Italy Sojourn – September 2027

Discover Italy through its art, wine, food, and countryside on an eleven-night journey through Rome, Tuscany, and Florence. Designed for a small group, this sojourn pairs extraordinary cultural experiences with unhurried afternoons and time to explore on your own.

This journey is designed around marquee experiences — private wine tastings, incredible dining experiences, and access to the people and places that make Italy's food and wine culture so extraordinary — yet it leaves space for what matters most: time to breathe.

Itinerary at a Glance

Sept 6

Arrive in Rome

Sept 7-10

Rome

Sept 10 - 15

Tuscany

Sept 15 - 17

Florence

Sept 17

Duomo + Fly Home

Eleven nights across three of Italy's most extraordinary destinations

Rome

Highlights in Rome, the Eternal City

Welcome to Rome

Discover Rome’s historic heart with a nationally certified Italian Arts Expert, exploring Piazza del Popolo, the Spanish Steps, Trevi Fountain, and the exterior of the Pantheon. Along the way, uncover the stories behind the city’s art, architecture, and everyday traditions. This welcoming introduction offers historical insight and practical orientation, helping you feel at home in Rome before exploring on your own.

Opera at Doria Pamphilj

Encircled by masterpieces of art and the echoes of nobility, guests will be serenaded by world-class voices resonating through rooms that have hosted generations of aristocracy. Each note of the performance is a thread in the fabric of history, in a space where every detail—from the classical furnishings to the opulent artworks—whispers of a bygone era of splendor.

After Hours at the Vatican

An expert-led after-hours tour of the Vatican Museums, providing an opportunity to explore the renowned galleries outside of public visiting hours. Stroll through the historic halls and exquisite frescoed galleries of the Vatican.

This exclusive visit offers the chance to view some of the world’s most celebrated sacred artworks in a peaceful and reflective setting. Encounter masterpieces such as the Apollo Belvedere, the Raphael Rooms, and the Sistine Chapel.

Flexible Time

Enjoy the city on your own with CITY GRIT recommendations for where to snack, sip, & shop.

Discover Rome's piazzas, linger over lunch, or find a favorite neighborhood café.

Tuscany

Welcome to Wine Country

Explore Wine Villages

Castelnuovo dell’Abate, Montalcino, Montepulciano, & Greve in Chianti

Hike through the Vineyards

Explore the town of Castelnuovo dell’Abate, then savor a tasting at Ciacci Piccolomini d’Aragona.

Enjoy a free day

Relax in Thermal Spa, enjoy a picnic in the vineyards, sip wine at Italy's Best Wine Bar 2025, or choose your own adventure


Florence

Finale in Florence

Florentine Steak Dinner

Gather for Tuscany’s signature culinary traditions: bistecca alla fiorentina, served with accompaniments and an incredible dessert cart.

Sunset Boat Ride

See Florence from the Arno as the sun sets over its historic bridges and riverside palaces.

Exclusive Open the Duomo Experience

Be the first to enter the famous Duomo for a spectacular views of the artwork and the city.

Free time is relaxed with time for art, shopping, snacking, and personal discoveries.

Budget // $11,600 per person, double occupancy


What’s included

  • 11 nights at five-star hotels including breakfast
  • Private group transportation between cities and for scheduled excursions; airport transfers in Rome and Florence arranged separately per couple
  • All winery visits, tastings, and pre-planned excursions
  • Entrance fees for scheduled cultural and historical sites
  • Two dinners and two lunches
  • Winery visit and tasting en route; wine-country hike; Ciacci Piccolomini d’Aragona tasting
  • Excursions to Montalcino and Montepulciano; dinner at Mastrojanni
  • Greve in Chianti stop; Florentine steak dinner; Arno sunset boat ride; “Open the Duomo”
  • Gratuities

What’s not included

  • International Airfare
  • Meals and beverages not listed as included
  • Optional outings, including the Tuscany wine-bar evening
  • Spa treatments and optional hotel services
  • Transportation and activities during free time
  • Personal purchases, laundry, minibar charges
  • Travel insurance {required}


Payment Schedule

$5,000 deposit per person to book made payable to Feed The City, CITY GRIT Hospitality Group's 501c3.

Remaining payment due by March 15, 2027.