PRIVATE . BESPOKE . PLANNED BY ITALY SPECIALISTS

Luxury Custom Italy Vacations

Live Italy. Do not just see it.

Private, tailored journeys designed around you by Italians who know the country as only locals can.

Custom itineraries from $8,500 per person.

Fully Private

Your own guides, drivers, and pace

Fully Custom

No packages, no group tours, ever

Founded by Italians

Planned by people who call Italy home

Effortless Luxury

Every detail handled, end to end

Crafted by Italians Who Call It Home

Our team is made up of first-generation Italians who know where to go, what to do, and how to experience Italy the way locals do. That is the difference between seeing Italy and truly living it.

Whatever you envision, we design it from a blank page: the private access, the rare tables, the quiet upgrades, the seamless logistics. A handcrafted itinerary that belongs to you alone and creates memories that last a lifetime.

Where Your Private Italy Awaits

From the cliffs of the Amalfi Coast to the vineyards of Tuscany and the shores of Lake Como, every region becomes yours to experience privately.

AMALFI

TUSCANY

ROME

LAKE COMO

VENICE

FLORENCE

PUGLIA

THE DOLOMITES

Journeys Designed Entirely Around You

No two travelers want the same Italy. We craft each private journey around the occasion you are celebrating and the experiences you dream of.

Bespoke Private Journeys

The heart of what we do. A completely custom itinerary, privately guided, built from the ground up around your interests and your pace. Private transfers between regions, doors opened that stay closed to the crowds, and reservations at the tables worth crossing a country for.

You travel. We take care of everything else.

Honeymoons and Milestone Celebrations

Your honeymoon or anniversary deserves more than a standard itinerary. Picture your first sunset as newlyweds over the rolling hills of Tuscany, a private dinner above the Amalfi Coast, or a quiet morning on the canals of Venice before the city wakes.

We listen to what the moment means to you, then design a journey worthy of it.

Private Food and Wine

Savor Italy with every sense. Private tastings in the country’s most celebrated wine regions, hands-on afternoons with local chefs, and exclusive access to artisanal producers who rarely open their doors.

Each culinary experience is crafted just for you, so every meal becomes a memory and every glass tells a story.

Multigenerational Private Travel

Italy is meant to be experienced together. The wonder in a grandchild’s eyes at ancient ruins, stories shared over a long lunch, laughter echoing through a sunlit piazza. We design private journeys that delight every generation, with seamless logistics so you can focus entirely on each other.

Privately guided, perfectly paced, and uniquely yours.

See Italy Through Our Eyes

They say all roads lead to Rome, unless you had the privilege to grow up there and simply call Italy home. As children we walked the cobblestone streets. As adults we married in the vineyards of Tuscany, prayed in the Sistine Chapel, sailed Lake Como, and skied the Italian Alps. Italy made us who we are. For over two decades we have designed private journeys for travelers with an adventurous spirit and a taste for the exceptional. From your first conversation with us, you will feel our commitment to crafting the finest Italy vacation, designed uniquely for you. Unlike internet travel sites or even our competitors, our team is comprised of first-generation Italians who know where to go and what to do. Do not just see Italy. Live it.

Why Choose Trips 2 Italy

Traveling is not just about places. It is about stories, and the moments you cannot plan.

Tailor Made

Every journey designed from a blank page, never a package.

A Friend in Italy

First-generation Italians who open doors locals only know.

Private and Exclusive

Your own guides and access reserved for the few.

Two Decades of Expertise

Nearly twenty years crafting Italy’s finest vacations.

Begin Your Private Italy Consultation

There are no packages to choose from and no call centers. Share a few details and one of our Italy specialists will reach out personally to start shaping a vacation built entirely around you.

Our custom journeys begin at $8,500 per person, reflecting the private guiding, seamless logistics, and rare access that define a Trips2Italy experience.

What happens next: a personal conversation, a tailored proposal, and an itinerary refined until it is exactly right.

Your Italy, Designed Around You

Begin with a private consultation. No packages, no pressure, simply a conversation about the Italy you have always pictured.

Custom journeys from $8,500 per person.