​Hi everyone!

​I’m planning a family trip for May 2027 (I know, plenty of time, but I like to plan ahead to catch flight deals!). We are a group of 5 adults (my wife and I, my sister, and our parents, who are around 60 but active and ready for a "full tourist/walking mode" trip). This will be the first time in Italy for all of us.

We absolutely love history—especially everything related to the Roman Empire and ancient ruins. We are currently planning to spend the first few days in Spain to recover from the long flight and then focus heavily on Italy.

​Here is the tentative itinerary we came up with. I’d love your critique on the pacing and the destinations.

The Itinerary (24 Days / 23 Nights)

​Days 1-5: SPAIN (Madrid) (4 Nights)

● ​May 1st - 5th: Arrive in Madrid. Day trip to Toledo.

​Days 5-7: VENICE (2 Nights)

● ​May 5th: Fly from Madrid to Venice (VCE).

​Pacing: Is 2 nights enough just to see the main highlights (St. Mark's, Doge's Palace) and get a feel for the city?

​Days 7-11: FLORENCE / TUSCANY (4 Nights)

● ​May 7th: High-speed train to Florence.

​Plans: Uffizi, Duomo, and rent a car for one day to visit Siena/San Gimignano.

​Days 11-18: SORRENTO / AMALFI COAST / POMPEII (7 Nights)

● ​May 11th: High-speed train from Florence to Naples, then local train to Sorrento.

● Plans: Using Sorrento as a base to visit Pompeii, Herculaneum, Naples Archaeological Museum, Capri, and relax on the Amalfi Coast (Maiori/Positano).

​Days 18-24: ROME (6 Nights)

● ​May 18th: Train from Sorrento -> Naples -> Rome.

● ​Plans: Deep dive into Roman history (Colosseum, Forum, Appian Way, Ostia Antica, Pantheon) and the Vatican. We left Rome for the end to have an "epic" finish and an easier trip to FCO airport on our departure day.

● ​May 24th: Fly out of Rome (FCO) back to my country.

​Specific Questions for the Community:

​Stealing nights from Madrid: We definitely want to keep Madrid as our starting point, but we could cut 1 or 2 nights from it if there is a "must-see" region or city in Italy we are missing. Where would you add those nights in Italy?

​Missing "Must-Sees": As first-timers who love Roman history, is there any major site we are skipping? (For example, should we try to fit in Milan, the Dolomites, or Paestum, or would that make the trip too rushed?)

​Redistributing Nights: Should I take a night away from somewhere and add it elsewhere? Is 7 nights in Sorrento too much for the Amalfi Coast/Pompeii area?

​Group Accommodation (5 Adults): We are planning to book 2-bedroom or 3-bedroom apartments (Airbnb/Booking) in each city to save money and have breakfast together. Is there good availability for apartments of this size in the central areas of these cities (especially Venice and Sorrento)?

​Budgeting for 5: In your experience, does traveling as a group of 5 (sharing apartments and using group train discounts like Trenitalia's "Insieme") make the per-person cost significantly cheaper compared to traveling just as a couple?

​The Order: Does the flow of Florence -> Sorrento -> Rome make sense to avoid a long travel day right before our flight home from FCO?

​Any tips, critiques, or reality checks are more than welcome. Thank you!