Rome is the perfect place to begin a trip to Italy. The city is vibrant, historic, and endlessly beautiful.

Spend your first two days wandering ancient streets, sipping espresso, and taking in some of the world’s most iconic sights.

Start by exploring the historic center.

Visit the Colosseum and the nearby Roman Forum. A private guide makes the experience much more enjoyable and helps bring the history to life.

Later, wander through the gardens of Villa Borghese and visit the Borghese Gallery to see works by Bernini and Caravaggio.

Rome is wonderful for luxury shopping. Spend some time browsing along Via Condotti where many of Italy’s most iconic fashion houses have boutiques.

Roscioli — legendary Roman pasta
Pierluigi — elegant seafood
Armando al Pantheon — classic Roman cuisine

On the morning of Day 3, take the high-speed train from Rome to Florence.

Travel time: about 1 hour 30 minutes.

Florence is smaller and more intimate than Rome, making it perfect for two relaxed days of art, food, and wandering.

Florence has some of the most beautiful historic hotels in Europe. If you love traditional luxury, these are three wonderful choices.

Four Seasons Hotel Firenze
This extraordinary hotel is set inside a Renaissance palace surrounded by the largest private garden in Florence. The property is breathtaking, with frescoed ceilings, beautiful suites, and exceptional service.

The St. Regis Florence
Located directly along the Arno River, this historic palace hotel offers spectacular views and classic Italian elegance with frescoed interiors and chandeliers.

Belmond Villa San Michele
If you want a hotel with unforgettable views, this former 15th-century monastery sits on a hillside overlooking Florence. It feels like a Tuscan villa retreat while still being just minutes from the city.

Florence is home to some of the world’s greatest art.

Visit the Uffizi Gallery and the Accademia Gallery where Michelangelo’s David is displayed.

Spend time walking through Florence Cathedral, Piazza della Signoria, and the historic Ponte Vecchio bridge.

Florence is famous for leather goods and artisan craftsmanship. You’ll also find luxury boutiques along Via Tornabuoni.

Enjoy a sensational meal at one of the following restaurants, each offering a unique experience.

La Giostra — romantic Florentine dining
Trattoria Cammillo — classic Tuscan lunch
Enoteca Pinchiorri — Michelin-starred experience

From Florence, drive about an hour into the rolling hills of Tuscany.

This part of the trip is all about slowing down. Think vineyard views, incredible food, and long relaxed afternoons.

Pause in the charming hill town of Montepulciano.

Have lunch at Osteria Del Conte and enjoy a glass of Brunello before continuing on to your hotel.

Three exceptional countryside properties include:

Rosewood Castiglion del Bosco
A beautiful vineyard estate in the heart of Brunello country with incredible views, an infinity pool, and outstanding dining.

Borgo Santo Pietro
A luxurious countryside retreat set on a historic estate with gardens, farm-to-table dining, and a serene spa.

Castello di Vicarello
A romantic castle hotel perched high above the Tuscan countryside with sweeping views and elegant suites.

Spend one day exploring nearby hill towns such as Pienza and Montalcino.

Arrange wine tastings at Brunello producers including Biondi-Santi and Castello Banfi.

Other wonderful experiences include:

truffle hunting
cooking classes
horseback riding through vineyards
olive oil tastings

Or simply spend the afternoon enjoying the pool and the countryside views.

Enjoy one final slow breakfast overlooking the vineyards.

Then drive to Florence Airport for your flight home.

Travel time from Tuscany to Florence Airport is about 1–1.5 hours.

From Florence, most flights connect through major European hubs before continuing to the United States.

This itinerary flows naturally through three of Italy’s most beautiful destinations.

Rome gives you history and culture.

Florence offers art, fashion, and incredible food.

Tuscany allows you to slow down and enjoy the countryside.

It’s the perfect balance of city energy and countryside calm—and a trip you’ll remember forever.