2 destinations 2-01 Destinations
2+ 2+ Guests
Pace - Relaxed pace Relaxed Pace
Customizable Customizable-01 Customizable

Customize Your Luxury Vacation

• Experience the best of rural Tuscany and Florence on a fully-tailored journey

•  Share intimate moments with a special someone in a place  known for extraordinary food and exceptional wine 

• There are no set dates—the best times of the year to travel are May through September

• This itinerary can be customized to your interests, specifications and group

• Pricing is per person, based on double occupancy, for a group of two or more

2 destinations 2-01 Destinations
2+ 2+ Guests
Pace - Relaxed pace Relaxed Pace
Customizable Customizable-01 Customizable

A Romantic Getaway in Italy

Explore the journey

Itinerary

  1. Days 1 - 3
    Tuscany
    View details
    Overview

    Begin your getaway in Tuscany’s romantic countryside.

    Meet your English-speaking driver at Florence International Airport for a private journey through the Italian countryside to Castiglion Del Bosco, one of the oldest and best-preserved estates in Tuscany. Located in the heart of the UNESCO World Heritage site Val d’Orcia, the estate is an essential part of the famed Brunello di Montalcino winemaking region and an outstanding culinary destination. It’s also an exceptional place to reconnect with one another. You choose the activities that please you, so it’s easy to slow your pace and truly enjoy each other’s company.

    Curated Experiences
    Curated Experiences
    Private Spa Experience

    After settling into your suite, let your everyday concerns fade at Rosewood Castiglion Del Bosco’s well-appointed spa. Begin with a 50-minute classic massage, followed by an hour-long sauna and steam bath for two. Finally, escape to the hotel’s secret garden to enjoy a private buffet. It’s the perfect way to say hello to Italy and set the mood for your Tuscan getaway.

    spa
    Curated Experiences
    Hot Air Balloon Ride

    Few landscapes evoke romance as well as Tuscany. Experience it from your private hot air balloon in an early-morning flight above the region’s patchwork fields, red-roofed villages and charming medieval cities.

    balloon
    Curated Experiences
    Discover Charming Tuscan Towns

    Meet your local guide amid the 14th century towers of San Gimignano, considered the best-preserved medieval village in Tuscany. The town once flourished as a center of trade, attracting the creators of artwork and architecture still visible today. For lunch, try the specialties of nearby Siena, including local Chianti wine. Then join your guide to stroll the Piazza del Campo, the heart of this proud city.

    Italy_San Gimignano
    Curated Experiences
    Attend a Gregorian Chant

    Only a few dozen monasteries continue the practice of Gregorian chanting. One is the community of Benedictine monks at the Abbey of Monte Oliveto Maggiore, concealed between deep canyon walls in central Tuscany. Make your way to the abbey to experience the intimate beauty of the monks’ song at evening vespers where the pure, almost austere tones often prove deeply moving to listeners.

    Gregorian
    Curated Experiences
    Private Wine Tasting

    The Ricasoli family has ties to Chianti winemaking that stretch at least as far back as 1141, the date on the first record showing their ownership of a nearby castle. Tour the home of Ricasoli wines, then sample a special selection of the very best in a private tasting room reserved just for you. For lunch, take a four-course tour of Tuscan cuisine led by the chef at Osteria del Castello, the restaurant in the castle adjacent to the vineyards.

    wine
    Curated Experiences
    Chianti Culinary Experience

    After your visit to Ricasoli, spend a decadent afternoon experiencing the pleasures of Chianti, one of the world’s great culinary destinations. Your private car and English-speaking assistant give you the freedom to focus on flavors and culture as you sample local olive oil, cheese, salami and gelato at a series of private tastings presented by the region’s most esteemed producers.

    Chianti
    Previous 1 of 6 Next
    Accommodations
    Rosewood Castiglion Del Bosco
    Perched atop a Tuscan hilltop with vineyards nearly at its doorstep, the Rosewood Castiglion Del Bosco is a luxurious retreat set among the historic buildings of Il Borgo, the region’s former farming center. Watched over by the ruins of the medieval castle that gives the estate its name, the Rosewood Castiglion Del Bosco marries the best in modern amenities—including relaxing spa treatments, fine dining and sumptuous suites—with the beguiling history and culture of Italy.
  2. Overview

    Hunt for truffles and the soul of the Italian Renaissance.

    In a few short hours, a leisurely drive takes you from the delightful Tuscan countryside to the amber-tinted center of the Italian Renaissance, Florence. Along the way, farm families continue a tradition of Italian life, training dogs to sniff out truffles, the delicacy of the local woods. In the city, traditions remain strong too, especially when preserving Florence’s famed Renaissance art.

    Curated Experiences
    Curated Experiences
    Truffle Hunt

    Join a truffle-hunting dog and its handler on an entertaining search for these culinary gems of the Tuscan woods, a staple of the slow foods movement in Italy. Learn how the dogs are trained to sniff out the prized underground fungi, where to hunt for them and how to clean and store your harvest.

    truffle
    Curated Experiences
    Tuscan Cooking Class

    Once the truffles are found, it’s time to taste. Join an expert in truffle cuisine at a private, hands-on cooking class. Use local products—including truffles, of course—to prepare your lunch, with appetizers, fresh pastas and sauces, and dessert.

    Tuscan cooking
    Curated Experiences
    Italian Renaissance Walking Tour

    The Duomo and the Baptistery. The churches of Santa Maria Novella and Santa Croce. The Uffizi Palace, the Piazza della Signoria and the Ponte Vecchio across the river Arno. It seems every turn on the streets of Florence presents you with another Renaissance masterpiece. Enjoy them on a private walking tour with your expert guide.

    Florence
    Previous 1 of 3 Next
    Accommodations
    Four Seasons Hotel Firenze
    Stroll the tranquil grounds of this historic hotel—Florence’s biggest private garden—before retiring to your luxurious suite. As your getaway to Tuscany draws to a close, indulge yourself in a locally inspired spa treatment, a meal in the Michelin-starred restaurant or a soak in the outdoor pool and whirlpool, open year-round.
Tuscany
Florence