Find deals on 41 top-rated, price matched, sightseeing, tours, and cruises around Chianti and beyond. Explore, compare, and book inspirational adventures for every type of trip and every type of traveler.

Beautiful hikes along the Chianti vineyards
Private Hike And Wine Experiences In Chianti
Chianti, Tuscany, Italy
5.0 (2)
from $97
Much loved
Olive Oil Tours And Tasting At Frantoio Di Montalcino
Chianti, Tuscany, Italy
5.0 (72)
from $57
Often booked
Truffle Hunting In Chianti, Pasta Class And Lunch
Chianti, Tuscany, Italy
5.0 (25)
from $181
Montepulciano Pienza Montalcino Tour From Siena
Tuscany, Italy
5.0 (5)
from $1,118
Wine tasting
Greve In Chianti Wine Tasting And Winery Tour
Chianti, Tuscany, Italy
4.7 (110)
from $57
Discovering Chianti, E-bike Tour - Daily Experience
Chianti, Tuscany, Italy
5.0 (20)
from $317
Brunello Bike Tour
Brunello E-bike Tour
Chianti, Tuscany, Italy
5.0 (8)
from $283
Chianti Truffle Hunting With Lunch Or Dinner
Chianti, Tuscany, Italy
4.2 (5)
from $221
Lunch wine experience
Montalcino Wine Tour
Chianti, Tuscany, Italy
4.2 (6)
from $396
Pienza
Grand Tour Of Pienza, Montalcino, Montepulciano + Wine And Cheese Tasting
Chianti, Tuscany, Italy
5.0 (1)
from $396
Discovering Chianti: Sunset Ebike Tour And Dinner
Chianti, Tuscany, Italy
5.0 (2)
from $187
Likely to sell out
Two Wine Tastings And Visit To A Historic Cellar Inside Old Walls Of Montalcino
Chianti, Tuscany, Italy
5.0 (2)
from $75
Glimpses of the medieval village of Montefioralle
Chianti: Eno-excursion Through The Vineyards
Chianti, Tuscany, Italy
5.0 (1)
from $68
wine tasting lunch
Gourmet Wine Tour
Chianti, Tuscany, Italy
5.0 (1)
from $295
Brunello tasting
Likely to sell out
Discover Montalcino Through Its Best Productions: Brunello & Saffron!!
Chianti, Tuscany, Italy
5.0 (2)
from $215
Points of View, First Women Walk - Casato Prime Donne
1-hour Experience With Brunello. Visit To The Vineyard And Cellar
Chianti, Tuscany, Italy
4.5 (4)
from $38
Montalcino Essence: Your Privat E-bike Experience, Top Quality!
Chianti, Tuscany, Italy
5.0 (4)
from $395
Livorno Shore Excursion: Chianti and Tuscany Countryside Private Wine Tour
Much loved
Livorno Shore Excursion: Chianti And Tuscany Countryside Private Wine Tour
Chianti, Tuscany, Italy
5.0 (45)
from $519
Siena drone pic!!!
Private Guided Tour: Siena, San Gimignano And Chianti Day Trip From Florence
Florence, Tuscany, Italy
4.8 (21)
from $996
Likely to sell out
Chianti Wine Tastings And Visit To 3 Cellars With Lunch&transfer
Chianti, Tuscany, Italy
New
from $244
Likely to sell out
Wine Tasting And Dinner In Chianti
Chianti, Tuscany, Italy
New
from $97
Olive Harvest In Tuscany
Chianti, Tuscany, Italy
New
from $442
Montalcino Private Guided City Tour
Chianti, Tuscany, Italy
New
from $147
Trekking in the vineyard and artistic installations
Montalcino, Trekking In The Vineyard, Enomusicale Tasting And Cacio Di Pienza!
Chianti, Tuscany, Italy
New
from $223
Likely to sell out
Brunello Wine Tasting With Typical Tuscan Lunch
Chianti, Tuscany, Italy
New
from $65
Lunch with a view in our Exclusive Brunello wine Tour
Luxury Brunello Tour
Chianti, Tuscany, Italy
New
from $622
Electric Vespa Rental
Chianti, Tuscany, Italy
New
from $159
Vespa Tour With Chianti Winery Tasting
Chianti, Tuscany, Italy
New
from $210
Discovering Chianti: Sunset Vespa Tour With Dinner
Chianti, Tuscany, Italy
New
from $238
Truffle Hunting: Guided Tour And Pasta Cooking With Lunch
Chianti, Tuscany, Italy
New
from $419
Claudia Callegari
Private Tuscany Wine Tour Experience In Montalcino
Chianti, Tuscany, Italy
New
from $430
truffle_hunting_montalcino
Searching For Truffles
Chianti, Tuscany, Italy
New
from $283
Montefiorale
Full Day Tour In Chianti With Transportation Included
Chianti, Tuscany, Italy
New
from $679
Immerse In Tuscany's Life: Market Visit & Cooking Class With Meal
Chianti, Tuscany, Italy
New
from $181
Cellar operations
Chianti Family Owned Organic Wine Tasting
Chianti, Tuscany, Italy
New
from $71
truffle_hunter_montalcino
Searcing For Truffles: Black Or Scorzone
Chianti, Tuscany, Italy
New
from $289