Episode #088: The Grand Tour

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Listen to “Trip report: The Grand Tour” on Spreaker.


The Grand Tour of Italy is a tradition that dates back hundreds of years to the 17th century when well-to-do English gentlemen and later American men and women would travel to Europe as a rite of passage on becoming an adult.  As steam trains arrived in Europe in the 19th century, this opportunity opened up to the middle classes and later Thomas Cook took the concept and converted it into some of the world’s first tour packages which many tour companies like Trafalgar, Perillo, and others copy to this day, with many people starting their adventures in Italy on a tour like this – a modern-day version of the Grand Tour. While our guest’s trips took them to France and Greece, they would spend most of their time exploring Italy – in particular Rome, Florence, and Venice.

Show notes
We talk to Kathleen Guglielmo, who, along with her cousins did her own Grand Tour of Italy – 18 days traveling around the country on a tour with a private driver, with all accommodation, lunches, and excursions included – organized by friends of Untold Italy – Joe Banana Limos & Travel. We learn about the many advantages of traveling this way through cities, to the coast, and the Tuscan countryside. 

What you’ll learn in this episode

  1. A custom pre-designed tour is a wonderfully relaxing way to travel. A trip can be designed around your own personal interests and in terms of locations, tours and excursions. With almost every aspect taken care of, you are left to sit back and enjoy. 
  2. A private tour might not be for everyone, but there are also companies that do similar tours for groups, such as Central Holidays, Gate One Trave, Collette Tours, and Perillo tours. Check out our recommendations for the best tour companies and what style of traveler they are best for in Best Italy Tours
  3. A boat tour in Venice is a great idea and often a lot easier than taking the Vaporetto, which can get very busy and with schedules and routes being a little confusing.  A private boat tour means you can just sit back in the boat, enjoy the scenery, listen and learn
  4. The dinner at the Tuscan Hotel Borgo di Cortefreda hotel includes the option for wine tastings as well as, rather wonderfully – olive oil tastings
  5. Pienza and Lucca are both Tuscan walled hilltop towns that are full of character and history
  6. Having a driver who speaks English, and of course, is fluent in Italian, can open a lot of doors on your journies. Opportunities to go to places that are off the beaten path where less English is spoken and knowing the tips and tricks for maneuvering the cities
  7. A private boat tour is a fantastic way to explore the island of Capri. The Blue Grotto is famous, but also gets very busy – a private tour can take you to the lesser-known but equally as magical green and white grottos
  8. Including food experiences in your trip can lead to some unique adventures – Kathleen visited a mozzarella farm and olive mill, as well as learning (or being reminded of) how to prepare a real pizza – with all the most amazing local ingredients
  9. Of course, Italy makes the best pizza and Naples then lays claim to making the best pizza in Italy. Kathleen did a tour and enjoyed pizza with one of our favorite podcast guests and pizza expert Pierpaolo of Joe Banana Limos. Pierpaolo is a massive foodie as you can hear in his drool-inducing episode all about pizza from Naples: Episode 73: Pizza from Naples – The Full Story. He’s also shared with us list of the best pizza in Naples – collated from years of painstaking research! 
  10. It’s well worth taking tours of places like the Vatican and Roman Forum. Going alone can actually be quite hard work – when things aren’t well marked or you have no idea of the significance of many things. A guide can really help you understand the stories and history behind the pieces
  11. Trastevere is a trendy and vibrant neighborhood in Rome with many divine restaurants
  12. Having a driver to take you from A to B across the country is obviously a relaxing experience and being able to stop off at various locations along the way is a clear bonus – but also having a driver available in a city can be a real winner – someone to pick you up from a long day touring and walking – when your feet have given up!
  13. Traveling with a driver can be an advantage if you have mobility problems or if you are in family groups, of say older parents, and younger children

About our guest – Kathleen Guglielmo

A lifetime New York resident, Kathleen is a citizen of both the United States and Italy.  Kathleen’s career was in finance and human resources. She recently retired as Director of Finance for an architectural firm in New York after 19 years to spend more time with her children and 4 grandsons.

Kathleen has strong ties to Italy, and received the community leadership award from the Andrettesse Club in New York.  They represent her grandparent’s home town of Andretta in Campania. 

Kathleen served on the Board of the National Organization of Italian American Women (NOIAW) since 2005, and was President for New York from 2010 to 2013.  She was part of Italy’s cultural exchange program with NOIAW for many years, housing and accompanying young Italian women selected by the Italian Ministry to participate in the program.

You can find Kathleen on these channels:

The private, custom tour that Kathleen and her cousins enjoyed was created by Joe Banana Limo & Travels, run by brothers Giovanni and Pierpaolo. 

You can find Joe Banana on these channels:

Places mentioned in the show

  • Montebello Splendid Hotel – a hotel set in a 19th-century villa in Florence
  • Academia – gallery in Florence, home to Michelangelo’s David
  • Piazza Santa Croce – square in Florence taking its name from the Basilica of Santa Croce that overlooks the square
  • Ponte Vecchio – famous bridge in Florence with jewelry stores above it
  • Uffizi gallery – art museum adjacent to the Piazza della Signoria
  • Lucca – town in Tuscany
  • Forte dei Marmi – elegant beach town in Tuscany with a beautiful pontile 
  • Lido di Camaiore – Tuscan beach town 
  • Monaco and Grand Canal Hotel – hotel in Venice with gorgeous views over St Mark’s Square with an outdoor restaurant overlooking the canal
  • Doges Palace – in Venice, formerly the seat of Venetian government and a masterpiece of Gothic architecture
  • Rialto Bridge – Venice’s most famous bridge
  • Burano – an island on the Venetian lagoon known for its colorful buildings
  • Murano – the second largest island in the Venetian Lagoon famous for its glass making
  • Val d’Orcia – region in Tuscany
  • Hotel Borgo di Cortefreda – hotel in the Val d’Orcia countryside 
  • Montepulciano and Montalcino – towns famous for their wine
  • La Crociona – vineyard estate 
  • Siena and San Gimignano – characterful medieval Tuscan towns
  • Regina Hotel – quaint hotel in Sorrento overlooking the Bay of Naples, with a lovely rooftop bar. Great central location to be able to walk everywhere
  • Positano, Ravello and Amalfi – famous gems along the Amalfi Coast
  • Veneto Palace Hotel – boutique hotel in Rome
  • Janiculum Hill –  is a hill in western Rome – the second-tallest hill
  • Grazia & Graziella – pizza place in the charming Trastevere neighborhood of Rome

Food and Drink

  • Pecorino cheese – sheeps milk from Pienza
  • Brunello, Chianti Classico – wines from Tuscany
  • San Marzano tomatoes – the world’s most famous tomato – coming from the region of Campania
  • Rum Babas – classic dessert from Naples


  • Andrea Bocelli – Italian opera singer (who has a private beach at Forte dei Marmi)
  • vaporetto – the water bus in Venice
  • Duccio – a late 13th and early 14th century Italian painter from Siena

Resources from Untold Italy

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