Hill town days
Consider Siena, San Gimignano or smaller towns according to your route, keeping daily driving realistic.

Hill towns, country stays and long lunches.
Plan your holidayTuscany can be a rural escape, a sequence of historic towns or a mix of both. Choose a manageable area and give yourself time to enjoy the place you are staying, not just the roads between stops.
TuscanyConsider Siena, San Gimignano or smaller towns according to your route, keeping daily driving realistic.
Look closely at access roads and nearby dining when choosing a rural property.
Build in a market visit, cooking experience or tasting where it fits your interests and transport plans.
Use these prompts to start a useful conversation about your trip.
Explore Italia.itUse our checklist to organise your dates, travellers and budget for Tuscany. Check current official advice for entry requirements and travel updates.
Prepare your holiday brief Check official travel adviceDiscuss parking outside historic centres and any driving restrictions. A rural stay may need a car even when a town looks close on the map.
Describe the walking, driving and outdoor activities you are comfortable with. Ask about terrain, equipment and guide arrangements, including easier alternatives for anyone who wants a gentler day.
Outdoor plans can change with conditions. Leave some flexibility and discuss what happens if an excursion cannot run, rather than making the whole holiday depend on a single activity.
Share your ideas for Tuscany with the community team. We can help identify a community agent to discuss the route, accommodation and arrangements that suit your plans.
Talk to the communityBegin with your priorities: hill town days, a countryside base or food and local produce. Tell the community team your dates and total nights so an agent can help decide what fits comfortably.
Yes. Include the amount of walking, driving and moving between hotels you enjoy, together with any access needs. Your enquiry starts a conversation; the itinerary and availability are confirmed separately.
Tell us your preferred dates, departure airport, budget and who’s coming. Your enquiry will go to the community team with Tuscany included, so we can help connect you with the right specialist.
These pages offer inspiration. Prices, availability and arrangements are confirmed when you discuss your trip.