Ultimate 18-Day Italy Adventure: Rome, Dolomites, Venice & Tuscany Experience

Day 1: Rome Classics

Rome, Italy on June 22, 2025

8:00am

Breakfast at Roscioli Caffè

Start your day with traditional Italian pastries and coffee at Roscioli Caffè, open from 7:30am to 7:00pm, located near Campo de' Fiori.
EUR5, 1h

9:30am

Colosseum and Roman Forum Visit

Explore the iconic Colosseum and adjacent Roman Forum. Book tickets in advance to avoid queues. Open 8:30am-7:00pm.
EUR16, 3h

1:00pm

Lunch at Trattoria da Enzo al 29

Enjoy authentic Roman cuisine in Trastevere, known for its carbonara and cacio e pepe. Open 12pm-3pm.
EUR25, 1.5h

3:00pm

Vatican Museums & Sistine Chapel

Book a late afternoon guided tour to the Vatican Museums to avoid crowds. Open till 6pm on Sundays.
EUR30, 3h

7:30pm

Dinner at Osteria da Fortunata

Savor freshly made pasta dishes in this well-loved spot near Piazza Navona, open till 11pm.
EUR35, 2h
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Day 2: Historic Rome

Rome, Italy on June 23, 2025

8:30am

Breakfast at Pasticceria Regoli

Start with artisanal pastries and cappuccino from Regoli, open at 7:30am.
EUR6, 45m

9:30am

Pantheon and Piazza Navona

Visit the Pantheon and then stroll to Piazza Navona to admire its fountains and street artists.
Free, 2h

12:00pm

Lunch at Pizza ai Marmi

Famous for delicious Roman-style pizzas, open 12pm-12am.
EUR20, 1.5h

2:30pm

Trevi Fountain and Spanish Steps

Walk to the Trevi Fountain and toss a coin, then relax by the Spanish Steps.
Free, 2h

5:00pm

Galleria Borghese

Book a ticket to see Renaissance art in the Borghese Gallery. Booking required. Open until 7pm.
EUR20, 2h

8:00pm

Dinner at La Pergola

Indulge in Michelin-star dining with panoramic views of Rome. Reservations essential.
From EUR150, 2.5h
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Day 3: Leisure & Travel

Rome to Dolomites, Italy on June 24, 2025

7:00am

Early Breakfast at your hotel

Enjoy a light breakfast before your transfer to the Dolomites.
Included, 1h

8:30am

Travel to Dolomites

Drive or take a train to a suitable start point for Alta Via 4, such as Belluno or Pieve di Cadore. The journey takes approximately 5-6 hours.
EUR60-90, 6h

3:00pm

Check-in and Preparations

Check-in at your mountain accommodation like Rifugio Chiggiato or Hotel Alla Cascata near Belluno to begin your trek the next day.
EUR80-120, 2h

7:00pm

Dinner at Hotel Restaurant

Enjoy hearty alpine cuisine to fuel your Alta Via 4 trek. Most mountain hotels offer dinner by reservation.
EUR25, 1.5h
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Day 4: Alta Via 4 Trekking

Dolomites, Italy on June 25, 2025

7:30am

Breakfast at Rifugio or Hotel

Early breakfast to prepare for your trekking day on Alta Via 4.
Included, 1h

8:30am

Begin Alta Via 4 Trail

Start your hike on the Alta Via 4, enjoying spectacular Dolomite scenery. Plan segments based on your fitness; mountain huts offer resting points.
Free, 6-8h

5:30pm

Evening at Rifugio

Check-in at a mountain refuge along the trail for overnight rest.
EUR60-80, Overnight
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Day 5: Continue Alta Via 4

Dolomites, Italy on June 26, 2025

7:00am

Breakfast and Trekking

Start with breakfast then continue on Alta Via 4 trail. Stop at scenic viewpoints and mountain huts for meals and rest.
Included / EUR20 snacks, 6-8h

6:00pm

Evening Relaxation

Arrive at next accommodation or refuge to rest and enjoy alpine dinner.
EUR60-80, Overnight
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Day 6: Finish Alta Via 4

Dolomites, Italy on June 27, 2025

7:30am

Final Trekking Day

Complete the last section of Alta Via 4, soaking up final mountain views.
Free, 4-6h

1:00pm

Travel to Venice

After trekking, take transport to Venice, approximately 3-4 hours by car or train.
EUR40-70, 4h

5:00pm

Check-in at Venice Hotel

Settle into your hotel in Venice's historic centre for a relaxed stay.
EUR120-200/night, Rest
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Day 7: Venice Exploration

Venice, Italy on June 28, 2025

8:30am

Breakfast at Pasticceria Tonolo

Enjoy pastries and coffee at this popular Venetian café, open from 7am.
EUR8, 1h

9:30am

St Mark's Basilica & Square

Visit the stunning basilica and wander St Mark's Square. Basilica opens 9:30am-5pm.
Free, 2h

12:00pm

Lunch at Trattoria Alla Madonna

Savour fresh seafood dishes near the Rialto Bridge. Open 12pm-3pm.
EUR30, 1.5h

2:00pm

Gondola Ride

Relax on a classic gondola ride through Venice’s canals for approximately 30-40 minutes.
EUR80, 45m

4:00pm

Explore the Doge's Palace

Tour the ornate Doge's Palace, open 9am-7pm.
EUR25, 2h

7:00pm

Dinner at Osteria Ae Sconte

Dine on Venetian classics at this relaxed osteria open until 11pm.
EUR35, 2h
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Day 8: Venice Relaxed

Venice, Italy on June 29, 2025

9:00am

Breakfast at Rosa Salva

Enjoy traditional Venetian breakfast pastries and coffee. Open from 7am.
EUR7, 1h

10:00am

Murano and Burano Visit

Take a vaporetto to explore Murano’s glassmaking and colourful houses on Burano. Ferries run from 9am.
EUR20 roundtrip, 4h

3:00pm

Relax in Cannaregio District

Return to Venice and unwind in the quieter Cannaregio area with cafes and canals.
Free, 2h

7:00pm

Dinner at Antiche Carampane

Enjoy romantic seafood dinner made from fresh local catches, open until 11pm.
EUR45, 2h
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Day 9: Venice Leisure

Venice, Italy on June 30, 2025

8:30am

Breakfast at Farini

Try Venetian-style coffee and breakfast snacks, open early every day.
EUR6, 1h

10:00am

Explore Jewish Ghetto & Fondamenta della Misericordia

Discover historic Jewish heritage and enjoy quiet canal views in this area.
Free, 3h

1:30pm

Lunch at Osteria Al Squero

Have casual lunch with cicchetti (Venetian tapas) near a gondola workshop.
EUR15, 1h

3:00pm

Free Afternoon for Shopping or Museums

Choose to shop for Murano glass or visit minor museums like Ca' Rezzonico and Peggy Guggenheim Collection (both open till 7pm).
EUR15-20, 3h

7:00pm

Dinner at Ristorante Quadri

Gourmet dinner on St Mark’s Square terrace, reservations recommended.
EUR70+, 2.5h
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Day 10: Travel to Tuscany

Venice to San Gimignano, Tuscany, Italy on July 1, 2025

7:00am

Breakfast at hotel

Enjoy a leisurely breakfast before departure.
Included, 1h

8:00am

Travel to San Gimignano

Drive or take train + bus to San Gimignano, the best base for Tuscany horse riding, wineries and Vespa rentals. Journey takes 4-5 hours.
EUR60-100, 5h

1:30pm

Check-in and Lunch at Cum Quibus

Check into your charming hotel in San Gimignano and enjoy lunch at famed Cum Quibus restaurant (open 12pm-2:30pm).
EUR40, 1.5h

3:30pm

Vespa Pickup at Tuscany Motorcycles

Collect your 2 Vespas from Tuscany Motorcycles rental in San Gimignano. They provide helmets and safety briefings.
EUR80/day per Vespa, 1h

5:00pm

Vespa Ride Around San Gimignano

Enjoy an easy ride around the medieval town and nearby countryside to get familiar with the Vespas.
Included, 2h

8:00pm

Dinner at La Mandragola

Casual Tuscan dining with local wines and organic ingredients, open till 10pm.
EUR35, 2h
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Day 11: Horse Riding & Winery

San Gimignano, Tuscany, Italy on July 2, 2025

8:00am

Breakfast at Hotel

Start with a hearty breakfast preparing for your riding day.
Included, 1h

9:00am

Horse Riding Tour with Agriturismo Il Casale

Enjoy guided horse riding through vineyards and olive groves near San Gimignano.
EUR80-120 for half day, 3-4h

1:30pm

Lunch at Osteria Selvapiana

Rustic Tuscan lunch in the countryside near wineries, open 12pm-3pm.
EUR30, 1.5h

3:00pm

Winery Visit & Tasting at Fattoria San Donato

Take a guided tasting tour at this family-run Chianti winery a short Vespa ride from San Gimignano. Tours last 1.5-2h.
EUR25 tour fee, 2h

6:00pm

Evening Vespa Ride Back

Return leisurely to San Gimignano by Vespa, admiring the sunset.
Included, 1h

8:00pm

Dinner at Ristorante Dorando Pietri

Traditional Tuscan fare downtown with excellent local wines and cheeses.
EUR40, 2h
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Day 12: Vespa Wine Tour

San Gimignano & Chianti Region, Tuscany, Italy on July 3, 2025

8:00am

Breakfast at Hotel

Fuel up with breakfast before today’s full Vespa wine tour.
Included, 1h

9:00am

Self-Guided Vespa Wine Tour

Ride your Vespas through the Chianti wine region visiting wineries such as Castello di Verrazzano and Castello di Querceto. Consider a guided tour for drinking stops or drive yourself to selected locations. Driving is feasible but requires a designated driver; otherwise, book a small group wine tour which includes transport from San Gimignano.
Vespa rental EUR80/day; Winery tastings EUR15-30 each, 6h

3:30pm

Return to San Gimignano

Relax and unwind in town after your ride.
Included, 1h

7:00pm

Dinner at Cum Quibus

Fine-dining to celebrate your Tuscan adventure with seasonal dishes and local wine.
EUR50+, 2h
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Day 13: Relax & Explore Tuscany

San Gimignano, Tuscany, Italy on July 4, 2025

9:00am

Breakfast at local café

Enjoy a relaxed breakfast in town, sampling fresh pastries and espresso.
EUR7, 1h

10:00am

Explore San Gimignano

Stroll the medieval streets, visit the Torre Grossa and local artisan shops. Open 10am-6pm.
EUR9 for Torre entrance, 3h

1:00pm

Lunch at La Vecchia Latteria

Savour traditional Tuscan dishes with a casual vibe.
EUR25, 1.5h

3:00pm

Leisurely Vespa Ride to Nearby Villages

Visit nearby Certaldo or Monteriggioni by Vespa for light sightseeing.
Included, 3h

7:00pm

Dinner at Ristorante San Martino

Enjoy a final Tuscan dinner featuring farmhouse ingredients.
EUR35, 2h
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Day 14: Departure or Extension

San Gimignano, Tuscany, Italy on July 5, 2025

Morning

Breakfast and Pack

Enjoy your final morning in Tuscany with a leisurely breakfast before packing.
Included, 1h

Travel

Departure or Continue Italian Adventure

Arrange transport to your next destination or airport from San Gimignano. Florence or Pisa airports are closest, about 1.5 hours away.
EUR50-70 taxi or bus, Variable
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