Classic Tuscany Experience: Pisa, Siena & Wine Tasting

Duration: 12h

Group: Max 50 people

Oct 17, 2026

About This activity

Coach transportation between destinations

Free time at Pisa’s Piazza dei Miracoli to view the Leaning Tower, Cathedral and Baptistery

Lunch at a Chianti winery

Wine tasting of local varieties at the winery

Free time to explore Siena and San Gimignano

Return travel to Florence

VIP small-group option includes guided Siena tour with entry to Siena Cathedral, private gourmet lunch and small-group transport from central Florence

Entry or admission fees

Tips or gratuities

Hotel pick-up and drop-off

This full-day excursion showcases the very best of Tuscany, taking you through an extraordinary blend of iconic landmarks, medieval architecture and rolling vineyard-covered hills.

Begin the day with the striking vistas of a celebrated piazza where a world-famous leaning campanile, an imposing cathedral and an ornate baptistery dominate the skyline. Photograph these historic monuments and soak up the unique atmosphere of this UNESCO World Heritage Site.

Travel onward into the Chianti countryside, where the gentle slopes and cypress-lined lanes create the classic Tuscan panorama. Midday is devoted to a relaxed lunch in a traditional countryside setting, paired with carefully chosen regional wines that reflect local winemaking traditions.

The afternoon offers time to wander the narrow, medieval streets of a fortified city whose shell-shaped main square is a marvel of urban design, and then to ascend to a hilltop town famed for its skyline of ancient towers, artisan shops and panoramic viewpoints.

Expect ample opportunities to sample local produce, browse independent craft stores and savour authentic gelato. The day concludes with a comfortable coach journey back to Florence, leaving you with lasting memories of Tuscany’s architecture, gastronomy and landscapes.

Coach transportation between destinations

Free time at Pisa’s Piazza dei Miracoli to view the Leaning Tower, Cathedral and Baptistery

Lunch at a Chianti winery

Wine tasting of local varieties at the winery

Free time to explore Siena and San Gimignano

Return travel to Florence

VIP small-group option includes guided Siena tour with entry to Siena Cathedral, private gourmet lunch and small-group transport from central Florence

Entry or admission fees

Tips or gratuities

Hotel pick-up and drop-off

Before You Go

Meet at Florence Gate Caffetteria inside Villa Costanza Coach Station (see voucher for exact meeting time)

Accessible from Santa Maria Novella by tram T1 (approx. 20 minutes); tram tickets cost €1.50 and can be purchased at station machines

Comfortable shoes recommended for walking on cobbled streets and uneven surfaces

Order of itinerary may change while all scheduled destinations will be visited

VIP option departs from central Florence

No reviews yet

Iconic sights: Experience renowned piazzas and striking towered skylines.
Chianti experience: Enjoy a leisurely countryside lunch with local wine sampling for an authentic regional flavour.
Authentic towns: Free time in Siena and San Gimignano to explore artisan shops, viewpoints and historic squares.
Flexible options: Choose the VIP small-group upgrade for enhanced access and exclusive dining.

Perfect for travellers who want a comprehensive taste of Tuscany with comfortable transport and plenty of time to explore each destination.

Classic Tuscany Experience: Pisa, Siena & Wine Tasting

Best of Tuscany Pisa, Siena and San Gimignano with Chianti Wine

About This activity

Meeting Point

You might also like

Siena to Montepulciano: Wine Tasting & Gourmet Lunch

Lisbon Surf & Yoga Experience at Costa da Caparica

Munich Private 4 Hours Walking Tour with English Speaking Guide