Brainstorming a 2-Week Italy Itinerary: An Actual Client Email

Are you considering booking our travel planning services but are unsure of how that service translates into a full, customized Italy itinerary? Here we share with you an initial email to a client that came out of our “first step” introductory phone call/email exchange to give you an idea of how we take each client’s general (or, sometimes, very specific) ideas and aspirations and use it as a framework for creating their on-the-ground trip.

When we start working with a new client who wants to travel to Italy, we start with questions:

And so on. Once we have a good understanding of the travelers’ goals, interests, amount of time, and travel style, we start sending ideas. Based on their feedback, their Italy itinerary comes together.

To give you an idea of what that actually looks like, here’s an email we sent to a new client recently to kick off the Italy itinerary creation process. Note that this traveler was very open to all suggestions. Many new clients arrive already knowing a few places they definitely want to include in their itinerary.


I read over my notes from our phone call and reviewed what you wrote in your initial email to me, and I have some ideas I think you’ll like for your Italy itinerary.

You said 2 weeks, and that you like to have a home base and travel out for day trips. In 2 weeks, it’s completely realistic to have 2 home bases.

Since you liked the Amalfi Coast scenery but not the steepness of the towns, and since Pompeii isn’t a priority, and since you want somewhere well connected by public transportation (which the Amalfi Coast isn’t), I would consider the seaside area in and around the Cinque Terre, which is a few hours west of Florence, about 6 hours up the coast from the Amalfi Coast.

There are 2 areas specifically that I would recommend. If you like them both then there are your two weeks!

Or, you could combine a week in the Cinque Terre with another spot. This could give you a seaside-countryside option or a seaside-small town balance. Two additional places come to mind that I think you might enjoy. Both would be good as a base, and no driving needed. These are great towns for wandering and exploring, and different from the coast culturally. They’d also work well geographically. I won’t keep you guessing any longer — I’m thinking Parma and area, and the city of Venice.

Below, I’ve listed highlights of each area, with some links for you to look at and you can let me know your thoughts.

The Cinque Terre & Surroundings

The Cinque Terre (translation: Five Towns) are five fishing villages on the sea, and they are connected by mule paths that have become famous hiking trails. The names of the villages are Monterosso al Mare, Corniglia, Vernazza, Manarola and Riomaggiore. The 5 villages are connected by 4 trails, two of which are proper hiking trails and 2 of which are short and easy ambles. The villages are also connected by boats, trains, and buses. This area also came to mind when I was talking to you because you said you like small B&Bs and this area has some great ones.

In particular, I was thinking you might like this place:

Iconic photo of Vernazza
Iconic photo of Manarola

The towns are fun to explore, and there’s good food, local wine, good fish and local pesto.
It’s worth noting that this is NOT an off the beaten track area and gets very busy with travelers. However, October is one of the best times of year to go. Also, as soon as you go one town up the coast or one town down the coast, you get away from most of the travelers.

From a base in or near the Cinque Terre, I would also recommend visiting the Gulf of the Poets which is under an hour away and easy to get to by train. The towns I think you’d like – and you’d get there by train and then boat are:

Lerici, Portovenere (image), and the island of Palmaria, which is a 2-minute ferry ride from Portovenere. The island is small, and and there are walking trails, nice views, go for lunch.

Another place you might like that is easily reachable from the Cinque Terre is Carrara.

Carrara is not far — probably under an hour, and if there are cool jeep tours that take you through the marble quarries that Michelangelo used. The scenery is spectacular (photo).

Or, head north to the Portofino Peninsula.  Portofino is about 90 minutes north of the Cinque Terre, along the same coast and includes the towns of Portofino, Camogli, Rapallo, and Santa Margherita Ligure (photo). Then another 20 minutes further up the coast is the city of Genoa.

I love the fishing village of Camogli. There are some wonderful hiking trails, but even if you’re not hiking, it’s a great base.

The Portofino peninsula juts out into the sea and the whole thing is full of hiking trails (here’s a map). There are lots of great places to go for lunch and so many spots with pretty views over the Mediterranean

Getting around by train is easy, but the towns are also connected by boats (info here), although October is often when the schedules flip. But we’ll check all that for you. Seamless logistics are the secret sauce of the trip! 

I also recommend a visit to the Abbey of San Fruttuoso — it’s a tough hike or you can take a boat (photo).

And finally, the city of Genoa is a hidden gem!

Apart from the town of Portofino itself (incredibly picturesque but very chi-chi with yachts and overpriced touristy restaurants with mediocre food) this area is quite off the beaten track.

Parma & Surroundings

Parma is a gorgeous small town, very walkable, with a ton to do. Here’s why we love Parma.

Getting there: From the Cinque Terre, you could get to Parma by train in about 3 hours. 

Getting Around: It’s easy to explore this area of Italy by train.

This area of Italy is where parmesan cheese is made so if you are interested in that I definitely recommend visiting a parmesan factory. It’s also the area where prosciutto ham is from and not far from where balsamic vinegar is from. You can do food tours that include all three if you’re interested.

Worthwhile towns to visit by train that are nearby include Modena, Bologna and Mantova. I especially love Bologna, a major foodie destination and college town with great vibe.

If you are interested in Ferrari, Lamborghini, Pagani or fast cars in general, the area near Modena is referred to as Motor Valley. You can visit the museums, see the factories, test drive cars…. if you’re interested in this let me know and I’ll send recommendations.

I also really like the countryside around Parma, it’s full of great castles!
These castles are not easy to get to without a car, so I would either include them on a tour or just get a driver for a 1/2 day. Or you could do taxis as well.

Venice & Surroundings

Since you haven’t been to Venice, and since Venice is such a great city, it would work well. It’s also home to only one of 3 Italian airports that have direct flights to the US. A great option if you are interested in Venice.

You could also base yourselves in the nearby (~20 minutes by train) town of Padova, another of my favorite Italian cities.

From Padova, you could visit the city of Verona (famous for Romeo & Juliet’s balcony) by train

If you’re interested in wine, there are two amazing wine regions nearby, the Prosecco region north of Venice and the area where Amarone comes from (called the Valpolicella) which is near Verona.

But, day tripping into Venice isn’t ideal. The city really has a different atmosphere in the evenings after all the many daytrippers have left, so a week-long base in Venice would be great too.

Marjorie, I think I’ll leave it there and let you give me some feedback. Please tell me what sounds great and what doesn’t sound so great. Or let me know what you’d like more information about.

In every place, I can send you recommendations for sights, classes, tours, shopping, hikes, concerts, markets, etc.

Depending on what resonates with you (hopefully something does!), you could combine any two of the above for your Italy itinerary. You could fly into Florence or Pisa (easy from Paris) and out from Venice or Bologna.


What happens after this email? We move into step two. That means honing down the locations of your Italy itinerary so we can begin to suggest the ideal hotels, tours, activities, and other experiences. We end up with a trip perfectly tailored to you and your family or group. If you’d like more information, please contact us! We’re always happy to explain how our trip planning process and service can help you explore Italy…beyond the obvious 😉

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