Custom Italy Trip Planning

Plan My trip

Describe the Trip You Want

Fill out a 2-mins form about how you like to travel, which we’ll use to plan a trip to Italy tailored exactly to what you want to do & see.

Get Matched

We pair you with your own personal Travel Designer to custom build your dream trip complete with reservations, bookings and recommendations.

Book Your Custom Italy Trip

Once you are happy with the tailor made itinerary, it’s time to book your trip. You hop on a plane, we take care of the rest.

Getting to Know You

The first and most important step is to learn about you and what you’re looking for in this trip.

We may be travel experts but before offering personalized insights, we’ll learn about your interests, priorities, and travel style.

Designing Your Custom Itinerary

Our collaborative travel design process begins with an initial consultation, which your own personal Travel Designer will use to plan your dream trip exactly how you want it.

Then we begin designing your private trip taking both your stated preferences and our first-hand destination expertise into account.

We Customize Everything to Your Vision

Together, we’ll refine your itinerary until is just right. Your entire trip from the destinations to accommodations, immersive experiences and transport choices is designed just for you.

Unlike other travel agents, we don’t require hotels as a part of the package. Already have a place to stay? Using points? Prefer Airbnb? Fine - we’ll still help you plan the rest of your trip.

Book Your Custom Trip

As soon as you’ve approved the itinerary we’ve designed for you, it’s time to book your trip and begin preparing for your Italian adventure.

We’ll handle the behind-the-scenes process of meticulously coordinating all the details of your trip, so you can just relax, and begin living the dream.

Private Tuscany Wine Tour from Florence to Chianti

This was one of the absolute best parts of our honeymoon. We had a very nice and informative driver guide who took us to the town of Greve, and showed us the different wines, cheese and salami in one of the local stores. He gave us background information on all of the wines there, explaining the different grades of Chianti. Then, he took us to a very young, up and coming winery where the owner showed us a lot about the process and getting a winery started in today's market in the Chianti region. Then, we went to an amazing restaurant in the middle of the most gorgeous scenery that we had ever laid eyes on. Afterwards we went to an older, family-owned winery. Seeing such a wide range of the business and talking to the owners was unforgettable. We learned a ton. He even pulled over so we could take some very memorable pictures of the incredible scenery. It was a perfect trip. I know my husband and I will always have a special place in our hearts for Chianti, and we always look for the rooster label! Kathy & Aaron M. Tampa US


Custom Italy Family Vacation

My family and I have been on many tours, worldwide. I must say Enrico put together one of the best experiences I’ve ever had, bar none. We loved all of our hotels and the trip was SO great. Each stop was met with well-versed professionals who never missed a beat. Each excursion was well planned and customized to our specifications. Thanks for everything Nancy Aiello Tours! Rebecca M Chicago, IL


Custom Trip to Southern Italy

Dear Stefania, I just wanted you to know how wonderful our trip to Southern Italy was and cannot thank you enough for all the hard work you did to make this trip truly a “once in a lifetime experience.” The hotels were exquisite, the service was impeccable, and the guides and drivers were amazing. We truly enjoyed the culture, people, and of course the food and wine to its fullest. We would love to plan our next trip to Italy as soon as things calm down in our life. Again, thank you and your team so much for everything you did for us make this trip happen. Emma A Delray USA

Custom Trip Planning FAQs

How much does the custom Italy trip planning service cost?

There is no cost to this custom Italy trip planning service, except for last minute requests. For custom itinerary requests placed twelve (12) weeks or less from the arrival date, a non-refundable planning deposit is required. The amount varies depending on various factors (such as trip length, itinerary intricacy, etc.) and is fully applied towards the final trip cost.

What’s included in the trip?

Each Italy trip we design is unique, but our custom trips typically include all of the following travel services:

  • Bespoke design. We plan your trip around your vision, not around an off-the-shelf tour.
  • Accommodations in boutique and luxury properties. We make insightful recommendations based on your taste and priorities.
  • Fun & immersive private tours & experiences with local experts, curated around your interests along with as much free time as you’d like.
  • Expertly planned logistics & in country transport - via first-class train and private vehicle with driver where appropriate.

Note: Unlike traditional travel agencies, it is not mandatory to book the hotel through us. Therefore, if you prefer Airbnb lodgings or using points, we’ll still help you plan and book the rest of your trip.

How much is the cost of a custom Italy trip?

As not two trips are alike, we are unable to provide exact costs. Typically, our custom trips start at Euro €600 per person per day and up (based on a 2-person trip). The cost includes:

  • All your accommodations.
  • Seamless in country transport logistics in line with your preferences.
  • Private local guides, fun activities and experiences.
  • Plus, all the other essential details involved in expertly coordinating a perfect trip.

Note: Flights and travel insurance are not included.

Obviously, the final price of your trip can change based on the itinerary itself, and all that is included, along with factors such as your travel days and dates (for example, during peak seasons pricing may be higher), and the number of travelers in your party.

Why should I use a travel agent to plan my trip to Italy?

Glad you asked! There are a few great perks to working with us, if we do say so ourselves.

  1. We are absolute experts in Italy travel. We’ve been in the business for over 13 years, and we can be the insider connection to the people, places and things that make this destination come alive.
  2. At Nancy Aiello Tours, we live, breathe and sleep Italy the country we proudly call home. When you work with us, the firsthand knowledge of our entire Italian team is at your fingertips. Instead of spending hours sifting through conflicting information online, you can simply receive personalized trip recommendations from your own travel expert.
  3. We find that travel to Italy is a bit more complicated to book online than many people realize, especially when visiting multiple destinations. There is so much to see and do here that travel planning can be overwhelming and time-consuming. With Nancy Aiello Tours, there are no such complications, and you won’t have to visit 50+ websites to book everything individually. Consider us your one-stop shop for seamless land transfers, accommodations, and touring.
  4. Whatever your motive in visiting Italy, whether you are traveling as a family with kids or looking for the perfect holiday to celebrate an occasion in style, we consult, guide, create and deliver a seamless trip.
  5. Having been in the business so long, we have an outstanding network of partners that goes above and beyond to take care of our clients.
  6. We eliminate the hassle of travel and leave you with the fun parts! You’ll receive a personalized final itinerary for your trip, and all you have to do is show up at the place and time listed.

Nancy Aiello's

Custom Italy Trip Planning

Plan My Trip