Cathedral of Florence in Piazza del Duomo, Florence, Italy

Tailor-Made Travel to Italy

Rome, Tuscany, the Amalfi Coast, Venice, Sicily, Puglia, Umbria, and the Dolomites

Beautiful view of historic Church of St. Johann of Nepomuk with famous Odle Group mountain peaks in the Dolomites in beautiful evening light at sunset, South Tyrol, Italy

Alpine Peaks, Imperial Cities, Sun-Drenched Coastlines

Hike to mountain lakes, sip wine at esteemed vineyards, try your hand at truffle hunting, and lounge on the Mediterranean’s iconic white-sand beaches

The coast in Italy

Exceptional Hand-Picked Properties

Historic palazzos, clifftop villas, mountain lodges, and some of Europe’s finest boutique hotels

Ceiling fresco in Palazzo Barberini, Rome, Italy

History and Culture Come Alive

From Roman ruins to Renaissance masterpieces, discover Italy alongside private guides who are experts in all things Italy

A vineyard / winery in Tuscany, Italy

Your Italy Journey Starts Here

Speak to a specialist and we’ll start building your itinerary

History, Culture & Tailor-Made Travel to Italy

Italy is a destination where history, culture, food, and landscape come together in ways that are difficult to find elsewhere. From ancient cities and Renaissance art to vineyard-covered hillsides and dramatic landscapes, there is more here than most travelers manage to cover in a single trip. A well-planned itinerary often blends iconic destinations with regional depth: Rome’s layers of history, the slow pace of the Tuscan countryside, the clifftop villages of the Amalfi Coast, the baroque cities of Sicily, and the alpine scenery of the Dolomites. The food and wine shift with every region, and so does the architecture and the pace of life.

Every itinerary we build is designed around your interests and pace, using properties and guides chosen from firsthand experience. Our specialists know Italy intimately and understand how to sequence a trip that makes the most of each region without rushing through it. Browse the sample itineraries below and contact a Vaya specialist to start planning your Italy journey.

Regions at a glance:

  • Rome — The Imperial City that needs little introduction, from the Colosseum and the Roman Forum to the Vatican Museums and the Sistine Chapel
  • Tuscany and Umbria — Hill towns, cypress-lined roads, vineyards, and medieval cities including Florence, Siena, and Orvieto
  • The Amalfi Coast and the South — Clifftop villages, turquoise water, Greek temples at Paestum, the ruins of Pompeii, and the baroque cities in Sicily and Puglia
  • Venice and the Dolomites — A city unlike any other, not too far from the world-class hiking, skiing, and alpine villages in the Dolomites
  • The Lakes — Lake Como, Lake Maggiore, and Lake Garda, flanked by alpine peaks and elegant Belle Époque villas
  • Emilia Romagna — A worthwhile foodie destination, with Parmigiano Reggiano, prosciutto di Parma, fresh tagliatelle, and some of the country’s best ragù

Best-Selling Italy Trips

Essential Italy

Essential Italy

Days: 10 | From: $14,950/per person

The Best of Italy: Venice, Florence & Rome

Classic Italy: Rome, Florence, and Cinque Terre

Classic Italy: Rome, Florence, and Cinque Terre

Days: 12 | From: $16,990/per person

Journey from Rome to Florence, then to the Coastal Cinque Terre

Culinary Italy

Culinary Italy

Days: 12 | From: $17,950/per person

Taste Your Way Through Verona, Bologna, Tuscany, and Rome

“The areas we visited were absolutely incredible! Great choice of activities and excursions. Our guides and drivers were top notch! Food was fabulous as well as our accommodations. Just can't say enough about this trip!”

Lisa Migneault

Italy

Gems of Sicily

Gems of Sicily

Days: 10 | From: $11,150/per person

Explore Italy's Cherished Island

Sardinia Off the Beaten Path

Sardinia Off the Beaten Path

Days: 9 | From: $15,150/per person

Discover Sardinia's Villages, Coast, and Mountains on the Path Less Traveled

“Vaya was wonderful and easy to work with in planning and executing our Italy trip. I plan to use you again in the future as well as recommend you to others.”

Riann Taylor

Italy

Southern Italy: Rome, Amalfi Coast, and Puglia

Southern Italy: Rome, Amalfi Coast, and Puglia

Days: 11 | From: $12,390/per person

The Best of Rome and Italy's Southern Coasts

Enchanting Umbria

Enchanting Umbria

Days: 8 | From: $9,690/per person

Discover Umbria, a Region Rich with Culture and History

Dolomites Explorer

Dolomites Explorer

Days: 9 | From: 10,650/per person

Hike, Pedal, and Taste Your Way Through the Very Best of the Dolomites

Sicily & Puglia: Culture and Culinary Adventure

Sicily & Puglia: Culture and Culinary Adventure

Days: 11 | From: $12,690/per person

An Odyssey for the Senses in Southern Italy

Off the Beaten Path in Friuli & Venice

Off the Beaten Path in Friuli & Venice

Days: 9 | From: $9,690/per person

See Firsthand the Crossroads of Culture in Northern Italy

”Our trip was fabulous! Vaya's execution made the trip an absolute pleasure for all of us. Every driver was there as expected, every guide was knowledgeable and entertaining.

Susan Quinn

Italy

Discover Piedmont & Val D'Aosta

Discover Piedmont & Val D'Aosta

Days: 10 | From: $11,590/per person

Delve Into Italy's Spectacular Piedmont and Val D'Aosta Regions

Austria Trekking: From the Alps to the Dolomites

Austria Trekking: From the Alps to the Dolomites

Days: 9 | From: $6,870/per person

Explore Tyrol and the Dolomites on Foot

Italy Family Adventure

Italy Family Adventure

Days: 10 | $9,690/per person (based on a group of 4 people)

A Family-Focused Journey Through Rome, Florence, Venice, and Lake Como

5-Star Reviews

Find out why our discerning travelers consistently rate us with 5-stars.

Frequently Asked Questions: Italy

Planning an Italy trip with Vaya Adventures means working with specialists who understand how Italy actually works on the ground. Our team brings first-hand experience across regions such as Rome, Tuscany, the Amalfi Coast, Sicily, and northern Italy, allowing us to design itineraries that flow naturally rather than feeling rushed or overpacked.

At Vaya Adventures, we specialize in pairing travelers with exceptional private guides who bring history, art, food, and local culture to life. Our itineraries emphasize small, character-rich hotels, thoughtful routing between regions, and experiences that go beyond the surface, such as private vineyard visits, walking tours with local experts, and time built in to simply enjoy a place. Reviews consistently highlight our attention to detail, responsiveness, and ability to craft trips that feel personal rather than templated.

When travelers ask about the best places to visit in Italy, our specialists at Vaya Adventures focus on matching destinations to interests rather than offering a one-size-fits-all list. Popular itineraries often include Rome for history, Tuscany for food and wine, and the Amalfi Coast for scenery and relaxation. Other journeys may explore Venice, Florence, Sicily, or the Italian Dolomites.

Experiences commonly woven into Italy trips include guided city walks, food and wine tastings, hands-on cooking experiences, scenic hikes, and coastal exploration. Vaya Adventures designs Italy tours that balance iconic highlights with quieter moments, helping travelers experience Italy in a way that feels both enriching and unhurried.

The best time to visit Italy depends on where you plan to go and how you like to travel. At Vaya Adventures, we often recommend spring and fall for travelers seeking pleasant weather and fewer crowds, especially in cities like Rome and Florence. Summer can be ideal for coastal regions such as the Amalfi Coast, while winter offers a quieter atmosphere in cities and excellent conditions in alpine regions. Our specialists tailor timing to your itinerary rather than following blanket recommendations.

In our experience at Vaya Adventures, most Italy trips are best enjoyed over 10–14 days. This allows travelers to explore multiple regions without rushing and to truly settle into each place. Shorter trips may focus on one or two areas, while longer journeys can include deeper regional exploration or slower travel through countryside and coastal regions.

Italy trips designed by Vaya Adventures typically include boutique or luxury accommodations, private guides, ground transportation, and curated experiences such as food tastings, cultural visits, and guided excursions. Our itineraries are fully customized, meaning inclusions are shaped by your interests, travel style, and desired pace.

Yes. Vaya Adventures regularly designs Italy vacations that emphasize refined comfort, exceptional service, and meaningful access. Luxury in Italy often comes through location, character, and expertise rather than excess. This may include elegant city hotels, countryside estates, or cliffside properties on the Amalfi Coast, paired with expert guiding and exclusive experiences. Italy is also an excellent destination for those interested in food and wine, with culinary-focused tours intertwined with many of our top luxury accommodations and experiences.

Absolutely. At Vaya Adventures, Italy travel is often combined Mediterranean journeys and neighboring countries such as France or Switzerland. Nearby Slovenia and Austria and also easily be combined with an Italy trip for those interested in more mountain and cultural highlights, as well as more off the beaten path experiences. These combinations are planned carefully to ensure smooth transitions and a cohesive overall experience. Italy can also be combined with Croatia for an incredible Mediterranean coastal trip filled with rich history, stunning islands, and great food throughout. Italy can also be combined with Greece; many direct flight connections link these two countries for history and culture lovers.

Traveler in Italy

Superb Private Guides

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Swimming pool and gardens at Hotel Le Fontanelle in Tuscany, Italy

Boutique and Best-in-Class Hotels

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Thoughtfully Designed Itineraries

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“Hotels very nice with awesome attentive staff. Enjoyed the sightseeing, museums, Vatican tours, Truffle hunting and making pasta was so much fun! Wonderful overall trip!”

Mervianna Thompson

“We had an exceptional vacation in Florence and the Tuscan Countryside. Our accommodations were ideal locations with amenities that were exactly as we requested. Our drivers, tour guides and staff were professional, knowledgeable and pleasant.”

Nancy Marie Sandbrook

“The trip was wonderfully planned and beautifully executed. The drivers, guides, hotels and hotel staff where gracious, knowledgeable, and attended to our every wish or need.”

Rochelle Zuroff

“Every day was a great experience. Vaya Adventures came through again.”

John Monroe

“Great trip. Always good to know Vaya has the details covered.”

Stephen Williams

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