Evening Experiences

TUSCANY

3 Best Evening Experiences In Siena

Most booked first.

Our shortlist of the 3 most-booked evening experiences around Siena, ranked by what travellers actually rated. Who runs them, how long they take, what they cost.

3 Best Evening Experiences In Siena

From Siena: Chianti and San Gimignano Sunset Tour

From Siena: Chianti and San Gimignano Sunset Tour - Monteriggioni’s fortress walls: short time, big wow factor

1.From Siena: Chianti and San Gimignano Sunset Tour

Most Popular★ 4.8

Small-group Chianti winery tasting, Monteriggioni fortress, and San Gimignano sunset, finished with Vernaccia or Chianti at a farm dinner.

“Guillermo was outstanding! Fun, knowledgeable and wonderful company.( and an excellent driver!) This tour covered so much of what you want to see and experience of the Tuscany country. The group size of 6 was perfect. The winery visit and farmhouse dinner were “bravissimo!” A highlight of our 2 week trip covering Rome, Siena and…”

67 reviewsFrom $203.91by Tuscan Escapes by Papilio

Check Availability →Read the review →

Small-Group Chianti and San Gimignano Sunset Trip from Siena

Small-Group Chianti and San Gimignano Sunset Trip from Siena - Monteriggioni stop: the fortress-town walls you can still walk around

2.Small-Group Chianti and San Gimignano Sunset Trip from Siena

★ 5.0

Small-group Chianti and San Gimignano sunset trip from Siena with wine tastings, Monteriggioni walls, and a farm dinner with sunset views.

“We loved the whole experience from the commentary on the history of wine in the Tuscany area by our Tour Guide Danielle to the wine tasing stops. We visited a wine cellar on the winery/ farm used by several generations of the same family. The dinner served at the end was delicious and the wine…”

63 reviews8 to 9 hours (approx.)From $217.23by Tuscan Escapes by Papilio SRL

Check Availability →Read the review →

Sunset Summer Dinner Among the Vines – Small Group from Siena

Sunset Summer Dinner Among the Vines – Small Group from Siena - Monteriggioni at Dusk: The Hill-Town Warm-Up

3.Sunset Summer Dinner Among the Vines – Small Group from Siena

★ 3.5

Sunset summer dinner near Siena with wine tastings, barbecue in the vineyards, and a stop in Monteriggioni. Small group, English.

“Pros: lovely evening in a BEAUTIFUL winery with a gracious host who really welcomed us and took great care of our group. Transportation was from Siena by bus, easy breezy. I was really looking forward to eating outside but b/c the weather was cool, they moved us inside. We tasted a LOT of wine and…”

30 reviews5 hours (approx.)From $130.97by myTour in Italy

Check Availability →Read the review →

Explore Siena & Tuscany

Siena

Day Trips

Wine & Food

Experiences