Rosewood Castiglion del Bosco
Rosewood4.7598 reviews
via Google
800-year-old estate in the Val d'Orcia with its own Brunello vineyard and restored medieval borgo.
See weddings at the resortWhy it fits you
You get that romantic, rustic feel here, with a touch of luxury and Mediterranean warmth that suits a wedding with heart. It also asks you to think through guest logistics early, and most couples keep the ceremony symbolic, which keeps the focus on the experience itself.
Budget snapshot
$34K-$108K estimate
Based on Tuscany average ($25K-$80K) for an 80+ guest wedding
What drives this estimate
- Guest count: an 80+ guest party - more guests means more catering and room nights
- Resort tier: luxury properties; all-inclusive vs à la carte swings this the most
- Season: peak months (May) cost more than shoulder season
Best timing
Best
MayJuneSeptemberOctober
Avoid
NovemberDecemberJanuaryFebruary
Weather: Open-Meteo Historical Weather API (2019-2023 averages). Updated 2026-04-15.
Your Fall window in Tuscany, month by month
September
59-80°F
5 rain days
no storm riskOctober
52-70°F
6 rain days
no storm riskNovember
45-59°F
10 rain days
no storm riskYour guests (Mixed US guests)
Flight time
~10.5h
Avg flight cost
~$750
Hotel/night
~$250
Guest burden
5/10
manageable
Visa
No visa required
Legal requirements
Symbolic ceremony recommendedSame Italian marriage law as the Amalfi Coast: a Nulla Osta from your embassy, Atto Notorio, translated/apostilled birth certificates, and declaration of intent at the local comune are required. The process takes 3-6 months. Most couples handle the legal ceremony at home and hold a symbolic celebration in Tuscany. This is especially common for vineyard estate weddings, which often prefer the flexibility of symbolic ceremonies.
Marriage laws and document requirements change. Confirm with your planner or the country's consulate before you book.
Your planning timeline
- Step 112 mo
Lock your destination + book a planner
- Confirm destination and rough date
- Book a local wedding planner
- Set the guest list and budget
- Step 210 mo
Save-the-dates + start your room block
- Send save-the-dates (guests need lead time to book travel)
- Start a hotel room block for group rates
- Step 38 mo
Legal paperwork
- Research marriage requirements at your destination
- Decide: legal ceremony abroad vs legal at home
- Step 46 mo
Book your core vendors
- Photographer, florist, officiant
- Tasting / menu planning
- Step 54 mo
Details + guest logistics
- Invitations
- Welcome bags, transfers, excursions
- Step 62 mo
Confirm everything
- Final headcount to resort/vendors
- Confirm legal documents and travel insurance
- Step 71 mo
Final month
- Pack documents (apostilles/passports)
- Reconfirm vendors and timeline
Where couples stay in Tuscany
A feel for the resort scene - nothing to book yet. Most couples pick their resort with their planner's help, about 10 months out.
The five-star shortlist
The flagship properties for a luxury Tuscany wedding. Each link goes to the resort's own wedding pages, not a booking site.
Belmond Castello di Casole
Belmond4.8499 reviews
via Google
Hilltop castle estate with chapel, vineyard, amphitheatre and wine-cellar venues.
See weddings at the resortCOMO Castello Del Nero
COMO4.8455 reviews
via Google
12th-century Chianti castle with a private chapel and 12 venue spaces; buyouts host up to 120.
See weddings at the resortFour Seasons Hotel Firenze
Four Seasons4.82,769 reviews$$$$
via Google
Renaissance palazzo with Florence's largest private garden; garden ceremonies and receptions to 200.
See weddings at the resortGroup rates, comp nights + perks at these properties
Five-star resorts negotiate wedding room blocks privately; the real numbers never show up on booking sites. We pull rate and perk proposals for your date and guest count, free. Resorts pay us a commission; you and your guests never do.
Unlock rates with a free 15-min consultVetted vendors in Tuscany
Request an intro and they reach out to you - free, no obligation.
Wedding Planner
Above & Beyond Tuscan Weddings
Full-service destination wedding planning in Tuscany. Coordinating ceremonies, vendors, and logistics so couples can enjoy every moment.
Request introTransportation
Airport Shuttle Pick Up point
Tuscany transportation company specializing in wedding groups. Airport pickups, bridal-party transfers, and late-night shuttles with bilingual drivers.
Request introFlorist
Biancospino Flowers Atelier
Floral design studio in Tuscany specializing in wedding arrangements. Sourcing local and tropical blooms for ceremonies and receptions.
Request introPhotographer
D2 Photography Tuscany Wedding Photographers
Destination wedding photographer based in Tuscany. Natural light, candid moments, and the beauty of the location woven into every image.
Request introPhotographer
Davide Poggi Fotografo | Wedding Photographer Tuscany - Fotografo di matrimoni Firenze Toscana.
Destination wedding photographer based in Tuscany. Natural light, candid moments, and the beauty of the location woven into every image.
Request introDJ / Entertainment
Deejay Led - Sposa Dj ( Dj per Matrimoni, Dj for Wedding )
Wedding DJ and entertainment in Tuscany. Keeping the dance floor alive from ceremony through last dance.
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