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Family-Friendly Italy Itinerary: Wine Tours, Historic Sites & Scenic Adventures

Viewed by 89 travelers

Day 1: Arrival and Relax

Montepulciano, Italy on August 25, 2025

3:00pm

Arrival at Puglia Airport and Transfer to Montepulciano

Land at Puglia airport and take a pre-arranged transfer or rent a car to Montepulciano, a charming hill town famed for its wine and panoramic views. Settle into accommodation and relax after travel.
EUR100 (transfer), 2h0m

7:00pm

Dinner at Osteria Acquacheta

Enjoy a family-friendly dinner featuring traditional Tuscan dishes and Montepulciano wine at this locally loved osteria. Open 7pm-11pm.
EUR15 per person, 1h30m
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Day 2: Wine Tour & Scenic Views

Montepulciano, Italy on August 26, 2025

9:00am

Breakfast at Local Bakery

Start the day with fresh pastries and coffee from a nearby bakery, ideal for budget-conscious breakfast.
EUR5 per person, 0h30m

10:00am

Wine Tour at Avignonesi Winery

Take a family-friendly guided tour of Avignonesi, one of Montepulciano’s top vineyards specializing in Vino Nobile wines. Learn about the winemaking process and enjoy tastings.
EUR25 per adult, free for under 18, 2h0m

1:00pm

Lunch at La Porta di Bacco

Eat lunch with stunning views, serving affordable Tuscan meals and local wines. Open noon to 3pm.
EUR20 per person, 1h0m

3:00pm

Walking Tour of Montepulciano Historic Centre

Explore the Renaissance architecture and stunning views over the Val d’Orcia. Free walking tour or self-guided visit to Piazza Grande and local shops.
Free, 2h0m

7:30pm

Dinner at Supermarket Picnic

Pick up fresh produce and local cheeses from the supermarket for an affordable and relaxed family picnic back at your accommodation.
EUR15 per family, 1h0m
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Day 3: Day Trip to Pienza and Bagno Vignoni

Montepulciano, Italy on August 27, 2025

8:00am

Breakfast at Accommodation

Enjoy a simple breakfast with groceries purchased locally to save budget.
EUR5 per person, 0h30m

9:00am

Day Trip to Pienza and Bagno Vignoni

Drive or take local transport to the nearby Renaissance town of Pienza, famous for pecorino cheese and stunning countryside views. Continue to Bagno Vignoni to see its unique thermal pool in the town square.
EUR10 transport per person, free entry sites, 6h0m

3:30pm

Return to Montepulciano: Snack at Local Café

Stop at a café in Montepulciano for coffee and sweet treats after an active day.
EUR7 per person, 0h45m

7:00pm

Dinner at La Grotta

Dine at this family-friendly restaurant serving well-priced Tuscan meals, open 7pm to 10:30pm.
EUR20 per person, 1h30m
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Day 4: Relax & Explore Montepulciano

Montepulciano, Italy on August 28, 2025

8:30am

Breakfast at Bakery

Grab fresh pastries and coffee at a local bakery to start the day.
EUR5 per person, 0h30m

9:30am

Visit Cantina Contucci Wine Cellar

Take an underground wine cellar tour focusing on history and aging processes. Tastings included, open 9:30am-12pm.
EUR20 per adult, 1h30m

12:30pm

Lunch at Supermarket for Picnic Lunch

Shop for picnic supplies at local supermarket, enjoy lunch at Montepulciano’s scenic parks.
EUR10 per family, 1h0m

2:00pm

Leisure Afternoon at Montepulciano Parks & Views

Relax with family at Belvedere di Montepulciano viewpoint to capture beautiful photos.
Free, 2h0m

7:00pm

Dinner at Ristorante Il Giglio

Experience traditional dishes with a moderate price range; open from 7pm to 10:30pm.
EUR22 per person, 1h30m
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Day 5: Travel to Florence & Explore

Florence, Italy on August 29, 2025

8:00am

Early Breakfast at Accommodation

Pack a quick breakfast at your accommodation to save time.
EUR5 per person, 0h30m

9:00am

Travel Montepulciano to Florence

Drive or take a train from Montepulciano to Florence, approximately 1.5 to 2 hours journey.
EUR20 per person, 2h0m

12:00pm

Lunch at Mercato Centrale

Enjoy a variety of affordable Florentine food from stalls in the famous central market, open 10am-11pm.
EUR15 per person, 1h0m

1:30pm

Walk to Florence Cathedral (Duomo) & Historic Centre

Visit iconic landmarks including the Duomo and Baptistery; outside exploration is free though interior entry costs EUR20.
Free to walk; optional EUR20 entry, 2h0m

4:00pm

Gelato Break at Gelateria La Carraia

Taste some of Florence’s best gelato at a family favourite spot, open until late.
EUR4 per person, 0h30m

7:30pm

Dinner at Trattoria Mario

Eat delicious traditional Florentine cuisine at this family-friendly trattoria, open 12pm-3pm & 7pm-10pm.
EUR20 per person, 1h30m
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Day 6: Florence Museums & Parks

Florence, Italy on August 30, 2025

8:00am

Breakfast at Accommodation

Prepare an easy breakfast with groceries bought locally to save money.
EUR5 per person, 0h30m

9:30am

Visit Uffizi Gallery

Experience Renaissance masterpieces in one of the world's most famous art museums. Booking online in advance recommended. Open 8:15am-6:45pm.
EUR24 per adult, students discount available, 2h0m

12:00pm

Lunch at Pizzeria O’VeScialle

Enjoy tasty and budget-friendly pizzas near Uffizi Gallery, open 12pm-3pm and 7pm-11pm.
EUR12 per person, 1h0m

2:00pm

Walk in Boboli Gardens

Stroll through Florence’s historic Boboli Gardens, full of sculptures, fountains and scenic views. Open 8:15am-7:30pm.
EUR10 per adult, 1h30m

6:00pm

Relax and Light Dinner at Supermarket Picnic

Head to a local supermarket to pick up fresh items for a casual evening meal at accommodation.
EUR15 per family, 1h0m
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Day 7: Day Trip to Siena

Florence, Italy on August 31, 2025

7:30am

Breakfast at Accommodation

Prepare an early breakfast with groceries for travel day.
EUR5 per person, 0h30m

8:30am

Travel to Siena

Take a train or bus to Siena, about 1.5 hours from Florence.
EUR12 per person, 1h30m

10:00am

Visit Piazza del Campo and Siena Cathedral

Explore the famous Campo square and visit the majestic cathedral; cathedral entry costs EUR8.
EUR8 per adult, 2h0m

12:30pm

Lunch at La Taverna di San Giuseppe

Dine at family-friendly trattoria with Tuscan specialties, open 12pm-3pm.
EUR20 per person, 1h0m

2:30pm

Return to Florence & Rest

Travel back to Florence and relax at accommodation.
EUR12 per person, 1h30m

7:00pm

Dinner at Trattoria Antico Fattore

Classic Tuscan meals in a welcoming setting, open 7pm-11pm.
EUR22 per person, 1h30m
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Day 8: Travel to Venice & Explore

Venice, Italy on September 1, 2025

7:30am

Breakfast at Accommodation

Quick breakfast before travel day.
EUR5 per person, 0h30m

8:30am

Travel Florence to Venice

Take a direct train from Florence to Venice, approximately 2h15m journey.
EUR35 per person, 2h15m

11:00am

Check-in and Light Lunch nearby

Settle into accommodation and grab a quick light lunch at a nearby café serving panini and salads.
EUR10 per person, 1h0m

1:00pm

Stroll around Piazza San Marco

Visit Venice’s iconic square, enjoy the scenery, and visit St. Mark’s Basilica from outside (entry fees optional).
Free; Basilica entry optional EUR3, 2h0m

4:00pm

Gondola Ride

Enjoy a classic gondola ride through Venice’s canals for a memorable family experience.
EUR80 per gondola (4 people), 0h30m

7:00pm

Dinner at Osteria al Mascaron

Budget-friendly Venetian dishes served in a cozy spot, open 7pm-11pm.
EUR25 per person, 1h30m
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Day 9: Venice Historical & Scenic

Venice, Italy on September 2, 2025

8:30am

Breakfast at Bakery near Accommodation

Enjoy fresh pastries and cappuccino to start the day.
EUR6 per person, 0h30m

9:30am

Visit Doge’s Palace

Explore the historic palace with its beautiful art and prison cells; open 9am-7pm.
EUR25 per adult, 2h0m

12:00pm

Lunch at Dal Moro's Fresh Pasta To Go

Quick, affordable fresh pasta takeaway enjoyed in a nearby park.
EUR10 per person, 1h0m

1:30pm

Explore Rialto Bridge and Market

Wander the lively market area and famous bridge, great for photos and local flavour.
Free, 1h30m

3:00pm

Visit Peggy Guggenheim Collection

See modern art in a beautiful palace setting, open 10am-6pm.
EUR15 per adult, 1h30m

7:00pm

Dinner at Local Pizzeria

Relax with casual pizza dinner, open until late, budget-friendly for families.
EUR15 per person, 1h30m
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Day 10: Venice Leisure & Departure Next Day

Venice, Italy on September 3, 2025

8:00am

Breakfast at Accommodation

Prepare a simple breakfast to save time and budget.
EUR5 per person, 0h30m

9:00am

Visit Murano Island for Glass Blowing Tour

Take the vaporetto to Murano and watch skilled artisans create famous Venetian glass. Open 10am-5pm.
EUR20 transport, free viewing, 3h0m

1:00pm

Lunch at Murano Café

Enjoy light lunch by the lagoon with pizza or sandwiches.
EUR15 per person, 1h0m

3:00pm

Return to Venice & Rest

Head back to Venice for a relaxed afternoon and pack for next day.
Included in transport cost, 1h0m

7:00pm

Dinner at Supermarket Picnic

Shop for affordable ingredients to enjoy a budget-friendly dinner indoors.
EUR15 per family, 1h0m
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Day 11: Travel to Sestri Levante

Sestri Levante, Italy on September 4, 2025

8:00am

Breakfast at Accommodation

Simple breakfast before travel.
EUR5 per person, 0h30m

9:00am

Travel Venice to Sestri Levante

Take train south to the coastal town of Sestri Levante, approx 4 hours with transfer.
EUR40 per person, 4h0m

1:30pm

Lunch at Trattoria da Oscar

Enjoy seafood and local Ligurian dishes at this affordable family spot, open 12pm-2:30pm.
EUR20 per person, 1h0m

3:00pm

Explore Baia del Silenzio (Bay of Silence)

Relax at this beautiful beach known for clear waters and scenic views, perfect for family relaxation.
Free, 3h0m

7:00pm

Dinner at Supermarket Picnic

Pick up fresh local produce and bread for a budget-friendly picnic dinner.
EUR15 per family, 1h0m
Find Hotels in Sestri Levante

Day 12: Join Young Adult & Cinque Terre Day Trip

Sestri Levante, Italy on September 5, 2025

8:00am

Breakfast at Accommodation

Prepare breakfast for family including new young adult arrival.
EUR5 per person, 0h30m

9:00am

Travel to Cinque Terre

Take short train ride to explore Riomaggiore and Manarola, part of Cinque Terre’s famous seaside villages.
EUR15 per person return, 5h0m

1:00pm

Lunch at Trattoria in Manarola

Enjoy fresh seafood and regional Ligurian dishes at family-friendly prices.
EUR20 per person, 1h0m

3:30pm

Return to Sestri Levante

Relax at accommodation or beach after returning from day trip.
Included in transport cost, 1h30m

7:00pm

Dinner at Ristorante Gianni

Enjoy Ligurian specialities in a welcoming environment, open 7pm-10:30pm.
EUR22 per person, 1h30m
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Day 13: Relaxation & Local Exploration

Sestri Levante, Italy on September 6, 2025

8:30am

Breakfast at Bakery

Purchase fresh bread and pastries for a light breakfast.
EUR5 per person, 0h30m

9:30am

Visit Local Markets and Explore Town

Enjoy visiting the local market and quaint shops in Sestri Levante’s old town.
Free, 2h0m

12:00pm

Lunch at Supermarket Picnic

Grab affordable lunch supplies for a picnic at the beach or park.
EUR10 per family, 1h0m

2:00pm

Afternoon at Baia delle Favole

Spend relaxing time on this sandy beach, perfect for swimming and sunbathing.
Free, 3h0m

7:00pm

Dinner at Ristorante Vittorio

Dine on Ligurian cuisine in this popular eatery, open 7pm-11pm.
EUR25 per person, 1h30m
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Day 14: Travel to Puglia & Departure

Puglia, Italy on September 7, 2025

7:00am

Early Breakfast at Accommodation

Prepare for travel with a quick breakfast.
EUR5 per person, 0h30m

8:00am

Travel Sestri Levante to Puglia Airport

Take train and/or flight back to Puglia to catch flight to London.
EUR50 per person, 5h0m

1:00pm

Lunch at Puglia Airport

Grab a quick and budget-friendly lunch at the airport cafe.
EUR12 per person, 1h0m

3:00pm

Flight from Puglia to London

Depart Puglia for London, concluding the family trip.
Paid separately, 2h30m
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