A Signature Cherish Journey

Italy

Let your travel dreams fly

Experience local cuisine, rich traditions, and the midnight sun. This unforgettable adventure offers a perfect blend of nature, history, and modernity in two of Northern Europe’s most captivating countries.

This itinerary highlights Rome and the Umbria wine region, but we also specialize in other regions of Italy, including Tuscany, Venice, the Almafi Coast, and more. Reach out to us to learn more, or to build a custom itinerary around a different region.

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trip highlights
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Who is the trip for
all the details
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Trip Highlights

  • Fully planned journey through Rome and the Umbrian countryside

  • Explore Rome's ancient history, art, and architecture, with the freedom to choose your own path

  • Retreat to a woman-owned boutique guesthouse restored within a medieval hill town

  • Participate in a traditional Italian wine harvest (vendemmia) alongside local vineyard partners

  • Guided wine tasting and food pairing as the sun sets over the Umbrian countryside

  • A full day exploring Orvieto's Etruscan history, cathedral, and underground caves

  • Hands-on pasta and tiramisu making with a local Italian Nonna

  • Family-hosted Welcome Dinner in the historic village of Allerona

  • A farewell cookout celebration with your Italian hosts

  • Learn from women preserving culinary traditions, hospitality, and rural Italian life

  • Support women-owned and locally-owned businesses simply by traveling with Cherish

  • Simply show up, the rest is taken care of for you

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WHO IS THIS TRIP FOR?

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WINE & FOOD ENTHUSIAST

HISTORY ENTHUSIAST

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COUNTRYSIDE ROMANTIC

SLOW
TRAVELER

PURPOSEFUL TRAVELER

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the ITINERARY

day one

ARRIVE IN ROME

Benvenuta in Italia! Arrive in Rome and settle into Hotel Damaso, a family-owned boutique hotel tucked on a quiet street near Campo de' Fiori, with a private transfer included from the airport. Take time to rest or explore the surrounding streets before gathering with the group for a Welcome Dinner at a local, family-owned restaurant.

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day two

CHOOSE YOUR ROME EXPERIENCE​

Choose your own adventure in the Eternal City: join a history-focused walking tour through Rome's iconic landmarks and layered past, or a food-focused experience centered on local flavors and hidden culinary gems. In the evening, we'll come back together for a relaxed group activity before a free evening to explore Rome's dining scene on your own.

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day three

TRANSFER TO UMBRIA

Mid-morning, we'll depart Rome for the hilltop village of Allerona in Umbria, arriving at a woman-owned boutique guesthouse restored within a medieval village. Settle in over a warm welcome lunch hosted on the property, with free time after to browse the village's shops. In the evening, a guided walk through Allerona introduces you to the village's history before a family-hosted Welcome Dinner with your local hosts, Liz and Paolo.

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day FOUR

EXPLORING ORVIETO

This morning, a guided tour introduces you to Orvieto, a striking medieval hill town known for its Etruscan history, winding streets, and cathedral. Lunch is included at a favorite local trattoria, followed by a visit to one of the town's centuries-old underground cave systems. In the evening, we'll return to Allerona for a relaxed dinner at a casual local restaurant.

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day FIVE

HARVEST TRADITIONS & WINE COUNTRY

This morning, join in the traditional Italian vendemmia, or wine harvest, alongside local friends and vineyard partners. Enjoy a hearty local lunch afterward, with free time to rest, read, or explore the village at your own pace. As the sun sets over the Umbrian countryside, we'll visit a nearby winery for a guided tasting paired with local flavors.

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day 6

TRADITIONAL ITALIAN COOKING EXPERIENCE

Spend the morning in the kitchen with Nonna Franca, learning to make two types of handmade pasta and a classic tiramisu before sitting down together to enjoy the meal you've prepared. The afternoon is free to relax, read, or wander the village. In the evening, we'll gather for an outdoor cookout and farewell celebration with your Italian hosts.

day 7

BACK TO ROME

After a relaxed breakfast, we'll depart Umbria mid-morning for the journey back to Rome, arriving in time for lunch and check-in. The afternoon is yours to explore on your own, or upgrade to an optional historic outing to one of Rome's famous sites paired with lunch at a local café. The evening is free to enjoy Rome at your own pace.

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day 8

Departures

Enjoy breakfast before your departure. Cherish will provide one group transfer back to Rome Airport, with additional transfers available at an added cost for those on different flight schedules.

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how do i book this

step 1

Let's have a conversation!

Chat with Cherish's Founder directly about everything you'd like to get out of your Private Travel Experience.

Answer some questions about the details and we'll put together a custom trip estimate for you.

step 2

planning

Work together with Cherish to finalize your itinerary and select the perfect dates for your trip.

Once all the details are finalized, we will finalize the trip proposal and cost per person for your exclusive getaway.

BOOK NOW

step 3

confirmation

We'll send you your customized booking page for your group's trip. Start sharing the page with your guests to get everyone signed up.

When the date comes, simply show up for your fully curated private group experience.

More ways to travel with us

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Custom

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PRIVATE TRIPS

Fully curated for your own group, where every detail is tailored to your pace, preferences, and purpose.

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Signature

small group trips

Our guided journeys bring together like-minded women looking to share meaningful experiences

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