
Two Week Mediterranean Itineraries
A vast array of ecosystems, cultures, and experiences can be found in this special place on Earth. From ancient monuments and island paradises to amazing cuisine and colorful landscapes, a two week Mediterranean itinerary from one of Zicasso’s travel specialists will be a vacation unlike any other. Your exploration of this incredible region is made better through a personalized trip.
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Let these itineraries inspire your personalized travel experience

14 Day Trip IdeaFrom $5,600
Gems of the Mediterranean: 14-Day Italy and Greece Tour

14 Day Trip IdeaFrom $4,600
Two-Week Greece Tour: Wine, History & Legends

14 Day Trip IdeaFrom $4,400
Immersive 2 Weeks in Spain Tour: History, Culture & Food

14 Day Trip IdeaFrom $5,100
14-Day Ultimate Italy Highlights Tour

14 Day Trip IdeaFrom $5,100
Two-Week Highlights of Southern Italy Tour
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1.Share Your Travel Dreams
Zicasso specializes in custom tours, vacations, and safaris tailored to your interests and preferences. From private African safaris to culinary experiences in Europe, submit a trip request to share your ideas and travel style.
2.Meet Your Travel Specialists
To ensure a personalized experience, we'll carefully handpick and introduce you to two of our top travel specialists, each with unsurpassed destination knowledge and local insight aligned to your luxury travel dreams.
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Compare the expertise of two specialists with itineraries crafted exclusively for you. You can refine these further and choose your preferred proposal. Our unique process ensures a more creative, personalized, and expertly crafted trip.
Reviews of Zicasso's Two Week Mediterranean Itineraries
Based on 4708 verified traveler reviews.
My husband and I, along with our 2 children (age 20 and 17), enjoyed a wonderful Italian vacation booked through Zicasso and this travel agency. Our travel consultants listened to my ideas and arranged for us a fantastic custom itinerary. They stayed within the budget allotted, offered choices for beautiful hotels and private tours, and made several revisions as per our request. We departed from New York on our 25th anniversary, and spent 10 days traveling the country within the month of November. This off-season time proved to be a great decision as reservations were easy to obtain, crowds were minimal (mostly all locals), and the weather was conducive for walking and sightseeing (average 60 degrees F). Transportation and the personal drivers were top notch; with Mercedes SUVs or minivans to take my family from Milan-Chianti-Florence-Verona-Venice and then the high speed train down to Rome. Accommodations arranged for us were phenomenal! We stayed in a 12th century castle in Chianti, in the heart of the city center in Florence, and near the Spanish Steps in Rome. The personal tour guides were friendly and knowledgable, and were happy to recommend eateries preferred by locals. All in all, everything was flawless. We plan to return some day to see the Amalfi coast, Positano and Capri. We would absolutely recommend these travel consultants, and the travel company team to anyone who is looking for a personalized Italian vacation.
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Our family of five just got back from the most wonderful vacation in Tuscany and Rome. Our agent crafted a set of amazing experiences for our family from the private tour guides to Florence, Pisa and Lucca; a private wine tasting lunch at the Capannelle Winery and vineyards in Chianti; tickets to the Papal mass at the Vatican; to a tour beneath the church of San Clemente to see the excavations of a byzantine and then a Roman street neighborhood; a day excursion to the Amalfi coast to visit Positano, Sorrento and Pompeii; and more! Our agent and the guides found excellent restaurants from a simple salumeria where the locals ate to some high end restaurants. The hotels were right in the center of Florence – on the piazza della Repubblica - and Rome – between the Piazza del Popolo and the Spanish Steps. Our agent was attentive to our plans and made excellent suggestions. Everything went extremely smoothly. All the guides drivers were very friendly, spoke English and were very knowledgeable about art, history and the local culture. We saw so much every day because everything was so well planned. Simply the best travel experience ever!
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I have to begin by saying I've told everyone how pleased I am with Zicasso and the travel agent they recommended. I also have to say that I was very hesitant to book my trip with a company that I had only communicated with via email. Turns out I had nothing to worry about.
The initial response I received from my agent was immediate and continued right up until our actual trip while we were in Italy. I let her know where I wanted to go, what I wanted to see, told her I was interested in a mix of arranged tours and time on our own. She listened and also made great suggestions. I honestly can't say enough about how wonderful she was to work with, along with her co-worker.
They arranged for all our hotels, transportation and tours. Every driver and guide we had was top notch. They made a point of keeping us in small groups, sometimes only the two of us and the guide.
Our 19 day trip began in Venice where we were met at the airport and driven to a private water taxi. That driver walked us out of the boat and made sure we knew how to find our hotel. Our departure was just as seamless. A guide met us in our lobby, walked with us to the water taxi, came into the train station with us and explained the board to us, pointing out our train and track number.
We continued on to Verona, Cinque Terre, Tuscany, Florence, Naples, the Amalfi Coast and Rome. Since we weren't in any one place longer than three days it was extremely helpful to have guides, even for just a couple of hours to orient us, which saved us a lot of time. We had guides for a walking tour in Venice, a morning in Cinque Terre traveling with us between the villages, the Accademia in Florence, Pompeii, an Amalfi Coast drive and the Vatican in Rome. Every one of the them was passionate and proud and we learned so much. We had a car in Tuscany and saw many other places on our own, Lucca, Pisa, San Gimignano, Siena, Montalcino, Montepulciano. We stayed in Sorrento, spent one day on Capri and another full day on a tour to Positano, Amalfi and Ravello, which included a short boat ride along the coast. Spectacular. Our only tour in Rome was the Vatican but we saw all the other major sites on our own, taking the metro, bus, taxis and walking, lots of walking. It was the perfect mix of free time and arranged tours.
And, they also worked with our children who surprised us with a dinner in Venice for our anniversary after a gondola ride!
One great advantage to having your tour guide in the country you're visiting, you're in the same time zone. We had one mishap with a train and were able to talk to them right away. Other than that, everything worked liked clockwork.
I would definitely use them again and have told everyone I know what a wonderful job they did for us.
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My daughters and I had an amazing 12 day trip to Greece! In January, we made up a long list of all the places we wanted to see. We wanted focus on the scenic beauty and archeological history of different Greek sites, and we were not disappointed! We started in Santorini, then progressed to Mykonos, Delos, Hydra, Poros and Aegina, before turning our attention to the mainland, and covering sights in Athens, Sounion, ancient Corinth, Mycenae, Epidaurus, Nafplia, Olympia, Delphi, Kalambaka and Meteora. Armed with that very long list, I contacted a few different travel agents. I asked a local Hong Kong travel agent as well as sending off an inquiry to Zicasso. Zicasso came back with two travel agency referrals, one of them was this travel company.
From the very beginning,our travel agent was very professional and helpful. He worked around my travel schedule and our time difference to find a good time to Skype, and I sent him my list of places and sights that we wanted to include on this trip, along with our desired emphasis on the history and culture of Greece (rather than the wineries and shopping). He assured me that he would work on the best itinerary, given our desire to visit various islands as well as archeological sights on the mainland, and that he would also recommend the good hotels for us. My travel agent was willing to speak with me and also replied emails promptly, answering every small question in details in the itinerary as we went back and forth over a few weeks time. He assured me that he would arrange for knowledgeable private guides and we would be able to soak in all the archeological and scenic sights that we wanted. All of our tours with guides were private, and included all entrance fees and transfers. The only group outing we had was a one day cruise to Hydra, Poros and Aegina. Our guides were all knowledgeable and eager to share their passionate interests on the areas we were visiting. They adapted to our pace and interests well.
We were greeted by our travel company's Santorini representative when we arrived in Santorini. Our private transfer whisked us to our hotel and we were briefed on our prearranged tours for the time in Santorini. Our hotel was a wonderful boutique hotel that our travel agent had assured us would have incredible views of the caldera. We were floored by the breathtaking views and gorgeous sunsets!! Our suite (a renovated sea captain's quarters built into the cliffside) included enough space all three of us, and we had delicious and wonderfully prepared breakfasts on a private patio each morning. The hotel and its facilities were well maintained and we loved the three nights we stayed there. We were within five to ten min walking distance of shopping in both Fira and Firastefani. We had a five hour private tour the first day, driven by our young, friendly and exceptionally courteous driver. Our guide gave us the tour around different areas of the island, including Profitis Ilias, Megalochori, Perissa and the black sand beaches, and then our expert historian guide, met up with us for the visit to Minoan Bronze Age archeological site of Akrotiri. We then went back to meet up with the boat company, and took a three hour boat ride around the caldera, including visiting the Paila Kameni and Nea Kameni islands and the hot springs in between, and taking a short walk on the volcano crater (still active!). This boat ride was arranged at the last minute by our guide at our request to "see Santorini from the water" and he was very helpful in arranging this. In addition our guide was able to help us make reservations for meals and extend our tour times to accommodate some last minute requests - and he would follow up by WhatsApp to ensure that everything was going smoothly. On our second full day our driver took us to Oia, introduced us to some classic Santorini views, shops and unique finds (such as the book store and the nuts and pistachio store in Oia) and then to Imerovigli, where we hiked to Skaros Rock, to breathtaking views of Oia and the whole caldera. We then went to pre-historic and Archeological museums, Emporio and all the way to Cape Akrotiri to see the Venetian light house. Each day, our driver greeted us with a big warm smile and with offers for ice cold water whenever we returned to our car after each sightseeing stop. By the time we left Santorini, we had fallen in love with the island! We would highly recommend our driver and our guide to anyone looking for privately guided tours with a historical/cultural emphasis on Santorini.
We traveled by high speed ferry (all arranged by our travel agent) to Mykonos and were picked up by our travel company's representatives and brought to our hotel. After the warm and courteous greeting and follow up in Santorini, we were a bit surprised by the quicker (more rushed) pace of Mykonos, which was reflected in our interactions with the agency representatives. Our hotel in Mykonos was nice, but not as convenient as our Santorini hotel had been. We felt a little worried walking the road (no pedestrian path) with busy traffic into Mykonos town, even though it was just 10 minutes away. We only stayed one night in Mykonos, and our highlights were a boat ride and private guide to the UNESCO Delos Island and a walking tour with a private guide of Mykonos (including a museum visit). Coincidentally, our guide to Delos is the daughter of our walking guide in Mykonos, so we had both mother and daughter guiding us during our short Mykonos stay. Our Delos guide, had had a long hot day with different tours by the time she met up with us for our 5pm tour, and it showed, as she gave us the information of Delos, but wasn't keen to stop or pause when we wanted to take photos or just soak in the atmosphere a bit longer. Her mother, who gave us the walking tour the next morning, seemed more passionate about sharing the unique aspects of Mykonos' history and we enjoyed our walking tour with her.
After Mykonos we took a short flight to Athens, and our guide and driver were waiting for us. Once settled into the spacious minivan (clean, Mercedes minivan) Our guide shared historical and anecdotal details of Cape Sounion, and the Temple of Poseidon, which we visited. After the three hour tour, and she dropped us at the hotel in Athens. Here, I must mention that our travel agent was willing to allow us to directly book with the hotels that I have loyalty status with so that I would receive my SPG points and travel benefits (some travel agents would not allow this). This hotel has a great reputation and our interactions with the staff during this visit was great. We only stayed 2 nights at this hotel, with our one full day in Athens being spent taking a one day cruise to Hydra, Poros and Aegina. Of those three islands, Hydra was the most scenic. We took advantage of a short walking tour on Hydra and also the panoramic tour offered by the cruise company on Aegina. Apart from the initial boarding chaos (our transfer bus from our hotel to the port was one of the last to arrive and so we got onto an already crowded cruise ship without much information before leaving port on where to sit or what to expect), the one day cruise turned out to be a good one. The following morning we checked out and started our four day private road trip with our driver and our guide. We traveled in a Mercedes minivan with plenty of room for luggage as well as space inside the van for the long drives. Each stop along the way was uniquely picturesque, historically significant, and a feast for our senses as well as our hunger to learn more about Ancient Greek civilisation and how it impacted Greece and western civilisation today.
Our travels took us to the following sights:
Day 1 - Corinth, Mycenae, Epidaurus and Nafplio. We had to unfortunately skip Acro Corinth as the weather was very wet that day (the only rainy day in our otherwise sunkissed Greek holiday). The chance to visit these UNESCO World Heritage sites was thrilling for all three of us. and our guide provided in-depth historical and cultural context as we visited each location. Finishing up with our day with a one night stay in Nafplio at a hotel which is situated in the middle of an ancient Venetian fortress, was perfect. We learnt that Nafplio was the second capital of Greece (after Aegina and before Athens became the capital) and enjoyed walking through its winding streets with the Venetian influences, which give Nafplio the nickname “the Naples of Greece”.
Day 2 - drive to Ancient Olympia - touring the UNESCO site which was the home for the Ancient Olympic Games and the Sanctuary of Zeus. Again, our guide excelled in sharing his historical knowledge and his passion for sharing about the social and cultural impacts as he pointed out different archeological features and highlights was very apparent. We even had a chance for the girls to do a short sprint in the Olympic stadium!
Day 3 - We stayed overnight after Olympia in Delphia, where we stayed at a boutique hotel. We had not realised that Delphi was situated high in the mountains, and were floored by the views from our hotel room balcony, and enjoyed warm Greek hospitality. The next morning, we went to visit the UNESCO site, including the Ancient Sanctuary of Apollo and the Delphi Museum. After the tour, we took the scenic route from Delphi to Kalambaka, where we stayed overnight in a quaint B&B. The owners welcomed us warmly and had homebaked goods for our breakfast the next morning.
Day 4 - Kalambaka is a short drive from Meteora, another UNESCO World Heritage site. An absolutely amazing feast for our eyes and cultural/historical curiosity, as we soaked in the views of monasteries perched on clifftops and mountain faces, and visited two of the largest ones, Great Meteora and Varlaarm Monasteries. On the way back to Athens, we also stopped off quickly to learn about the historical significance of Thermopylae. Our guide continued to be a wealth of historical information, interesting facts, and anecdotal stories to bring the historical and cultural contexts alive for us.
Our last two nights in Greece were spent in Athens, staying at the same hotel again. We explored Athens on the penultimate day with our guide, taking a private Athens walking tour. This included Monastiraki Square, the Acropolis, the Parthenon, the Erectheion, the Acropolis Museum, and seeing other sights such as Hadrian’s library, Hadrian’s gate, the Plaka, and the historic/tourist district of Athens. We saved our last day to do some shopping before being picked up by our driver for our transfer back to Athens airport for our flights home.
In summary, this travel company and our agent, did a fabulous job making all the arrangements for us, from transfers, to hotels, and every little detail for our private tours. Our agent was available before the trip by Skype and email, and during our time in Greece by phone and WhatsApp. In addition, our agent ensured that our time on the islands was supported by able partner agencies. In particular, the Santorini partner agency are to be commended for the memorable stay we had in Santorini.
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