Tuscany Day Trip From Florence With Chianti, Siena and San Gimignano

Experience the best that Tuscany has to offer on this carefully-planned itinerary, taking you to two of the most beautiful (and historic) towns of the region & an authentic family-run vineyard/farmhouse for lunch. With an experienced driver on hand you don't have to worry about winding roads - or drinking too much of that wonderful Chianti wine!

Your driver and tour leader will pick you up in a private, air-conditioned transport in central Florence (depending on the group size, there might be two vans which the tour leader will shuttle between) and spirit you out into the hills above the city. First stop: Piazzale Michelangelo, a small piazza offering the most jaw-dropping views of Florence. You may not have heard of it yet but you'll recognize it when you see it; this is where most postcard photos are taken from.

Then it's back into your minibus and over the rolling hills of Tuscany to the town of Siena, one of the most beautiful, and historically important in the area (if not the country). Here your leader will guide you through beautiful Medieval streets (their great condition is a rarity in this region, so heavily shelled during WWII), telling you stories from the city's long history, and take you to the enormous central square where the world-famous Palio horse race takes place. Before you leave you'll have a chance to pop into the stunning cathedral (except on Sundays and festivities, when its closed) with pre-reserved tickets. Your guide will stay outside but they will give you an overview of the architecture and tell you what details to look out for once inside.

All this exploring will give you an appetite so after Siena you'll head to a local vineyard for a tour of the cellars, a wine tasting, and a delicious homemade lunch of locally-sourced ingredients. Once upon a time Tuscany's food was considered cucina povera, or poor food, for its reliance on ingredients like tomatoes, bread, and olive oil. Thankfully today we know better. Eat your lunch on the terrace overlooking the rolling hills and vineyards of Chianti. Of course there will be plenty of wine to wash it down with - we highly recommend the red.

Finally, you'll spend the afternoon in the hilltown of San Gimignano. This is one of the best-preserved of the medieval villages, built high atop hills to keep a lookout for hostile armies. Your time here is your own, so feel free to shop for souvenirs, enjoy a coffee in one of the charming piazzas, or climb to the top of the church's belltower for incomparable views of the countryside.

This trip is all about seeing as much of Tuscany as possible without any of the difficult planning and navigation. We'll take care of the logistics so all you have to do is enjoy the food, the scenery and the sightseeing.