Custom Italy Trip Planning

Plan My trip

Do IT Uniquely!

At Nancy Aiello Tours we custom-design private Italy trips around you backed by our first-hand experience & knowledge.

Get Matched

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

Custom Trip to Italy 2024

Dear Stefania, Our time in Italy was fascinating with your help. We had a great time and were able to enjoy all Italy had to offer with the easy navigation. We are truly spoiled with all the service we had from the tours and drivers you arranged. The chef in Tuscany was so inviting and took such good care of us... We had a great day learning so much, not just about cooking but about the area, the farming and the Italian lifestyle. The boys were just thrilled with the experience. Rome was fascinating with all the history and we absolutely loved the hotel and the rooftop patio. The tours in Rome were so helpful to teach us the history. The travel to Positano was easy as the driver had all the work to do while we enjoyed the views and became familiar with the area. We had great weather and enjoyed the beach, hiking and shopping while we explored the area. Thank you for planning such a great trip. We very much enjoyed our time in Italy and cannot wait to go back. Sincerely, Bob and Evelyn V. Columbus, OH


Custom Trip to Italy 2024

We've returned, Enrico, and before I get mired in several hundred emails in my inbox, I want to offer my compliments and thanks for what you arranged for us. Castello di Casole was simply lovely -- such a peaceful, relaxing, comfortable place in a delightful setting. The Maalot was a magnificent place. We thought it was perfectly located as well. The staff was friendly and helpful. So thanks for your arrangements and assistance with our questions and preferences. All in all, we view this as having been a really wonderful vacation. Ray C. Arlington, VA


Custom Family Trip to Italy 2023

Buongiorno Enrico, We are now back in Boston recovering from a fabulous trip. I thank you very much for your excellent choices of hotels and sights to visit. Rome: The Golf cart tour was a very big success and given how tired the children were from their day of flying it was a perfect way to spend their first evening. Hotel: This was my favorite. The location and ambience were exactly what I had hoped for. Vatican tour: This was exceptional and our guide for this also joined us the next day for the ruins. Florence: Our day in Tuscany was wonderful. Our driver made arrangements for us to have a lunch at a local winery and it was delightful. This children loved the view and the lunch. Cooking class: The chef was so good with the children. Lou and I watched, this was our choice, we wanted to watch the children cook. We stayed quite late because our host was so interesting and did not rush us at all. The Academia and Pisa were both successful and enjoyed. Venice: Although you could not order us perfect weather. Venice gave us the relief from the heat and we had a very successful walking tour. The hotel was very nice and the location was so easy to locate and enjoyable with the view of the water. It is my hope that we will be able to use your skills again. You were so easy to work with and made this trip stress free for us. Spero che Stephanie continui a sentirsi meglio. Augurandoti una sana e felice estate. Our very best to you and your family, Lou and Dianne B. Boston MA

Custom Trip Planning FAQs

How much does it cost to plan a trip?

At Nancy Aiello Tours we charge planning fees for our services that are quoted based on the length of the trip, number of people traveling, and overall intricacy of your vacation. Trip requests with less than 90 days’ notice from the trip dates will be considered last-minute and additional design fees will apply to cover the additional time and resources required to navigate the challenges of making last-minute reservations.

How do you select hotels for me?

Over the last 15 years, we developed an amazing list of tried and tested hotels that satisfies our stringent requisites for high quality service, style, location and facilities. We only work with 4-and 5-star hotels we have personally approved and think you will love. During the trip planning process your Travel Advisor will make insightful recommendations based on your travel style and present lodging options for you to consider.

How much is the cost of a custom Italy trip?

At Nancy Aiello Tours we create holistic custom traveling plans that start at Euro €900 per person per day and up (based on a 2-person trip). Each Italy trip we design is unique, but the cost of our bespoke trips typically include all of the following travel services:

  • Detailed, comprehensive, and specialized itineraries 100% customized to your interests and schedule
  • Firsthand, sophisticated destination knowledge and recommendations from your Italian Travel Advisor
  • Stays at 4-star and up vetted hotels selected based on your taste and priorities
  • Fun & immersive private touring with your own personal local guides and drivers
  • Unique, insider travel experiences and access to our local network of experts
  • All the other essential details involved in expertly coordinating a seamless travel experience, including all logistics, skipping lines during touring whenever possible, private airport transfers, and in country transportation
  • Personalized support before and during your trip

As not two trips are alike, we are unable to provide exact costs. Fill in the tailor made Italy trip request and get your custom quote. Cost depends on your needs and the travel duration.


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

Some people enjoy the inspirational part of travel, doing destination research, planning trip logistics and making reservations. But sometimes it can be overwhelming and time-consuming, especially if something goes wrong, or not as it should have. At Nancy Aiello Tours we incorporate your travel style, needs and desires into a custom travel plan that maximize your time and minimizes your hassle. Here are a few great perks to working with us.

  1. We are absolute experts in Italy travel. We’ve been in the business for over 15 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 a real headache. 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 local 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