Umbria, Tuscany, Florence

Italy Golf Retreat

August 31 to September 7, 2026
7 nights | 5 nights in Umbria and 2 nights in Florence

Hosted by Coach Shayain

This retreat is

Almost Full

Only 3 double rooms remain for this Italy retreat.

All single rooms are sold out.

If you’d like to join us, please email shayain@coachshayain.com as soon as possible.

Imagine an Italy escape where every detail feels like it was chosen just for you...

A castle stay in Umbria, golden hour golf, truffle hunting and vineyard lunches, pasta and aperitivo evenings, spa time in Assisi, organic wine tastings in Tuscany, and a breathtaking finale in Florence with Michelangelo’s David and rooftop views at sunset.

This is a rare boutique retreat experience, personally curated by Coach Shayain after traveling the region herself, designed to bring you the beauty of Italy on a silver platter... with a private driver, seamless planning, and the perfect balance of luxury, culture, and play.

La Vita Italiana Golf Retreat Itinerary ⛳🇮🇹

Monday, August 31 | Arrival Day

Rome → Orvieto → Perugia ✨

Group transfer from Rome at 10:30 AM
Stop in Orvieto for lunch and a short town visit
2:00 PM - 4:00 PM Private Basilica tour
5:30 PM Check in at the castle in Umbria
Settle in and enjoy the property
8:00 PM Welcome group dinner in Perugia 🍷

Tuesday, September 1 | Golf + Golden Hour ⛳🌅

Relaxed morning at the castle
Breakfast and time to enjoy the gardens, pool, and library
Free time to explore the city center of Perugia
2:00 PM Depart for Antognolla Golf
3:30 PM Tee time at Antognolla (sunset round)
Dinner and drinks at the golf course after the round 🍝🥂

Wednesday, September 2 | Villages + Wellness Day 🕊️🧖‍♀️

Morning visit to Spello
10:00 AM to 11:30 PM Tour and explore
Continue to Assisi for a cultural experience
Explore the historic streets and gelato shops
2:00 PM - 4:30 PM Private Walking Tour Assisi with Basilica of Saint Francis
Use of Spa Facility at Nun Assisi
A stunning wellness experience inside a beautifully restored former monastery. Massages and Facials can be booked as an additional package
7:30 PM Group dinner in Assisi ✨

Thursday, September 3 | The Umbria Experience 🍷🍄

9:30 AM-ish Depart for Chiesa del Carmine
Private truffle hunting experience
Wine tasting and lunch on the property
Experience wraps around 3:00 PM-ish
Optional stop at Rocco Ragni Cashmere (beautiful countryside setting)
Free evening in Perugia for:
- Shopping, Chocolate Making, Aperitivo, Optional dinner in town

Friday, September 4 | Golf + Pasta Night ⛳🍝

Morning golf at Antognolla
10:00 AM Tee time
Return and relax
Evening pasta making experience with aperitivo and dinner
A signature Italian night together 🇮🇹✨

Tuscany Wine Tasting Day 🍇🍷

Saturday, September 5

10:00 AM Check out from the castle
Scenic drive through Umbria into Tuscany (approx. 1.5 hours)
Arrive in Greve in Chianti
12:30 PM 3 course Italian lunch and wine at Ristoro di Lamole
Wine tasting at Lamole di Lamole Winery
5:00 PM Drive to Florence
Check in and evening at leisure in Florence ✨

Florence Finale 🎨🥂

Sunday, September 6

Morning in Florence
11:30 AM to 12:30 PM Guided tour of Michelangelo’s David (arrive at 11:00am to meet the Guide)
Free afternoon to enjoy Florence at your own pace:
- Duomo, Shopping, Ponte Vecchio, Cafés and wandering the city
6:00 PM Sunset aperitivo and snacks at Aria Rooftop
A beautiful closing celebration with views over Florence 🌇

Monday, September 7 | Departure Day ✈️🚆

Stay longer in Florence if you wish
Train to Rome
Fly home
Or continue your Italy travels

✨ What’s Included:

Umbria

5 nights & breakfast in a castle in Umbria
2 rounds of golf at Antognolla
4 of 5 dinners in Umbria
Private truffle hunting experience
Umbria wine tasting with lunch
Pasta making experience with aperitivo and dinner
Assisi spa experience and dinner
Guided cultural touring in Orvieto and Assisi
Private driver and group transportation throughout the retreat itinerary

Tuscany

Chianti wine tasting
Full Tuscan lunch overlooking the countryside

Florence

Guided tour of Michelangelo’s David
Aria Rooftop sunset aperitivo and snacks

✨ Important Notes

Guests should plan to arrive in Rome the night before the retreat begins
The retreat begins with the scheduled group transfer from Rome on August 31
Hotel in Rome the night before is not included
Transportation after the retreat ends is not included (Florence airport transfer or train to Rome)
Flights and most lunches are not included (except the included Umbria and Tuscany lunches)

Please note: In accordance with local Italian regulations, hotels may charge a city tax of approximately €2.50 per person, per night, payable locally. The exact amount may vary by property and is subject to change.

Who This Retreat Is For

This retreat is designed for travelers who want a beautiful, elevated experience in Italy that blends golf, culture, wellness, and connection.

It is perfect for you if you are:

✨ A beginner or intermediate golfer who wants to play in a welcoming, low pressure environment

✨ Someone who loves luxury travel, meaningful experiences, and unforgettable food and wine

✨ A solo traveler who wants to feel supported, comfortable, and part of a great group

✨ A couple or pair of friends looking for a unique golf and lifestyle escape

✨ Someone who wants a curated, seamless trip where the details are thoughtfully handled

✨ A traveler who wants to build confidence on the course while enjoying Italy in a truly special way

This is not a rushed golf trip. It is a thoughtfully designed experience with space to play, explore, relax, and soak in the magic of Italy.

If this feels like your kind of trip...

beautiful golf, incredible food, meaningful connection, and the ease of having everything thoughtfully arranged... you are in the right place.

This Italy retreat is intentionally intimate, and spots are limited.

We would be honored to share this experience with you.

Your Coach,
Shayain

Italian Golf Retreat Itinerary

Umbria , Tuscany, Florence 2026

FREE