Best Greek Island Hopping Vacation for Travelers Over 50

We had a wonderful experience with our Zicasso travel specialist while planning our vacation in Greece. We had a group that consisted of two families; in total, eight people. Our travel specialist gave us recommendations based on the types of activities we wanted to do and the types of islands we were hoping to experience.

We stayed two nights in Athens, three nights on Naxos, and three nights in Santorini. The accommodations were fantastic! Every tour guide and driver was helpful and so kind.

When we wanted to add a stop in Naxos for an impromptu lunch, our guide was happy to detour and bring us to a place with the best gyros that the locals really enjoy! Everyone made us feel at home. Thank you for a beautiful trip and all the lovely memories!

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Zicasso's travel expert was very professional. She answered all my questions promptly and made sure to book the tours and hotels that fit our needs. Highly recommend.

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Our 11-day honeymoon in Greece was nothing short of magical—and we owe so much of that to our Zicasso travel specialist and the entire team at her company. From the very start, they worked within our budget and offered a flexible payment plan that made planning feel manageable and stress-free.

As our trip approached, we had a thorough planning call with our specialist. She walked us through every detail of our itinerary, which completely put us at ease. That level of preparation meant we could focus on enjoying the moment instead of worrying about logistics.

Once we landed in Athens, the travel company was just a WhatsApp message away. Anytime we had a question—no matter how small—they responded within minutes. That kind of real-time support made us feel cared for the entire time.

The accommodations they booked were absolutely out of this world. Each hotel felt handpicked just for us—luxurious, romantic, and incredibly welcoming. It was clear the company has strong relationships with local vendors because we were treated like royalty everywhere we went.

As a gay couple, we also appreciated how safe, inclusive, and celebrated we felt throughout the trip. Every detail was thoughtfully planned with us in mind.

We’d recommend our travel company 1,000 times out of 10. If you're planning a gay honeymoon—or any trip to Greece—look no further. This was truly the trip of a lifetime.

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Zicasso's travel specialist and her company did an amazing job of planning the most incredible and memorable trip for my family of five.

Every detail was meticulously thought out and perfectly executed. Every transfer was spacious and, thankfully, air conditioned. Each boutique hotel booked was unique and beautiful, with stunning views and amenities offered. Every excursion with English-speaking guides was incredible. The guides were knowledgeable and super-friendly.

We can't thank our travel specialist and her team enough for this amazing trip. We have memories for a lifetime!! I highly recommend using her for your next trip to Greece or Europe.

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It was our family's first time visiting Greece. We've always wanted to see the country and there were so many good things we'd heard about Greece.

There were a couple of things that made this trip very special. First, our youngest daughter's request for her 16th birthday was to go as a family and celebrate it in Greece. Second, none of us had ever been to Greece (on our previous trips, either my husband and/or I had been there or it was our family's second time there), so experiencing it together for the first time was really special.

Zicasso gave us two very good Greek travel companies. Both presented interesting itineraries to us. It was a year of planning and I'd gone back and forth with both travel companies with revisions of itineraries and, of course, the cost.

What made us choose this travel company was that the specialist was very honest, upfront, and very accommodating. He gave his honest opinion when I asked him about certain excursion activities or even restaurants (social media makes it really look good, especially for people who have not been there), and he did not pressure or force us into doing activities that did not interest us. He wanted to make sure we got to experience the best, but he was also very mindful of the costs. I had many back and forth conversations with him via texts, emails, or phone calls. He wanted to get to know our family. When I told him about our daughter's 16th birthday requests, he made sure he got every detail of what would make her birthday special. He also asked me about the interests of our eldest daughter because he wanted to surprise her with something special from Greece. That says a lot about the travel specialist and his company; they are personal and it's not just pure business for them.

A few days before we left the US, he called us so we could reschedule our flights (Santorini to Athens) to an earlier time going back home because he was concerned we may miss our connecting flights. Who does that? This just shows he checks every detail and wanted to make sure that even before we left the US, up to the time we arrived back home, everything was taken care of.

We had the best vacation in Greece. We did not worry about anything the entire time. The travel company was in constant communication with us. They created a WhatsApp group chat which made it so much easier. They gave us daily reminders and they arranged everything for us. We felt that the entire trip was customized for our family. The "Mamma Mia" island tour and birthday celebration for our daughter was perfect. The restaurant in Kolios was a great recommendation, and when I asked him to reserve the specific table and have a little birthday decoration for my daughter, it was accomplished.

Chania was amazing; both me and my husband loved this place. The view from our hotel room on Zampeliou Street, overlooking the old harbour and the Cretan Sea with the lighthouse, was breathtaking. We enjoyed walking through the streets of the Old Town of Chania.

We thought Santorini would be overcrowded, but we had a great tour guide who knew where to take us first to avoid crowds, and he gave us really helpful advice to go around the island. He took us to the little hidden alleys and showed how locals live. We ended up really loving the island.

We enjoyed every activity planned for us. We enjoyed our stay at our hotels. Mine and my husband's favorite were the hotel in Kalamata and the one in Chania. We really liked the view of the Acropolis from our rooms at the hotel in Athina, and that hotel was very convenient. We also enjoyed their breakfast there. The girls enjoyed the hotel in Skiathos because of how close it was to the beach, and they loved the "Mamma Mia" boat tour.

We each have our own favorite activities/tour/tour guides, but overall, our family had an amazing time in Greece – the way the travel agent and the entire team did a phenomenal job. The way the itinerary was put together and the timing for each place/island was just perfect for us. They exceeded our expectations. We fell in love with Greece, the culture, and the people, who were all so kind, nice, and very hospitable (not once did we have a bad encounter). We will definitely go back; there is so much more to explore and we'll definitely be working with this travel company in the future.

We only have good things to say about our Greece vacation and we highly recommend this travel agency. We've been to other countries and worked with other travel companies. In our opinion, this one was the best travel company we've ever worked with.

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Zicasso's travel agent took great care of my family, planning an excellent trip, with revisions based on our interests, and was quick to respond to my emails. He took care of the necessary arrangements when the ferry was unexpectedly cancelled.

We stayed in beautiful hotels and enjoyed our tours with knowledgeable guides and drivers. Our trip to Delphi and Meteora was a highlight of our trip. We had a great driver there.

Highly recommend!

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