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 1 double room remains 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 + Pasta Night ⛳🍝

  • Pick up 7:45 AM for Antognolla Golf

  • Morning golf at Antognolla — tee times 9:30, 9:40, 9:50 AM

  • Return and relax at the castle

  • 5:00 PM Evening pasta making experience with aperitivo and dinner — a signature Italian night together 🇮🇹✨

Wednesday, September 2 | The Umbria Experience 🍷🍄

  • 9:00 AM Depart for Chiesa del Carmine

  • Private truffle hunting experience

  • Wine tasting and lunch on the property

  • Wraps around 2:30 to 3:00 PM

  • Optional stop at Rocco Ragni Cashmere (beautiful countryside setting)

  • Free evening in Perugia: shopping, chocolate, aperitivo, optional dinner in town

Thursday, September 3 | Villages + Wellness Day 🕊️🧖‍♀️

  • Morning visit to Spello — 10:00 to 11:30 AM explore the town and shops

  • Continue to Assisi for a cultural experience

  • 2:00 to 4:30 PM Private walking tour with the Basilica of Saint Francis

  • Spa time at Nun Assisi — a former monastery turned wellness sanctuary (Massages and facials can be booked as an additional package)

  • 7:30 PM Group dinner in Assisi ✨

Friday, September 4 | Golf + Golden Hour ⛳🌅

  • Relaxed morning at the castle — breakfast, gardens, pool, library

  • Free time in the city center of Perugia

  • 1:45 PM Depart for Antognolla

  • Warm up: driving range, putting green, snacks

  • Tee times 3:40, 3:50, 4:00 PM (sunset round)

  • Dinner and drinks at the golf course aft

Tuscany Wine Tasting Day 🍇🍷

Saturday, September 5

  • 9:45 AM Check out from the castle

  • Scenic drive through Umbria into Tuscany (approx. 2 hours)

  • Arrive at Antinori nel Chianti Classico, one of the most stunning wineries in Italy

  • 12:00 PM 3 course Italian lunch and wine at Rinuccio 1180, overlooking the Chianti hills

  • 4:00 PM Drive to Florence (approx. 45 minutes)

  • 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 to €3.50 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

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Italy Golf Retreat Itinerary

Aug 31–Sept 7 · Sold Out

FREE