Sicily, Italy Discovery Tour 2023

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  • Regular price $8,400.00

NEW! Join our no-obligation, no-pressure informational Zoom meeting on Saturday, February 4th, at 10:00 AM Pacific where you can meet your hosts and guides, and ask questions. Click here to RSVP.

Dates: September 25th to October 6th, 2023, (12 days)

Pick up and drop off in Rome, Italy (FCO). The tour prices INCLUDES the domestic round-trip flight from Rome to Palermo, where our adventure begins...

Sicily, or Regione Siciliana, is a cultural melting pot – full of diversity and unique culture found nowhere else in Italy. Of course, Sicilian cuisine is renowned, and the presence of ancient Greek temples and Mount Etna – the biggest active volcano in Europe, make a dramatic backdrop for people watching in street cafés. Opposite the mountains, you have the crystal clear coastline and sandy beaches framing the largest island of Italy and the Mediterranean Sea.

To truly appreciate the variety of treasures in Sicily in only 12 days requires the insight and knowledge of experienced and professional Italian guides, and we have partnered with some of the best: Max & Cristiana, owners of Ciao Andiamo.

Our Adventure tour will take us to some of the most iconic landmarks, through some of the most beautiful scenic vistas, and have us wining and dining in some of the most delicious and culturally unique places in Italy. You will be able to relax and enjoy, knowing that every detail of your adventure is being taken care of for you.

Our intentionally small groups of travelers allow us to travel discretely (no huge tour buses), visit places that bigger groups cannot, and have intimate experiences that you would typically enjoy with just a close group of friends. In fact, we are sure you will feel you’ve made some new ones by the first day of our adventure together!

This is not a mass-produced tour. Max and Cristiana work with us to curate a unique and intimate experience that is rich with cultural connection and diversity.

Check out the itinerary tab for a full overview of what we’ll be experiencing together.

Tour highlights:

  • An active adventure with lots of walking and some hiking. A good state of health is important. All are welcome, so please feel free to contact us if you have any physical or mobility issues. 
  • Beautiful 4-star hotels that reflect the unique culture of the areas we'll be staying in.
  • A perfect combination of discovering iconic landmarks, experiencing food & wine culture, exploring and shopping the Sicilian markets, and taking in the natural beauty of the beaches and mountains. 
  • Hosts and guides whose sole focus is your comfort and a beautiful overall experience.
  • Customized and intimate experiences that you simply cannot get with larger, mass-produced tours.


Sicily, Italy Discovery Tour 2023

DAY 1, Sept. 25th - ROME - TRAPANI

We’ll fly from Rome to Palermo (cost of this flight is included in the tour price) Our adventure begins with a visit to the town of Erice. Towering over the west of Sicily at 751m above sea level and often covered in its own personal cloud, Erice is a wonderfully preserved medieval town offering a breathtaking view of the valley below. Amongst the most visited sites there is the Venus Castle, a Norman construction with imposing towers that derives its name from the nearby ancient Temple of Venus, said to be founded by Aeneas. We’ll stay the night at a wonderful Baglio, a typical winery and farm resort, where we’ll enjoy our first aperitivo and dinner.  

Meals included: lunch and dinner

DAY 2, Sept. 26th - TRAPANI

We’ll enjoy breakfast at the Baglio, then head out with our guides to experience the saline of the Laguna Marsala. Situated along the coast of Marsala, the saline is a fully functioning famous Sicilian salt mill. The picturesque site, with its windmills set against the backdrop of the sea, makes a lovely place to stop and take photos. Travelers interested in traditional production methods will enjoy learning about how this company harvests salt. We’ll then visit a historical winery in the area for a tour and lunch. We’ll enjoy another night and dinner at the farmhouse.

Meals included: Breakfast, wine tasting & lunch, and dinner

DAY 3, Sept. 27th - AGRIGENTO

After breakfast, we’ll check out of our hotel and head towards Agrigento with a lunch stop on the coast. After checking in to our new hotel we’ll tour the famous UNESCO site, Valley of the Temples, where you will walk among almond and olive trees, prickly pears, and agaves and learn about Sicily and Agrigento, their culinary traditions, wine, local culture, and people. The Temple of Concordia is a must-see at this site. Built-in the 5th century BC by the Greeks, it is one of the most well-preserved temples in the world and an important Greek monument in Italy. Dinner will be together at our hotel.

Meals included: Breakfast, lunch, and dinner

DAY 4, Sept. 28th - AGRIGENTO

We’ll have breakfast at our hotel, then head out for a unique Sicilian experience. The small villages of the Sicilian hinterland provide a great opportunity to immerse yourself with the locals. You can immediately see in the eyes of those you meet along the little streets their warm hearts and Sicilian hospitality. Here you are not going to meet tourists or visit famous places, the real attractions are the human relationships and the great heart of the people. The day will include a local culinary experience for lunch. Dinner will be at our hotel.

Meals included: Breakfast, lunch, and dinner

DAY 5, Sept. 29th - TAORMINA

Following breakfast, we’ll check out of our hotel in Agrigento, and make our way to the town of Taormina. We’ll stop on the way in Ragusa and Noto, true Baroque Sicilian gems splendidly set on a rocky plateau overlooking the valley below. Ragusa is one of the most picturesque towns in Sicily. We’ll have private tours in both towns. After checking in to our hotel in Taormina we’ll enjoy dinner as a group.

Meals included: Breakfast, and dinner

DAY 6, Sept. 30th - TAORMINA

Enjoy breakfast at our hotel before a half-day excursion to Mount Etna. We’ll make our way up the volcano to meet our guide for some easy trekking through the unique landscape of Etna’s lava tubes and craters. Following our hike we’ll head back down to the lower slopes to tour a winery and sample wines made in the area around Etna. Lunch at the winery will include local culinary specialties. After we return to our hotel you can enjoy dinner on your own in town.

Meals included: Breakfast, wine tasting & lunch at a winery

DAY 7, Oct. 1st - TAORMINA

Enjoy a relaxing day in Taormina. Idyllically perched on a rocky promontory high above the sea, Taormina is full of beautifully restored medieval buildings, breathtaking views around every corner, and a network of winding streets strewn with shops, bars, and restaurants.

Meals included: Breakfast and dinner

DAY 8, Oct. 2nd - TAORMINA

After breakfast we’ll head to Siracusa – a city full of charm, history, and beautiful natural landscapes. It became a UNESCO World Heritage Site in 2005. The city is divided into two different parts: the newer, modern part of the city, and Ortigia, a characteristic island and the historical heart of the city. Within its area of one square kilometer, you can admire the architectural beauties of many different historical periods: from the first prehistoric settlement to the numerous remains of ancient Greeks, Byzantines, and Normans. We’ll have time on our own before driving back to our hotel in Taormina.

Meals included: Breakfast and dinner

DAY 9, Oct. 3rd - PALERMO

After breakfast we’ll check out of our hotel and head to Palermo. We’ll stop in Cefalù for a light lunch and a stroll through the narrow streets of this beautiful coastal city. Once we arrive in Palermo and check into our hotel we’ll relax and enjoy dinner with the group.

Meals included: Breakfast, lunch, and dinner

DAY 10, Oct. 4th - PALERMO

Embark on a full-day private guided tour of Palermo starting at one of the oldest and most famous markets in Europe. Street food was invented here! After a colorful and tasty lunch in the heart of the town, we’ll visit the Cathedral of Monreale, a masterpiece of Arab, Norman, and Byzantine art. Dinner will be on your own.

Meals included: Breakfast, lunch

DAY 11, Oct. 5th - PALERMO

After breakfast we’ll explore the different souls of this incredible town with our guide. Palermo is a cultural melting pot being the crossroads for civilizations for millennia. We’ll see Teatro Massimo, one of the largest theatres in Europe and Quattro Canti, the octagonal square located at the intersection of via Maqueda and Vittorio Emanuele, one of the truly picturesque locations in Palermo. Lunch will be on your own. We’ll celebrate the end of a memorable tour with our group dinner.

Meals included: Breakfast, dinner

DAY 12, Oct. 6th - PALERMO TO ROME

After breakfast we’ll head to the airport to fly back to Rome. Arrivederci Sicily!

Includes: Breakfast





    Main Tour: $8400 per person, based on double occupancy. $9200 for singles with a private room. This INCLUDES the domestic flight from Rome to Palermo.

    Note: If you are single and open to sharing a room with a same-gender participant, we will do our best to pair you and offer the double-occupancy rate. Pairing is not always possible based on other participants, but we'll do our best!

    You may reserve your spot now by paying the $1000/person deposit. We will contact you later for balance payment options.


    • Internal flights (Rome to Palermo and back to Rome) and airport taxes.
    • Private ground transportation during the entire trip
    • Most meals (noted on the itinerary where not included)
    • Expert bi-lingual local guides and dedicated hosts


        Not Included:

        • International airfare to Rome.
        • Some meals (see itinerary).
        • Extra alcoholic beverages.
        • Some tips


        Payment Schedule:

        We limit our adventures to small groups in order to provide the best, most intimate, and most engaging experiences. Each person is an integral part of making our trip successful and affordable for all!

        A reservation fee of $1000 per person is required to reserve your spot. Initial reservation fees of $1000 are fully refundable for 7 days after payment if made more than 67 days prior to departure. If booking less than 60 days prior to departure, the full fee is due.

        When booked more than 120 days prior to departure, the balances due are as follows:

        • 120 days prior to departure – 50% of balance due.
        • 60 days prior to departure – final balance due.


        Participant Cancellation:

        Seven days after your initial reservation fee, full refunds are not available. However, if we can refill your canceled seat, we do our best to refund any recovered payments (minus any transaction fees, change fees, administration fees, or unrecovered costs).

        We make payments in advance to our guides to secure the best locations, booking options, prices, and experiences. Refunds from our vendors cannot always be collected when cancellations are made at the last minute.

        Personal trip cancellation insurance is highly recommended. We are happy to recommend providers we've used.

        Cancellation by us:

        We will refund the money you have paid, or transfer your reservation to a future trip, at your discretion, unless canceled due to a Force Majeure event, described below.

        Cancellation due to Force Majeure (unforeseeable circumstances beyond our control):*

        If our trip is canceled due to Force Majeure event, we can offer you full credit for monies paid towards a future tour, OR refund monies paid MINUS any unrecoverable costs we incur.

        • A “Force Majeure Event” includes but is not limited to: acts of God; war; civil commotion; riot; blockade or embargo; fire; explosion; breakdown; union dispute; earthquake; epidemic, pandemic or other health emergency; flood; windstorm or other extreme weather event; lack or failure of courses of supply; passage of any law, order, proclamation, regulation, ordinance, demand, requisition or requirement or any other act of any government authority, beyond the reasonable control of the parties, which would make it dangerous or not viable for a trip to commence or continue.

        In the event of any cancellation, there will be no claim for damages by either party against the other and we are not responsible for any incidental expenses that you may have incurred as a result of your booking including but not limited to visas, vaccinations, travel insurance excess or non-refundable flights.


        Many of our travelers are repeat customers, join us once and find out why! We take pride in offering a sincere and personal vested interest in your enjoyment and experience. We'll do everything we can to make sure you're a satisfied customer, too!

        "I LOVED the whole trip it was amazing everything from where we stayed to the food and the company the trip was perfect. Great Job guys!! There is no other way to travel, you get the intimate backstage pass to the area." – Catrina Scott

        "I loved this adventure because it was off the beaten track, and we were privileged to experience the Umbria and Tuscany regions of Italy in a way most tourists don't get to enjoy. The people you meet become friends, the places you stay are small local gems, the food you enjoy is awesome, the sights you experience and photograph are indescribable and the attention to detail and the way they work in activities that interest everybody is phenomenal. This was my first travel adventure with the Kubotas, and I look forward to participating in others!" – Benita Clarke

        "EVERYTHING! The motos were so much fun! The weather was PERFECT- I feel like we got so lucky there. The food was incredible. I loved the places we stayed and all the places we visited. I didn't want it to end. The Italy motophototour 2016 was an epic adventure of a lifetime and food for the soul. I am leaving feeling alive and inspired in a way that I didn't know was possible." – Frances Marron

        "The Secret Italy trip was fantastic! The convenience of having everything planned out for us, from each stop along our way that offered incredible photo ops, all the way down to the wonderful Italian dinners we shared together. All we had to do was show up! My wife, who is not a photographer, had an awesome time as well. We made many friends and continue to stay in touch. A big thanks to Kevin, Clare, Max and Cristiana for their planning and hospitality. I would do it again in a heartbeat." – Shane Rodimel

        "Where do I begin? I loved the entire trip throughout Italy with Kevin, Clare, Max and Cristiana. They knew what photographers would be interested in seeing. Best of all, there was no one saying "why do you have to take so many pictures where ever we go?" It was great to be with so many people with exactly the same interests as me. There was a wonderful variety of places to photograph. There were endless photo ops whether you like photographing people, landscape, close-ups, architecture, or food. And there was endless food as well. The accommodations were beautiful and spacious. Max and Cristiana are so warm and knowledgeable about the history and culture of the various towns we visited. I loved their home town of Stroncone the best. I hope to go to Italy again with Kevin and Clare's tour some day." – Marilyn Hunt

        "This was, indeed, a trip of a lifetime. Everything we experienced was carefully, professionally and compassionately mapped out.  Even the extra last-minute side trips (roof tile-making, bakery, pork soup restaurant) side trips were joyfully interspersed with the itinerary.  Clare and Kevin are perfect hosts - caring, accommodating, respectful, happy, patient, etc., etc., etc!  Our guides, Washi and his brother, Rogelio (Rocker),  were outstanding!  Even Washi's wife, Pammela joined us from time to time to support our travels.  So much knowledge to share, and as with Clare and Kevin, our guides were caring, accommodating, respectful, happy, patient, etc., etc., etc!  As an example, Washi's skill, knowledge and kindness were evident in his ability to give a few of us the confidence we needed to safely walk to the top of Rainbow Mountain in spite of the thin air.  Washi had us hold hands as if in a chain.   We walked 20 steps, rested and continued in this manner to the top of the mountain - altitude 16,313!  What a sense of accomplishment!  As promised we were introduced to fabulous foods above and beyond expectations (well, maybe not the cuya😳).  The spiritual aspect of this journey was life-changing. Our time with our Shamans, the local people and the entire experience stirred my soul. I will be forever changed (in a good way).  Difficult to put into words.  You just have to experience the magic of this adventure for yourself to get the full beautiful impact.  Would I travel again with Kevin, Clare, Washi, Rocker, and Pammela again??? Yes - to the ends of the earth!!!" – Lorraine S., Peru 2022 Adventure

        THE TEAM

        Kevin & Clare Kubota

        Aloha! We have been leading workshops and tours around the world since 2001 when I, Kevin, was asked to teach my first International photography workshop in Italy. Ever since then, the love of sharing our travel experiences with others has been an inspirational piece of why we do what we do. I've been a professional photographer for over 30 years and have taught photography workshops since 1998.

        Clare is our "Queen Bee", who joyfully and eloquently manages our team, co-leads our tours, and inspires me, and many others, with her zest for life and love for rich connection with people.

        We have led travel experiences in Rwanda, South Africa, Kenya, Thailand, Brasil, Italy, Hawaii, and Bolivia. We have also traveled and taught photography courses in many more places nationally and internationally.

        We know one thing to be true: traveling with an open mind and open heart leads to amazing experiences and profound personal growth. We call this the "Traveller's Mindset" – where you allow yourself to be open to meeting new people, trying new things, and seeing life from a different perspective. You do more than allow, however, you take the first steps. You take the initiative to say "hello", ask to try, and listen more than you talk.

        Inevitably, when you bring your Traveller's Mindset home to your own community, you find treasures in your own backyard.


        Max Brunelli & Cristiana Chiacchierini

        Kevin & Clare have been friends with Max & Cristiana for over 20 years. They met when Kevin & Clare did their first workshop in Italy at the medieval village Inn that Max & Cris owned at the time. Soon after that fortuitous meeting, Max & Cris began guiding photography tours for Kevin and Clare, and have been doing so ever since. 

        Max is an amazing connector, having worked in the film industry as a location expert and traveled to almost every corner of Italy throughout the years of constant work in the travel and tourism business for most of his life. 

        Cristiana is a shining light of hospitality and cheer. She is a chef, a sommelier, coordinator extraordinaire, and an expert on finding beautiful places to dine, shop, learn, and share with friends! 

        The reputation of Max & Cristiana spread rapidly, and their guiding business grew to a complete Tour company, Ciao Andiamo – with employees, partners, and clients around the globe! Despite their growth, Max & Cris and Ciao Andiamo have maintained their intimate connection with their clients, unique offerings, and off-the-beaten-path adventures. 

        We have yet to meet any Italians that have a more in-depth knowledge of Italy, or deep passion for sharing the unique culture and beauty, than Max and Cristiana. 

        We are fortunate to have Max and Cristiana as our guides on our hosted adventures.

        MORE INFO