Italiaoutdoors | Italy Vacation and Travel Planner

Plan A Small Group, Family, Couple or Individual Adventure To Italy

  • Venezia

  • Trentino Alto Adige Region

  • Friuli Venezia Region

    Friuli Venezia Region

  • Tuscany Region

  • Umbria Region

Italy's 20 regions are more like 20 independent states, each with its own dialects, traditions, architecture and exceptional food. Combined with the country's incomparable artistic treasures, which amount to more than the rest of the world put together, it's hard not to fall in love with the country. What makes Italy so unique is its geography, the mountainous landscape and mild climate has created unlimited varieties of eco zones. The best way to explore Italy is by bike touring, trekking, walking, and even running. For those wanting an active vacation but do not want to ruff it in the outback Italy is the perfect destination choice.

Get Insider's Knowledge on Traveling Italy with Italiaoutdoors

Italy has historically been known as a place were you will find Paradise or Purgatory. Travel to Italy can fall into similar categories, it can be an experience of a lifetime or an expensive vacation that you just want to get over. Having lived, worked, and studied in Italy for over 25 years we have the knowledge of where to go, what to do, and how to maneuver through the labyrinth of Italian culture. This knowledge we share with you to help make your Vacation Exceptional.

Travel Planning Services

Vacation Planner and Travel Consultant Services: what you can expect

From the first contact with Italiaoutdoors and throughout the entire process you work with one person. For us to create a Custom Italy vacation we use our 20+ years to make your “custom” program fit your travel goals! We have never created the exact same itinerary twice and each phase is adjusted to fit time, goals, budget, and to help you learn new things about where you are exploring.

Some reasons a Custom Italy Vacation is the right for you

There are specific things you want to see, ride, walk, or do. Sometimes, that’s the classic vacation spots like Rome, Florence, and Venice. Other times, it’s an off the beaten track itinerary. You may know where you want to go, but not how long to spend in each place, or the best way to get from A to B. Tell us what you want to see, give us a budget if you have one, let us know how many days you have, and we’ll do the rest.

You’re just not a “tour” person.  I hear this all the time. There are lots of types of Italy tours: large bike tours, small hiking tours, private tours, small group tours with no support vehicle… the list goes on. Italiaoutdoors creates your Custom Italy Vacation, starting with your input and travel goals. There are no pre scripted templates we are trying to sell you or sub contracting programs. You can decide what you’d like to do, and what you’d like to skip, and we’ll make it happen.


You just don’t have time to create this trip. We work with lots of people who are well-traveled and have put together their own trips in the past. The amount of information online about Italy is overwhelming. You know how to research, plan, and book, but you don’t have the time to do it.

Your group or family has specific needs. Maybe you’re traveling with someone with different fitness level or skill sets and not sure how to make the trip friendly for all parties. Or maybe one of the travelers has severe food allergies or other medical considerations. Or you have a group with diverse interests that you’re not sure how to incorporate into one trip. We specialize in mixed group programs with a module system of events that you can always add on more and have some options in your day based on how you feel and what you have found new during your travel.

Creating your Custom Trip

Italy custom vacation

  • How we create your Italy Custom Vacation:
    When you hire us to create your Travel Planning, we follow an easy to follow step by step travel planning process in order to create the Italy trip that is the best fit for you and your travel companions. We have been using this process for over 20 years making adjustments based on travel restrictions or current events, and we’ve followed it over and over again to create hundreds of personalized Italy itineraries over the years.
  • The First Step is quite simple, we want to know about you and your travel thoughts.
  • We want to know how many people will be traveling, ages, interests, and anything you think we should know in order to make the best recommendations.
  • We want to know whether you have any must-visit places or experiences that you want to include on this trip. These may be as specific as “biking Passo Stelvio” or as general as “bike the wine roads and relaxing with a glass of wine, after the ride”.
  • Tell us how much time you have, and whether you have a budget (we’ll work within your budget).
  • Describe a perfect day as you envision it on this trip.
  • Let us know whether you’ve been to Italy before. (If so, when did you go and what did you see. If not, have you been abroad before).

This can be communicated though our online form, in an email to mailto:This email address is being protected from spambots. You need JavaScript enabled to view it., or schedule a time to link up with us online for a short chat.

After this information has been sent and we can speak with you directly via phone or skype, in order to get a personal feel of your travel goals and resolve any question, we can then start the planning process.  We will send you a few skeleton outlines for you to consider and once a general outline is established we will then began the Travel Contract and start organizing your Vacation. THIS IS THE MOMENT YOU OFFICIALLY HIRE US TO DESIGN YOUR VACATION WILL BE ASKED TO START THE PAYMENT SCHEDULE.  CHECK OUT OUR PAYMENT PAGE OF SPECIFICS.

FOOD AND WINE PROGRAMS IN ITALY