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Help me decided between these three itineraries?

Trip is planned for late May through first week of June. I'm basically trying to do a bit of everything while avoiding huge tourist spots, as well as hot/muggy days. We are not interested in nightlife, but love food, nature, sightseeing, history.

Option 1: South of Italy

Depart US for Bari (overnight flight)
Day 2
Arrive in Bari
Bari to Ostuni via train
Stay in Ostuni (night 1)
Day 3
Stay in Ostuni (night 2)
Day 4
Day trip to Polignano a Mare via train
Return to Ostuni
Stay in Ostuni (night 3)
Day 5
Day trip (still contemplating on where)
Return to Ostuni by EOD
Stay in Ostuni (night 4)
Day 6
Travel to Matera
Ostuni to Bari via train
Bari to Matera via bus
Stay in Matera (night 1)
Day 7
Stay in Matera (night 2)
Day 8
Travel to Castelmezzano...via Potenza?
Seems there is no train, so contemplating bus/car.
Stay in Castelmezzano (night 1)
Day 9
Stay in Castelmezzano (night 2)
Day 10
Return to Puglia via train
I need to think of a side quest once I am here (night 1)
Day 11
(night 2)
Day 12
(night 3)
Day 13
Travel to Bari
Ostuni to Bari via train
(night 1)
Day 14
Fly home from Bari

Option Two: North of Italy

Route: Milan → Lake Orta → Camogli → Sestri Levante → Bologna → Parma or Modena → Milan
Day 1 – Arrival → Lake Orta
Day 2 – Lake Orta
Day 3 – Lake Orta
Day 4 – Lake Orta → Camogli
Day 5 – Camogli
Day 6 – Camogli → Sestri Levante
Day 7 – Sestri Levante
Day 8 – Optional day trip
Sestri Levante → Levanto
Day 9 – Sestri Levante → Bologna
Day 10 – Bologna
Day 11 – Bologna
Day 12 – Bologna → Parma or Modena
Option A (Parma):
Bologna Centrale → Parma
Option B (Modena):
Bologna Centrale → Modena
Day 13 – Parma or Modena
Day 14 (June 6) – Parma/Modena → Milan
Fly Home

Option Three: Bit of both South and North

Day 1
Depart US (overnight flight)
Day 2 – Arrive Bari → Ostuni
Arrive in Bari
Stay in Ostuni (night 1)
Day 3 – Ostuni
Stay in Ostuni (night 2)
Day 4– Day trip
Day trip to Polignano a Mare via train
Return to Ostuni
Stay in Ostuni (night 3)
Day 5 – Day trip
Day trip to Lecce (recommended)
Return to Ostuni
Stay in Ostuni (night 4)
Day 6 – Travel to Matera
Train Ostuni → Bari
Bus Bari → Matera
Stay in Matera (night 1)
Day 7 – Matera
Stay in Matera (night 2)
Day 8– Travel to Castelmezzano
Travel Matera → Castelmezzano (bus or car via Potenza)
Stay in Castelmezzano (night 1)
Day 9 – Castelmezzano
Stay in Castelmezzano (night 2)
Day 10 – Travel to Bologna
Stay in Bologna (night 1)
Day 11 – Bologna
Stay in Bologna (night 2)
Optional: Day trip to Modena or Parma
Day 12– Travel to Dolomites (Ortisei)
Bus Bolzano → Ortisei
Stay in Ortisei (night 1)
Day 13 – Dolomites
Stay in Ortisei (night 2)
Day 14 – Depart
Fly home

Posted by
9486 posts

Two weeks is way too short for Option 3. Look up how big of a chunk of time it would take to go between these locations.

A general comment about Ostuni. If you are traveling by train as you mention (and it’s the way I travel), you will get off at the Ostuni train station which is on the valley floor, but the city is up on a steep hill. So, you need to take the train and then transfer to a bus to go up into the city. It’s one of the least handy stops in that area. I would consider staying in Monopoli or another city where the train station is in the city. Then take a day trip to Ostuni, so you only have to do that connection once.

Posted by
9486 posts

For Option 1 and your request to stay away from tourist hot spots, I would head south of Lecce, spend time there, work your way back up with places like Ostuni, Monopoli, Martina Franca, etc. and then head to Matera. Afterwards go to Castelmezzano - looks very interesting! I haven’t been to that city. Then possibly it’s easier to connect to Salerno (see Paestum Greek ruins), take the train back to Rome and fly home from there. (If this is for 2026, it’s getting very late for hotel reservations.)

I would vote for Option 1 because May is an excellent month for this area, and unfortunately, it seems like the Puglia region is getting more popular on social media lately. I’m heading back there for the third time to enjoy it before it gets too crowded.

Have a fantastic trip in Italy with whatever you choose! : )

Posted by
6706 posts

Option 1, but before you go to Matera, go somewhere in the Salento like Lecce.
Don’t be worried about driving, it’s very rural and that would be the best way to see the mountainous area.