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
$5,700 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 611 reviews
We had a wonderful and memorable trip to Greece, thanks to the Zicasso travel specialist’s excellent planning. In addition to exploring Athens, she designed a seamless road trip across the Peloponnese Peninsula that took us to beautiful beaches and ancient castles in Messinia, Voidokilia, Pylos, Methoni, Monemvasia, and Nafplio. She also provided clear directions and recommended great stops to break up our drives, including Mystras Castle and the beautiful Polylimnio Waterfalls.
Our hotel accommodations were excellent throughout the trip and we really enjoyed our stay in beautiful Santorini. We also appreciated her restaurant recommendations, which saved us from having to search for places to eat and always led us to great food. She stayed in touch via WhatsApp the entire time, checking in on us and answering our questions whenever they came up. There is so much to see in Greece that we’ll definitely need to go back for another visit.
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We recently returned from an incredible two-week Coral Anniversary trip to Greece and it exceeded every expectation. From the ancient wonders of Athens to the whitewashed villages of Mykonos, the dramatic cliffs of Santorini, and the authentic traditions of Crete, every stop offered something unique and unforgettable. Most importantly, the people we met along the way transformed a beautiful vacation into a truly special experience. The journey took us through Athens, Mykonos, Santorini, and Crete.
Outstanding Planning and Service
Every transfer, hotel, tour, ferry, flight, restaurant reservation, and activity was flawlessly coordinated by Zicasso's travel partner. The itinerary struck a perfect balance between guided experiences and personal exploration, allowing us to enjoy Greece without ever worrying about logistics.
Athens – History, Culture, and Exceptional Hospitality
Our stay at our hotel in Athens gave us incredible Acropolis views and a perfect base for exploring the city. Walking through the Acropolis with our guide and standing before the Parthenon was breathtaking. The Acropolis Museum and city highlights tour helped bring thousands of years of history to life.
One of the highlights of our anniversary celebration was dinner at a restaurant atop Lycabettus Hill. Watching the sun set behind the Acropolis while enjoying excellent Greek cuisine and wine was a magical experience and one we'll never forget.
We would especially like to recognize our driver in Athens. He was professional, knowledgeable, and genuinely invested in making our trip memorable. During our day exploring the Argolis region, Epidaurus, Mycenae, and the Nemea wine country, he provided insights that helped us better appreciate the history and culture of Greece.
What truly distinguished our driver was his attention to detail. While we were traveling along the Athenian Riviera toward Cape Sounion and the Temple of Poseidon, he realized we were hoping for a true seaside lunch experience. Without being asked, he contacted the travel company and coordinated everything to make a last-minute adjustment so we could enjoy lunch by the sea. That thoughtful gesture perfectly reflects the level of service he provided throughout our stay. It turned a wonderful day into one of our favorite memories of Athens.
Mykonos – Relaxation and the Beauty of the Aegean
Mykonos provided the perfect contrast to the historical focus of Athens. Staying at our hotel in Mykonos overlooking the Aegean Sea allowed us to fully appreciate the island's beauty.
We spent time exploring the charming streets of Mykonos Town, admiring the famous windmills, and enjoying the relaxed island atmosphere. A major highlight was our private catamaran cruise to Delos and Rhenia. Sailing through the crystal-clear waters of the Aegean while visiting the UNESCO World Heritage Site of Delos gave us a fascinating glimpse into one of the ancient world's most important religious centers. The secluded waters around Rhenia were stunning and provided some of the most beautiful scenery of our trip.
Santorini – Spectacular Views and Unforgettable Sunsets
Santorini is every bit as beautiful as the photographs suggest and somehow even more impressive in person. Our stay in Oia overlooking the caldera was breathtaking. Whether enjoying breakfast with panoramic views or simply walking through the village, every moment felt special.
The wine-tasting experiences at a winery were outstanding. Sampling the island's distinctive Assyrtiko wines while learning about Santorini's unique volcanic terroir gave us a new appreciation for Greek winemaking. The carefully paired food-and-wine experiences were among the culinary highlights of the entire trip.
Our private sunset catamaran cruise around the caldera, White Beach, Red Beach, Black Beach, hot springs, and the volcano was another unforgettable experience. Watching the sunset from the water while enjoying dinner and local wine created one of the most memorable evenings of our anniversary trip.
Crete – The Heart of Greece
As amazing as Athens, Mykonos, and Santorini were, Crete became our favorite part of the journey.
Our quick stop at Knossos Palace and the historic city of Rethymnon allowed us to learn about the Minoan civilization and experience the rich blend of Venetian and Ottoman influences that define the island. The old Venetian harbor in Chania was equally impressive and provided a spectacular setting for our stay.
Samaria Gorge
One of the most rewarding experiences of our entire trip was hiking the Samaria Gorge. Covering 11 miles through one of Europe's most spectacular natural settings was challenging and incredibly rewarding. The dramatic cliffs, pristine landscape, and sheer scale of the gorge were unlike anything we had experienced before.
A tremendous part of that experience was our guide. Our guide brought expertise, enthusiasm, and a genuine passion for Crete that elevated the hike far beyond a typical excursion. His knowledge of the region, local culture, and natural environment made every step more meaningful.
Kissamos Villages and Cooking Class
Our final full day in Crete may have been the most authentic and memorable day of the entire trip.
The tour of the traditional villages of Kissamos provided a fascinating look at everyday Cretan life. Learning about olive oil production, tasting regional products, and experiencing rural villages gave us a perspective on Crete that most visitors never see.
The cooking class that followed was exceptional. Our host created an atmosphere that felt less like a tour and more like spending a day with friends. Together with his mother, he shared not only recipes, but the stories, traditions, and values that make Cretan culture so special.
For anyone traveling to Crete, we cannot recommend this tour company highly enough. Their commitment to authentic local experiences is truly outstanding.
This trip exceeded our expectations in every possible way. We experienced world-famous historical sites, breathtaking landscapes, incredible food and wine, beautiful hotels, and unforgettable adventures. Yet what we will remember most are the people who made the experience so special.
We returned home with wonderful memories, a deeper appreciation for Greek culture, and gratitude for everyone who helped make our anniversary celebration the trip of a lifetime.
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Our trip to mainland Greece, organized by Zicasso's tour agency, was the best luxury trip my husband and I have enjoyed to date. Every hotel and site tour guide was carefully selected for our needs and interests, and they were all outstanding! Our driver for the entire trip was warm, courteous, and highly professional. We saw all the sites we'd requested and a couple of fun surprises along the way.
We travelled from Athens to various spots in the Peloponnese, then through the lush plains of Thessaly to Meteora, and then, finally, Thessaloniki. The accommodations were superb, with special shout-outs to the hotels in Athens, Nafplio, and Thessaloniki. We spent our last night at the Athens airport hotel and were so glad we did. The suite was stunning and completely soundproof. The food during our trip was incredible (especially at the hotel roof restaurant in Thessaloniki) and traveling by car allowed us to fully appreciate the gorgeous mountain and sea views. The Greek people were warm and super-friendly. Nearly everyone spoke English.
When we arrived in Athens, our travel consultants met us at our centrally located, fabulous hotel with all the info we needed, as well as a Greek cell phone and lovely gifts. All instructions were clear and details perfectly arranged. We really can't exaggerate how wonderful this trip was and we'll definitely return to this company for our next trip to Greece. 10/10 stars, though they deserve an even higher rating.
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This was one of the best-organized trips my wife and I have taken in Europe. Zicasso had put us in touch with Zicasso's travel specialist. She called us to ask about the dates, interests, islands we wanted to see, sights, etc. She formulated a travel plan including hotels, transfers, and tours (including food tours). We discussed the plan, chose hotels based on our budget, and finalized a tour plan with her.
Right from the moment we arrived at Athens airport, everything was taken care of for us. We had a limo waiting, even though it took time to go through the EU's new immigration system. Our hotel in Athens was right next to the city center, with a beautiful Acropolis view from our balcony. The room was comfortable and spacious, and ready when we arrived at 2 pm. Our travel specialist even suggested a restaurant to celebrate our anniversary and made reservations for us, as we were unable to do it online.
The next day, we had a tour of the Acropolis conducted by a professional tour guide. It was a good two-hour walking tour and we enjoyed it very much. The tour guide was very knowledgeable, took time to explain the history, which we are interested in, and also took some amazing pictures for us. We had free time to go to the city center to shop and try out some of the Greek taverns.
From Athens, we went to Mykonos by ferry. Ferry tickets were sent on a WhatsApp group chat created by her. Our limo came at the designated time and our ferry trip was easy and very enjoyable. On arrival, our limo was waiting to take us to our hotel in Mykonos, located on top of the hill, with a balcony overlooking the central area and a scenic sea view. It was easy to go down and see the shops, windmills, Little Venice, and explore the city center that day. Nighttime was party night, with almost everything open late.
The next day, we had a private Jeep tour of the island. We went to different parts of the island to explore. Our driver and tour guide were very thorough and patient, and it was a very enjoyable tour.
The following day, we were taken by a tour bus to the port, where we went on a private tour of the Delos and Rhenia islands. The tour guide was very knowledgeable and pointed out the sights of an ancient civilization. Lunch on the boat was basic, but on the whole, it was a very informative tour.
We then left for Santorini by ferry. Again, ferry tickets arrived a day before on WhatsApp. We requested an upgrade from basic tickets to Club Class/Platinum Class for the rest of the tour, which was immediately arranged and payment was accepted by credit card. In Santorini, we stayed at our hotel, which had a beautiful view from the balcony and the breakfast was superb, made to order, with the rooftop restaurant having spectacular views of the caldera. It was just awesome! In the afternoon, a tour guide took us in a van and showed us the sights, including the Three Bells of Fira. We did not have to wait anywhere, as the guide knew exactly how and where to go to see the sights and take photos. We learned a bit of history of the island.
The next day, we had two wine-tasting tours, first to a premium vineyard and then to the oldest winery in Santorini. Our tour guide and van arrived on time everywhere for a well-conducted and planned private tour.
On the third day, we went on a semi-private sunset cruise to the volcano, hot springs, and beaches. It was a well-conducted tour with a BBQ on the boat! The crew even accommodated my shellfish allergy by cooking the chicken before cooking the seafood on the BBQ. The food was good and, more importantly, the crew was friendly and very caring. The crew members took some beautiful pictures of us against the spectacular Santorini sunset.
We left for Crete the following morning by ferry. Everywhere, we had private transfers waiting to take us and we did not wait anywhere to be transferred. In Heraklion, we were staying at our hotel in the city center and therefore had access to some very nice traditional Greek restaurants where the locals went for dinner. The following day, we had a private tour of Knossos Palace with a very friendly and knowledgeable tour guide. On our return, our limo was waiting for us to take us to Chania in Crete.
Our journey to Chania took us two hours and was very informative and enjoyable, as our driver pointed out a number of sights on the way. Our check-in at our hotel in Chania was quick and efficient. The hotel even sent us a bellboy to the drop-off point (cars are not allowed inside) to help with our luggage. The hotel room was spacious and had a balcony overlooking the waterfront, the lighthouse, and all the restaurants in the area. The next day, we were taken on a private olive oil tour and, in the evening, a food tour with a tour guide who spoke seven languages and knew the city inside and out!
The following day, a private limo and a private boat took us to Glyka Nera, Loutro, and Marmara. We were able to swim and see some of the beautiful azure-blue water and sights, again in the company of the same tour guide from the previous night. Lunch in Marmara was exceptional. At no time during this tour were we rushed and everything moved at a very easy pace. We checked out from the hotel the following morning for a flight to Athens. The hotel manager helped us with our luggage to the pickup point. Boarding passes were sent on WhatsApp and our check-in and travel were smooth. Everything went like clockwork. Our limo was waiting on arrival and we were taken back to our hotel in Athens, where we stayed the night before our travel home the following day.
At all the sites we visited, our travel specialist even suggested some restaurants to try. These were special in their own ways and not touristy. This tour was very detailed, meticulously planned, and executed by her and the team, who kept in touch with us every day throughout the tour to make sure we had a great time. Thank you for making this a memorable, special, and personalized tour.
This was our 35th-anniversary celebration trip and, thanks to Zicasso's travel specialist and the team, it was a memorable trip for us.
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Excellent! Everything was meticulously planned. All of our tours were very interesting and the drivers were courteous. We went to Athens, Naxos, and Santorini during our 11-day trip. Overall, I think our favorite place was Naxos, with Athens and the Acropolis being second, although the weather that morning was not the best. But our guide was excellent and kept us engaged while fighting rain and wind. As I mentioned, all the drivers and guides were excellent and I would highly recommend this trip. Santorini was beautiful too and the wine tour was extremely interesting. We highly recommend Zicasso.
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We loved our trip! My recent trip to Greece was truly unforgettable and I cannot say enough good things about the Zicasso travel company that helped make it happen.
From the moment we arrived in Athens until our final day, every detail was thoughtfully planned and organized. The itinerary was the perfect balance of sightseeing, relaxation, and experiencing the local culture. We visited incredible destinations, including Athens, Mykonos, and Santorini, and each stop offered something unique and memorable.
The accommodations were excellent, transportation between islands was seamless, and the recommendations for restaurants, activities, and attractions were outstanding. Having everything arranged ahead of time allowed us to fully enjoy the experience without worrying about logistics.
One of the things I appreciated most was how responsive and helpful the team was throughout the planning process. They made the trip feel personalized to our interests and ensured everything ran smoothly.
Greece exceeded every expectation and I am so grateful for the expertise and attention to detail that went into planning this adventure. I would highly recommend this company to anyone looking for a stress-free, well-organized, and unforgettable travel experience. We made memories that will last a lifetime!
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