Discover Tuscany’s rolling hills, medieval towns, scenic coastlines, and world-renowned wine regions on a captivating journey from Rome through Chianti, Cinque Terre, Pisa, and beyond.
Starting from $.
Tuscany n 5 Terre Escorted Tour
4 Days/3 Nights
Starting from
$
per person*
Unforgettable Italian Journeys, Designed for You
Curated by passionate Italy experts, this sample itinerary is just the beginning of your Italian adventure. Every journey we design is unique, crafted around your interests, pace, and dreams so you can experience Italy’s beauty and culture like a true insider. Let us transform your vision into a one-of-a-kind travel experience, filled with authentic moments and lasting memories
Day 1
ROMA – MONTEPULCIANO – PIENZA – SIENA
From Roman Grandeur To Tuscan Grace
- 7:00 a.m. pickup at a designated central meeting point in Rome
- Travel with multilingual tour leader through the Chianti hills
- Stop in Montepulciano, medieval village famous for Vino Nobile di Montepulciano
- Visit a charming wine cellar with wine tasting plus salami and cheese
- Continue to Pienza, Renaissance town renowned for pecorino cheese
- Proceed to Siena
- Visit Siena’s old city center and Piazza del Campo, one of Europe’s finest medieval squares
- Group dinner at your hotel in Siena
- Overnight stay in Siena
Day 2
SIENA – SAN GIMIGNANO – TAVERNELLE –CHIANTI WINE REGION – PISA – LA SPEZIA
Tuscan Icons Before The Coast Steals The Show
- Breakfast at your hotel in Siena
- Depart for San Gimignano, walled hilltop town with medieval towers
- Free time to explore lanes, squares, churches, and Gothic/Romanesque architecture
- Continue to Tavarnelle Val di Pesa area
- Visit farmhouse “La Tancia” for Chianti Classico “Gallo Nero” wine tasting and light lunch
- Afternoon transfer to Pisa
- Walking tour of Pisa’s historic center
- See the Leaning Tower, Cathedral, Baptistery, and monuments in Piazza dei Miracoli
- Evening arrival in La Spezia, coastal city in Liguria
- Group dinner and overnight stay in La Spezia
Day 3
LA SPEZIA – PORTOVENERE – GOLFO DEI POETI – CINQUE TERRE – LA SPEZIA
Boat-View Scenery with a Storybook Finish
- Breakfast at the hotel in La Spezia
- Full‑day excursion along the Gulf of Poets and Cinque Terre
- Boat tour along the coastline (weather/season permitting)
- Stops and free time in Portovenere, Vernazza, and Monterosso al Mare
- Panoramic views of colorful cliffside villages and terraced vineyards
- Alternative (low season/bad sea): tour by train and minibus instead of boat
- Return by train from Monterosso to La Spezia
- Group dinner and overnight stay in La Spezia
Day 4
LA SPEZIA – CARRARA MARBLE CAVES – MONTECARLO DI LUCCA – ROME
Arrivederci With Marble Dust in your Imagination
- Breakfast at the hotel in La Spezia
- Depart for Carrara, famous for its marble quarries
- Visit the marble caves used since Michelangelo’s time
- Optional visit to the quarry museum with ancient tools and sculptures
- Continue to Montecarlo di Lucca, hilltop town still surrounded by ancient walls
- Stop at a farmhouse for tastings of local wines, olive oil, cheese, pasta, and breads
- Afternoon departure back to Rome
- Arrival in Rome and end of tour and services
MAKE THIS ITINERARY YOURS
Turn this sample itinerary into your dream Italy vacation – tailored to your pace, passions, and budget.
Day 1
ROMA – MONTEPULCIANO – PIENZA – SIENA
From Roman Grandeur To Tuscan Grace
Your journey begins with a 7:00 a.m. pickup in central Rome. A multilingual tour leader will guide you through the rolling hills of the Chianti region to Montepulciano, an ancient village world‑famous for its Vino Nobile. Visit a charming wine cellar to taste local wines paired with salami and cheese. Continue to Pienza, a Renaissance gem best known for its delicious pecorino cheese, then travel on to Siena. Explore the old city center and reach Piazza del Campo, considered one of Europe’s most beautiful medieval squares. Enjoy dinner at your hotel in Siena and an overnight stay.
Day 2
SIENA – SAN GIMIGNANO – TAVERNELLE –CHIANTI WINE REGION – PISA – LA SPEZIA
Tuscan Icons Before The Coast Steals The Show
After breakfast, depart for San Gimignano, a beautifully preserved walled town perched on a hilltop, famous for its medieval towers that dominate the skyline. Stroll through its lanes and squares, admiring Gothic and Romanesque architecture. Continue to the Tavarnelle Val di Pesa area to visit the farmhouse La Tancia, where you’ll taste wines from the Chianti Classico “Gallo Nero” region accompanied by a light lunch. In the afternoon, head to Pisa for a walking tour of Piazza dei Miracoli, where you’ll see the iconic Leaning Tower, the Cathedral, and the Baptistery of St. John. After exploring this remarkable complex, travel on to La Spezia, where you’ll enjoy dinner and spend the night.
Day 3
LA SPEZIA – PORTOVENERE – GOLFO DEI POETI – CINQUE TERRE – LA SPEZIA
Boat-View Scenery with a Storybook Finish
After breakfast, set out for a full day of discovery along the Gulf of Poets and the Cinque Terre. Weather and season permitting, you’ll tour the coastline by boat, enjoying panoramic views of the colorful villages clinging to the cliffs above the sea. Dock in Portovenere, Vernazza, and Monterosso al Mare, with free time in each village to explore at your own pace. (In low season or in case of rough seas, the itinerary will be operated by train and minibus instead of by boat.) In the evening, take the train back from Monterosso to La Spezia, where you’ll enjoy dinner and an overnight stay.
(Your descriptive notes about each village—Riomaggiore, Manarola, Corniglia, Vernazza, Monterosso—can be kept as an “About Cinque Terre” sidebar on the page or brochure, since the core day description already covers the logistics.)
Day 4
LA SPEZIA – CARRARA MARBLE CAVES – MONTECARLO DI LUCCA – ROME
Arrivederci With Marble Dust in your Imagination
After breakfast, travel to Carrara to visit its renowned marble quarries, the same ones that provided the marble for many of Michelangelo’s masterpieces. Learn about the extraction process and, if included, visit the quarry museum to see ancient tools and sculptures. Continue to Montecarlo di Lucca, a well‑preserved hill town encircled by historic walls, set amid vineyards and olive groves. Stop at a delightful farmhouse to sample regional wines, extra virgin olive oil, cheeses, pasta, and breads that showcase Tuscan flavors. In the afternoon, return to Rome, where your tour and our services come to an end.
