Make this trip your own
Create your own free, personalized itinerary in seconds — then sign up to save and edit it.
Create my version

4-Day Dog-Friendly Foodie Adventure in Italy's Medieval Towns

Viewed by 95 travelers

Day 1: Medieval Lucca

Lucca, Italy

8:00AM

Breakfast at Caffè Condor

Start your day at Caffè Condor, enjoying their delicious pastries alongside a strong Italian espresso, perfect for fueling an adventure.
Walk to the café just 10 minutes from the city walls.
EUR15, 1 hour

9:30AM

Explore Lucca's City Walls

Take a stroll with your dog around the historic city walls, delivering stunning views and a breath of fresh air.
Walk around the walls which encircle the old town.
Free, 1.5 hours

11:00AM

Visit the Lucca Cathedral

Marvel at the breathtaking architecture of the Lucca Cathedral, dating back to the 11th century.
The cathedral is located in the heart of Lucca, easily accessible on foot.
EUR5, 1 hour

12:30PM

Lunch at Trattoria Da Benvenuti

Savor authentic Tuscan cuisine featuring local ingredients while seated outdoors with your dog.
Short walk back into the town center.
EUR40, 1 hour

2:00PM

Hiking in Parco Regionale di Monte Pisano

Head towards Parco Regionale di Monte Pisano for a scenic hike through hills adorned with olive trees and forests, welcoming your dog to join.
Drive 20 minutes to the park entrance.
Free, 3 hours

6:00PM

Dinner at Ristorante Da Pasquale

Delight in traditional dishes while enjoying the warm atmosphere and position just outside the busy tourist paths.
Drive back to Lucca to the restaurant.
EUR60, 2 hours
Find Hotels in Lucca

Day 2: Charming Barga

Barga, Italy

8:30AM

Breakfast at Caffè Della Piazzetta

Indulge in local baked goods in the charming piazza, getting a taste of the town’s friendly atmosphere.
Driving to Barga takes about 1 hour.
EUR20, 1 hour

10:00AM

Explore Barga's medieval architecture

Wander through Barga's narrow streets, taking in its medieval buildings and breathtaking views.
Easily walkable from breakfast spot.
Free, 2 hours

12:00PM

Lunch at Ristorante Pizzeria Da Riccardo

Enjoy a hearty pizza or pasta dish while soaking up the sun at the patio surrounding this casual eatery.
Just a short walk from the historic area.
EUR35, 1 hour

1:30PM

Hiking on the nearby trails

Venture out on one of the picturesque hiking trails surrounding Barga with your pup, offering stunning views and local flora.
Head to the trailhead, accessible by car in 10 minutes.
Free, 3 hours

5:30PM

Dinner at Ristorante La Torre

Savor delightful regional dishes prepared with fresh local ingredients in the heart of Barga.
Drive back to town for dinner.
EUR50, 1.5 hours
Find Hotels in Barga

Day 3: Artistic Cortona

Cortona, Italy

8:00AM

Breakfast at Caffè Tuscher

Enjoy delightful pastries and coffee in this cute café, warming up for the day ahead.
A scenic drive from Barga to Cortona.
EUR15, 1 hour

9:30AM

Visit the Museo Diocesano di Cortona

Explore Cortona's ancient art dating back thousands of years; dogs are allowed on leashes!
Located a short walk from the café.
EUR6, 1.5 hours

11:30AM

Walk through Cortona's Piazza della Repubblica

Wander through the town square where history, culture, and local shops blend beautifully.
Located conveniently close to the museum.
Free, 1 hour

12:30PM

Lunch at Osteria del Teatro

Enjoy exquisite Tuscan flavors in a cozy setting, accompanied by your furry friend on the terrace.
Just a short walk from the town square.
EUR45, 1.5 hours

2:00PM

Hiking around Cortona's hills

Embark on a scenic hike in the rolling hills surrounding Cortona, allowing your dog to enjoy the fresh air.
Access trails within 10 minutes of driving.
Free, 3 hours

5:00PM

Dinner at La Bucaccia

Dine in this acclaimed restaurant that showcases local wines and gourmet dishes, perfect for concluding your day.
Driving back into Cortona.
EUR70, 2 hours
Find Hotels in Cortona

Day 4: Wine in Montepulciano

Montepulciano, Italy

8:00AM

Breakfast at Bar Di Neri

Kick-start your day with a traditional Italian breakfast accompanied by a cup of local coffee.
Drive takes about 40 minutes to Montepulciano.
EUR15, 1 hour

9:30AM

Visit the Piazza Grande

Explore the stunning main square of Montepulciano, lined with shops and beautiful Renaissance architecture.
Short walk from the breakfast spot.
Free, 1 hour

11:00AM

Wine tasting at Avignonesi

Visit this winery to taste some of the best local wines together with your furry friend.
A pleasant 15-minute drive from the city center.
EUR30, 1.5 hours

1:00PM

Lunch at Osteria Acquacheta

Savor rustic Tuscan fare in this traditional eatery, a local favorite renowned for its delicious pastas.
Head back to the city center; it's nearby.
EUR40, 1 hour

2:30PM

Afternoon hiking at Parco Pienza

Enjoy a trek in the nearby Parco Pienza with stunning landscapes, open to leashed dogs.
Drive takes about 20 minutes.
Free, 3 hours

6:30PM

Dinner at La Grotta

Conclude your incredible Italian adventure with a memorable dining experience in this rustic, award-winning restaurant, celebrating the spirit of Tuscany.
Back to Montepulciano after hiking.
EUR65, 2 hours
Find Hotels in Montepulciano
0
Like this trip? Make your own version.
A free, personalized itinerary in seconds — sign up to save and edit it.
Create my version

More About italy

Trip Packing List: Italy (Late February — early spring conditions)
Packing List
Trip Packing List: Sligo, Ireland (20–27 June 2026)
Packing List
Summer Climate Guide for Italy: Mid-June to Mid-July
Weather Guide
Mediterranean Late Spring: A Weather Guide for June Cruises
Weather Guide
European cities list with countries — quick reference
Travel Expert
Ultimate Guide to Traveling Between Major European Cities
Travel Expert
Itinerary created by AI-assisted, human-reviewed

Plan Your italy Trip

Cost Estimator
Estimate your trip budget
Packing List
Get a custom checklist
Weather Expert
Check weather & best time to go