Riomaggiore in the Cinque Terre, Italy
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Milan and Cinque Terre Itineraries & Tours

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Blend the luxury of the House of Savoy with the charisma of hidden seaside towns overlooking the Tyrrhenian Sea with Milan and Cinque Terre itineraries. Wander along coastal paths that connect secluded cobblestone lanes and witness the marvels of classic masterpieces by the likes of da Vinci. Find hidden canals, embrace local flavors, or embrace the glamour of luxury shops. With thousands of custom trips planned to Italy, a Zicasso travel specialist tailors your itinerary to your wants, desires, and needs. Find inspiration for your personalized trip with our sample itineraries.

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Tailor Made Itineraries

Get inspired with our sample trips below. Let our travel specialists customize a trip just for you.

Happy couple enjoying romantic dinner with wine at a vineyard in Italy
Romantic Getaway to Northern Italy and Cinque Terre Tour

8 Day Custom Tour

Dynamic pricing from $2,859

Share the secrets of Italy with your partner during a romantic excursion from the snow-capped Italian Alps to the sun-drenched cobblestone streets of the Cinque Terre villages. The Mediterranean Sea laps at the rugged coastline as ships sail along the turquoise waters to weigh anchor in the small marinas and the natural harbors of these often overlooked towns. Scents of basil and parmesan linger in the air and give way to the aroma of lemon trees and vineyards. Your custom tailored tour encompasses the elegance of luxurious villas and the enchantment of castle ruins to provide you with the perfect romantic landscape to indulge in.

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Fishing Village in Cinque Terre in Riomaggiore, Italy.
Culture and Coastal Treasures of Northern Italy

10 Day Custom Tour

Dynamic pricing from $3,575

Northwest Italy is yours to explore on this tailored tour that leads from the rich city of Turin to the spectacular coastline of the Cinque Terre and the magic metropolis of Milan. Every step of the way, you will treat yourself to the tantalizing flavors of Italian cuisine and witness the breathtaking unspoiled backdrops of Italy’s countryside while learning more about the local culture and heritage.

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Vineyards surround the comune of Serralunga d'Alba in the Piedmont region of Italy
Marvelous Piedmont, Cinque Terre, and Milan Tour

12 Day Custom Tour

Dynamic pricing from $4,291

Embrace splendid flavor and graceful scenery during your 12-day Italy food tour taking you through the towns of Piedmont and Liguria. Bask in an ancient spa and sample the inspiring wines of Barolo. Witness da Vinci’s Last Supper and indulge in cuisine outlined by the Slow Food Movement. You can relax with a panorama of Cinque Terre and craft a meal in a historic palazzo during your flavorful Italy tour.

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Guisti Garden in Verona, Italy
Northern Italy Trip Between Opera and Culture

12 Day Custom Tour

Dynamic pricing from $5,071

From music to cuisine, seaside serenity to alpine treasures, your 12-day Italy tour will immerse you in the famous culture of the north from Cinque Terre to Milan. The sounds of opera will permeate a preserved Roman amphitheater and the La Scala Theater. Artistic marvels will capture your imagination with Giotto and da Vinci. Each new destination will reveal Italy’s unrivaled beauty as you embrace villages, cities, opera, and culture.

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Riomaggiore and the coastline of the Cinque Terre, Italy
Italy's Lakes District Tour with Cinque Terre

12 Day Custom Tour

Dynamic pricing from $4,291

This Italy tour is for everyone who’s ever wished for two weeks of utter relaxation; for everyone who’s ever sought out the tiny towns and hamlets instead of the well-worn tourist trails; for everyone who’s ever longed for an authentic travel experience. This is the experience for everyone dreaming of a two-week Northern Italy trip that you’re sure to remember for the rest of your life.

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Verenna on Lake Como, Italy
Spirited 17-Day Journey through Italy: Highlights and Hidden Culture

17 Day Custom Tour

Dynamic pricing from $6,081

Unbridled beauty veils Italy and its awe-inspiring countryside and spectacular coastline, scenes that will backdrop your educational exploration during this extensive 17-day tour from Venice to Rome. Whether it's the sprawling glimmering waters of Lake Como or the romantic skyline of Verona, Italy will dazzle and seduce you as you delve into its spirited culture and honored history along the journey.

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Gabbiano Castle with vineyards and cypress trees in Tuscany, Italy
Cultural Immersion Tour of Northern Italy & Cinque Terre

9 Day Custom Tour

Dynamic pricing from $3,217

Northern Italy takes you out of the ordinary and into the exceptional, from the grandiosity of once noble families to the delicate flavors of balsamic drizzled over fresh strawberries. Rugged mountains run along the coast to turn fishing villages into secluded getaways. The Tuscan hills roll along the horizon and glow emerald in the sunlight. Castles rise out of old vineyards and monasteries hide between seaside cliffs. Your custom tailored tour will show you the unique and enveloping splendors of Northern Italy and Cinque Terre as it’s embodied in the landscape and emanating from the culture.

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Gothic Church of San Pietro on the Italian Riviera in Portovenere, Italy
A Perfect Seven-Day Itinerary to Cinque Terre

7 Day Custom Tour

Dynamic pricing from $2,501

Raise your glass and make a toast to the unbridled beauty of the Italian Riviera at Cinque Terre. The five secluded towns are near legendary in their natural splendor and the perseveration of culture situated between the Maritime Alps and the Mediterranean Sea. Precipitous cliffs frame gorgeous pebbled beaches as strawberry patches and olive trees grow alongside beautiful historical trails. Medieval churches border cobblestone piazzas and castle ruins continue to overlook the water that protects the villages. Absorb the charm of the national parks and the local cuisine as you bask in the luxuries of the villas and the secluded beaches. Relish your time as you sip your wine with cheers to Cinque Terre.

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Malcesine on Lake Garda, Italy

Escape from the crowd and explore a new perspective during your 9-day Italy tour of Cinque Terre, Lake Garda, and Venice. The trails of the Italian Riviera hide beneath lush oak forest as medieval castles overlook the cobalt waters of a glassy lake and the historical neighborhoods of Venice remain frozen in time. You will travel the shorelines, lakeshores, and canal banks for a luxurious, custom-tailored Italian experience.

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More About Milan & Cinque Terre Itineraries

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Our Italy Travel Guide provides helpful tips and inspiration from must-see destinations and top activities to the best time to visit. Discover traditional food and wine, inspirational culture, and amazing cities on a personalized vacation.

For more information on how to make your dream journey a reality, get connected with a top travel specialist by filling out a Trip Request.

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How to Plan a Trip to Italy: Frequently Asked Questions

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Whether you are designing a first-time Italian vacation as a couple or returning to the Mediterranean jewel with family, we share how to plan a stress-free trip.

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Top 15 Things to Do in Italy
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Manarola village in Conque Terre, Italy
How To Spend 2, 5, or 7 Days in Cinque Terre

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The location, a UNESCO World Heritage Site along the pristine Ligurian coast, provides endless views and vibrant sunsets. Built among the rocks, with unique layouts etched into the contours of the cliffs, discovering any of the five towns of the Cinque Terre will leave you with incredible memories.

Discover the best experiences for your trip to make the most of your adventures in this gorgeous, charismatic corner of Italy.

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Reviews of Zicasso's Referral Service

4.89 stars based on 61 reviews.

Italy Vacation Review: Shopping in Milan, Pompeii Excavations,...
"Start to finish, the outright best travel planning experience...

Reviewed By Jim M.

Luxury Italy Trip Review: Milan, Venice, Porto Venere, Cinque...
"[Our travel agent] created the perfect balance of private...

Reviewed By virginia e.

Vacation Review: Italy Mother/Daughters Trip, Civita di...
"Everything we did was PERFECT!"

Reviewed By Aurelia L.

Italy Vacation Review: Milan, Cinque Terre, Alba Area, Truffle...
"We thought the trip was well organized and the company...

Reviewed By Jeffrey H.

Italy Vacation Review: Venice, Lake Como, Milan, Cinque...
"Our travel agency did a fantastic job with the planning...

Reviewed By Paul P.

Italy & Switzerland Trip Review: Cinque Terre, Bellagio,...
"We were very impressed with Rose, and how she listened...

Reviewed By Jon S.