Recently, I was asked to design a ten-day travel itinerary in Italy for a couple who wanted to spend there their second honeymoon. At first sight, nothing could be easier. Italy is a relatively small country in terms of distances between cities, it is packed with touristic attractions, it has a perfect infrastructure, and we know it very well as it is one of our favorite countries to visit. The Italian challenge for tourists and those designing itineraries comes from combining sightseeing expeditions with authentic gourmet and relaxation experiences as if you go to Italy and do not try “la dolce far niente” you might as well stay home. So I thought I would use this itinerary as an example to also give you a glimpse of what we can do for your next holiday. I hope it will convince you to fill in the contact form to your right here.
The decision of where to holiday is a complex one and for every person, it finally amounts to an amalgam of fulfilled dreams, allocated budgets, time considerations, availability, and weather. I have explained here our process and I have also written extensively about its implications. When designing personalized itineraries I keep in mind that travel is not only about sights and checklists, but also about what one learns about oneself during the process. We all search for our better selves while traveling. We want to feel free and open in order to make new memories, experience different things, get out of the comfort zone, and enrich our lives. This is exactly what I mean when I say Dream, Book, and Travel is about making each destination unique for you. When approached by a new customer I ask the usual questions regarding time, budgets, et co, but I also try to understand what the holiday would mean for this person’s personal story, what are their expectations, how can I help them make the most powerful memories
So let’s look at the particular Italian challenge I mentioned above. A couple from the USA approached me to help plan their annual holiday. What was challenging about this itinerary were their expectations for the trip – they had a very clear and non-negotiable list of things to see – the main touristic sights in Florence, Cinque Terre, Rome, the Vatican, and the Amalfi coast. They asked for an authentic Italian experience in terms of enjoying themselves at nice restaurants, having time for gelato, and participating in a wine tasting. They wanted to walk as much as possible on foot and then be pampered for a few days on the Amalfi coast (while still seeing the sites), as this was going to be their second honeymoon.
Honestly, when I realized the importance of my task I felt overwhelmed, pretty much like a wedding planner on their first job. The biggest issue was the fact that they wanted to cover 4/5 destinations in ten days including transatlantic flights. I could not recommend renting a car and driving around, as the logistics involved would have meant spending half their time on the road, finding parking places, etc. Add to that four hotel check-in/check-out, and I could already see this couple’s memories of Italy consisting primarily of carrying luggage around.
There were two things working to my advantage: their medium range budget, which helped provide travel speed and comfort, and their flexibility in terms of the timing of the trip. Thus, I recommended the shoulder season with fewer tourists in the hope that it would result in a more authentic experience. My strategy focused on three main directions.
One, reduce traveling time to a minimum – I suggested overnight flights and took advantage of the fastest trains in Italy and only booked direct trains.
Two, include a couple of organized tours in Florence (wine tasting and a day trip to Cinque Terre that included stops at some of the best beaches in Cinque Terre), a good compromise for getting an authentic wine tasting experience without having to drive to Chianti, as well as for saving one hotel check-in/check-out.
Three, find hotels that are easily accessible, but also provide unique and memorable stay. For Florence, I recommended our favorite hotel Corte dei Medici/Solo Experience in the beautiful and lively San Lorenzo neighborhood. One can reach this hotel walking from a different direction every day, thus allowing to discover different shops and restaurants every time. It is what we did during our stay in Florence. While we sometimes recommend a stay in a convent in Rome, but this was not applicable here. Therefore, a friend recommended Hotel Centrale within walking distance of all main attractions, in a beautiful neighborhood of cobbled small streets and across the street from the best gelato shop in Rome. For the stay on the Amalfi coast, I needed a special hotel that would offer transfer from Salerno train station, a spa package, a private cruise along the Amalfi coast, and be situated in an authentic location. I finally decided for the Aquaboutique located in Vietri sul Mare, a town famous for its ceramics and fishing tradition, but not as well known as to be overcrowded. Once this part was done, adding in suggestions for walking tours as well as our favorite restaurant in Florence – the Trattoria Le Mossacce, was the easy part. I could not stop and include a few reading suggestions similar to Eat, Pray, Love in my recommendations.
The final outcome of this endeavor can be seen below. My customers additionally get a more detailed document that includes check-lists, maps, and every other piece of information they might need during their trip.
Of course, if you decide for such an itinerary you would only have time to see the main sights during a walking tour and take a few photos. To properly explore Florence or Rome with all its attractions (such as the Colosseum), three-day itineraries are usually ideal. That is why it was very important for me to make sure the hotels and restaurants were the best possible, and that there was enough time to unwind upon changing locations (like the spa treatment after the arrival on the Amalfi coast). I also put it the three days of relaxation in the middle of the trip as a buffer for end-to-end sightseeing expeditions.
In the end, my customers were extremely satisfied with this itinerary, which made me very happy. So all that is left is to dare you, my readers, to challenge me in planning your perfect holiday!