Private
Taormina Private Half Day Walking Experience
Overview
Discover the ancient city of Taormina and the majestic Greco-Roman theatre with our English speaking guide who will show you the best of this incredible Sicilian city.
Duration
2 hours
30 minutes
Pricing
On request
Tailored to your dates and group.
Discover the ancient city of Taormina and the majestic Greco-Roman theatre with our English speaking guide who will show you the best of this incredible Sicilian city.
- Tour Style
- Private
- Meeting Point
- Hotel - Port or Rail
Where this journey has been featured
National Geographic Traveller (UK)
On Page One of National Geographic Traveller (UK), September 2026
September 2026
Open the September 2026 Italy issue of National Geographic Traveller (UK) and you will find us on page one, with three words that sum up why we plan journeys: places change us.
Read the story
Magic Towns Italy
Featured in Magic Towns Italy: The Story Behind Italy Vacation Specialists
December 2025
Magic Towns Italy tells the story of our founder Jesse Andrews, who arrived in Calabria in 2003 with 50 euros and a teaching contract, and stayed to build Italy Vacation Specialists.
Read the story
ValiantCEO
Our Founder in ValiantCEO: Why No Algorithm Can Replace Local Knowledge
August 2025
Our founder Jesse Andrews talks to ValiantCEO about AI in travel: where it helps, where it falls short, and why trips built on local knowledge and real relationships matter more than ever.
Read the story
Appetito
Our Founder in Appetito: A Culinary Journey Through Calabria and Basilicata
May 2025
Our founder Jesse Andrews writes for Appetito on the food and coast of southern Italy, from the sea caves of Praia a Mare in Calabria to Maratea, the town of 44 churches in Basilicata.
Read the story
Italian American Life with Frankie D
Our Founder on the Italian American Life Podcast: 20 Years of Living and Breathing Italy
March 2025
Our founder Jesse Andrews joins Frankie D on Episode 144 to tell the story behind Italy Vacation Specialists, from a summer job in Calabria to planning custom trips across Italy.
Read the story
Inclusions & Exclusions
What's Included
- Bilingual and Totally Fluent Guide(s)
- Excellent Photo Opportunities
- Friendly and Professional Service
- Hotel Pick up and Drop Off
- Personalized Service
- The Most Fun Possible!!!! :)
What's Not Included
- Gratuities of any type
Traveler Reviews
Emily and David DavisonMy husband and I just took a two week trip to Italy that was planned for us by Eleanor Kinchin-Smith. It was a fantastic trip and we could not have been more thrilled. We worked together with Ele to let her know about our interests and our style of travel. She planned the perfect trip with excellent private guides at all of our sites, professional drivers and lovely hotels. We arrived in Italy with all of our train and ferry reservations made by Ele, with tickets in hand. She was in touch with us daily throughout our trip to make sure that things were going smoothly. She was able to make a few changes to our itinerary as needed. We look forward to working with Ele again on our next trip and have put her in touch with another family member to help plan their trip as well.
Ron and Deb CrosbyDear Guiseppe and Jesse,
We just returned from our most wonderful vacation to Italy and wanted to first thank you for putting together such a wonderful trip, and second to provide some feedback for the future.
Hotels
1. Hotel Sovestro in San Gimignano was wonderful. The staff were very friendly and helpful and made the first portion of our journey very stress free. They made us feel like we were part of their family. I would recommend it to anyone and would specifically ask for it if we were to make a return visit.
2. Hotel La Baia in Monterosso was nice and it's location was very good especially for us older folks humping luggage from/to the train station.
3. Hotel Lucchesi in Florence- what can I say expect FANTASTIC. The rooftop view at sunset is well worth it. Again very friendly and helpful staff. Would recommend it to everyone.
Wine Tour
Money well spent. We had a great time overall. The driver Mario was OUTSTANDING. He had lots of local knowledge as well as about winemaking. USE HIM AGAIN!!!
The various wineries we visited on tour:
Altesino- fantastic and they were not cheap on their pouring. Great experience.
Azienda Agricola Patrizia Cencion Sloaria- Again a great tour by one of the owner's daughters. We felt like we were the only thing on their mind although there were other customers there. A great way to complete the day.
Again we had a fantastic time and are very appreciative of everything you booked for us. We wish you continued success and if our travels should bring us back to Italy, we know who to call.
Leon and MicheleThe trip was great we appreciate all the hard work you and your team invested to make our experience a once in a lifetime trip. We appreciate all the attention to the details in particular Giuseppe spending the time and the focus with us on the road and as we were exploring your great country.
Bob & SandyJesse & Giuseppe,
Sandy and I have been looking through my slides of our trip to Southern Italy. We had such a good time with you and Giuseppe that we wanted to let you know again. You were the best guides ever.
Location
Italy Taormina
Taormina and beyond
2 hours 30 minutes through Italy, with every stop chosen by the people who live here.
Where we meet
Hotel - Port or Rail
Nearby Experiences
Secrets of Sicily: Unesco Sites, Wineries, Food and Beaches
Private Tour of Sicily's Unesco World Hertiage Sites, Food, Wine and Magnificent Coastal Towns
Isola Bella and the Coast of Taormina Morning Tour By Boat
Catamaran Tour of Castellammare del Golfo & Scopello
Sicily: Private Full Day Tour of Erice - Castellammare del Golfo and Lo Zingaro Nature Reserve
Harvest Time in Sicily: Experience a Sicilian Wine Journey - 7 Days of Vino, Volcanoes & Villages
A Private Journey with Local Hosts through Southern Italy and Malta including the Amalfi Coast, Capri, Pompeii, Sicily and the Island Nation of Malta
Frequently Asked Questions
Is this a private tour, or will we join a group?
Private. You travel with your own guide and driver, and the only people on the itinerary are the ones you bring with you. Nothing is shared with strangers, and the pace of each day is yours to set.
Can the itinerary be changed to suit us?
Yes. What you see here is a starting point, not a fixed departure. Tell us how long you have, what you love and what you would rather skip, and we will reshape it around you. A slower morning, an extra night somewhere you fell for, a different region entirely.
How do we start planning?
Send us a note using the form on this page, or call us on 1-866-779-2565. A travel specialist replies within one business day, usually with a few questions of their own. There is no cost and no obligation in asking.
When should we book?
The earlier the better, particularly for travel between May and September, when the guides worth having are taken first. That said, we have put together beautiful trips at short notice, so ask and we will tell you honestly what is still possible for your dates.
Start the Conversation
Quick Enquiry
Our travel specialists reply within one business day.
Recommended Tours
From the journal
Our Recent Blog
Latest
Peaks, Palaces & Prosecco® Venice Is Only the Beginning…
Read article-
Who Really Benefits When You Book Your Italy Experiences Through GetYourGuide, Viator or Tripadvisor?
-
Join Us for Italy’s Flavorful Fall Festivals!
-
Italy’s Best Autumn Food Festivals: Where to Eat, Drink and Celebrate in 2026
-
Italy’s Most Delicious Season Has Arrived
-
From Grandparents to Grandchildren—Beautifully Planned Italian Journeys
Explore More of Italy
Curated Italy journeys and travel inspirations.
Ready to plan your journey?
Connect directly with a member of our team for expert guidance and fully customized travel across Italy and the Mediterranean.
- Direct in Italy: +39 375 823 5314
- Toll Free: 1-866-779-2565