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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
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.

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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 tour of Chianti, surrounded by San Gimignano’s medieval towers, then be treated to a fabulous winery lunch with delicious regional products.

DAY 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
    Arrive in Rome for a two-night stay, with time to soak up the atmosphere of its cobbled piazzas and fountains.
  • 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 south 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 yacht 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’S INCLUDED

Everything taken care of

  • Private drivers for every airport 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 and private tours led by expert local guides
  • Skip-the-line access at keys sites
PRICING

Prices from

  • 2 people travelling
    $5,090 pp
  • 4 people travelling
    $4,390 pp
  • 6 people travelling
    $4,490 pp
(with private driver instead of car rental)

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

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 much does a trip to Italy cost per person?

This itinerary starts from $4,390 per person for six travelers, rising to $5,090 for two. Pricing includes boutique hotels, luxury trains, private transfers, and selected dining. International flights are not included.

What is the best time of year to visit Italy?

June and September are ideal months to enjoy both cities and the beach. July is the hottest month, and April to May are the wettest. For cooler temperatures, consider October.

Can this itinerary be customized or extended?

Our signature itineraries are designed to be taken as they are. If you have a specific vision, that’s exactly what our Bespoke Journey service is for. Bespoke trips are built from the ground up around your preferences and are completely customizable.

Is Italy a good destination for a honeymoon?

One of the world’s best! Venice and Positano are among the most atmospheric places on the planet to celebrate a new marriage. This itinerary features a boat tour under the Faraglioni arch to the island of Capri, candlelit dining, and a sunset gondola ride.

What is the difference between a private itinerary and a group tour?

A group tour runs on fixed dates, and you are traveling with other tourists. A private itinerary runs entirely on your schedule, with your group. Every trip we design is for your party only. Some of your individual tours are small-group tours.

What happens if something goes wrong on our trip?

You will be given the phone numbers for each of your drivers and guides to reach them on local time. Our team is available during EST hours. We reconfirm every reservation before you leave to minimize the chance of problems in the first place.

Is there a payment plan?

Your 35% deposit (plus applicable flights) confirms your booking with us. The final balance is due 60 days prior to your departure, and you’re able to pay by credit card or bank transfer. (Pro tip: you receive a 3% discount for paying via bank transfer!)

How much luggage am I allowed to bring?

During your travels, our expectation is that you will have one large (up to 50 pounds) rolling suitcase and one carry-on bag per person. If you have train or ferry travel, we do not recommend exceeding this amount, as it would hinder your boarding and disembarking.

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.
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.

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 take care of the complexity so you can be fully present from the moment you arrive.

NOT SURE WHERE TO START?

Let us point you in the right direction.

Tell us about your travel style, your crew, and what lights you up. We’ll match you with a journey that feels like it was made just for you.

THE PEOPLE BEHIND YOUR TRIP

Meet the team

Every WAC journey has a dedicated travel designer and a whole team working in the background. From booking suppliers, reconfirming every transfer and reservation, preparing your travel documents, and making sure nothing is left to chance, we’ve got you covered.

Hilary Altman

FOUNDER & CEO
I match travelers with their dream places. The best trips are fun, life-changing, and leave you connected to the world and each other in new ways.

Sharon Albin

DIRECTOR OF OPERATIONS
I love experiencing new things and helping others do the same. Morocco has my heart, with its amazing mix of landscapes, architecture, art, and people.

Chrissy VanScoten

HR & BUSINESS DIRECTOR
Life is short and there’s so much world to soak in. Egypt was a lifelong dream, and finally seeing it only made me want to explore even more.

Christine Turoczi

TRAVEL DESIGNER
Travel has always been part of who I am. I love helping people turn dream trips into unforgettable memories they’ll cherish for a lifetime.

Grace Campagna

PRODUCT MANAGER
I studied history, so I love researching places. Finding hidden gems in ancient cities and staying in historic hotels are my favorite parts of travel.

Kimberly Espinosa

TRAVEL DESIGNER
I love speaking the language with locals. Rome is my favorite city for its energy and magic, and it’s where I befriended an artisan who makes mirrors!

Kristin Harwood

PRODUCT EXECUTIVE
Travel is about unexpected moments, like kids blowing bubbles in Innsbruck’s main square at sunset. Everyday life around the world inspires me.

Grace Monteleone

CLIENT CONCIERGE
Travel takes me out of my routine to experience new sights, cultures, and foods. Italy, my motherland, will always be my favorite place to return to.

Katie Watson

PRODUCT EXECUTIVE
Malta is my favorite hidden gem, with sea, history, culture, and food at an affordable price. Make time for the Silent City of Mdina and Valletta!

Julie Koenig

BOOKING AGENT
Travel is an endless adventure. I’ve fallen for India’s people, Italy’s in-the-moment attitude, and Japan’s mix of old and new. Tokyo has my heart!

Sera Lewis

BOOKING AGENT
I love how travel connects you to places and people. Chania, Greece is my favorite spot, but my best memories come back to the people I’m with.

Kelley Ko

PRODUCT EXECUTIVE
As a self-proclaimed foodie, local cuisine is a big part of why I travel. Japan has some of the best food, and its cities stay rooted in tradition.

Gabriela Coffey

PRODUCT EXECUTIVE
My parents instilled a love of travel in me as a baby. My favorite place is Orvieto, Italy, where I studied abroad and became a true ‘local.’

Joy Cunanan

BOOKING ASSISTANT
Seeing clients happy makes this job rewarding. Kind strangers who helped me in Taiwan and Singapore showed me what makes travel so special.

Emma Wallace

PRODUCT EXECUTIVE
In Genoa, a pesto class host told me her dream was to visit New York, where my sister lives. It reminded me that we’re all living someone’s dream.

Venice King

ACCOUNTING ASSISTANT
Travel introduces me to people I’d never meet otherwise. On one trip, our local guide became our friend and even invited us to his daughter’s baptism!

Faye Canillo

OPERATIONS ASSISTANT
My favorite place is Siargao, our first-ever family trip. The beaches were beautiful, but the memories we made together are what I’ll always cherish.

Sarah Kanavos

PRODUCT EXECUTIVE
I lived in Andalucía for two years and made friends from all over the world. Now I help others plan trips that build connections like the ones I made!
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