SIGNATURE ITINERARY

Italy: Ruins, Rolling Hills & Golden Sands

9 NIGHTS · FLEXIBLE DATES · PRICES FROM $4,390 pp

20 YEARS OF CRAFTED TRAVEL

6,000+ TRAVELLERS SERVED

PERSONALLY VETTED BY OUR TEAM

92% REPEAT AND REFERRAL CLIENTS

Italy: Ruins, Rolling Hills & Golden Sands · 9 nights

From · $4,390 pp

BOOK THIS TRIP

ABOUT THIS JOURNEY

For families and curious travelers who want ancient history, slow Tuscan afternoons, and Mediterranean bliss.

Over nine days, revel in the sights, sounds, and flavors of Italy’s most dynamic landscapes. The adventure begins in Rome, the world’s most captivating city filled with elegant fountains, ancient ruins, and bustling piazzas. Next, enjoy a peaceful respite among the rolling hills of Tuscany, where idyllic nature meets the world’s most beloved food and wine. By the end of the trip, you’ll find yourself watching the sun set over the Italian Riviera, feet in the sand and wondering how one country can hold so much.

DAYS 1 – 2

Rome

Your journey begins in Rome: The Eternal City. Just steps from Piazza Navona, stay in a boutique hotel with a rooftop terrace and dazzling views of the city skyline. The first evening is yours to wander through ancient streets, explore lively piazzas, and gaze upon Trevi Fountain aglow at night. On the second day, stand in the footsteps of gladiators as you visit the Colosseum, then learn of Rome’s captivating origins at the Roman Forum. In a delicious finale, you’ll traverse one of the most atmospheric neighborhoods to savor the city’s most delicious cuisine.

DAYS 3 – 5

Tuscany

Bid farewell to the tourists and the vigor of the city as you depart Rome and enter Tuscany. In Val d’Orcia, a stunning display of rolling hills, tall cypress trees, and lush vineyards unfolds before you. You’ll explore a local farm to hang with the sheep, taste gourmet pecorino cheese, and savor fine wine. Also awaiting you is a stay at a 16th-century country house whose infinity pool overlooks the picture-perfect countryside. Enjoy leisure time to relax on the property and wander the charming streets of Montepulciano. You’ll have a full day to explore Chianti, surrounded by San Gimignano’s medieval towers, then be treated to a fabulous winery lunch with delicious regional products.

DAYS 6 – 9

Sestri Levante

The adventure continues north through Tuscany, pausing in Pisa to explore the iconic Leaning Tower. You’ll arrive in the Italian Riviera at a hotel perfectly set on the golden shores of Sestri Levante. Bask in the sunshine as you swim in the azure Mediterranean waters, then wander about town. You’ll enjoy a day of coastal splendor aboard a private boat to Portofino and Camogli, admiring pastel-colored houses, gleaming superyachts, and dramatic rocky cliffs. Your final day begins deliciously with an authentic Ligurian cooking class where you’ll craft handmade focaccia and fresh pesto. On the last evening, with your feet in the sand, you can watch the sunset over the water, reflecting on this incredible journey.

DAY BY DAY

The highlights

DAY 1

Arrive in Rome for a two-night stay, with time to soak up the atmosphere of its cobbled piazzas and fountains.
DAY 2

Step back in time on a small group tour of the Colosseum and ancient Rome, then savor an evening of authentic tastings on a food-lovers’ walk through Trastevere.
DAY 3

Collect your rental car and wind your way from Rome into the Tuscan countryside for a three-night stay, stopping for a leisurely lunch at a family-run pecorino cheese farm.
DAY 4

Sip and savor at a Tuscan winery, where a guided tasting leads into a relaxed lunch among the vines.
DAY 5

A free day to explore at your own pace, perhaps with a wander through the hilltop streets of Montepulciano.
DAY 6

Drive north to Sestri Levante for a four-night stay, with time to explore its colorful harbor and pastel buildings.
DAY 7

A leisure day to enjoy the beaches of the Riviera.
DAY 8

Set sail on a private boat along the Gulf of Tigullio, taking in the towns of Portofino and Camogli, with refreshments on board.
DAY 9

Roll up your sleeves for a hands-on Ligurian cooking class paired with wine.
DAY 10

Transfer to the airport for your flight home.

WHAT OUR CLIENTS SAY

“We had an amazing experience in Italy thanks to Hilary and WAC travel!! The vacation was a wonderful variety of relaxation and activities. Everything went incredibly smoothly (the private transportation, train travel, excursions and tours). Highlights for us were: hotel on the water in Sestri Levante, lunch in Portofino, boat tour, wine tasting in Tuscany, touring the Colosseum. All the guides were amazing! We will use WAC for our next vacation!”

KIM H. · GOOGLE REVIEW

“Hilary and her team thought of every last detail, recommended resources and services and places we would not otherwise have found on our own. The wine tasting tour in Tuscany was a highlight for our family. The cooking class was also a highlight. So glad we stayed in Sestri Levante, which she recommended. It was tropical, beautiful and not overrun with American tourists. The boat tour they booked for us too was wonderful.”

NINA D. · GOOGLE REVIEW

WHAT’S INCLUDED

Everything taken care of

Door to door, from the moment you land until you fly home. Your airport transfers are booked and your car is waiting for you in Tuscany, so there are no tickets to buy and no connections to figure out.

Private drivers for every airport and train station transfer
Automatic car rental in Tuscany (or private driver for 6 people)
Boutique hotels, carefully chosen, in the heart of each destination
Daily breakfast included
A cooking class lunch, winery lunch, and food tour dinner
Small group tours led by expert local guides
Skip-the-line access at key sites

Meals not listed above are yours to enjoy wherever you like. International flights are not included.

PRICING

From $4,390 PER PERSON

Based on four people traveling together

2 people traveling

$5,090 pp
4 people traveling

$4,390 pp
6 people traveling

$4,490 pp

With a private driver instead of a car rental

WHY THE PRICE CHANGES

Private drivers and many of your arrangements are priced per vehicle or per booking, not per person, so the more of you who travel together, the lower the price for each person. Groups of six travel with a private driver in Tuscany rather than a rental car, which is why that price is a little higher.

PREFER A DRIVER?

This itinerary is also available with a private driver in Tuscany for two or four travelers. Just let your travel designer know.

Prices are subject to change depending on your preferred dates of travel. Price does not include international flights.

BOOK THIS TRIP

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COMMON QUESTIONS

Everything you want to know

A selection of questions about this itinerary and planning a trip to Italy. For more, visit our full FAQ page.

How do we start planning a trip with WAC?

With a conversation. We ask about how you like to travel, what’s brought you to this trip, and what would make it feel right, before suggesting anything specific.

What if members of a group are flying from different cities?

Very common, especially for multigenerational trips. We coordinate arrival windows and arrange group transfers once everyone lands, regardless of where each flight originates. Where it’s possible, we’ll also help align flights so part of the group can fly together for a leg of the journey, or failing that, so everyone lands around the same time.

Does WAC require travel insurance to book with us?

We don’t require it, but we recommend it for every trip, and especially for bespoke and multi-generational itineraries where more is at stake if plans change.

Can I bring my regular hairdryer or curling iron?

We’d recommend leaving standard hairdryers and curling irons at home, as European voltage is too strong for most of them unless they’re specifically dual voltage. Most of our hotels can provide a powerful hairdryer on request, or you can bring a dual-voltage travel version if you’d rather have your own.

What should we pack for Italy?

Comfortable shoes for cobblestones, layers for variable weather, and modest clothing for visiting churches, a lightweight scarf works well for covering shoulders. Smarter clothes for evenings with leather shoes for men rather than sneakers.

Can dietary restrictions be accommodated on a private villa stay?

Yes, we collect dietary needs in advance and build them into any private chef arrangements or restaurant bookings.

Can we combine a city stay with the Italian countryside?

Yes, this is one of our most popular itinerary shapes, several days in a city like Florence or Rome followed by a stay in Tuscany or Piedmont.

What happens if something changes once we’re in Italy?

There are frequently small changes when you travel, our team is on hand to keep you updated, and they’ll update your documents in your phone app so you always have the latest version.

ASK US DIRECTLY

PREFER SOMETHING ENTIRELY YOUR OWN?

We build bespoke journeys too.

When your vision calls for something entirely custom, it deserves to be designed from the ground up. Our bespoke process begins with an unhurried discovery conversation.

BESPOKE JOURNEYS

WHY TRAVEL WITH US

The details that make the difference

We’ve been there.

Every hotel, tour, and experience we recommend has been personally vetted by our team. We don’t send you somewhere we wouldn’t go ourselves.

Our connections are yours.

Years of relationships with exceptional guides, trusted drivers, and the right people on the ground across Europe and Africa.

Nothing gets left to chance.

Before you travel, we reconfirm every booking, every transfer, and every detail to make sure the pieces fit together exactly as planned. You’ll also receive your full itinerary, hotel confirmations, guide contacts, and emergency support loaded into your personal travel app before departure.

Someone picks up the phone.

While you’re away, we’re available. If something shifts, we handle it so you don’t have to.

Your time is the point.

We’ve been arranging travel across Europe and Africa for 20 years, and more than 92% of our clients come back or refer a friend.