Ultimate Greek Island Hopping Getaway for Seniors

Paros, a fishing village in Greece.

What to expect on this itinerary

This 8-day island-hopping tour of Greece has been handcrafted to allow you to partake in some of the most incredible experiences that an island-hopping excursion can afford. From the famed shores of Santorini and Paros to Naxos and Mykonos, this epic journey will immerse you in volcanic landscapes, natural hot springs, charming fishing villages, amazing cuisine, and much more.

Countries Visited

Greece

Places Visited

Mykonos, Santorini, Paros, Naxos, Rhenia, Delos

Suggested Duration

8 Days

Customizable Itinerary

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Day 1

Santorini – Arrival

When you land on Santorini, your private driver will greet and escort you to your accommodation in the heart of the city. You will have a moment to relax and refresh after your long flight. Nothing specific will be planned today, but your guide can provide you with excellent dining recommendations so that you can get a sample for the local culture. You can dine with the locals or from the respite of your accommodation.

What's Included:

Tour
Accommodation
Transfer
Day 2

Santorini – Santorini’s Highlights

Day 3

Santorini – Private Catamaran Cruise

Day 4

Paros – Volcano and Hot Springs

Day 5

Naxos – Sunset Dinner Sail

Day 6

Mykonos – Naxos & Mykonos

Day 7

Mykonos – Rhenia & Delos

Day 8

Mykonos – Departure

Trip Highlights

  • Witness the incredible sites of Santorini on a private tour
  • Receive your first impressions of Naxos on a sunset dinner sail
  • Discover the delights of Rhenia, Delos, and Mykonos
  • Rub elbows with friendly locals during a farm-to-table feast
  • Embark on a luxurious private catamaran cruise and sail along Santorini’s coast
  • Witness the wonders of Santorini’s volcanic landscapes and bask in the island’s natural thermal hot springs
  • Stroll around the Old Town on Paros and peruse the island’s most charming fishing villages

Detailed Description

This 8-day island escape will begin in Santorini. For your first evening in Greece, you will indulge in a meal of delicious Greek fare. It can also be complemented with a excellent glass of wine

The next day, your private guide will lead you on an exciting tour of the island’s most iconic landmarks. This adventure will include visits to Firostefani, Fira, the Blue Domed Church, Oia, and much more. Following your highlights tour, you will embark on a catamaran cruise. During your sail, gorgeous you will have the luxury to visit Red Beach, White Beach, and Palea Kammeni.

Day four will find you beginning the morning with a visit to Santorini’s volcano and thermal hot springs. Here, you will learn fascinating facts about the island and its  amazing landscape before indulging in a pampering session. Paros will be your next destination. Here, you can take a stroll around Parikia’s Old Town for your first evening.

The morning of day five will begin with your guide leading you to discover Paros’ charming fishing villages, including Naoussa and Lefkes. Following your tour, a ferry will whisk you to nearby Naxos, where you can indulge in a sunset dinner cruise.

Day six will begin with a private tour of Naxos’ most revered sites. Then, you will sail to Mykonos for an immersive tour. Your final full day in Greece will find you sailing away from Mykonos for a delightful day trip to Rhenia and Delos.

Starting Price

$3,400 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

The starting price is based on travel during the low season for a minimum of two travelers staying in shared 3-star accommodations. Please inquire for a custom trip quote based on your travel preferences and travel dates.

4.9

Verified Traveler Reviews

Based on 542 reviews

Greece Anniversary Vacation Review: Athens, Mykonos, Santorini, Crete, Catamaran Cruise, Cooking Class, Wine Tasting, Hiking, Local Cuisine, 2-Week Trip

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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Greece Tour Review: Athens, Mykonos, Santorini, Crete, Chania, Acropolis, Delos, Rhenia, Knossos Palace, Wine Tasting, Sunset Cruise, Food Tour, Olive Oil Tour, 2 Weeks

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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Greece Tour Review: Athens, Paros, Antiparos, Naxos, Santorini, Crete, Olive Oil Tasting, Wine Tasting, 18 Days

I could not ask for a better partner and travel company than this one. I reached out on short notice, looking to plan a two-and-a-half-week trip to Greece to explore Athens and some islands (Paros, Antiparos, Naxos, Santorini, Crete). I provided our Zicasso travel specialist with some of my interests, guidelines for my travel style, and the kind of trip I was looking to plan, and she delivered all of that and more!

She developed an itinerary that provided me with exactly what I was looking for and gave me some specific recommendations for restaurants, experiences, and things to do in each location. It was an absolutely incredible trip, all made possible by our travel specialist and her team. Her assistance, guidance, and the time and attention to detail that she put in made it an amazing journey. She was incredibly responsive and even checked in with me throughout the trip to make sure everything was okay and to provide me with any updates. Everyone should only be so lucky to have our travel specialist help plan such a wonderful experience, and I can't wait to work with her again to plan another fantastic adventure!

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Greece Trip Review: Athens, Crete, Chania, Santorini, Paros, Ferry Ride, Wine Tasting, 12 Nights

We loved our Greece trip and had so much fun with our activities. Of the referred travel companies from Zicasso, we gravitated to this travel company because of its personal attention to detail regarding our vacation wishes. Our travel specialist took the time to listen and tailored an itinerary that captured our interests. It did not disappoint. This was our second trip through Zicasso and, as with the first, the guides, drivers, and support were on point.

The travel company lined up excursions with the nicest and most engaging people. From our arrival at the airport, they made us feel welcomed and special. We went to the head of the line again and again, and avoided much wasted time. The guides and drivers were genuinely glad we were there and our enjoyment was of the utmost importance. They always seemed to go above and beyond expectations with the knowledge they imparted and the amount of personal attention they provided.

In general, we found the people of Greece to be so nice and that really made the difference on this trip. Need a restaurant suggestion, just text our guide, as he was always right. Need a reservation, just text the travel company through WhatsApp and it was made. We are still texting a couple of the guides for additional information and recommendations for friends traveling to Greece.

Traveling by boat was one of the best decisions we made. The overnight ferry from Athens to Crete was an unexpected pleasure, and we would recommend it over air travel anytime, as it was very relaxed. Chania was engaging, Santorini was beautiful, and Paros was the ultimate place to chill out before traveling home.

We can't stop talking about how much fun we had in Greece. Thank you, the travel company, our travel specialist, and Zicasso. We will be in touch about our next adventure!

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Greece Vacation Review: Athens, Naxos, Santorini, Acropolis, Wine Tasting, 11-Day Trip

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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Greece Vacation Review: Naxos, Athens, Cuisine, Walking Tour, 10 Nights

Zicasso's travel company made our bucket-list trip to Greece come to life! They organised all our tours and transportation, worked with us to provide activities that were in line with our interests, and even gave detailed information on suggested itineraries for our free days.

Some highlights included the walking tour(s) of Athens, our trip to see Santorini, and the best steak I have ever had at a beach hotel in Naxos! Our only suggestion is that we went on a day tour to Delos which was self-guided. There is so much history there though that a guided tour would have been helpful. I would definitely recommend booking your tour with them!

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Customizable Itinerary

This is a sample itinerary to inspire a personalized trip designed with your travel specialist.

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