The Best Hotels, Apartments & Agriturismos in San Gimignano, Italy (Historic Centre & Countryside)
Timeless Wanderers: Posted January 25, 2026
Where to Stay in San Gimignano: Historic Centre vs Countryside Agriturismos
San Gimignano is one of Tuscany’s most atmospheric hill towns, known for its medieval towers, vineyard-covered countryside, and slow traditional lifestyle.
Staying here is about choosing between sleeping inside the stone walls or waking to vineyard views just beyond them.
From boutique hotels in historic palazzi to countryside agriturismos surrounded by olive groves, San Gimignano offers a wide range of stays suited to couples, families, and travellers seeking space and calm.
This guide covers the best 14 hotels, apartments, and farm stays, all carefully selected for location, comfort, and character.
Each option is ranked by budget, luxury, family-friendly, or countryside farm stay, helping you choose the right base for exploring San Gimignano and the surrounding Tuscan hills.
Table of Contents
Best Parts of San Gimignano to Stay
Historic Centre: Best for walkable access to towers, cafés, and museums.
Countryside hillsides: Scenic agriturismi views of vineyards and olive groves.
Near Strada Chiantigiana: Close to wine routes and day trips.
Just outside town: Quiet settings with easy car access.
We can help you plan your dream trip to Tuscany, with a personalised itinerary designed just for you.
After more than 20 years of travelling to Tuscany—and loving it so much we decided to make it our home—we now live here and explore the region at a relaxed, local pace.
Planning a trip to Tuscany is exciting, but choosing where to go, how long to stay, and how to get around can quickly become overwhelming.
That’s where we come in. We offer a personalised planning service that helps you decide exactly how to explore Tuscany, based on your travel style, budget, and pace.
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How We Chose These Luxury Hotels and Apartment Rentals in San Gimignano
Each property in this guide was selected for its combination of location, comfort, and overall quality.
We focused on luxury hotels and apartments within San Gimignano’s historic centre or just beyond the city walls, where access to major sights, restaurants, and quieter streets is easy.
All stays are consistently well-reviewed, bookable on trusted platforms, and known for thoughtful service, elegant interiors, and a sense of place that reflects San Gimignano’s historic character.
Don’t have time to read the whole post? Here’s the quick version:
1. Hotel Bel Soggiorno – offers large rooms and an on-site restaurant serving typical Tuscan dishes.
2. Hotel San Michele – offers a peaceful location, Tuscan-style accommodation with free WiFi and views of the surrounding countryside.
3. Hotel Casolare Le Terre Rosse – have rustic or modern furnishings. Each includes satellite TV and minibar.
4. Leon Bianco is in Piazza della Cisterna, one of San Gimignano’s main squares. During summer, breakfast is served on the quiet, relaxing terrace.
5. Palazzo Al Torrione in San Gimignano is housed in a historic building, offering a unique setting with a view of the city.
6. Le Fonti di San Gimignano Room in San Gimignano offers family rooms with private bathrooms, air-conditioning, and city views
7. Antico Casolare offers a farm stay with a beautiful garden and free WiFi, a lounge, and family rooms.
8. Casa Milena in San Gimignano offers a serene garden and a spacious terrace.
9. L’Antico Pozzo is a 15th-century building .This charming hotel offers stylish, unique rooms with free Wi-Fi.
10. Hotel La Cisterna is set in a picturesque namesake square. The rooms offer air conditioning, free Wifi and a flat-screen satellite TV.
11. Relais Santa Chiara is set just 400 metres from the medieval walls of San Gimignano,It offers elegant rooms, a garden, and an outdoor pool.
12. Mormoraia features an outdoor pool with hot tub, a sauna, and a Turkish bath. Free WiFi is available in the Tuscan-style rooms.
13. Tenuta Sovestro offers comfortable rooms with air-conditioning, private bathrooms, and garden views. Each room includes a work desk, TV.
14. Podere La Quercia in San Gimignano offers a farm stay with a garden, open-air bath, and free WiFi.
BUDGET HISTORIC STAYS
1. Hotel Bel Soggiorno
Historic Centre | €130–€170 |
A long-established, family-run hotel inside the city walls, Bel Soggiorno offers traditional rooms with charming stone features and rustic décor.
Its terrace provides sweeping views of the Tuscan countryside. Perfect for travellers prioritising location and authentic character over luxury amenities.
Within minutes of Piazza della Cisterna and San Gimignano’s main towers, it’s one of the best budget-friendly historic options for guests wanting immersive town-centre experience without stretching the budget.
2. Hotel San Michele
Outside Historic Centre | €120–€160 |
Set in a converted convent, Hotel San Michele combines simple, clean rooms with a serene atmosphere.
Just steps from main sights and restaurants, it’s ideal for short stays or for travellers spending most of the day exploring.
The classic interiors preserve the historic charm of the building, giving guests a sense of being part of the medieval town while remaining affordable and practical.
3. Hotel Casolare Le Terre Rosse
Countryside | €140–€170 |
Located a short drive from town, this budget countryside property offers comfortable rooms, a pool, and a garden.
Ideal for travellers with cars, it balances affordability with outdoor space.
While rooms are simple, the views over the surrounding hills provide a true Tuscan atmosphere.
Guests can easily drive into San Gimignano for dinner or sightseeing, making it a practical and scenic budget pick.
MID-RANGE HISTORIC STAYS
4. Hotel Leon Bianco
Piazza della Cisterna | €190–€260 |
Overlooking the main square, Leon Bianco blends historic charm with comfort.
Rooms feature classic décor and some include views of the towers.
Its prime location means restaurants, cafés, and museums are all within steps.
Ideal for couples or small families seeking a mid-range stay inside the medieval walls, offering convenience, service, and authentic town-centre atmosphere.
5. Palazzo al Torrione
Historic Centre | €180–€250 |
Palazzo al Torrione provides spacious apartments with kitchenettes inside the city walls.
Perfect for families or longer stays, these well-appointed units allow flexibility and independence.
The historic building retains character with stone walls and period features, yet modern comforts make it a reliable mid-range choice.
Walk to restaurants, shops, and towers in minutes.
6. Residence Le Fonti
Near Historic Centre | €170–€240 |
Apartment-style units with kitchenettes and outdoor areas, Le Fonti is ideal for families or independent travellers.
While slightly outside the busiest streets, it is an easy walk into town.
Comfortable, practical, and well-reviewed, it balances space, flexibility, and proximity to San Gimignano’s main sights for mid-range guests.
Read my full guide
San Gimignano’s Ultimate Travel Guide 2026: Tuscany’s Best Medieval Town
7. Antico Casale
Countryside | €190–€260 |
This charming farmhouse offers rooms and apartments in olive-grove surroundings.
Guests enjoy a pool and peaceful setting while being a short drive from the town.
Suitable for couples or families seeking a tranquil countryside experience with easy access to historic San Gimignano, combining rustic charm and modern conveniences in a mid-range price point.
8. Casa Milena
Near Historic Centre | €150–€250 |
Just outside the city walls, Casa Milena offers well-reviewed apartments with terrace and garden.
Modern conveniences meet historic charm in these comfortable units.
Perfect for couples or small families wanting independence with proximity to restaurants, piazzas, and sights, all while enjoying a relaxed environment.
LUXURY HISTORIC STAYS
9. Hotel L’Antico Pozzo
Historic Centre | €280–€450 |
L’Antico Pozzo is set inside a restored medieval tower house, offering stone walls, elegant décor, and refined interiors.
Rooms often feature views of towers or the main piazza, providing an immersive historic experience.
Guests enjoy polished service, sophisticated furnishings, and central access to restaurants, shops, and museums.
Ideal for couples seeking romantic luxury in the heart of San Gimignano, blending medieval character with modern comfort.
10. Hotel La Cisterna
Piazza della Cisterna | €260–€400|
Overlooking the main square, La Cisterna delivers classic Tuscan style with refined interiors and historic charm.
Rooms and suites often include views of rooftops and towers.
Guests benefit from direct access to cafés, shops, and sights.
This boutique luxury hotel is perfect for travellers seeking a combination of central location, period features, and upscale comfort.
Read this Guide next
The 14 Best Things to Do in Tuscany: The Complete Guide (2026)
11. Relais Santa Chiara
Just Outside Walls | €280–€420 |
Relais Santa Chiara blends contemporary luxury with a peaceful countryside setting near the town walls.
Rooms are spacious, interiors stylish, and many offer panoramic views of the Tuscan hills.
The property features a pool and tranquil gardens.
It’s ideal for couples or travellers seeking comfort, elegance, and a quiet retreat within walking distance to San Gimignano.
COUNTRYSIDE AGRITURISMOS & FARM STAYS (RURAL EXPERIENCE)
12. Mormoraia – San Gimignano Countryside
Countryside (about 4 km from San Gimignano) | ~€300–€500+ per night |
Mormoraia sits in the rolling Tuscan hills surrounded by vineyards and olive groves, offering a peaceful and refined rural escape.
The property features an outdoor pool with hot tub, spa facilities including sauna and Turkish bath, and wellness treatments — excellent for travellers who want space and relaxation in nature.
Its on-site restaurant serves local cuisine and wine, and tours of the estate’s wine cellar are available.
With its high guest ratings and serene setting,
13. Tenuta Sovestro
Countryside | €150–€220 |
Tenuta Sovestro offers a tranquil agriturismo experience with gardens, pool, and vineyard views.
Rooms and suites open to the outdoors, creating a relaxing environment for couples or small families.
Guests enjoy proximity to town while staying immersed in the rolling Tuscan hills.
Its combination of authentic farm atmosphere and convenience makes it a favorite for slow, countryside stays.
14. Podere La Quercia
Countryside | €180+ |
Podere La Quercia is a traditional Tuscan farmhouse with comfortable, characterful rooms and garden spaces.
Surrounded by olive trees and fields, it’s ideal for longer stays and scenic relaxation.
Guests enjoy a peaceful rural base while still being within short driving distance of San Gimignano’s historic centre, perfect for exploring local vineyards and countryside roads.
Things to Do in San Gimignano
San Gimignano is small, but there’s plenty to fill a relaxed one or two days, especially if you slow down and time things well.
Walk the Historic Centre
Start by simply wandering. San Gimignano’s medieval streets are compact and easy to explore on foot, with stone towers, quiet corners, and small piazzas connecting naturally.
Early morning or early evening is when the town feels most authentic.
Visit Piazza della Cisterna & Piazza del Duomo
These two main squares sit side by side and form the heart of the town.
Piazza della Cisterna is lively and photogenic, while Piazza del Duomo feels calmer and more residential.
Sit for a coffee, watch daily life, and take in the medieval architecture.
Climb Torre Grossa
For the best views in town, climb Torre Grossa, the tallest remaining tower.
The stairs are manageable, and the reward is a full panorama over the Val d’Elsa countryside and surrounding hills — especially clear on a bright day.
Explore the Duomo (Collegiata di Santa Maria Assunta)
The frescoes inside the Duomo are one of San Gimignano’s highlights, covering stories from the Old and New Testaments.
It’s well worth stepping inside, even if churches aren’t usually a priority.
Taste Vernaccia di San Gimignano
This local white wine is produced only in the surrounding hills.
Many enotecas and wine bars offer tastings by the glass, making it easy to try without committing to a full winery visit.
Stroll Along the Town Walls
Walk sections of the old town walls for a quieter perspective and countryside views.
It’s a simple way to escape the crowds without leaving the historic centre.
Visit the San Gimignano 1300 Museum
This small museum offers a scale model of the town as it appeared in the Middle Ages, when dozens of towers still stood.
It provides useful context and takes less than an hour.
Enjoy Gelato (Yes, It’s Worth It)
Gelateria Dondoli is famous and often busy, but the quality lives up to the reputation.
Go early or late to avoid queues, or try a quieter gelateria nearby for a more relaxed stop.
Have Dinner After the Day-Trippers Leave
Evenings are when San Gimignano shines. Once tour buses depart, restaurants feel calmer and the streets soften.
A slow dinner inside the walls is one of the best experiences the town offers.
Use San Gimignano as a Base for Short Trips
If staying longer, consider a half-day trip to:
Monteriggioni (bus from Siena)
Volterra (bus via Colle Val d’Elsa)
Both work well without a car with a little planning.
San Gimignano vs Siena vs Chianti: Where Should You Stay in Tuscany?
Choosing where to base yourself in Tuscany can shape your entire trip.
San Gimignano, Siena, and Chianti each offer a very different experience, depending on whether you want walkable towns, countryside views, or a balance of both.
San Gimignano: Best for Atmosphere & Short Stays
Best for: First-time visitors, couples, short stays (1–2 nights)
San Gimignano is compact, walkable, and packed with character.
Staying inside the medieval walls lets you experience the town once the day-trippers leave, when the streets quieten and restaurants feel local again.
Accommodation is limited, which means prices are slightly higher for the space you get, but the atmosphere makes it worthwhile.
Countryside stays nearby offer pools and views while keeping the town within easy reach.
Stay here if you want: Medieval charm, easy sightseeing, evening ambience
Skip it if you want: Large hotels, nightlife, or long stays in one place
Siena: Best for Culture, Food & Longer Town Stays
Best for: Culture lovers, food-focused travellers, 2–3 night stays
Siena feels more lived-in than San Gimignano, with a stronger local rhythm and a deeper food scene.
The historic centre is larger, offering more accommodation choice and better value, especially at mid-range and luxury levels.
Siena works well as a base for day trips to Val d’Orcia, Chianti, and Crete Senesi, particularly if you prefer staying in one place rather than moving frequently.
Stay here if you want: Historic depth, great dining, transport links
Skip it if you want: Small-town intimacy or vineyard views
Chianti: Best for Countryside, Wine & Slow Travel
Best for: Couples, drivers, longer stays, wine lovers
Chianti is all about space, views, and pace.
Staying here usually means agriturismos or villas surrounded by vineyards, with pools and on-site dining.
It’s less about sightseeing on foot and more about slow mornings, winery visits, and scenic drives.
A car is essential, but accommodation offers better value for space and comfort than town stays.
Stay here if you want: Vineyards, privacy, pools, and relaxation
Skip it if you want: Walkable towns or public transport
Quick Comparison Table
| Area | Best For | Nights | Need a Car | Accommodation Style |
|---|---|---|---|---|
| San Gimignano | Atmosphere & charm | 1–2 | Optional | Boutique hotels, apartments |
| Siena | Culture & dining | 2–3 | Optional | Hotels, apartments |
| Chianti | Wine & countryside | 3–5 | Yes |
Recommended Split Stay: San Gimignano + Siena + Chianti (7 Nights)
This itinerary gives you atmosphere, culture, and countryside, without rushing or excessive driving.
Nights 1–2: San Gimignano
Why here: Medieval charm, compact size, magical evenings
Stay style:
Inside the walls for atmosphere or
5–10 minutes outside for pools and parking
What to do:
Afternoon arrival + walk the historic centre
Evening dinner after day-trippers leave
Taste Vernaccia di San Gimignano
Morning visit to Torre Grossa and Duomo
Enjoy Gelato
Evening dining ideas (casual, non-luxury):
Cum Quibus
La Mandragola
Chiribiri (wine bar style)
Nights 3–4: Siena
Why here: Culture, food scene, and depth
Stay style:
Historic centre for walkability
Near Piazza del Campo or Duomo
What to do:
Explore Piazza del Campo and the Duomo complex
Wander Contrade neighbourhoods
Optional half-day trip to Monteriggioni
Evening dining ideas:
Osteria Le Logge
Osteria Da Divo
Il Pomodorino (simple and local)
Nights 5–7: Chianti Countryside
Why here: Space, views, slow travel
Stay style:
Agriturismo or vineyard estate with pool
What to do:
Scenic drives between Greve, Panzano, Radda
Winery visits (1 per day max)
Pool afternoons and relaxed dinners on-site
Dinner options:
On-site agriturismo restaurant
Panzano: Officina della Bistecca or Dario Cecchini’s wine bar
Greve: La Cantina (simple, reliable)
How to Get Around Tuscany
A rental car is essential for staying at luxury farm stays in Tuscany.
Most farm stays are located along country roads with limited public transport.
Florence and Pisa airports are the easiest arrival points, with car hire available directly at the terminals.
Driving allows flexibility, scenic detours, and access to villages, wineries, and viewpoints not reachable otherwise.
For more comfort and convenience, compare these car rentals: DISCOVER CARS or RENTALCARS
FAQs
What is the best time to visit San Gimignano?
Spring (April–June) and autumn (September–October) offer mild weather, smaller crowds, and beautiful landscapes.Can you explore San Gimignano without a car?
Yes. The town centre is walkable, but countryside agriturismos require a taxi or car to reach the historic centre.Are these accommodations family-friendly?
Yes. Many mid-range apartments and farm stays have space for children and offer pools or gardens.Do luxury hotels offer town views?
Most historic luxury hotels feature tower or piazza views, providing authentic medieval ambience.Are there options for budget-conscious travellers?
Yes. Several town and countryside hotels provide value-focused rooms without sacrificing charm or comfort.Can I book directly through Booking.com or VRBO?
All 14 properties listed are available on these trusted platforms.Are meals included in the farm stays?
Some agriturismos offer breakfast or wine-tasting experiences, but most do not include full meals by default.Is it safe to walk around the town at night?
Yes. San Gimignano is a quiet, safe town with low traffic, particularly inside the historic walls.
Do You Need Travel Insurance for Tuscany?
(Short Answer: Yes — It’s Still a Smart Idea)
Travel insurance isn’t legally required to visit Tuscany, but it’s one of the smartest things you can have when travelling in Italy.
Even in a relaxed destination like Tuscany, things can go wrong — from delayed flights and lost luggage to medical issues, rental car damage, or unexpected trip cancellations.
And while Italy has excellent healthcare, medical treatment for visitors can still be costly without proper coverage.
As long-term travellers living in Italy, we’ve found SafetyWing to be a practical option for trips around Europe, offering coverage for medical care, travel delays, and lost belongings without complicated fine print.
SafetyWing
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It’s the kind of insurance you hope you never need—but you’ll be very glad you have if something unexpected happens.
Final Thoughts
San Gimignano blends medieval history with Tuscan charm, offering travellers a range of accommodations from budget-friendly historic hotels to luxurious boutique stays and authentic countryside agriturismos.
Staying inside the walls immerses you in the town’s towers, piazzas, and restaurants, while the countryside farm stays provide rolling hills, vineyards, and space for relaxation.
This curated list of 14 properties balances convenience, comfort, and authenticity, ensuring options for couples, families, or groups.
It’s easy to plan your trip and enjoy San Gimignano’s timeless appeal, vibrant culture, and scenic landscapes without compromise.
PLAN YOUR TUSCANY ADVENTURE
These are our favorite companies we use when planning a trip, they consistently have the best prices, great customer service, and overall, are better than their competitors.
BOOK YOUR FLIGHT – Going is a great search engine if you are flexible about your travel destination and dates. Sign up for their newsletter and get the latest deals on destinations around the world. GOING is our new go to.
CAR RENTAL – We recommend using Discover Cars or Rental Cars when booking a car rental, they work with hundreds of companies worldwide to help you find the best car for your needs.
TRAINS – OMIO – is our favorite, this site is very reliable and easy to use.
BUS – OMIO – this website allows you to book train or bus tickets to travel from city to city the best and cheapest way. FLIXBUS is another terrific website with routes between 20 European countries.
ACCOMMODATIONS
BOOKING.com – is our go to for hotel searches around the world, we find they always have the cheapest rates and offer different payment options. In addition, VRBO is another terrific website for all types of accommodations.
HOSTELWORLD – is great if you’re traveling on a budget, and if you need a cheap place to stay.
SIGHTSEEING TOURS
GET YOUR GUIDE – is our favorite; they have stacks of tours and excursions available in cities all over the world. VIATOR is another great website for all types of tours.
TAKE WALKS – This walking tour company provides inside access to attractions and places you can’t get elsewhere.
TRAVEL INSURANCE
SAFETY WING – is our go to travel medical insurance company, especially for longer trips. You can either purchase a monthly plan or a plan for specific trip dates (i.e. 1-2 week trips). They cover people from all over the world, while outside their home country.
ARC’TERYX – is a go to reliable brand for outdoor adventure and travel, their wide range includes light weight durable, easy to clean travel gear.
Check out our RESOURCE PAGE for more additional planning.