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Italy Travel Planning Sample Itineraries

2024 is poised to break records for crowds, particularly in the most popular destinations: Florence, Venice, Rome, the Amalfi Coast, and the Cinque Terre. Here are four sample itineraries we designed for our Bespoke Travel Planning clients in 2023 that you can model to make your Italy travel planning easier.

Iconic Florence and Rome

Florence sample itinerary
Florence reflected in the Arno river

Client brief: Busy, professional couple who wants to experience the best sites and tastes in two iconic locations. Private tours with expert guides and skip-the-line tickets, the best possible hotels within their defined budget, private drivers when transferring between cities, and some key restaurant reservations made for them. Early spring trip to avoid the massive crowds.

What we planned: This trip was scheduled for early spring to enjoy Florence and Rome without the high-season crowds. They had a private tour of Florence's historical center, a food tour, and a day in the Chianti countryside for lunch and wine tasting. To take advantage of the low season, we organized a day trip to the Cinque Terre with a private driver and a local guide to manage a light hike, lunch, and a boat ride.

Next, they traveled to Rome by private car with stops in Pienza and Montepulciano. In Rome, they enjoyed a food tour of Trastevere, private tours with skip-the-line tickets to the Colosseum and the Vatican, a free day for exploring and shopping, and dinner at a Michelin-starred restaurant.

What the clients had to say: "Loved the trip; everything went very smoothly. The guides were all warm and wonderful very knowledgeable. The Trastevere food tour was also excellent."

Emilia-Romagna and Tuscany

Client brief: A couple visiting Italy for the first time, traveling during high season, but very crowd averse and not city people. Happy to rent a car and explore rural locations. Flying in and out of Milan and wide open to our suggestions, though are very interested in Tuscany and would like one day in Florence to see Michelangelo's David.

What we planned: This ten-day trip included Emilia-Romagna and Tuscany, staying at two different agriturismi and one hotel, with day trips into smaller cities. They had private tours in Modena and Parma, a Vespa tour of Chianti with lunch, and a day trip to Florence to see David with our Florence guide, and a private driver to avoid driving and parking in the city center. The hotel in the center of Lucca allowed them to explore the streets of the medieval city on foot and ride bikes along the city walls.

What the clients had to say: "Your services relieved so much of our worries and stress. You listened to what we wanted to see and how we wanted to experience Italy and absolutely nailed our itinerary. The guide in Parma took her cues from us and adapted her pace with our interest. She also assisted us in getting tickets to a local soccer game! We loved Parma and ended up going back the next day on our own and exploring a little more."

Cilento Coast

Party at Borgo La Pietraia in Cilento
Enjoying a family dinner on the Cilento Coast

Client brief: Three very busy families coming from Denver and Boston. The grown-ups were all close friends before marriage and kids so this trip is an opportunity to reconnect and have fun together, as well as give the kids (very young to pre-teen) experiences of history and culture. They are all foodies, so amazing food and wine experiences are a top priority.

What we planned: A private driver picked up all three families at the Salerno train station for five days of planned activities with Borgo La Pietraia as the home base. They had a private tour of the temples at Paestum led by an archaeologist, a catamaran tour of the Cilento Coast, a visit to a buffalo farm to taste mozzarella and gelato, and a memorable sunset dinner at a mountaintop vineyard. On returning to Naples train station, they had a private tour of Pompeii.

What the clients had to say: "The grounds at the Borgo kept the kids entertained at the pool, exploring and chasing lizards while the adults relaxed. We appreciated that the kids could feel independent without straying far. Chef Mario had kid-friendly options for dinner every night, and my daughter still talks about his gnocchi. We had a great time exploring the surrounding area, including the beach, Paestum, vineyards, and farms. Most importantly, we ate as well as we could possibly have hoped for on an Italian vacation."

Puglia, Matera, Sicily

Locorotondo, jewel of Puglia
View of Locorotondo

Client brief: First-time Italy travelers interested in visiting Sicily to connect with family roots and Puglia for beautiful coastal scenery and relaxation. They want many restaurant reservations made for them and all airport transfers arranged via private car. Flying in and out of Rome with internal flights from Bari to Palermo and back to Rome.

What we planned: This two-week trip included two nights in Rome, starting with a private tour of the Colosseum. They transferred to Puglia by train with a hotel Monopoli as their base to explore Alberobello, Ostuni, and Polignano a Mare with our local guide. They then moved to Matera for two nights of history and culture, flew from Bari to Palermo for sightseeing, and beach time in Cefalù.

What the clients had to say: "We can’t say enough how much we enjoyed this trip. Having you help with all of the planning, transportation, suggestions, hotel, and living arrangements would’ve been near impossible if we did it on our own. So many good stories to share with friends and family, especially the people we met, the food we ate the sites we saw in the overall experience of the various regions of southern Italy and Sicily. My favorite part we agreed was “cooking with mama“. Angela was a fantastic tour guide and we love her."


Italy Travel Planning: Trip Consultation & Planning Services

Self-planners who want to tap our resources may book a Trip Consultation via Zoom. Over one hour, you can strategize your entire trip with Danielle and get access to our vetted recommendations for restaurants, sites, and small group tours.

Bespoke Trip Planning clients have their itineraries designed for them, all private tours led by our local guides, and the entire trip managed for them. We work on a fee model as opposed to participating in a commission network so that we can plan highly customized trips with your best interests in mind before anything else.


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