Are you dreaming of a wedding where your closest friends and family can truly immerse themselves in the romance of Tuscany? Where the celebration doesn't end at midnight because everyone's already home? You've come to the right place!

Florence and its surrounding countryside offer some of the world's most spectacular wedding venues that combine historic charm, breathtaking landscapes, and the convenience of on-site accommodation. For September / October celebrations, you're choosing the perfect time – autumn in Tuscany means golden light, crisp air, truffle season, and fewer crowds.

Here are seven extraordinary venues that will make your 60-guest wedding an unforgettable multi-day celebration:

1. Villa Pozzolo - The Ultimate All-Inclusive Experience

Location: Montaione, Tuscany (45 minutes from Florence)
Accommodation: Up to 50 overnight guests in 23 bedrooms
Capacity: Up to 60 wedding guests
Starting Price: €14,380 for 35 guests (additional guests €490/person overnight)

Villa Pozzolo is a wedding planner's dream – everything is included from the moment you arrive. This Renaissance estate spans 40 hectares of gardens, vineyards, and forests, offering complete exclusivity for your celebration.

What Makes It Special:

True All-Inclusive: Unlimited food and drinks, wedding planning, flowers, decorations, cake, hair and makeup (up to 5 people), live music, and DJ all included
Renaissance Chapel: Perfect for intimate ceremonies
International Cuisine: Chefs from Italy, Germany, and Vietnam create diverse menus
Activities Galore: Yoga, cooking classes, wine tastings, heated saltwater pool, petting zoo
October Bonus: Autumn foliage creates a magical backdrop for photos

Perfect For: Couples who want everything handled seamlessly with no surprise costs.

2. Castello di Gabbiano - Medieval Romance in Chianti

Location: San Casciano Val di Pesa, Chianti (30 minutes from Florence)
Accommodation: Up to 40 guests in 10 rooms/suites + 4 apartments
Capacity: 20-50 wedding guests (perfect for your 60)
Setting: Medieval castle with 900-year history

This authentic medieval castle in the heart of Chianti offers breathtaking views over vineyards and olive groves. The intimate scale makes it perfect for creating lifelong memories with your closest circle.

What Makes It Special:

Complete Privacy: Exclusive use of the entire castle
Historic Charm: Stone courtyards, medieval lounge, authentic architecture
Flexible Spaces: Gardens, courtyard, reception rooms, swimming pool
Minimum Stay: 2-3 nights ensures a proper celebration
October Magic: Prime truffle and wine harvest season

Hidden Gem Status: Less commercialized than larger venues, offering authentic medieval atmosphere.

3. Villa San Michele (Belmond) - Legendary Luxury

Location: Fiesole, overlooking Florence (15 minutes from city center)
Accommodation: 45 rooms and suites (accommodates 90+ guests)
Capacity: Up to 70 guests (Cloister), 150 guests (Michelangelo Terrace)
History: 15th-century monastery with façade attributed to Michelangelo

This is where luxury meets history. Famous for hosting celebrity weddings (Elizabeth Taylor, Sophia Loren, Sting), Villa San Michele offers unparalleled elegance with panoramic Florence views.

What Makes It Special:

Celebrity Pedigree: A-list wedding venue with impeccable service
Multiple Ceremony Options: Gardens, historic cloister, or panoramic terrace
Michelin-Star Dining: Exceptional Tuscan cuisine with contemporary flair
Spa & Wellness: Full-service spa for pre-wedding pampering
October Views: Crystal-clear autumn air offers the best Florence panoramas

Perfect For: Couples seeking ultimate luxury and sophisticated elegance.

4. Villa Le Fontanelle - Intimate Medici Villa

Location: Careggi Hills, Florence (20 minutes from airport)
Accommodation: 7 elegant rooms and suites (up to 16 guests on-site)
Capacity: Up to 60 guests indoor, 110 guests outdoor
History: 15th-century Medici family residence

This boutique venue offers the perfect balance of intimacy and elegance. With only 7 rooms, it feels like your own private villa while still accommodating your full guest list for the celebration.

What Makes It Special:

Medici Heritage: Former residence of Florence's most powerful family
Italian Terraced Gardens: Picture-perfect ceremony settings
Stone Pool: Unique reception backdrop
Intimate Scale: Feels like a private home, not a hotel
October Advantage: Gorgeous autumn colors in the terraced gardens

Perfect For: Couples wanting an exclusive, intimate feeling with historic significance.

5. Borgo Divino - Authentic Tuscan Agriturismo

Location: Montespertoli, Chianti Hills (30 minutes from Florence)
Accommodation: 21 Tuscan-style rooms and suites
Capacity: Flexible for intimate weddings
Specialty: Truffle hunting and authentic farm-to-table experiences

This hidden gem agriturismo offers the most authentic Tuscan experience, complete with working vineyards, olive groves, and seasonal truffle hunting.

What Makes It Special:

Truffle Season: October is peak white truffle season – imagine truffle-hunting with your wedding party!
Farm-to-Table: Ingredients from their own organic garden, wine production, olive oil
Authentic Activities: Cooking classes, wine tastings, yoga sessions
Infinity Pool: Stunning views over Chianti countryside
October Bonus: Harvest season means wine-making demonstrations and tastings

Hidden Gem Status: True working farm experience rarely found at wedding venues.

6. Lupaia - Boutique Perfection in Val d'Orcia

Location: Montepulciano area, Southern Tuscany (1.5 hours from Florence)
Accommodation: 12 rooms (all guests can stay on-site for groups up to 36)
Capacity: Up to 36 guests (perfect for ultra-intimate celebrations)
Setting: Restored 1622 farmhouses with panoramic views

If you're considering a smaller celebration, Lupaia offers the ultimate in intimacy where every single guest stays on the property, creating an unforgettable shared experience.

What Makes It Special:

Everyone Stays: All guests under one roof for maximum bonding
UNESCO Views: Overlooks the famous Val d'Orcia landscape
Sustainability Focus: Eco-conscious luxury
Seasonal Operation: March-November only, making it exclusive
October Glory: Peak season for the iconic Tuscan landscape photography

Perfect For: Couples prioritizing intimacy and shared experiences over larger celebrations.

7. Castello di Reschio - Secret Castle in Umbria

Location: Umbria-Tuscany border (1.5 hours from Florence)
Accommodation: 36 luxury suites in restored 10th-century castle
Capacity: Up to 50 guests for intimate celebrations
Estate: 3,700 acres of pristine wilderness

This recently opened castle hotel is Italy's best-kept secret – a 1,000-year-old castle lovingly restored into the ultimate luxury retreat.

What Makes It Special:

Ancient History: 10th-century castle with modern luxury
Vast Estate: 3,700 acres of private wilderness for exclusive use
New Opening: Less discovered, ensuring exclusivity and personalized service
Multiple Venues: Castle dining rooms, gardens, restored farmhouses
October Tranquility: Peak season for the surrounding countryside without crowds

Hidden Gem Status: Newly opened luxury venue with authentic medieval atmosphere.

Why October 2026 Is Perfect Timing

Weather: October offers ideal conditions – warm sunny days (65-75°F), cool evenings perfect for dancing, minimal rain risk
Light: Golden hour light lasts longer, creating magical photo opportunities
Harvest Season: Wine and olive harvests, truffle season, peak flavors
Fewer Crowds: Tourist season winding down means more exclusive feel
Availability: Book now for 2026 – October is popular but not yet fully booked

Planning Your All-Inclusive Wedding

Budget Expectations:

Villa Pozzolo: €14,380 base (35 guests) + €490 per additional overnight guest
Castle venues: €30,000-60,000 for full exclusivity with accommodation
Luxury hotels: €50,000-100,000+ depending on guest count and services

Booking Timeline:

Contact venues 18-24 months ahead (perfect timing for October 2026!)
Most require 25-50% deposits to secure dates
October is peak season – book early for best selection

Questions to Ask Each Venue:

What's included in the base package vs. additional costs?
How many guests can stay on-site vs. reception capacity?
Are there preferred vendor restrictions?
What's the cancellation/postponement policy?
Can we see the venue during October for accurate planning?

Your Next Steps

Narrow Your List: Choose 2-3 venues that match your vision and budget
Schedule Virtual Tours: Most venues offer virtual walkthroughs
Plan a Venue-Seeing Trip: Visit Florence in October 2025 to experience the season
Book Early: October 2026 dates at the best venues are booking now
Consider a Wedding Planner: Italian venues often work best with local expertise

Final Thoughts

Your dream of an all-inclusive Florence wedding where everyone stays together isn't just possible – it's magical. These seven venues each offer something unique, from medieval castles to working farms to luxury monasteries. The key is choosing the one that matches your vision of the perfect celebration.

October 2026 will arrive faster than you think, and these exceptional venues book up quickly. Start reaching out now to secure your piece of Tuscan paradise!

Ready to start planning? Contact these venues directly or consider working with a specialized Tuscan wedding planner who can negotiate packages and coordinate the complex logistics of destination weddings with accommodation.

Contact Information: