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Home/Destinations/Chianti/Chianti highlights
Highlights · Chianti itinerary

Chianti Highlights: The Best Itinerary

See the very best of the region. Here is how to explore it — with the best-rated tours to book.

At a glance

  1. 1Towns
  2. 2Wine
  3. 3Vespa
  4. 4Best

Siena & San Gimignano

The medieval towns.

A wine tasting

Chianti Classico at a cellar.

A Vespa ride

The scenic back roads.

Book the experiences in this itinerary

Top-rated tours for exactly what this plan recommends in Chianti — prices per person.

Guided Winery Tour and Wine Tasting in Siena
Siena
Guided Winery Tour and Wine Tasting in Siena
5.0(77)·2h 30min
from$85/ person
via Viator
Rome 3-Hour Evening Vespa Sidecar Tour with Gourmet Pizza Tasting
Rome
Rome 3-Hour Evening Vespa Sidecar Tour with Gourmet Pizza Tasting
5.0(126)·3 hours
from$188/ person
via Viator
Private daytrip to Siena & Chianti wine country, with wine tasting from Florence
Florence
Private daytrip to Siena & Chianti wine country, with wine tasting from Florence
5.0(65)·8 hours
from$443/ person
via Viator
Vespa Tour in Rome Driven by Us with Optional Pick Up
Rome
Vespa Tour in Rome Driven by Us with Optional Pick Up
5.0(65)·2h 50min
from$216/ person
via Viator
Siena: Chianti Sunset Tour with Dinner & Wine Tasting
Siena
Siena: Chianti Sunset Tour with Dinner & Wine Tasting
5.0(58)·3 hours
from$108/ person
via Viator
Private Day Trip Siena, San Gimignano and Chianti from Florence
Florence
Private Day Trip Siena, San Gimignano and Chianti from Florence
5.0(268)·8–9 hours
from$387/ person
via Viator
Chianti Wine Tour from Florence to San Gimignano with 2 Wineries
Florence
Chianti Wine Tour from Florence to San Gimignano with 2 Wineries
5.0(33)·7–8 hours
from$313/ person
via Viator
Rome Morning Vespa Sidecar Tour in Rome with Cappuccino
Rome
Rome Morning Vespa Sidecar Tour in Rome with Cappuccino
5.0(1,847)·3 hours
from$170/ person
via Viator

Chianti highlights — FAQ

What is Siena known for?
Its shell-shaped square and grand cathedral.
What wine is Chianti known for?
Chianti Classico, the region’s famous red.
Do Vespa tours suit beginners?
Yes — passengers and easy routes suit beginners.

Explore more in Chianti

From FlorenceWine TastingTuscan CountrysideSiena & San GimignanoFood & Cooking