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Tuscany & the Italian Riviera

Discover charming, picturesque Tuscany countryside and explore the colorful villages of Cinque Terre. Stay in a classical villa for four nights and visit breathtaking locations in Tuscany each day. Stop in the medieval hill towns of Volterra, Cortona, and San Gimignano. In Florence, the birthplace of the Renaissance, visit the Duomo and the Galleria dell’Accademia, home to Michelangelo’s David. Tour Pisa and visit its famous Leaning Tower. Traveling north to the heart of the Italian Riviera for two nights, we explore the pastel-colored fishing communities of Cinque Terre and take a pleasant boat ride to quaint Portofino, the Pearl of the Italian Riviera.

Hosted By: Tom McIntyre

Veteran Reporter


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The Holiday Advantage
Airfare Included
Airfare Included
Exceptional Accommodations Included with Baggage Handling
Exceptional Accommodations Included with Baggage Handling
Most Meals Included
Most Meals Included
Premier Attractions
Premier Attractions
Professional Tour Directors
Professional Tour Directors
Motorcoach & Professional Driver
Motorcoach & Professional Driver
Low Deposit, Guaranteed Prices, & No Hidden Costs
Low Deposit, Guaranteed Prices, & No Hidden Costs
Call to Book 1-888-867-2190

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Day 1 : Ciao Italia!

Our tour begins with an overnight flight to Italy. Anticipation builds as we fly across the ocean.

Day 2 : Arrive in Rome

Upon arrival we are greeted by our Italian guide who accompanies us throughout our tour. We then begin our journey through the famous rolling hills of Tuscany to our home for the next four nights, the delightful Hotel Casafrassi. This Neoclassical villa is nestled among a panorama of landscaped gardens, olive groves, and vineyards offering us a chance to relax in an environment surrounded by the beauty of Tuscany. All rooms overlook the Chianti hills. This evening we get to know our fellow travelers over authentic Tuscan cuisine complete with local wine.


Day 3 : Volterra & San Gimignano

Today we visit two of Italy’s best preserved medieval hill towns. Both are surrounded by fortified walls and overlook rolling farmland. Pre-dating the Roman Empire, Volterra was once an important Etruscan city. Learn about its ancient history and see the more recent 12th-century Romanesque cathedral. In the afternoon we visit San Gimignano, famous for its medieval towers once used by feuding noble families. During our free time here, roam the quaint cobblestone streets and squares that make this ancient hill town so mesmerizing. Discover the tastes of the region with an included dinner tonight.

Breakfast, Dinner

Day 4 : Florence

Today we tour Florence, birthplace of the Renaissance. Visit the Galleria dell’Accademia and view incredible works including Michelangelo’s David. Find wonder at the Duomo, the largest brick dome ever constructed, and gaze upon Ghiberti’s bronze doors of the Baptistery, often called the Gates of Paradise. Take time to visit the iconic Ponte Vecchio Bridge with its unique hanging houses and shops, or enjoy a fresh gelato. This evening offers a special treat, the winery at Castello di Verrazzano. Learn the history of Giovanni da Verrazzano, celebrated navigator. We delight in an included dinner featuring a fantastic selection of wines for our sampling pleasure

Breakfast, Dinner

Day 5 : Cortona

After a splendid breakfast, we make our way to the hilltop town of Cortona. Our Italian guide will provide a fascinating tour of the medieval architecture of the Piazza Garibaldi, the sights and shops of the Via Nazionale, and the Palazzo Casali, displaying relics from the Etruscan, Roman, and Egyptian civilizations. The afternoon is yours for individual pursuits to enjoy the Renaissance churches, olive groves, and terraces that surround us in this picture-postcard town. After an included dinner we bid farewell to our time in Tuscany.

Breakfast, Dinner

Day 6 : Pisa & Portofino Coast

Enjoy breakfast on the terrace and say arrivederci to Tuscany as we travel north to Pisa, known for its opulent churches and palaces. Our guide introduces us to the area famously called "The Field of Miracles" where we see the world-famous Leaning Tower of Pisa. We continue to our overnight accommodations along the Portofino coast.

Breakfast, Dinner

Day 7 : Cinque Terre

Today we visit the Cinque Terre, an Italian National Park and UNESCO World Heritage Site. Arrive by rail on the Cinque Terre Express for a day exploring cities on this rocky coastline on the Mediterranean Sea. The pastel colors of the buildings in the tiny fishing villages make for stunning pictures. Enjoy superb views of the distinctive terraced vineyards that produce local wine. Dry whites are the specialty here. We start in the morning at the little village of Riomaggiore, continue on to Vernazza, and end our visit in Monterosso al Mare, the village with the best beach and beautiful lemon trees. We return to our hotel for an evening at leisure.


Day 8 : Italian Riviera

A short boat ride takes us to Portofino, known as the Pearl of the Italian Riviera. This enchanting fishing village with its picturesque harbor is frequented by some of Europe’s wealthiest and most discerning pleasure seekers. This afternoon we travel to Milan for our overnight accommodations near the airport where we gather for a Holiday Vacations Farewell Dinner and toast our new friendships.

Breakfast, Dinner

Day 9 : Arrivederci, Italia

After an included breakfast, we make our way home with fond memories of our Italian adventure.


Additional Tour Information

Your Holiday Vacations Experience Includes

  • All airfare
  • All fuel surcharges, government fees, airport & departure taxes
  • Holiday Vacations Tour Director
  • Motorcoach & professional driver
  • Baggage handling at hotels
  • $100 Loyalty Credit for a future tour

All Accommodations Featuring

  • 4 nights at the Hotel Casafrassi, Castellina in Chianti, Tuscany
  • 2 nights along the Portofino Coast
  • 1 night near the Milan airport

Attractions & Highlights

  • Tuscan countryside
  • Volterra guided tour
  • San Gimignano guided tour
  • Florence guided city tour
    • The Duomo
    • Galleria dell’Accademia
    • Michelangelo’s David
  • Cortona guided tour
  • Leaning Tower of Pisa & Field of Miracles
  • Cinque Terre
  • Boat ride to & from Portofino
  • Portofino Coast

13 Excellent Meals Featuring

  • Daily European breakfasts
  • Holiday Vacations Welcome & Farewell Dinners
  • Dinner & wine tasting at Castello di Verrazzano
  • Dinner on the Portofino Coast

Tour Dates & Pricing


Price Per Person





Final Payment Date: 06/27/2023

Tour Map for Tuscany & the Italian Riviera

Departure Cities

WMBD TV Pickup Locations:

Chicago, IL - O'Hare International Airport

East Peoria, IL - Holiday Inn & Suites

Normal, IL - Sam's Club

Tom McIntyre

Tom has been a fixture on Central Illinois radio and television for half a century, beginning with WGLT-FM in Normal and continuing over the years at WIOK, WIRL, WWTO, WEEK, and now the veteran broadcaster calls WMBD-TV his media home.

An ISU graduate and navy veteran, Tom has won awards from the Associated Press, United Press International, The Illinois News Broadcasters Association, and a regional Edward R. Murrow award. He counts among his highlights a trip to Saudi Arabia with Peoria army reservists before the first Gulf War, and going to the White House to quiz Bill Clinton.

Join Tom and WMBD/WYZZ viewers on this spectacular vacation.