Arrive in the Eternal City and walk through ancient wonders like the Colosseum and Roman Forum. End your day with a sunset stroll and dinner in charming Trastevere.
Overnight: Rome

Explore Vatican City, admire Michelangelo’s masterpieces, and climb St. Peter’s Dome. Toss a coin in Trevi Fountain and take in the Pantheon by night.
Overnight: Rome

Drive or transfer north to the Tuscan countryside. Settle into the charming spa town of San Casciano dei Bagni, surrounded by rolling hills.
Overnight: San Casciano dei Bagni

Enjoy countryside drives, vineyards, and small villages. Options include Montepulciano and Pienza. Return to your quiet Tuscan base.
Overnight: San Casciano dei Bagni

A slower day: walking paths, hot springs, and countryside picnics. Evening in the village.
Overnight: San Casciano dei Bagni

Arrive and settle into Otranto. Stroll the old town, see the cathedral mosaics, swim at Spiaggia degli Scaloni, and dine by the sea.
Overnight: Otranto

Stop at Torre Sant’Andrea for its striking limestone stacks and sea views, then drive inland to Alberobello to wander the UNESCO-listed trulli. Return via Ostuni, the White City, with time for a walk and dinner before heading back to Otranto.
Overnight: Otranto

Explore Monopoli’s old harbor and coves, then Polignano a Mare with its cliffside views and lively piazza. On the return, pause in Lecce to see its baroque squares before your last evening in Otranto.
Overnight: Otranto

Fly from Bari/Brindisi to Venice. Evening gondola ride or stroll along canals.
Overnight: Venice

Explore Piazza San Marco, Doge’s Palace, Rialto, and back canals. Evening cicchetti (Venetian tapas).
Overnight: Venice

Train via Milan to Menaggio on Lake Como. Relax on arrival by the lakeside promenade.
Overnight: Menaggio

Walk the Greenway del Lago di Como, passing lakeside villages and gardens. Visit Villa del Balbianello or Villa Carlotta.

Overnight: Menaggio

Rent a boat, swim in the lake, and stop in Varenna or Bellagio. Aperitivo by the water in Menaggio.
Overnight: Menaggio

Bid farewell to Italy with a suitcase full of memories, flavors, and photos from your grand European adventure.