Are there evening or sunset experiences ideal for romance?

Absolutely. The Chianti & San Gimignano Sunset Trip combines wine tasting with a farm dinner as the sun sets over Tuscany. Also, many food tours operate in the evening, letting you enjoy Siena's atmosphere after dark.

Can I arrange a special occasion like a proposal or anniversary in Siena?

Yes, many experiences can be tailored for celebrations. Consider a private walking tour to pop the question at a scenic spot, or book a sunset wine tour for a memorable anniversary toast. Contact the provider to arrange special touches.

We use only the cookies this site needs to work. Analytics (Google, PostHog) load only if you agree.

Cookie PolicyPrivacy Policy

LivingLocal

Every bookable experience in Italy, in one place — compared across GetYourGuide, Headout and Viator, ranked on reviews, booked on their site at their price.

Destinations

Explore

Company

About

Legal

Siena · Tuscany

Romantic Experiences in Siena

Average rating4.7Median price$148

Siena's medieval lanes and sun-washed piazzas set the stage for romance, especially as day fades into golden hour. Share a sunset toast over the Chianti hills on the Chianti & San Gimignano Sunset Trip from Siena: Wine Tasting & Farm Dinner, or savor the city's flavors hand-in-hand on the Siena's Ultimate Food Tour: A Full Tuscan Meal by Do Eat Better.

Quick match

Find the right experience in Siena — in 30 seconds

I only have 2 hours I want food, not another queue

Top experiences in Siena

475 experiencesranked by rating and review volume

Prices shown in USD, converted from € at an indicative rate.

Chianti & San Gimignano Sunset Trip from Siena: Wine Tasting & Farm Dinner

Frequently asked questions

Yes, the Private Siena Walking Tour offers an intimate, personalized exploration of the city's traditions, streets, and cathedral with skip-the-line access. It's perfect for couples wanting a tailored experience away from large groups.