easily be reached by train or bus from Florence. Do a day trip to Siena by bus. Take the train to Pisa and then onto Lucca. Take the train to Bologna for the day. You've used up most of the week.

If you have two weeks and a car maybe base yourself in Siena and tour the province.

Travel_Nerd

I still do not know exactly what of a trip you are looking for as your original posts mention "adventure" and I do not know what that means to you for any of us to suggest an itinerary. You have a lot of broad interests which is great, but makes it hard to pinpoint and suggest. Also, do not know what research you have done in any of these areas.

However, you've mentioned a huge strong bucket list and interest in Sicily, which sounds like is the area you have spend the most time researching. Go to Sicily, then. Figure out flights from Florence (and perhaps back if you need to return for your daughter's school). Or maybe you can get Sicily done first and then to Florence to get your daughter settled. If it were me with my daughter, I'd want to get her settled after the trip if the schedule allows. YMMV.

Adventuregal

Travel_Nerd no need to focus on the term “adventure”. Think of it as me asking your opinion or suggestions based on your own experience and must sees and must dos. Sicily or whatever you are suggesting.

I will figure out the rest, I just need the lay of the landscape in terms of moving around transportation.

Adventuregal

Traveler_Nick would you suggest any of those areas be overnight?

I did some research and I see that Sicily is accessible by Train through it is a long trip (12-14hours) so I may opt to fly.
I may also opt to rent a car to maximize my “freedom” to live how and where I want though I’d rather not.

Traveler_Nick

You can take the train to Sicily but it's a bad idea unless you want to say you did it.

The train would be at least 12 hours. You can fly it from Pisa for less money and a fraction of the time.

I'd happily spend a few days in Siena.

Adventuregal

Traveler_Nick Yes, realized that. Thank you 😊

what should I aim for in Sienna?

Travel_Nerd

I know I am not Nick, but maybe peruse Siena's (note the spelling - important for trains and public transport) official tourism office. It has a lot of ideas for landmarks in the city.https://visitsienaofficial.it/en/sie...icial-website/

Not quite sure if you want religious sites, but the Cathedral (edited) is lovely. Too bad you will miss the exposed floors, they're amazing (only at certain times they open them up). Timed entry might be required. Edit: I apparently was mistaken, they expose the floors beginning in mid-August, so you might catch them.

Adventuregal

Travel_Nerd ha. Thank you for that tip on paying attention to spelling…Siena (single “n”!) Anything else in addition to the Cathedral in terms of the road less traveled/ off the beaten path for Siena?

Travel_Nerd

I appreciate you asking a more specific question. It is sometimes hard to get a feeling when someone asks for "suggestions" because they really are personal to the person asking them as well as to the person answering them. Trip reports are fantastic for that "personal" touch that I think you are looking for, by the way. You will get a sense of the good, bad, and ugly (to the person), which may differ from what you want.

Siena will be quite busy during the time you would be there, probably (so will any place you go to). Siena is my favorite town in Tuscany just to wander, sit at an outdoor cafe with a glass of wine and people watch. I do not go to that town for a specific sightseeing agenda with the exception of the Cathedral, which I made a point to go to just to see the marble floors (in October). There are underground aqueducts in the city - which really were a marvel at the time of building, but I cannot be sure they are "off the beaten path, " especially during the time period you'd be there.

Anymore, everything seems to be absolutely overrun and Siena is no exception. If you can stay there for a night or two, you would see more of what the city is like when the day trippers have moved on. Much more enjoyable and charming, imho.

Adventuregal

thank you, Travel_Nerd

bvlenci

Planning two or three different one to two week itineraries is really more than I can take on. I can suggest some things to do or see in some of these areas. As I said, some would really require a car.

In northern Le Marche, Urbino Is a jewel of a small Renaissance city, with a ducal castle in the center of town. It's a typical hill town, the birthplace of Raphael. There's an excellent art museum in the palace, and you can admire the frescoed halls in the palace. One of the highlights is the "studiolo", richly decorated with intarsia. The subterranean rooms, which held the stables, the kitchen (uncomfortably near the stables), and the laundry are interesting. Urbino Is on top of a steep hill, so I don't consider it a good base for day trips, because getting in and out of these hill towns is a bit tedious.

There are lots of scenic and interesting things to see near Urbino. You might want to base in an agriturismo or other rural lodging a bit to the south of Urbino. The Furlo Gorge is very beautiful. The ancient Roman Via Flaminia highway ran through it, following the route of an even more ancient road. The decisive battle with the forces of Hannibal was fought nearby. There is an ancient tunnel carved in the rock in pre-Roman times and a more recent ancient Roman one next to it. There is also an ancient flood-control works along the road.

The town of Mondavio has a medieval fortress with a small museum of medieval armour and weapons.

The town of Fratterosa has some traditional pottery workshops.

Corinaldo is another beautiful hill town with an intact medieval wall.

If you're interested in fine dining, the seaside town of Senigallia has two Michelin starred restaurants, and the whole area has some excellent restaurants. Senigallia has a long sandy beach, with a shallow seabed. It also has an attractive center, with several beautiful piazzas and some some good shopping.

I'll try to add more in the days to come, but this is a bit time-consuming, and I'm leaving in a few days for a trip to the US.

bvlenci

If you want to use public transportation, Ferrara is a good choice. It's an attractive small city with a castle in the centre of town. It's very easy to get around by bike, and most residents use bikes for transportation. Your son might enjoy a Ferrari tour, but someone else can advise you better about that.

Nearby cities you can visit from Ferrara by train include Ravenna, famous for its ancient golden mosaics; and Bologna, famous for its cuisine and ancient university.

Another destination you might consider is Lake Garda, with beautiful mountain scenery and charming lakeside towns. Your son would surely enjoy taking the cable car to the top of Mount Baldo from the town of Malcesine. Boat rides from there to the northern end of the lake are very scenic. At the opposite end of the lake, Gardaland Is a fantastic amusement park. My granddaughter fell in love with it when she was 15 years old. You can get to the lower end of the lake by train, and proceed by bus or boat to the upper end of the lake.