Italy Connect Overview 2019-05-04T13:59:39-04:00

italy connect

Italy Connect is for solo travelers who want to experience the real Italy with others! This isn’t your typical Italy vacation package—instead it’s an experience that incorporates structure, personal time, spontaneity, and a shared experience with a diverse group. You won’t have to plan or book a thing. That’s right, leave worries behind and simply soak up each experience!

Culinary greatness, Michelangelo masterpieces, epic views, Tuscany, Umbria, local wine and everything Italian culture. More than a holiday, this is an opportunity to explore Italy up close and personal. Pack your bags for a trip of a lifetime!

Who is Italy Connect for?

  • Anyone, from anywhere, over the age of 21

  • Travelers who embrace inclusiveness and diversity

  • Those who have the ability to be easy-going and flexible and—most of all—understand that travel can be unpredictable (e.g. the weather)

  • Positive, independent, solution-oriented people with the willingness to offer their wisdom and skills for greater group enhancement

  • Ability to carry one’s own luggage—potentially up/down stairs

  • Any diet – we are mindful of vegetarian, vegan, halal, and other dietary needs

  • Participants must have the ability to walk up to 5 miles throughout a day on varied terrain

  • Travelers who speak English (other language skills are a bonus!)

Onsite Concierge and Cultural Expert for Italy Connect

Each trip is led by an experienced guide. She will lead all group excursions and serve as your concierge for solo adventures. We also partner with local businesses/experts for certain aspects of Connect trips–see individual itineraries for more information.

I loved traveling to Italy with Julie [guide]! She had great things planned but also left plenty of time to be flexible and to relax. I can’t wait to travel with her again! – Andrea (Traveled through Umbria/Tuscany, Rome, and the Amalfi Coast of Italy)

I appreciated our guide’s knowledge and calm and confident demeanor. – Jane (Greece Connect Traveler 2017)

2019 Itinerary


Italy Connect 2019 will start in Milan and end in Rome.

  • All accommodations are 4+ stars with no single supplement

  • Safety and security are a priority for all trips

  • Maximum group size: 12 people

  • Ages: Over 21

  • Must be able to handle your luggage up/down stairs and on uneven ground

Daily Itinerary

The following is the itinerary for Italy Connect – June 6-16, 2019:

Meals: Dinner

Italy Connect will begin in Milan, Italy. It is recommended that you fly into Milan and out of Rome.

Upon arrival in Milan, you’ll be driven to the hotel to get settled in and put your feet up or go for a stroll in the center of Milan. The group will meet in the hotel lobby at 6:00 p.m. to go to our welcome dinner and start getting to know one another. A local culinary expert will join us to talk about the history of Italian food and orient us to the tastes we’ll experience throughout Italy Connect.

+ Arrive to Milan no later than 3:30 p.m. (Italy Time)

+ Airport or train station pick-up times will be communicated to you after you send your travel information

At the welcome dinner, we’ll review the itinerary and you’ll receive a packet of information.

Meals: Breakfast, Lunch, Dinner

All aboard! After a morning in Milan, we’ll hop on a train and head to La Spezia – our gateway to Cinque Terre.

Cinque Terre, a natural wonder, is a UNESCO World Heritage site on Italy’s West coast. It is comprised of five villages that you’ll have the choice of getting to via train or on foot. You’ll be provided with a 2-day Cinque Terre Card that gives you unlimited train access and entry to the walking trails – you’ll have flexibility to go with the group or explore on your own today and Saturday.

Meals: Breakfastitaly connect

Spend the day exploring the villages and beaches of Cinque Terre. Get to know one or two villages, or hike or train to all five! The day is yours to go out on your own or with your host.

Meals: Breakfast, Lunch, Dinner

We’ll leave La Spezia today for Florence, but not without a stop in Pisa to see that leaning tower! After some sight seeing and lunch in Pisa, we’ll head to the home of Renaissance art and architecture. Soaking in our surroundings in the center of Florence, we’ll enjoy a dinner with a view and you’ll receive maps and information for exploring the city on Monday.

Meals: Breakfast

This is your day to experience Florence, the capital of Italy’s Tuscany region. Stand in the presence of some of the world’s masterpieces by Michelangelo and more. Bask in the grandeur of cathedrals. And be sure to sample the culinary delights along the way. You will have the option to explore on your own or go with a guided tour.

italy connectMeals: Breakfast, Lunch, Dinner

We’ll leave Florence today with a private driver and explore the Tuscany and Umbria countryside and hill towns. There will be no shortage of breathtaking views of vineyards, rolling hills, and Italian architecture. We’ll go off the beaten path and experience what “typical tours” skip over. You’ll get to see, touch and feel the real Italy!

In the evening, we’ll arrive at our accommodations in Umbria and get settled in for the next three nights.

italy connectMeals: Breakfast, Dinner

Pictures cannot describe the majesty and mystery of Civita. This hill town, built 2,500 years old, is often referred to as a “ghost village”. The only way to get to it is by walking up a footbridge, from the village of Bagnoregio, that makes you feel like you’re floating in a fairy tale. We’ll spend time wandering through the small town with only about 10 year-round residents! You’ll also have an opportunity to walk around Bagnoregio for shopping and photo-opps.

italy connectMeals: Breakfast, Dinner

Spend the morning relaxing poolside or going for a hike. And we’ll visit the picturesque hill town of Orvieto in the afternoon. Take in the sights, shop, eat Gelato…or simply stroll through the narrow streets and take it all in. In the evening, we’ll meet up for a candlelit Italian feast.

italy connectMeals: Breakfast, Lunch

Today we head to the ancient city of Rome. We’ll visit some famous spots as a group and get you oriented to the city. You’ll receive a Roma Pass that will give you access to public transportation, a couple entry passes, and more.

italy connectMeals: Breakfast, Dinner

Today is your day to explore Rome and Vatican City on your own or go on a guided tour – options will be presented.

We’ll all meet up in the evening for a farewell dinner.

Meals: Breakfast

You will be responsible to get yourself to the Rome airport for departure. Once Creative Travel Connections has your flight information we’ll recommend the best options for ground transportation and will help you get to it on Sunday.



USD $3,195 per person 

Deposit: $500 is due upon registration to save your spot

Registration Deadline: January 31, 2019

Trip balance is due 45 days prior to departure.

The fee is inclusive of single accommodation (non-smoking), ground and sea transportation, admission tickets, meals as noted on the itinerary, and gratuities.

  1. Participants are responsible for their own airfare to Milan and from Rome. And ground transportation to the Rome airport upon departure. (For an additional $50 fee, Creative Travel Connections will find airfare for you based on your budget and needs.)
  2. This trip requires a minimum of 8 participants (max 12).
  3. Participants are required to purchase individual travel insurance. (recommendations available upon request)

I traveled with Creative Travel Connections and would do it all over again! Every single aspect of the trip was top notch. That’s the highest recommendation I could give. – Jane (Greece Connect Traveler, July 2017)

Fees and Cancelation Policy

The fee is inclusive of accommodations, ground and sea transportation, admission tickets, meals as noted on the itinerary, and gratuities.

  1. A $500 USD non-refundable deposit is due upon registration.
  2. Full payment is required 45 days before the trip.
  3. Cancelations up to 45 days before the trip are subject to a 5% administrative fee based on the full registration cost. 20-45 days before the trip: 15% administrative fee. 0-20 days before the trip: 25% administrative fee. The $500 deposit is non-refundable.
  4. Participants are responsible for their own airfare to/from Italy and ground transportation to the airport upon departure.
  5. Participants are required to purchase individual travel insurance. (recommendations available upon request)

Other Important Information

  • Traveler’s passport must be valid for at least 6 months after date of travel in order to board flights.

  • You will be sent a packing list, optional pre-trip reading, and any other relevant information upon deposit. Really…you just need to pack and get on the airplane with your passport!

  • Travelers will meet each other virtually before the trip.

  • Questions are welcome.

If you’re looking for a customized trip for a group or family, please contact us.