Tuscan Classic Car Rally with Debbie Travis
About the Trip
September 26–October 4, 2025 | 9 Days
Indulge in luxury and heart-racing excitement with this CAA Exclusive Tuscan Classic Car Rally. Your grand adventure begins in Rome where you’ll experience the wonders of the Vatican Museums on a guided private VIP tour. Your next stop is the enchanting and luxurious Villa Reniella in Montefollonico, owned by lifestyle maven Debbie Travis. Here, your epic Classic Car Rally awaits. Hosted by Debbie Travis and auto aficionado Hans Rosenstein, you’ll spend four days driving 14 iconic, vintage sports cars through Tuscany’s picturesque landscapes. Each day of this unparalleled Italian escape will be filled with gourmet delights, exhilarating cars, charming villages, scenic routes and cherished new memories made under the Tuscan sun.
One-of-a-kind Experiences
This luxurious departure is part of the CAA Premier Collection tour, offering immersive and intimate group journeys.
- Every detail matters: From the moment you’re met at the airport to your farewell dinner, you’ll experience best-in-class service wherever you go.
- Our CAA Hosts lead you on incredible adventures to iconic destinations. They will take care of every detail on each journey.
- Travel in style: Stretch out on spacious motorcoach while exploring during the day and rest easy at night in the best hotels each destination has to offer.
- Memorable dining: Delicious local dishes and the season’s most flavourful offerings will have you savouring every bite.
CAA Exclusive Tuscan Classic Car Rally
Hosted by Debbie Travis and auto aficionado Hans Rosenstein, you'll explore the breathtaking Tuscan landscape from behind the wheel of 14 iconic, vintage sports cars. Each day includes 3-4 hours of leisurely driving through hidden gems of southern Tuscany, including UNESCO heritage sites like Crete Senesi and Val d’Orcia.
The tour’s fleet includes both standard and automatic transmissions, and guests will have the chance to drive each car as they rotate throughout the day. There will be a team of mechanics to help familiarize guests with the vehicles and accompany the group outings for added peace of mind.
Member Exclusive Benefits
We reward all our CAA Members on our Extraordinary Explorations® tours.
- Bon voyage gift†
- International Driving Permit Fees1
- 100 CAA Dollars®^
- 25% savings on CAA Travel Insurance◊
Package Includes:
- Pre-tour Rome
- 2-night stay in deluxe-class accommodation in Rome
- 2 breakfasts and 1 dinner
- Sightseeing and entrance fees as per itinerary
- Local English-speaking guide
- CAA Exclusive Classic Car Rally
- 6-night stay in deluxe-class accommodation at Villa Reniella
- Celebrity Villa Host Debbie Travis
- 3-4 hours of driving per day for four days in vintage sports cars
- Full vehicle insurance, maintenance and fuel included
- 7 breakfasts, 6 lunches and 6 dinners taken at the villa or local restaurants
- Complimentary bar − wine/prosecco & spirit plus filtered water, tea and coffee
- Midweek room refresh
- Infinity pool & open-air cinema
- Tuscan sightseeing
- Prepaid gratuities
- Destination transfers
- CAA Host
CAA Exclusive Tuscan Classic Car Rally with Debbie Travis
Activity Level: Moderate. Join Debbie Travis and Hans Rosenstein at their luxury villa where you’ll experience the thrill of driving iconic, vintage sports cars through Tuscany's landscapes.
Day 1
Rome – Arrive in Rome for the start of your grand adventure. Spend the day exploring on your own before meeting with your CAA Host and fellow travellers for a welcome dinner this evening. (D)
Day 2
Rome – Enjoy a VIP Early Entrance tour of the Vatican with an expert guide who will lead your group through the wonders of the Vatican Museums, Sistine Chapel and St. Peter’s Basilica before they open to the public. The balance of the day will be at leisure to explore Rome. (B)
Day 3 - 8
Villa Reniella and CAA Exclusive Classic Car Rally – This morning, transfer to Villa Reniella in Montefollonico for the start of the Classic Car Rally. The first two days are for meeting your special hosts, Debbie Travis and Hans Rosenstein, and relaxing with your fellow travellers at Villa Reniella.
Swim, take in a Tuscan cooking class, explore the local medieval village of Montefollonico or enjoy a leisurely walk with Debbie. This lovingly restored property in the heart of the Tuscan countryside offers the amenities of a luxury hotel set in a private home on 100 acres of olive groves and vineyards, with an infinity swimming pool, open-air cinema, hiking trails and more.
Over the next four days, you’ll explore the breathtaking Tuscan landscape from behind the wheel of 14 iconic, vintage sports cars. Each day includes 3-4 hours of leisurely driving along specially curated routes to landmark destinations where you’ll enjoy fascinating vistas and historic sights during pitstops and a well-earned gourmet lunch at some of the best restaurants in the area. After lunch, you’ll return to Villa Reniella to relax, swim and enjoy a sunset aperitivo followed by a truly Tuscan feast under the stars prepared by a private chef and paired with the finest wines of the region.
The tour’s fleet includes both standard and automatic transmissions, and guests will have the chance to drive each car as they rotate throughout the day. There will be a team of mechanics to help familiarize guests with the vehicles and accompany the group outings for added peace of mind. (B/L/D)
Day 9
This morning, say farewell to your incredible hosts and transfer to the Rome airport. (B)
B - Breakfast | L - Lunch | D - Dinner
Terms & Conditions
*All CAA Member prices are per person, based on double occupancy, in Canadian dollars unless otherwise indicated and are subject to change without prior notice until final payment is paid. All prices are correct at press time and apply to new bookings only, based on availability at time of booking. To receive CAA Member-exclusive benefits, there must be one valid CAA Member travelling per booking. Non-members booking Extraordinary Explorations will not receive Member-exclusive benefits.
†Bon Voyage Gift is 1 (one) per person.
1 CAA Gift Card will be provided at the time of final payment for purchasing an International Driving Permit from a local CAA store.
^CAA Dollars awarded per adult Member. To earn and redeem CAA Dollars, you must be a current CAA Member in good standing (CAA Membership dues paid in full by membership expiry date). CAA Dollars will be credited at time of departure. For more information on CAA Dollars, please visit www.caasco.com/caadollars.
◊CAA Travel Insurance, an Orion Travel Insurance product, is underwritten by Echelon Insurance. Twenty-five percent (25%) Member savings is made up of a ten percent (10%) Member savings as well as a promotional fifteen percent (15%) savings when you purchase an Extraordinary Explorations tour through CAA Travel, applies to CAA South Central Ontario and CAA Manitoba Members in good standing (CAA Membership dues paid in full by membership expiry date). This promotional offer is valid until December 31, 2025. Ten percent (10%) Member savings applies to Members in good standing of all other CAA clubs. Savings apply to the total premium excluding applicable taxes. Minimum premium applies. Visitors to Canada Insurance is limited to promotional savings. Certain exclusions, limitations and restrictions apply. Subject to change without notice. A Medical Questionnaire may be required to purchase travel insurance.
Extraordinary Explorations vacations are organized and booked by CAA Travel (South Central Ontario) Inc. and CAA Manitoba (“CAA Travel”) on behalf of CAA Club Group (o/a CAA South Central Ontario and CAA Manitoba). In the event of an increase in any of the cost factors, CAA Travel reserves the right to increase the price whereby the provisions of the Travel Industry Act shall prevail. CAA Extraordinary Explorations packages are 100% non-refundable at final payment. CAA Travel service fee for cancellation prior to final payment varies by program. For full payment terms and conditions, please ask your CAA Travel Consultant. CAA Travel reserves the right to cancel or re-schedule any tour departure in accordance with operating requirements (minimum number of participants) or circumstances beyond its control. Additional fees for checked luggage or other incidentals may be incurred and vary according to itinerary and airline. Air schedules with some tours are not available at press time and may include several connections or forced overnight at passenger’s expense. CAA Travel strongly recommends the purchase of trip cancellation and emergency travel and emergency medical insurance at the time of booking.
Please note: Participants must be able to embark and disembark cruise ships and coaches without assistance as well as have a good level of mobility for walking tours in destinations where stairs and traditional cobblestone streets can be challenging. International transportation vehicles and facilities may not meet accessibility standards.
Tour Itinerary
Day 1
Rome
Arrive in Rome for the start of your grand adventure. Spend the day exploring on your own before meeting with your CAA Host and fellow travellers for a welcome dinner this evening. (D)
Day 2
Rome
Enjoy a VIP Early Entrance tour of the Vatican with an expert guide who will lead your group through the wonders of the Vatican Museums, Sistine Chapel and St. Peter’s Basilica before they open to the public. The balance of the day will be at leisure to explore Rome. (B)
Day 3 – 8
Villa Reniella and CAA Exclusive Classic Car Rally
This morning, transfer to Villa Reniella in Montefollonico for the start of the Classic Car Rally. The first two days are for meeting your special hosts, Debbie Travis and Hans Rosenstein, as you and your fellow guests relax at Villa Reniella. This lovingly restored property in the heart of the Tuscan countryside offers the amenities of a luxury hotel set in a private home on 100 acres of olive groves and vineyards, with an infinity swimming pool, open-air cinema, hiking trails and more.
Over the next four days, you’ll explore the breathtaking Tuscan landscape from behind the wheel of 14 iconic, vintage sports cars. Each day includes 3-4 hours of leisurely driving along specially curated routes to landmark destinations where you’ll enjoy a well-earned gourmet lunch at some of the best restaurants in the area. After lunch you’ll return to Villa Reniella to relax, swim and enjoy a sunset aperitivo followed by a gourmet dinner under the stars prepared by a private chef and paired with the finest wines of the region.
The tour’s fleet includes both standard and automatic transmissions, and guests will have the chance to drive each car as they rotate throughout the day. There will be a team of mechanics to help familiarize guests with the vehicles and accompany the group outings for added peace of mind. (B/L/D)
Day 9
This morning, say farewell to your incredible hosts and transfer to Rome airport. (B)
B - Breakfast | L - Lunch | D - Dinner
Accommodations in Montefollonico, Tuscany
Day 3 - 8