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 Trip

Once you are happy with the itinerary we’ve designed for you, 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.

Jayanth V. Chicago, USA

Just got back to Chicago, after my wonderful family vacation. My overall experience has been nothing short of truly exceptional. Thank you very much in arranging for such a memorable family friendly luxury vacation and I will definitely recommend Nancy Aiello tours to all my friends planning to come to Italy.


Reemah S. New York, USA

I would be happy to put a review on TripAdvisor. Our overall experience couldn’t have been better. I would have no hesitation at all in recommending Nancy Aiello to my friends. Thank you again for a delightful experience for my family.


Hannah W. Dallas, Texas, USA

I wanted to follow up on our tours we had last week. We had an absolute wonderful experience with both of our guides. They truly made our trip to Italy wonderful. We will absolutely recommend your company to anyone traveling to Italy. We wish you were in more countries! Thanks again,

Custom Trip Planning FAQs

Is every trip customized?

Yes! Each itinerary is one-of-a-kind and takes into account your personal tastes and preferences. We consider who you’re travelling with, what you would like to see and do, what your budget is, your ideal pace of travel, and more to build your perfect trip. Your custom trip can be planned to the minute or can be more “open” with less planned activities The choice is yours based on your travel wishes.

What’s included in your trip?

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

  • Bespoke design. We personalize everything to your vision.
  • 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 where appropriate.

Note: Unlike other travel agencies, we don’t require hotels as a part of the package. Therefore, if you prefer Airbnb lodgings or using points, we’ll still help you plan the rest of your trip.

How much is the cost of a tailor-made trip to Italy?

As not two trips are alike, we are unable to provide exact costs. Typically, our custom trips start at Euro €600-€900 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.

When and how do I pay?

Once you have approved the itinerary unless otherwise specified, a deposit of 30% of the total price is required to reserve your trip. Final payment is due no later than 90 days prior to your trip start date (if your departure is within 90 days at the time of booking, full payment is required at that time), unless otherwise specified. Deposits and payments can be made by wire transfer or credit card.

Nancy Aiello's

Custom Trip Planning

Plan My Trip