Discover Italy with Brett Winterble

Growing up and learning about my family, I heard all the tales about my ancestors and I was always fascinated with my familial roots in Italy. My grandfather’s family was from the north and my grandmother’s family was from the south – they spanned the country, with Sicily included. I’ve always wanted to go to Italy and I almost went, a bunch of times…

In the 1990s I had the chance to live in Europe for 6 months. I saw Berlin, Munich, Brussels, Amsterdam, and even Budapest and Vienna. But I never got to Italy and I have regretted it ever since. I know I know, it’s crazy right!?! I could have hopped on the Eurail, but I never did it, I just ran out of time. Well, guess what – I am resetting the clock! Next summer ‘WE’ are going to Italy! That’s right, I said ‘WE.’ I want you to join me and my wife Sherri on this very special trip.

If you have never been to Italy, this is the itinerary for you. We will tour, we will eat and drink, be merry and learn, learn, learn! We will come back saying ‘Io amo l’Italia’ (‘I love Italy’)! So I want to invite you to go – so that you have no regrets! Let’s do this together and build memories for a lifetime!

Brett Winterble

Per Person Double Occupancy
Single Supplement Available

June 21-30, 2023

10 Days / 9 Nights


Wednesday, June 21, 2023

Depart USA
Relax on your overnight flight to Rome.

Thursday, June 22, 2023

Arrive Rome
Welcome to Italy, a country steeped in culture, history, iconic vistas and incredible food. Settle into your city center Rome hotel, just steps away from the Colosseum and Roman Forum. Tonight, get to know Brett and your fellow WBT travelers over a welcome dinner featuring local specialties. (D)

Friday, June 23, 2023

This morning after breakfast, discover the Vatican Museums on a guided tour. Then take in Michelangelo’s masterpiece frescoed ceiling in the Sistine Chapel. Finish your morning strolling through the towering columns of St. Peter’s Basilica to take in Bernini’s altar canopy. Later today, see the Colosseum, Circus Maximus and more on a panoramic drive through Rome. (B)

Saturday, June 24, 2023

Today, journey through the Italian countryside to the Umbrian capital of Perugia. En route we’ll stop in Assisi, the birthplace of St. Francis, for a walking tour. Here we will discover the Basilica of St. Francis, consecrated in 1253. This afternoon in Perugia, enjoy free time to discover the medieval city center. (B)

Sunday, June 25, 2023

A drive through the rolling hills of Tuscany today brings us to the hilltop town of Cortona, the idyllic setting for the movie Under the Tuscan Sun. Later today we’ll visit the Academy Gallery in Florence to see Michelangelo’s David. (B)

Monday, June 26, 2023

This morning after breakfast, take a walking tour to see Florence’s iconic Duomo, the Palazzo Vecchio and the Piazza della Signoria. Your afternoon is free to explore the city center on your own, sit down for a delicious lunch and do some shopping. Tonight we’ll venture off the beaten path to nearby Galluzzo for an evening of local wines, Tuscan food and entertainment. It’s an authentic family-style Italian feast that will leave you smiling for days! (B, D)

Tuesday, June 27, 2023

Today is your chance to tie on the apron and try your hand at cooking some Tuscan delicacies (over a glass of Tuscan wine of course) during a chef-led cooking class. After a delicious lunch we’ll journey across central Italy to the shallow lagoon in the northeast of Italy that is Venice. (B, L, D)

Wednesday, June 28, 2023

Venice–Murano Island
After breakfast, we’ll board a boat for Murano Island, affording magnificent views along the way. A glass blowing demonstration will uncover the mysteries of this ancient art. Later today we’ll learn about the historic center of Venice, seeing the Castello district, St. Mark’s Square and the Venetian Gothic Doge’s Palace. Then partake in one of Venice’s famous pastimes, a romantic gondola cruise. Enjoy! (B)

Thursday, June 29, 2023

Today we’ll make our way to Milan, the final stop on this unforgettable journey. And again, it’s up to you on how you want to see Italy’s most modern metropolis. Take a walking tour to visit the Duomo (Europe’s third largest) and Scala Opera House. Or tour Milan’s high-fashion district, Quadrilatero della moda, with a local guide. Finish the day over Italian wines and dinner as you say goodbye to Brett and new found friends. (B, D)

Friday, June 30, 2023

Fly Home



  • Economy class international airfare from Charlotte*
  • 13 meals (8 breakfasts, 1 lunch, 4 dinners)
  • All ground transportation in Italy
  • Expert local guides in Italy
  • Gratuities for guides & driver
  • Custom luggage handling
  • All taxes & fees as of 9/10/22
  • Complete services of Cruise & Tour including vacation host in Italy
  • Brett Winterble Exclusives

Brett Winterble Exclusives:

  • Get to Know Brett Winterble Over Drinks and a Q&A
  • WBT Welcome Session
  • Tuscan Feast in Florence
  • Gondola Ride in Venice
  • Travel Gift Set

*Other gateways may be available upon request. Additional charges may apply.

Not Included

  • Travel insurance
  • Business class air upgrade
  • Airline baggage fees
  • Items of a personal nature
  • Increases in taxes, fees or surcharges after 9/10/22

Currently, Italy does not require COVID-19 vaccination or testing to enter the country. However, if rules change, please be advised that all guests may be required to provide a negative COVID-19 test result and/or proof of full COVID-19 vaccination. Specific requirements will vary by destination governing bodies and travel vendor/operator and are subject to change at any time. Masks may be required to be worn during portions of your trip and specific requirements will vary by destination governing bodies and travel vendor/operator. Any costs associated with these requirements shall be at the travelers’ expense. This shall not release the passenger from the cancellation policy stated above or be grounds for adjustment of the price of the travel arrangements reserved.


The essence of a company is what they are, not just in the good times, but in the tough times. You all have come through with flying colors and are the model of how it "should" work. Yes, we have been on multiple wonderful trips with Cruise & Tour, but your customer care is what has just separated you from all others. We sadly had 3 international trips (with other companies) canceled in March of 2020 and are still wading through endless bureaucracy to get reimbursed; Cruise & Tour just displayed a WHOLE different and critical side of travel. No one EVER has said, "I hope my wonderful planned trip is canceled", but when it does, hopefully they have chosen Cruise & Tour! An ecstatic customer! :)
- Valori
From the communications that were emailed, to the availability of people when you had questions and all the sign holding people at the airport, Cruise & Tour took care of every detail. We didn't have to think about anything except having a good time and relaxing.
- Jeanine Bobber


Double Occupancy (Per Person)
Single Supplement
Business Class Air Upgrade
Call for Availability**
Travel Insurance
Quote Will Be Provided

*Limited Single Availability
**Business Class Air Subject to Availability at Time of Reservation

$1000 per person deposit required with your reservation
$2000 per person second deposit due 11/23/22
Final payment due 2/21/23

Initial $1000 deposit refundable through 11/23/22, less a $500 cancellation fee
11/24/22 to 2/21/23: Cancellation charge is 50% of deposits paid
After 2/21/23 or non-appearance on departure day: 100% of cost forfeited

Call 800-383-3131 to Reserve Your Spot Today!

How to Book

  1. Call Cruise & Tour at (800) 383-3131 or REQUEST A CALL
  2. Ask to have a place held on this trip
  3. You will receive an email with a link to our online registration form

Fill it out and you’re in!

It’s that easy. Give us a call today!

Travel Insurance Information

Travel Insured International
Worldwide Trip Protector

Cruise & Tour recommends that you purchase travel insurance.

To purchase travel protection insurance:

  1. Click here to view and print the Travel Insured International brochure which has a brief summary of coverage.
  2. After making your travel reservation and deposit, a Cruise & Tour representative will create an insurance quote for you. You will receive that travel insurance quote from Travel Insured International Customer Care.
  3. From here you will be able to view the quote, add additional coverage options such as Cancel for Any Reason, and purchase your policy all in the Travel Insured International Portal.

Please Note: Pre-Existing Condition Exclusion will be waived if you purchase the protection plan within 21 days of the date of your initial trip payment. Options such as Cancel for Any Reason or Interrupt for Any Reason must also be purchased within 21 days of the date of your initial trip payment.

To view and print the Explanation of Benefits, click here.

Covered events for trip
Sickness, Accidental Injury or Death of You, Your Travel Companion, Family Member, or Business Partner Job Loss or Lay Off Traffic Accident en Route to Departure Weather Natural Disaster at Destination Extension of School Year Terrorist Attack Revoked Military Leave Strike Bankruptcy of Travel Supplier Being Hijacked, Quarantined, Subpoenaed, or Asked to Serve on Jury Duty
* See Travel Insured International Description of Coverage for complete coverage details.