On our most recent adventure, my family and I spent one incredible week bouncing between Rome, Tuscany, and Venice.
Our twins are eleven and enjoy trying new foods and activities, but don't love lengthy or strenuous walks. We tend to be more active travelers and prefer to fulfill the bucket lists over fully unplugging. Our nonnegotiables are blackout curtains and included breakfasts. This was the perfect mix of excitement and rest for us. See more footage in this reel! Here was our rough itinerary:
Day 1 - Rome
Stay @ Palazzo Goldoni
Arrive 7:45am
Drop bags
Taxi to Vatican Museums 10:30
Taxi to Spanish Steps for gelato
Walk to Capuchin Crypts
Dinner @ Terraza Delle 5 Lune @ 7:30
Day 2 - Rome
Stay @ Palazzo Goldoni
9:30 Driving Tour with Aldo & Giorgio
Catch Pope Leo for his 12:00 Sunday balcony prayers @ St. Peter’s Square
Dinner @ Alla Rampa
Day 3 - Tuscany
Stay @ Borgo Pignano
3:29 drive, stop at Civita (crumbling city) otw
Explore grounds
Truffle hunting?
7:30 dinner @ Villa Pignano
Day 4 - Tuscany
Stay @ Borgo Pignano
10:30-12:00 cooking class
1 hr. drive to Pisa
Tower climb @ 3:00
Rick Steves walk
Walk the beach and grab dinner by the Marina
Day 5 - Tuscany
Stay @ Borgo Pignano
1 hr. drive to Florence (leave 8:30)
Shop @ Hermes and Scoula de Cuoio
Accademia @ 1:00 ✅
Lunch @ Giada's recommended sandwich shops
Walk by St. Maria Cathedral
Walk to Uffizi @ 2:00
Dinner in Volterra
Day 6 - Venice
Stay @ Hotel Aquarius
Park @ Piazalle Roma
Take the ACTV vaporetto line 1 or 5.2
Get off @ riva de biasio (2nd stop)
Rick Steves walk
St. Mark’s Basilica @ 4:00
Dinner around the square
Nighttime gondola with music
Day 7 - Florence
Depart after breakfast
Before you go:
My friend Ashley Esparza of Runways and Sky is in the early stages of launching a travel concierge business while living in Italy, and she was instrumental in helping us plan our time in Rome. She arranged our driving tour and shared invaluable hotel recommendations—I can’t recommend her enough if you’re planning a trip.
While most Italians speak English (and we managed in some places with Spanish), making an effort goes a long way. Here are a few helpful phrases.
We rely heavily on Rick Steves travel guides for recommendations, historical context, and especially his walking tours—they’re consistently spot on.
Packing-wise, we typically fit everything for our family of four into two large suitcases. However, between tiny European car trunks and hauling luggage over Venice’s many bridges, we’ll be switching to four rolling carry-ons next time.
We also prefer to drive when traveling—it gives us the freedom to explore at our own pace. That said, Italy’s restricted traffic zones (ZTLs) can be tricky and expensive if you’re not careful. Apps like Waze catch some of them, but not all—so keep an eye out for signage.
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