Italian Escapes

Discover Italy, Your Way

Five hand-crafted itineraries through Italy’s most captivating regions, each designed for private, seamless travel with the perfect balance of exploration and ease. Every one can be made your own.

every one can be made your own

Rome · Amalfi · Naples

Dolce Vita: Amalfi Edition

This is your Italian highlight reel. Rome, Sorrento, Positano, Amalfi, and Napoli all in one trip. You’ll sip espresso in Rome, take a private boat along the Amalfi Coast, and end each day with sunset views that feel unreal. It’s glamour, it’s color, it’s the kind of trip you’ll think about every time you see the ocean again.

Starting at: $6,450 per person
Length: 9 nights

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From the journal: Dolce Vita: Amalfi Edition →

Milan · Como · Venice

Lago di Luxe: Como

If you love style, this one’s for you. Milan, Lake Como, Verona, and Venice: the perfect mix of city chic and lakeside calm. You’ll shop Prada in Milan, sip prosecco by the lake, and glide through the canals of Venice. It’s polished, it’s peaceful, and it’s pure luxury from start to finish.

Starting at: $5,495 per person
Length: 7 nights

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From the journal: Lago di Luxe: Why Lake Como and Northern Italy Feel Like Pure Indulgence →

Siena · Florence · Lucca

Table to Terrace: Tuscany

This is the Italy you’ve been dreaming about. Rolling hills, vineyards, cozy trattorias, and endless views that look straight out of a movie. You’ll sip an Aperol Spritz on a sunlit terrace in Siena, explore Florence’s art and charm, and end your days watching the light fade over Lucca. It’s long lunches, deep red wine, and that perfect kind of slow.

Starting at: $5,995 per person
Length: 8 nights

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From the journal: Table to Terrace: Why Tuscany Feels Like the Italy You Have Always Imagined →

Watercolor of trulli houses on the Puglian coast

Lecce · Ostuni

The Puglian Secret: Lecce to Ostuni

If you want to feel like you’ve discovered the part of Italy no one’s talking about, this is it. Think whitewashed towns, olive trees for miles, and the slow, beautiful rhythm of the south. You’ll wander Lecce’s golden streets, stay in stunning countryside villas, and explore beaches and villages that feel completely untouched. It’s Italy’s best-kept secret and you’ll never want to leave.

Starting at: $5,295 per person
Length: 8 nights

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From the journal: The Puglian Secret: Why Lecce and Ostuni Feel Like Italy’s Best Kept Treasure →

Taormina · Catania · Rome

Sicily & the City

This one blends two completely different sides of Italy. You’ll start in Taormina and Catania where the views and food are next-level, then finish in Rome for that big city energy. Think beach clubs, pasta al mare, and a final espresso standing at a Roman bar before your flight home. Warm, vibrant, and full of energy, just how Italy should feel.

Starting at: $3,995 per person
Length: 7 nights

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From the journal: Sicily and the City: Why This Two-World Itinerary Is Pure Magic →

Beyond Italy

Italy is where we started. Europe is where we go next.

We design custom trips across Europe with the same care: the right hotels, the right pace and the logistics handled. Tell us where you’re dreaming of.

FranceGreeceSpainPortugalCroatia

not sure where to start?

Tell us the feeling. We’ll bring the map.

Six quick questions, about two minutes. Your advisor will suggest the regions, pace and hotels that fit.

Help me choose