Let Italy Beyond the Obvious create a personalized trip to Italy that you just can’t create on your own. We’ve created more than 300 custom Italy itineraries since 2008, and no two have been exactly the same. Below we’ve outlined some of our suggestions for iconic itineraries in Italy, including Rome, Tuscany, Venice and the Amalfi Coast.

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Three great Italy itineraries:

  • Rome to Tuscany to Florence to Venice: Yes, this Italy itinerary hits the Big Three, but Rome, Florence, and Venice are famous for a reason. Fly into Rome and fly out of Venice. Take trains in between. See the Colosseum, the Vatican museums and Sistine Chapel, the Uffizi Gallery and the Ponte Vecchio. Take a cooking class in Tuscany and go for a bike ride or vespa ride in the countryside and do some wine tasting. Explore the small streets of Venice, ride a gondola, and visit the glass-blowing island of Murano.
  • Florence to Parma to the Cinque Terre: Fly into Florence and out of Pisa. See the Uffizi Gallery and David and do a city walking tour, then pick up a rental car and drive up to Modena. Test drive a Ferrari and visit the Pagani or Lamborghini factories. Go on a parmesan tour and visit castles near castles near Parma, and see how balsamic vinegar is made near Modena. Climb the Leaning Tower if Pisa, if you want. Drop off the car, and take the train to the Cinque Terre and spend a few days in these small coastal towns, hiking, exploring, and eating pesto.
  • Rome to Positano to Capri to Naples: Fly into Rome and out of Naples. Visit the Colosseum, the Vatican and Sistine Chapel, then take the train to Salerno and a taxi to Positano. Hike coastal trails, drink limoncello, enjoy the views and the towns, and then take the ferry to Capri for a few days. Head back to the mainland, stopping to visit the archaeological site of Pompeii on your way to Naples. Spend a couple days in the gritty, fantastic city of Naples. Eat pizza.
  • Other Italy itineraries: We create Italy itineraries of any length for anywhere in Italy, including Sicily, Umbria, Puglia, the Dolomites, the Veneto, Piedmont and more. Our strengths are active trips, family trips, and luxury trips.

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Colosseum Rome Italy

Photo from Wikimedia Commons

 Itineraries in Rome

  •  Rome itinerary for museum lovers: Visit the Colosseum and the Roman Forum with a private guide; visit the Vatican museums, Sistine Chapel and St Peter’s with another private guide but not on the same day. On a third day, visit the Borghese Gallery. In the afternoons, visit Castel Sant’Angelo, the Jewish Ghetto or the Catacombs, the Baths of Caracalla, the Pantheon, and the famous outdoor sights – the Trevi fountain, Piazza Navona, the Spanish steps, and the Campidoglio.
  • Rome itinerary for the museum-averse: Go to Vatican city but skip the museums. Instead, climb to the top of St Peter’s Basilica for views over the city. Book the underground Scavi tour. In the morning, head to an outdoor market like in the Campo de’ Fiori. Do a 3 hour Rome overview tour on the back of a vespa! Do a late-afternoon wine tasting or cooking course. Walk up Aventine Hill and look through the keyhole to St Peter’s. Visit the famous outdoor sights: the Trevi Fountain, the Spanish Steps, Piazza Navona, and the Campidoglio.
  • Rome itinerary for a balanced visit: Start with an introductory city tour of Rome on the back of a vespa. Do a bit of shopping, and get an introduction to Italian wines with a wonderful wine tasting. Visit the Vatican museums and Sistine Chapel with a private guide, then climb up to the dome of St Peter’s, then go have lunch nearby. Visit the Trevi Fountain, the Spanish Steps, and Piazza Navona, stopping for lots of gelato.
  • Other Rome itineraries: we create Rome itineraries for families, for foodies, or with a focus on Jewish history. We can do a “hedonistic” itinerary. Just let us know about your interests. Contact us, and let’s get started!

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Itineraries in Venice

  • A one day Venice itinerary: Visit St Mark’s Square and Basilica, climb the bell tower or campanile in the square and walk past the Bridge of Sighs. Have lunch, and continue to the Rialto Bridge. Shop for glass or masks. Walk over the famous Accademia Bridge, exploring Venice’s small streets. Take a gondola or boat ride, have a long dinner, and enjoy the quiet evening after the day trippers have left.
  • A two day Venice itinerary: Visit St Mark’s Basilica and also book a Doge’s Palace tour. Instead of climbing the campanile in St Mark’s Square, take the short public boat over to the island of San Giorgio Maggiore and climb that bell tower instead, which is much less busy and has equally stunning 360 degree views over Venice. Visit the Scuola Grande di San Rocco’ for some jaw-dropping art. Go to a Vivaldi concert held in a church in the evening after dinner.
  • A three day Venice itinerary: with your additional day, head out to visit some of the islands in the lagoon: the glass-blowing island of Murano; the colorful island of Burano; and the historic island of Torcello.

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Itineraries in Italy

Itineraries in Tuscany

  • A Chianti, Tuscany itinerary: Visit and tour wine makers and olive oil makers, take a cooking course, visit a castle, explore medieval Tuscan hill towns, go for a bike ride or a vespa ride.
  • A Val D’Orcia, Tuscany itinerary: The Val D’Orcia is a UNESCO World Heritage site and is where photographers go for iconic Tuscany landscapes. Take a sunrise hot air balloon ride over this gorgeous countryside, see fields of poppies or sunflowers, explore quintessential Tuscan towns like Montepulciano or Montalcino. Go for hikes in the hills or for a challenging bike ride. Do a city walking tour in the incredible town of Siena. Have a long Tuscan lunch or a picnic in the countryside, visit a picturesque Abbey with chanting monks, or explore some of the towns from the movie Under the Tuscan Sun.
  • A Lucca, Tuscany itinerary: go for a truffle hunt or visit a chocolate factory. Cycle on the top of Lucca’s ancient walls and try some of its famous focaccia. Hit the beach. Go see an opera by Puccini. Climb the Leaning Tower of Pisa. Ride 4x4s in the countryside, go white-water rafting or canyoning, or visit the marble quarries Michelangelo used. Have long Italian lunches, take a cooking course, and browse in local markets.
  • Other Tuscany itineraries: You name it, we create it! Stay on a farm or in a castle or in a villa. Visit gardens and have your own private chef cook at the end of the day. Set the kids up with hands-on activities like pasta making or painting ceramics while the adults do a wine tasting. Go horseback riding, hang out at the beach, or spend half days hiking or biking and afternoons by the pool. Opportunities abound in Tuscany, so let us know what interests you, and we’ll start planning!

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itineraries in the Amalfi Coast Italy hotel Caruso


Itineraries in the Amalfi Coast

  • A one day Amalfi Coast itinerary: Visit the quintessential Amalfi towns of Positano and Ravello. Shop for handmade leather sandals, drink limoncello, and enjoy jaw-dropping coastal views.
  • A two day Amalfi Coast itinerary: Walk the Path of the Gods in the morning, have a long lunch with incredible views, then explore Positano in the afternoon. Visit the towns of Amalfi and Ravello, and listen to a classical concert under the stars. Drink limoncello and enjoy the scenery.
  • A three day Amalfi Coast itinerary: Add a morning visit to the archaeological site of Pompeii and a cooking class in Sorrento.
  • A four day Amalfi Coast itinerary: Add a day on the island of Capri. Boats don’t run late enough for you to return after dinner, so stay overnight at least one night.


Do any of these itineraries in Italy, Rome, Venice, Tuscany or the Amalfi Coast sound good? Contact us, and let’s get started planning your fantastic trip!

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