Custom Guided Tours of ItalyCrafted Just for You

With our in-depth insider knowledge, you'll experience the beauty of Italy like a local, not a tourist.

  • 100% custom itineraries

  • Crafted by native Italians

  • Local tour guides

Guided Tours from Trips 2 Italy

Perfectly planned, 100% unique

Just tell us where you'd like to go, or what you'd like to do. Our Italy travel experts will do the rest.

Describe your ideal trip

Start with a simple, 4 question survey that takes just 2 minutes to complete

We’ll design a custom itinerary based on your interests and no one else’s.

Get a custom itinerary

Including everything you’ll need for a perfect trip to Italy

Crafted by experts in Italian travel with over 30 years of experience

Take the perfect vacation

One of kind experiences you can’t get anywhere else

Backed by our exclusive Flexible Travel guarantee

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We take care of every detail

You get the perfect trip

Custom
Itineraries
Itineraries

Boutique
Hotels
Hotels

Local
Food & Wine
Food & Wine

Private
Guided Tours
Guided Tours

Flights +
Transportation
Transportation

Flexible
Scheduling
Scheduling

We take care of every detail

You get the perfect trip

Custom
Itineraries

Boutique
Hotels

Local
Food & Wine

Private
Guided Tours

Flights +
Transportation

Flexible
Scheduling

Why more people travel

With Trips 2 Italy

We know you have options when booking your trip. Find out what truly sets Trips2Italy apart from the rest.

One of a Kind

Guided Tours of Italy

Italy is a country that offers an abundance of sights, activities, and culinary delights to explore. With Trips2Italy, you can immerse yourself in the richness of Italian culture and indulge in all it has to offer. From iconic landmarks to hidden gems, our tours cover a wide range of attractions, ensuring that you don't miss a thing. With the option of private drivers and tour guides, you can navigate the cities and countryside with ease, receiving personalized attention and insider knowledge along the way. Whether you're exploring the ancient ruins of Rome, marveling at the art in Florence, or cruising along the picturesque Amalfi Coast, our tours cater to your interests and preferences. And let's not forget the culinary experiences! Italy is a paradise for food and drink enthusiasts, and our itineraries include visits to local markets, wine tastings, and authentic dining experiences that will tantalize your taste buds. With Trips2Italy, you can savor the best of Italy, guided by experts who ensure that every moment is memorable and enriching.

Discover One of a Kind

Crafted by a Team

That Specalizes in Italian Travel

With our unparalleled Italian-born expertise, Trips 2 Italy specializes in hassle-free vacations covering every aspect of your journey. From flights and transportation to handpicked accommodations and restaurant reservations, we ensure a seamless travel experience. Whether it's a romantic honeymoon, group trip, beach getaway, or ski adventure, our curated itineraries cater to your desires. Enhance your trip with private tour guides and drivers who provide insightful commentary and navigate you through Italy's treasures. Enjoy the peace of mind of our 24/7 assistance as you create cherished memories.

Discover Crafted by a Team

Book Your Guided Tour

With Complete Peace of Mind

Introducing our new flexible travel itinerary, exclusively offered by Trips 2 Italy. With this option, enjoy the freedom to change your departure date for your Italian vacation up to 30 days in advance, without incurring any penalties or registration costs. We understand that circumstances can change, and we prioritize flexibility to meet the needs of every traveler. If there are any changes to your itinerary or travel conditions, our dedicated team will proactively reach out to discuss necessary adjustments and explore various options, including rescheduling or canceling the trip. You can rest assured that Trips 2 Italy values your investment, as we will provide a letter of credit that covers the full amount paid for your reservation if you choose to postpone, ensuring comprehensive protection for your valuable travel plans.

Discover Book Your Guided Tour

Guided Tours

With Trips 2 Italy

Just tell us a little bit about where you'd like to go, and what you'd like to do. Our Italy travel experts will do the rest.

Architecture & History Tours

Italy's diverse regions offer captivating architectural and historical tours. In Rome, visit iconic sites like the Colosseum and Pantheon, and explore hidden areas of Castel Sant'Angelo. Florence's Renaissance treasures include the Cathedral of Santa Maria del Fiore and Giotto's Bell Tower. Venice offers walks through the Doge's Palace and St. Mark's Basilica, while Verona and Siena boast literary and architectural highlights. In Milan, explore La Scala Theater and the Galleria of Vittorio Emanuele II. Private guides enhance these experiences throughout Italy, making your journey truly extraordinary.

Religious Tours

Discover the profound spiritual heritage of Italy through a religious guided tour that encompasses the captivating wonders of the Vatican City and beyond. With Trips 2 Italy, our expert tour guides will lead you on an enlightening journey, exploring sacred sites like St. Peter's Basilica, the Vatican Museums, and the Sistine Chapel, where remarkable artistry and centuries of religious history converge. From the grandeur of Florence's Basilica of Santa Maria del Fiore to the timeless charm of Assisi's Basilica of Saint Francis, our guided tours offer a deep dive into Italy's religious legacy. Immerse yourself in the reverence of iconic cathedrals, ancient churches, and revered landmarks in Rome, Siena, Milan, and beyond, as our knowledgeable guides provide insightful commentary to enhance your spiritual exploration. Experience the profound connection between faith, culture, and art, creating cherished memories that will resonate long after your journey ends.

Food & Wine Tours

Indulge in the culinary delights of Italy through a captivating food and wine tour, carefully curated by Trips 2 Italy. Our expert guides will take you on a gastronomic adventure, where you'll savor the authentic flavors of Italian cuisine and explore renowned wine regions. From the bustling food markets of Rome to the charming vineyards of Tuscany, our tours offer an immersive experience into Italy's rich culinary heritage. Taste traditional dishes, sample exquisite wines, and learn about the art of pairing flavors. Whether you're discovering the secrets of authentic pizza in Naples, indulging in truffle delicacies in Piedmont, or enjoying the finest seafood on the Amalfi Coast, our knowledgeable guides will provide insights into the regional specialties and the stories behind them. Immerse yourself in the vibrant food culture of Italy, meet local producers, and create lasting memories as you embark on a culinary journey unlike any other.

Guided Tour packages

We've crafted for clients

Curious about what a custom itinerary from Trips 2 Italy is like? Explore these Guided Tour packages to see what we do.

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Starting at: $2,999.00

Gardens and Villas of Italy Deluxe Package | Vacation Packages for 2021 – 2022

Nature lovers planning a trip to Italy should consider an itinerary featuring some of the country's most impressive villas and gardens. This unique travel package focuses on several villas that can be admired in the areas around Rome and Florence. During the tour, travelers would have the opportunity to visit the Vatican Gardens, Villa Farnese and Villa Lante with their elegant gardens and fountains. Also included in the itinerary are two fine examples of Tuscan villas: Villa Gamberaria and Villa Peyron in the hills outside of Florence. In your free time, you will be able to visit the famous historical monuments of the city centers of Rome and Florence as well. Take in the beauty of Italy's most opulent villas and expansive gardens during this independent travel package featuring Rome and Florence.From ROME to FLORENCE

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Starting at: $1,392.00

The Chianti Experience With Private Driver 4 Days Customized Trip | Vacation Packages for 2021 – 2022

Considered to be one of the most beautiful parts of the Tuscan countryside, the Chianti area is perfectly positioned near the Italian cultural hot-spot of Florence. During this unique itinerary through the Tuscan countryside, travelers will discover exactly why this part of Italy is world-renowned as one of the premier areas for production of fine Italian wines. You will begin your Chianti experience with visits to the the beautiful medieval towns of San Gimignano, Monteriggioni and Siena, discovering their fascinating history and captivating monuments. Then it is off to visit the gorgeous vineyards and wineries of Chianti for a tour and wine tasting to be followed by an authentic Tuscan cooking class. We can't think of a better way to spend your time in the stunning Tuscan countryside!From FLORENCE to FLORENCE

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Starting at: $3,684.00

Rome and The Amalfi Coast Deluxe Package 8 Days Customized Trip To Italy | Vacation Packages for 2021 – 2022

This fabulous eight day vacation travel package will bring you to some of the most historic and scenic venues along Italy's southwestern coast.  Begin in Rome with leisure time to explore ancient iconic landmarks such as the Colosseum, the Villa Borghese Gallery, and the Vatican complex.  Then be whisked away to the ancient town of Pompeii before riding and trekking up the side of the Mount Vesuvius volcano.  The second half of the trip takes on a more relaxed and sunny vibe with visits to gorgeous seaside towns along the Amalfi Coast where travelers can explore, relax, and enjoy the natural beauty of the coastline. For a first-time trip to Italy, this tour combines the best of Rome's historical sightseeing with the laid back atmosphere of the Amalfi Coast.From ROME to SORRENTO

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Starting at: $2,699.00

Classical Italy Group Tour | Vacation Packages for 2021 – 2022

Rome, Florence and Venice are among Italy's most iconic cities and must-see destinations for first-time travelers. Rome, nicknamed the Eternal City, offers a plethora of famous historical monuments and remarkable collections of art to admire; from the Colosseum to the Vatican, Rome is filled with unforgettable gems just waiting to be discovered. Florence and its historic architecture will transport travelers back in time to the Renaissance, while a trip through the rolling hills of the Tuscan countryside allows for wine tastings at historic wineries among breathtaking panoramas. Last but not least, the beauty of the Island of Venice with its unique canals, winding streets and ornate architecture is sure to impress. This 11 day independent travel package offers the perfect mixture of local guided tours and time at leisure to ensure that travelers make the most of their once-in-a-lifetime vacation to Rome, Florence and Venice.TOUR HIGHLIGHTS:

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Starting at: $988.00

Customized Vacation to Turin and Piedmont Castles | Vacation Packages for 2021 – 2022

This independent itinerary will help travelers discover the heart of Turin, a stately city in northern Italy with an illustrious history. As the first capital of Italy and a key political hub for many centuries, Turin's affluence can be observed in its ornate architecture composed of unique landmarks and historical palaces, such as the Palazzo Madama and the Palazzo Reale. Not to be missed are the city's eminent museums such as the National Cinema Museum and the Egyptian Museum, among the most important of its kind. Take a day to explore the surrounding area where you will discover refined former residences and hunting lodges of the the Savoy Royal Family, the past Kings of Italy. The travel itinerary features one private guided walking tour in Turin to help you become acquainted with the historical city center. The rest of the travel package allows for leisure time to discover Turin and its rich surroundings independently. Further tours or activities can be added according to particular interests such as historical walking tours, food tours or wine tastings. No matter what you choose to see, be sure to savor your time in Turin, a remarkable city unlike any other in Italy.Day 1: TURIN

Your dream vacation starts here

No more endless scrolling through travel sites looking for the perfect fit. Tell us about your ideal trip and preferences, and let our Italian-born travel experts do the rest.

Your dream vacation starts here

Just share a few details about your ideal trip & let our travel experts do the rest.