Mainland & Island Hopping Greece Adventure Tour

What to expect on this itinerary
From the cradle of Western civilization to island hopping across the Aegean, welcome to two weeks of chic cafes, charming villages, lively heritage, and magnificent old ruins. Mix the classical past with the relaxed coastal present, then travel into time-warped settings, where you live out mythical tales. Handcrafted to incorporate a complete variety of Greek highlights, this is the very best of the mainland and island Greece in two weeks.
Customizable Itinerary
Athens – Keeping it Local in Plaka
Local tavernas entice you with aromas and clinking plates while artisanal shops engage through splashes of color and antiques. Decadent buildings juxtapose with 3,000-year-old relics showing their age. You will be in Plaka, a bustling local neighborhood beneath the glowing Acropolis. Time has moved slowly here, and it may seem that you are still in the 17th or 18th century, especially when you get lost in a whitewashed maze. In some ways, Plaka looks as you might imagine a blue and white Greek island village, however, it has a gritty local edge that most visitors find to be utterly charming. Your guide will meet you at the airport for your short transfer to your boutique hotel in Plaka. After a brief orientation, tour, you will have a free evening to make up your own impressions.
What's Included:
Athens – The Ancient Acropolis and More
Athens – Lesser Known Athens Highlights and Heritage
Nafplio – Legendary History On Route to the Coast
Nafplio – Exploring Psaromachalas Fishing Village and Epidaurus Theater
Meteora – More Venetian Charm and Mountaintop Monasteries
Santorini – A World-Famous Sunset and Setting
Santorini – Vineyards and Villages
Santorini – Catamaran Cruising and Coastal Highlights
Koufonisia – Off the Beaten Track Beach Indulgence
Mykonos – Chic Mazy Wonder of the Cycladic Island
Mykonos – Discovering the Wonder and Mystique of Delos
Mykonos – Departure
Trip Highlights
- Dive into 4,000 years of history with a two-night stay in Nafplio on Peloponnese
- Watch the famous Santorini sunset from your own infinity pool
- Explore the ancient world’s magnificence with a private tour of the Athens Acropolis and Agora
- Escape to Koufonisia and an off the beaten track island beach break
- Soak up the chic and charm of Mykonos, Greece’s celebrated island destination
- Ascend to the dramatic mountaintop monasteries of Meteora, islands in the sky that defy description
- Watch a summer performance in the fabulous Epidaurus Theater
- Savor the traditional Greek atmosphere, especially during three nights in Athenian Plaka and a stay in Oia, Santorini
- Connect the ancient eras by exploring Corinth and Mycenae
- Discover the mystical, sacred island of Delos, home to many Greek gods and fabulous old ruins
Detailed Description
Quintessential Greece is difficult to describe. It could be the remains of a classical era, found when exploring monuments like the Acropolis or Epidaurus Theater. Or it could be feeling the Greek heritage in blue and white neighborhoods, like Oia on Santorini or Plaka in Athens. For some, Greece is all about island hopping and beaches, along with a sunset cruise and some seafood indulgence. Others point to the uniqueness of destinations, such as Meteora’s mountaintop monasteries and Venetian histories in Nafplio. Ultimately, Greece is a destination that covers over 4,000 years, meaning ideas of quintessence are different for everyone.
This two-week highlights tour has been handcrafted for first-time visitors to Greece. It covers many of the major highlights, mixing six nights on the mainland with seven nights of Aegean island hopping. You will dive into the cradles of Western civilization, before jumping forward into the late-medieval charm of a whitewashed village. You will experience the chic contemporary atmosphere of changing villages, particularly on the island of Mykonos. In some places, you will be completely alone with history, marveling at how the stories have been preserved. In other places, you will be nearly alone on the beach or coast, watching the sunset or wiling an afternoon away.
Greece provides something for every kind of traveler, and this two-week itinerary ensures you fully explore what is on offer. Beginning in Athens, you can travel back in time, with the Acropolis and Agora beyond comprehension. The lively Plaka neighborhood provides an immediate immersion in the Greek tradition, and you will find that there is more to Athens than the famous temples. Travel to the Peloponnese peninsula on day four, stopping at the ruins of Corinth and Mycenae on route to Nafplio, a charming coastal town with 4,000 years of history. Meteora is your final mainland stop, where monasteries cling to rocky pinnacles as if they’ve been created by a fairytale.
Santorini is covered with whitewashed houses with bright blue shutters and domes, your bewitching setting for the next three days. Explore volcanoes and vineyards, walk the pedestrianized villages, find more boggling ruins, and take a cruise at sunset. Koufonisia is Greece from the past, a tiny island yet to be popularized by tourism. Spending two days here is all about lounging on the beach and doing very little, which is quintessential Greece in its own little way. End the vacation on Greece’s most famous island, Mykonos, where there are lively cafes and famous windmills, plus a day trip to the sacred island of the gods, Delos. Looking for the best Greece vacation ideas? Consider browsing our Greece travel reviews page.
Starting Price
$4,600 per person (excluding international flights)
Your Zicasso trip is fully customizable, and this sample itinerary is a starting place for your travel plans. Actual costs are dynamic, and your selection of accommodations and activities, your season of travel, and other such variables will bring this budget guideline up or down. Throughout your planning experience with your Zicasso specialist, your itinerary is designed around your budget. You can book your trip when you are satisfied with every detail. Planning your trip with a Zicasso travel specialist is a free service.
What's Included
- Accommodations
- In-country transportation
- Some or all activities and tours
- Expert trip planning
- 24x7 support during your trip
Your final trip cost will vary based on your selected accommodations, activities, meals, and other trip elements that you opt to include.
Verified Traveler Reviews
Based on 1616 reviews
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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We absolutely loved this travel company and Greece. Everything they did exceeded our expectations. We spent two days in Athens and two nearby, (1 in Delfi and one in Kalambaka for Meteora), then 4 in Crete and 1 1/2 in glorious Santorini. I stumbled upon Zicasso while looking for options in Greece. We usually arrange much of our own trips using VRBO for accommodations but since we wanted to see islands also and Greece was totally new to us, we decided to check out Zicasso. We got feedback from two agencies and both sounded great. However once we spoke to our agent at this travel company, we weren't really interested in talking to anyone else.
She really listened to us and from the beginning suggested a perfect itinerary with the ideal mix of guided and independent travel, all within our budget. We wanted to see all of the ruins and historical sights, but also meander about and check out the charming towns, shopping and incredible food ! I'm a bit of a picky eater, but had no problems in Greece. The food was fabulous, the people very friendly, and everyone speaks English as a second language. Check out this travel company. You won't be disappointed. Zicasso was a great way of finding qualified agents if you want to get quotes from multiple travel companies.
Your overall comments on Zicasso
I think your service was great and did exactly what you advertised. I would use Zicasso again for sure, for more countries.
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Terrific itinerary, wonderful personal service
We spent two weeks in Greece, Thessaloniki, Crete, Nafplion (with stops at Corinth and Marathon), Athens and Santorini, all travel by air not by boat. Our travel agent arranged it all with ease including our need for scent free rooms and a fitness centre that opened at latest 6am, and had good equipment. The tours and tour guides in each place were top notch as were the hotels. We discovered some excellent Greek wines and some amazing food. In fact the chef at the hotel in Santorini was the number one up and coming chef in Greece. Our agent even checked us in to all of our flights, emailed the boarding passes to our hotels and had them printed and put in our rooms. I would highly recommend this company and this travel agent for anyone wishing a wonderful trip to Greece.
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A carefree vacation in Greece - the things dreams are made of. And thanks to our travel company, in particular our agent, the trip was, indeed, a dream come true. Our agent saw to every detail. The trip was completely carefree for us because he planned it with such extreme care that we had absolutely no worries. Details, details, details - all planned in advance by our agent. All we had to do was show up, relax and enjoy. Day after glorious day.
I could go on and on about the splendors of Greece. It is an incredible place with ancient archeological sites, beautiful seaside villages and islands too many to count. Suffice it to say, it is a wonderful destination. But plan ahead to take it all in - or better yet - have this agent plan it for you! (I just might be his biggest fan right now.)
During our trip, we noticed people looking lost, unsure of where to turn for help; people pouring over maps trying to determine how to get from one place to the next; large groups, walking in lock-step, straining to hear their guide, or standing in line, waiting to get back on the bus. That was never our experience. Arriving at the airport, our driver was waiting to whisk us off to our hotel, holding a placard bearing our name. Ready for our tour of Athens, there was our guide waiting in the hotel lobby. Touring the Peloponnese? A private driver who was friendly, knowledgeable, helpful picked us up at our hotel in Athens and stayed with us for the better part of a week. Our driver didn’t just drive us from place to place. He carried our bags into the hotels and spoke to the desk clerks on our behalf, he told us interesting things about the areas we were driving through, he answered questions, he made suggestions, he laughed and talked with us. Arriving at archeological sites, we were always provided a private, state licensed guide. Our driver always made contact with that individual, walked us to where the guide was waiting, introduced us and then stepped back and waited for us to return. On a daily basis, while we were off seeing the sites, he confirmed our plans for the next day to be certain all was in order.
On the subject of the state licensed guides, arriving at Epidaurus, Olympia, Delphi and the rest, we had an educated, licensed guide all to ourselves. While others clustered in groups of 20 or 30, we casually walked and talked with our guide - just the three of us. And all of our guides were extremely knowledgable. They spoke with ease about the history of the site, answered our questions, added interesting details and stories we might never have otherwise heard. We didn't walk through the museums and sites reading placards, we had a guide pointing things out and chatting about them. Many times, we noticed individuals sidling up to us, getting close to listen in. I couldn’t blame them; I always felt we had the best of the best when it came to our guides. At one site, I thought three men from Germany were going to try to hire our guide away from us, but they asked for her card for another day - having overheard how good a guide she was. Our agent hand-picked every guide for us in advance and he certainly knew who to choose.
The hotels our agent chose for us were just perfect. I don't need a spa or even a swimming pool when I travel. I am there to see the sights. But I do need a very clean, very comfortable bed and I greatly appreciate a view that shows off the location. We got that in our rooms throughout the trip - and our agent had to choose lots of hotels for us. We spent one or more nights in Athens, Hydra, Nafplio, Olympia, Delphi, Kalabaka, Mykonos and Santorini. Our agent hand-picked every hotel and again, certainly understood what we were looking for.
Carefree is what we wanted and carefree is exactly what we got! A ferry strike necessitating a change in our plans? No worries, our agent is making alternate plans - handling a situation we would not have even known existed until we got to the ferry dock. A desire to change to a hotel in a slightly different location? No worries, our agent makes arrangements and sends a car. There may well have been other glitches we were never aware of - everything was handled behind the scenes as far as we were concerned. Everything ran smoothly, like clockwork.
The trip was a nice balance of planned activities and free time. We never felt lost or at a loss. We knew our agent was always just a phone call away, and others, (our guide in Athens, our guide on Santorini, our Peloponnese driver), were quick to say, “Just call me if you need anything.” And we knew they were sincere. The people we met in Greece were just wonderful. It was obvious they wanted us to enjoy and appreciate their country. It was the fabulous, carefree trip of our dreams. Thank you!
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