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The following trip itineraries are examples of the kinds of journeys we can create in Italy. Every trip we plan is fully customized to your travel style, pace, interests, and budget.

Whether you're dreaming of Renaissance cities, food and wine experiences, scenic coastlines, countryside escapes, luxury stays, family travel, or tracing your Italian heritage, our specialists design a personalized itinerary built around you.

Browse these ideas, or jump straight to the planning form to start designing your own Italy journey.

Sample Italy Itineraries. Find Your Inspiration.

Italy’s Greatest Hits
Venice | Florence | Rome (9 Days)

Italy’s Greatest Hits

  • Venice | Florence | Rome
  • 9 Days

This three-region Italian itinerary is a hit with first-time visitors, but these timeless cities never get old.

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Beautiful Italy
Florence | Tuscany | Rome | Amalfi Coast (12 Days)

Beautiful Italy

  • Florence | Tuscany | Rome | Amalfi Coast
  • 12 Days

Explore Florence, Rome, Tuscany, and Italy’s stunning southern coast on this moderate-paced journey.

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Romantic Towns of Italy
Cinque Terre | Florence | Tuscany (8 Days)

Romantic Towns of Italy

  • Cinque Terre | Florence | Tuscany
  • 8 Days

This week-long itinerary focuses on some of the most charming and famous towns in all of Italy.

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Northern Italy: Cities, Lakes & Mountains
Milan | Lake Maggiore | Lake Como | Lake Garda | The Dolomites | Venice (13 Days)

Northern Italy: Cities, Lakes & Mountains

  • Milan | Lake Maggiore | Lake Como | Lake Garda | The Dolomites | Venice
  • 13 Days

Experience the delights of cosmopolitan Milan and the Lakes of Northern Italy, finishing with the romantic canals of Venice.

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Heart of Tuscany
Florence | Tuscany (8 Days)

Heart of Tuscany

  • Florence | Tuscany
  • 8 Days

Popular with repeat visitors, this itinerary explores Florence and its surrounding art, culture, and wine regions.

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Italian Food & Wine Adventure
Bologna | Emilia-Romagna | Florence | Tuscany | Rome (11 Days)

Italian Food & Wine Adventure

  • Bologna | Emilia-Romagna | Florence | Tuscany | Rome
  • 11 Days

Taste your way through Italy’s culinary capitals, from Emilia-Romagna and Tuscany to Florence and Rome.

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Best of Southern Italy
Polignano a Mare | Lecce | Alberobello | Matera | Pompeii | Amalfi Coast (10 Days)

Best of Southern Italy

  • Polignano a Mare | Lecce | Alberobello | Matera | Pompeii | Amalfi Coast
  • 10 Days

Explore Italy’s deep south, from Puglia and Basilicata to the Amalfi Coast, on this off-the-beaten-path journey ideal for self-drive travel.

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Best of Sorrento & Sicily
Amalfi Coast | Siracusa | Taormina (11 Days)

Best of Sorrento & Sicily

  • Amalfi Coast | Siracusa | Taormina
  • 11 Days

Discover the coastal beauty of Sorrento and eastern Sicily on this Mediterranean escape.

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Sicily’s Highlights
Siracusa | Taormina (7 Days)

Sicily’s Highlights

  • Siracusa | Taormina
  • 7 Days

This is a great program for travelers who just have one week to discover two of Sicily’s most beautiful towns.

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All-Around Sicily
Palermo | Agrigento | Siracusa | Taormina (10 Days)

All-Around Sicily

  • Palermo | Agrigento | Siracusa | Taormina
  • 10 Days

This is a classic, moderate-paced itinerary hitting the major highlights around the island of Sicily, great for first-time visitors.

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Grand Tour of Sicily
Palermo | Marsala | Agrigento | Ragusa | Siracusa | Taormina (14 Days)

Grand Tour of Sicily

  • Palermo | Marsala | Agrigento | Ragusa | Siracusa | Taormina
  • 14 Days

This two-week adventure explores Sicily’s best hilltop villages, resort towns, and historic sites.

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Sicily & Malta
Palermo | Agrigento | Ragusa | Malta | Siracusa (11 Days)

Sicily & Malta

  • Palermo | Agrigento | Ragusa | Malta | Siracusa
  • 11 Days

Discover the cultural and historic treasures of Sicily and Malta on this enchanting Mediterranean journey.

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Where to Go in Italy Read more

Rome, though called the ‘Eternal City’, could answer to many other epithets: romantic, fashionable, opulent, pious, passionate, epicurean, aesthetic, artistic and timeless. Come to follow in the footsteps of gladiators and emperors, shop fashion houses and vintage finds, marvel at art from the masters, and live out your Roman fantasies in sun-soaked piazzas and charming trattorias.

The grandly ornate architecture and narrow canalways of the Venetian Lagoon are legendary, yet never fail to make the visitor stop in wonder. Come for water taxis and gondolas, priceless masterpieces, palaces along the Grand Canal, photography, cicchetti e vino, classical music, and romance.

The alluring city of Florence, the gateway to Tuscany, is synonymous with the Renaissance era. Come for statue-filled piazzas, world-class art museums, eye-catching architecture, culinary traditions, designer shopping, dazzling sunsets, and nearby Tuscan hills.

The Amalfi Coast, located in the region of Campania along with infamous Naples, is said to be the most breathtaking stretch of coastline the country possesses. Come to drive the spectacular coastal road between Sorrento, Positano and Amalfi, take a ferry to the islands of Capri and Ischia, hike the ‘Path of the Gods’, savor dishes rich with seafood and citrus, and step back in time at ancient Pompeii, Herculaneum and Paestum.

The hill towns of Tuscany and neighboring Umbria make an excellent area to taste adventure and freedom with a rental car. Come for wine, romance, evocative landscapes, photography, rustic cuisine, art cities like Siena and Pisa, small town charm with a medieval flair, pilgrimage stops along the Via Francigena, and even thermal baths.

The Ligurian Coast, or the Italian Riviera, offers stunning seascapes and is most known for its picture-perfect cliffside towns. Come to hike the trails between the Cinque Terre, watch the yachts in Portofino’s upscale marina, swim at sheltered pebble beaches and hidden coves, and visit other resort towns like Portovenere, Rapallo, Sestri Levante and Santa Margherita Ligure.

The north of Italy is home to the forward-thinking city of Milan and Italy’s stunning Lakes of Lombardy that sit at the base of the Alps to serve as a getaway for aristocrats and celebrities. Come to taste innovative cuisine, see modern Italian style and fashion, visit cultural centers including Brescia and Mantua, and take in the gorgeous natural backdrop of Lake Como, Lake Garda, and Lake Maggiore with their superb surrounding gardens and villas.

As the traditional foodie capital of Italy, Emilia-Romagna is positioned at the geographic and gastronomic heart of the nation. Come for the restaurants and colonnaded streets of Bologna, the parmigiano reggiano and prosciutto of Parma, the aceto balsamico of Modena, the mosaics of Ravenna, and the sweeping views from the village of San Leo.

The southern mainland regions comprising the “toe” and the “heel” of Italy’s “boot” offer some worthwhile destinations that are increasing in popularity. In Basilicata, visit the revitalized city of Matera with its Sassi cave dwellings. In Puglia, come for excellent beaches and interesting architecture including Baroque Lecce, Moorish Martina France, white-washed Ostuni, and the picturesque town of Alberobello with its unusual trulli abodes.

Italy’s northwestern Piedmont region lies on the road less traveled for most visitors, but it offers a lot in terms of history, nature and wine. Come for the stately city of Torino, the imposing mountain peaks that provide hiking and winter sports, the truffle-infused cuisine, and the acclaimed regional vineyards.

On the autonomous island of Sicily, the footprint of history is left behind in remarkable ancient monuments built to honor gods and kings, and the rich mix of past civilizations comes to bear on the present especially in exciting architecture and cuisine. Come to visit Palermo, the Cathedral of Monreale, the Aeolian islands, Taormina’s ancient theatre, the Godfather villages, Sampieri Beach, Noto Valley’s Baroque towns, the Valley of the Temples, historical Ortigia and Mount Etna.

 

Typical First-Time Itinerary for Italy Read more

Travelers visiting Italy for the first time usually request the three main art and culture powerhouses of Venice, Florence and Rome, interconnected conveniently by train. A mid-paced itinerary can fit in the highlights of these cities in around 8 days. Additionally, many clients like to add 3 or 4 nights in the Amalfi Coast if they have more time. We can also help you arrange a trip based on your special interests, such as food and wine, art and architecture, or tracing your Italian ancestry.

Where to Go in Sicily Read more

The boisterous capital of Palermo is known for its infamous city traffic, abundant street food and markets, opera and entertainment, and stunning architectural details. Come for the exquisite Byzantine mosaics of the Palatine Chapel and Monreale Cathedral, watch a show in Teatro Massimo, sample sweet cannoli and round rice balls called arancine, browse the historic bustling markets, and note the grand, elegant touches left behind by Arab and Norman rulers.

The West of Sicily is dotted with remnants of ancient cultures and home to traditional production of salt, wine and olives. Come to try sweet Marsala wine, see the salt pans and windmills of Trapani, taste the region’s spiced fish couscous, visit the fairytale hilltop castle of Erice, watch the sun set on the stunning white Scala de Turchi sea stairs, and reflect on history at scenic ancient sites like Segesta’s Greek theatre, Selinunte’s isolated ruins, and Agrigento’s impressive Valley of the Temples.

Central Sicily is one of the most unchanged regions where you can find authentic hill towns and sleepy villages sprinkled across rolling wheat fields and groves of olive and citrus. Come for the dreamy hilltop castles of Mussomeli, Caccamo, Sperlinga and Enna, explore the Madonie Mountains, discover a slice of Roman history in the preserved tile floors of Vila Romama del Casale, and shop for handmade ceramics in Caltagirone.

Sicily’s beautiful southern region is home to endless stretches of beach and idyllic pastures of grazing sheep and cattle. Foodies can come to taste special cheeses like caciocavallo and ragusano, enjoy the celebrated wines of Avola, and delight in Modica’s chocolate and Noto’s traditional breakfast of icy granita and brioche. The region’s aesthetic appeal is also huge with the beautiful Baroque towns of the Noto Valley, including RagusaModica and Noto, as well as Syracuse’s magnificent historical Greek center called Ortygia and the nearby archaeological park.

The northeast is a dynamic region providing a gateway from Italy’s mainland, and the active cities of MessinaCatania and Taormina. Come visit the historic fish market of Catania, admire the fabulous setting of Taormina’s Greco-Roman theatre, enjoy views of Mount Etna and taste wines from its volcanic soil, and join in spirited summer festivals in the cities.

The Aeolian Islands off of Sicily’s northeastern coast are a natural paradise of sparkling seas and unspoiled beaches. Come for outdoor activities and water sports, fresh local cuisine featuring capers, seafood and sweet wine, protected nature reserves, black sand beaches and a smoking volcano.

Typical First-Time Itinerary for Sicily Read more

To really do justice to the main attractions of this large island destination, it would require a good two weeks. We can help you arrange a trip based on what interests you most, whether it be history, gastronomy or even tracing your ancestry. The most requested spots in Sicily are Taormina, Mount Etna, Syracuse, Ragusa and the Baroque Valley, as well as the Valley of Temples and Trapani in the west, and the exciting capital Palermo.

What is Included? Read more

In general, our custom travel itineraries include everything needed to ensure a smooth trip. This can always be modified according to your needs and where you are in your stage of planning:

  • Hotel accommodation with breakfast daily

  • Airport transfers

  • Transfers between destinations (whether by car, van, boat, train, ferry, etc.)

  • Private or group sightseeing as requested (including entrance fees)

  • Personalized support, with contact before, during and after your trip

We are also happy to provide when requested:

  • Travel insurance

  • Assistance with Visa and ETIAS (upcoming entry requirement for Schengen countries)

Our programs do not include:

  • Optional gratuities to guides, drivers, yacht crew etc.

  • Laundry and personal items

  • Bottled beverages or alcohol, and meals where not listed

  • Hotel city tax

Start Planning Your Custom Italy Trip