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Tuscany Authentic Trip Planning

Plan your unforgettable Italy Trip with an Italian Insider

Plan your intimate, bespoke excursions and activities in Tuscany with Truly Italy

When planning for a trip to Tuscany, you want it to be easy and taken care of from the minute you decide.


Our excursion packages are for those who enjoy traveling authentically, in small groups, with real Italians. 


This is for you if:

  • You’ve never been to Tuscany. 

  • You have no expectations about your trip.

  • You are adventurous.

  • Your trip is planned 3 months out.

  • You trust that Katie will send you to authentic, intimate places.

  • You honor value, connections and culture.

  • You'd rather eat well at a family run restaurant off the beaten path.

  • You are open to Katie's suggestions.

  • You want to feel special, apart of a family.

  • You enjoy conversing with new people even in a different language. 

  • You want every excursion taken care of, you just want to show up.

  • You travel in small groups (4-6 people) and enjoy to immerse in each intimate experience with locals.

We book activities like wine-tastings, cooking classes, hiking paired with an artisan activity, private tours through the Chianti region, workshops like marble paper-making, book-making classes, and jewelry making.


Every experience is uniquely different and special. From the locals hosting you to the wine you will taste. 


Let us help you by doing all the research and supplying you with a plan that is easy to follow, already booked and paid for.


We're here to offer you the most authentic, bespoke, and intimate excursions.


Every place has a story, these excursions have been picked for you.

Fill out the questionnaire below to get started!

Do you need travel tips or some suggestions on your already planned itinerary?

We offer Travel Tip Consulting Calls for Self-Planners below.


We want to help you experience...

Authentic Italy

Custom Excursion Planning
Truly Italy Retreat Guests

Escape, Experience and Indulge in Intimate, Authentic Tuscany using Truly Italy as your personal guide!

How Custom Trip Planning works:

Easy as uno, due, tre....

Step 1: Fill out the questionnaire then you'll receive an email to book a call-30 minutes ($250).

Step 2: Are we a good fit?

This call has a non-refundable intro fee $250. The 30 minute call will include a review your excursion interests and other travel needs for your upcoming trip.


At the end of the call, if we decide to work together, the $250 will be 100% applied to the cost of your trip. 

After about 2 weeks, Katie will email you a draft of your custom excursions and costs per person (starting at $150 per person). From there, we'll work together to create your unique, authentic Tuscany Trip!

Note: Please note we do not offer a breakdown of prices on the packages.

Step 3: Book your flight and off you go to Bella Tuscany

Are you a self-planner? Then you'd like a 60 or 30 minute Trip Consulting or Travel Tip call, Book the call here

Badia a Passignano


Pay intro non-refundable fee when you book your call.


Are we a good fit?

Yes?! Let's get started!


After 2 weeks, you'll receive a draft itinerary to approve.


Once approved, pay 30% of balance.

how TO start YOUR Custom Trip planning

Custom Trip Packages

Price varies depending on: 
-How many travelers: 4-6 people 
-How many excursion days : from 1-7 days
-How much time we have for planning: 6 months before travel is recommended

  1. Booked activities like wine-tastings, cooking classes, guided hikes and bike tours in the Tuscan Hills. 

  2. Advice on Train, car rental, private driver transfers

  3. Insider Information & Tips

  4. Travel Preparation advice

  5. A Written Itinerary (pdf &/or app) with all contact information of excursions.

  6. Communication access through phone or message

  7. Support before & during 1-7 day itinerary

  8. 2 hours of face to face consultation over zoom

Trip Planning 
Pricing Includes:

Ponte Vecchio

Don't need that much support? 

Consulting calls
for Self-planners are available to book below.

Consulting Calls

Travel Tip Call

30 minutes

Wine Bottle

What's included in an Travel Tip Call? 

This 30 minute video call is for travelers with an itinerary already planned but just would like travel tips for getting around Italy. We want you to feel comfortable and ready to travel to Italy the first time. Please bring all your questions to this call so we can use our time wisely. 

Discussion topics:

  • Train travel, car rental, bus travel

  • How to purchase museum tickets on your own

  • General Travel Tips 

  • Trip Prep suggestions

  • Restaurant recommendations in and around Florence & Tuscany. 

  • Itinerary review

  • Recommendations of Tuscan Hill towns to visit

Not included:

  • Booking of excursions or tours

  • Names of tour guides, tour companies

  • Names or websites of accommodations

Please fill out the questionnaire below before your call.

After you fill out the questionnaire you'll get an email to book a call and pay.

Trip Consulting Call

60 Minutes


What's included in a Trip Consulting Call?

This 60 minute video call is for self planners, like you, who would like an accommodation and/or excursion recommendations to book on their own. This call will provide you with the contact information of the accommodation and tour to book on their own. We will share our favorite places in Tuscany to visit and experience.  

Accommodation & Excursion Recommendations: 

  • 2 accommodation recommendations for the area in Tuscany you are planning on staying. (pricing & contact information to book your stay)

  • 1 private driver recommendation

  • 1 vineyard recommendation (pricing and website included to book)

  • 1 outdoor excursion recommendation (hike, bike tour, cooking class, jewelry workshop) -pricing and website included to book.

Not included: 

  • Booking of excursions or tours

  • Booking of accommodations

  • Names of tour guides, tour companies

Please fill out the questionnaire below before your call.


After you fill out the questionnaire you'll get an email to book a call and pay.

What others are saying about Truly Italy Trip Planning...

"Katie has lived her knowledge of Italy. Her extensive travels and thorough research provides a lot of information that allow you to form an itinerary and she does it in a easy to follow fashion.  She's a wonderful listener and works with you for your unique experience.  After consultations she's provide follow up information specific to your trip.  Additionally she knows such a wide range of people in Italy that she'll assist you in getting to meet locals and smaller niche type places that are marvelous and off the beaten path.  This isn't a cookie cutter approach. It's a tailored approach.  Katie makes herself available and thoroughly follow up on any questions or needs. I believe I've saved 10-20 hours of work by utilizing her in addition to the fantastic places that she advised us to take in on our trip."


- John Livio

Buccelletti Villa

Guidelines of Custom Trip Planning

We offer customized travel to Italy for YOU! This is for you if you'd like everything taken care beforehand and would like help creating a custom, bespoke Italian vacation for you and your family. 

Contact Katie 3 months before your trip. 

Included in each Custom Excursion Planning Package is:

  • Behind the scenes research of your personal must-sees and activities to experience in & around Tuscany

  • A personalized, detailed itinerary with all your excursions.

  • Connections with Katie's personal network on the ground.
  • 2 hours of face to face consultation before your trip using zoom.

  • Personal advice and recommendations from Katie's experience of living in Italy for over 20 years.

  • Communication access through travel app before your trip and during your trip. (delayed response due to time zone).

  • Any booking requests/reservations by Katie on the behalf of the client.

  • FYI...Katie does not get commission from the vendors or experiences she recommends when you book. 

Are you ready to get started?

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