Tuscany in 4-Day with Florence, Cinque Terre, Winery & Siena

4 days (approximately)
Offered in: English

This 4-day experience combines the very best of Tuscany, Florence, and the Cinque Terre in one seamless journey. Unlike standard day trips, you’ll enjoy carefully curated itineraries with expert guides, exclusive wine tastings in the Chianti countryside, and overnight stays in Florence that let you truly soak up the Renaissance atmosphere.

From admiring Michelangelo’s David at the Accademia to savoring lunch in a Tuscan winery, exploring medieval Siena, climbing Pisa’s Leaning Tower square, and cruising past the colorful villages of the Cinque Terre, every day offers something new and unforgettable.

The balance of guided tours, cultural immersion, free time, and scenic travel makes this more than a tour — it’s a complete Italian experience that connects history, art, cuisine, and landscape into memories that last a lifetime.

What's Included

Full-day excursion to Pisa, Siena & San Gimignano.
Day 2 and Day 3 round-trip transportation by comfortable coach/bus.
Chianti wine tasting class and winery visit.
Lunch (Optional[2])
Lunch
Full-day Cinque Terre tour with lunch, boat, and train tickets included.
Breakfast (Optional[3])
Breakfast
3 nights in 3–4 star accommodation in Florence.
Daily continental breakfast and 2 lunches (Chianti winery & Cinque Terre)
Professional, English-speaking tour leader or driver.
Guided Florence walking tour with entry to Uffizi, Duomo Square & Accademia.
Florence and Siena guided walking tours.
Pickup and drop-off inside the city center of Florence.
Dinners and beverages not mentioned in the inclusions.
Gratuities for guides, drivers, and hotel staff (optional).
Airport transfers to and from Florence.
Entrance fees to attractions not listed as included.
Personal expenses such as souvenirs, extra drinks, or optional activities.
Optional activities not specified in the itinerary.
Lunch on Day 1 and Day 4.

Meeting and pickup

Meeting point

You will be greeted at the designated meeting point in central Florence and provided with all the necessary information, including your printed or digital itinerary with timings and instructions. Please note that pickup or drop-off inside the city center of Florence is not available.

End point
This activity ends back at the meeting point.

Itinerary

Duration: 4 days (approximately)
    Day 1

    Sightseeing in Florence - Arrival, Uffizi Gallery & Florence Walking Tour

    3 stops
  • 1

    Your adventure begins in Florence, where you’ll be greeted by your tour leader and checked in at your hotel.

    1 hour Admission ticket free
  • 2

    After settling in, start the morning with a guided visit to the Uffizi Gallery, home to Renaissance masterpieces by Botticelli, Leonardo da Vinci, and Michelangelo.

    1 hour 30 minutes Admission ticket included
  • 3

    Continue with a walking tour of Florence’s historic center, crossing Piazza della Signoria, Ponte Vecchio, and narrow medieval streets filled with history and charm. In the evening, enjoy free time to relax and dine at leisure. Overnight in Florence.

    1 hour 30 minutes Admission ticket free
  • Day 2

    Siena, San Gimignano with Wine Tasting & Pisa

    5 stops
  • 4

    After breakfast, depart early for Siena, where a professional guide will lead you on a walking tour through its winding streets, bustling Piazza del Campo, and the majestic Cathedral. After the tour, enjoy free time for a coffee or to wander at your own pace.

    4 hours Admission ticket free
  • 5

    The journey continues into the Chianti countryside, where a traditional farm or winery awaits. Savor a typical Tuscan lunch paired with excellent wines, surrounded by rolling hills and vineyards.

    2 hours Admission ticket free
  • 6

    In the afternoon, head to San Gimignano, famous for its medieval towers. Explore narrow cobblestone streets, browse craft shops, and soak in the unique skyline.

    3 hours Admission ticket free
  • 7

    The final stop is Pisa, where you will have time to admire the Cathedral, Baptistery, Monumental Cemetery, and of course the Leaning Tower. Return to Florence in the evening, often accompanied by a Tuscan sunset.

    2 hours 30 minutes Admission ticket free
  • 8

    Overnight stay in Florence.

    Admission ticket free
  • Day 3

    Cinque Terre Villages & Coastal Cruise

    5 stops
  • 9

    Start early for a full-day excursion to the Cinque Terre, a UNESCO World Heritage Site. After arriving from Florence, your first stop is Manarola, a charming village of pastel houses and vineyards. Stroll through narrow alleys and admire breathtaking coastal views.

    2 hours Admission ticket free
  • 10

    Continue by train to Vernazza, one of the most photographed fishing villages in Italy. Relax at the small harbor or enjoy a coffee overlooking the sea.

    2 hours Admission ticket free
  • 11

    Next, travel by train to Monterosso, known as the “Pearl of the Cinque Terre.” Here you’ll have free time to swim, sunbathe, or enjoy a leisurely lunch in a local restaurant.

    2 hours Admission ticket free
  • 12

    In the afternoon, board a boat to admire the dramatic coastline from the water. Arrive in Riomaggiore, where colorful houses cling to cliffs around a small natural port. Explore at your own pace before returning to Florence in the evening.

    2 hours Admission ticket free
  • 13

    Overnight stay in Florence.

    Admission ticket free
  • Day 4

    Sightseeing of Florence

    3 stops
  • 14

    On your final day, enjoy breakfast at your hotel before joining your guide for visits to two of Florence’s most famous landmarks. A visit to the Accademia Gallery, home to Michelangelo’s David, one of the world’s most famous works of art.

    1 hour Admission ticket included
  • 15
    Piazza del Duomo

    Then, discover the grandeur of the Duomo and its extraordinary architecture. Admire Brunelleschi’s dome, Giotto’s bell tower, and the Cathedral’s stunning interior, learning the stories behind this masterpiece.

    1 hour 30 minutes Admission ticket included
  • 16

    Afterwards, check out from your hotel. Your tour concludes, leaving you full of unforgettable memories of Florence, Tuscany, and the Cinque Terre.

    Admission ticket free

Additional info

  • Public transportation options are available nearby
  • Specialized infant seats are available
  • Not recommended for travelers with spinal injuries
  • Not recommended for pregnant travelers
  • Not recommended for travelers with poor cardiovascular health
  • Travelers should have at least a moderate level of physical fitness
Supplied by Star Florence

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Tags

Multi-day Tours
Bus Tours
Cultural Tours
Walking Tours
Food & Drink

Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

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