Best Greek Island Hopping Vacation for Travelers Over 50

Windmill and white house with clear blue sky and ocean in Santorini

What to expect on this itinerary

Your relaxing 8-day Greece vacation for travelers over 50 takes you across the luxurious lifestyles and enchanting scenery of the Greek islands. The ancient wonders of Athens will emerge from the Acropolis while divine images continue to decorate the island of Delos. You can swim in hot springs inside Santorini’s caldera and delight in views of the famous windmills on Mykonos as you bask in Greece’s beauty, prestige, and majesty.

Countries Visited

Greece

Places Visited

Athens, Mykonos, Delos, Naxos, Santorini, Nea Kameni

Suggested Duration

8 Days

Customizable Itinerary

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Day 1

Athens – Introductory Tour of Athens

Your vacation to these idyllic islands will begin when you land at Athens International Airport. A private transfer will whisk you away to your centrally located hotel, and after checking in, you can begin to discover the sights and sounds of Athens at your own pace. One of the oldest parts of Athens, Plaka, will be an excellent place to spend the majority of the day. The streets of Plaka are filled with intriguing shops and restaurants, and with the absence of vehicles in this area, you will be able to freely explore the winding roads.

What's Included:

Transfer
Accommodation
Tour
Day 2

Athens – Explore the Sights of the Acropolis

Day 3

Mykonos – Arrive in Mykonos for a Guided Tour

Day 4

Mykonos – Catamaran Cruise and Visit to Delos

Day 5

Santorini – Tour Naxos en Route to Santorini

Day 6

Santorini – Explore the Island and Relax at the Beach

Day 7

Santorini – Hot Springs of Nea Kameni and Wine Tasting

Day 8

Santorini – Depart for Home

Trip Highlights

  • Explore the wonderful shops and mouthwatering restaurants of Plaka, which is one of the oldest areas of Athens, during your two-night stay in the capital city
  • Marvel at the landmarks of ancient Greece, including the iconic Parthenon
  • Witness the magnificent windmills of Mykonos, which is a symbol of the island, during a privately guided tour
  • Delight in a catamaran cruise across the Aegean Sea along with an exclusive tour of the ancient island of Delos
  • Indulge in a visit to the beautiful island of Naxos, where you will explore its restored olive mills and handmade pottery
  • Relax and unwind at Perivolos Beach, which is one of Santorini’s breathtaking beaches
  • Swim in the amazing hot springs of Nea Kameni, which is a unique, volcanic island near Santorini
  • Enjoy a private wine tour of Santorini to discover and taste the premier blends of the island

Detailed Description

The stunning islands of Greece exude luxury and beauty and are the ideal destination for a senior’s trip. The amazing journey will begin when you land at Athens International Airport, and a brief stay in Greece’s capital city will be the perfect way to begin your trip before transferring to the islands. After you check-in at your luxurious hotel, you can begin to discover Athens at your own pace. A trip to Plaka, which is one of Athens’ oldest areas, will be an excellent place to spend your first afternoon and evening. With many unique shops and savory restaurants, you can begin to immerse yourself in the culture of the city. A private tour of the iconic Acropolis will be the highlight of your next day. You will feel as though you are traveling back in time as you discover the remains of ancient theaters and temples before setting your eyes on the remarkable Parthenon. As the sun sets over Athens in the evening, excitement will mount as you prepare to venture to the first Greek Island of your trip in the morning.

In the morning, the landmarks of Athens will fade into the background as you depart the mainland of Greece via speed boat and begin the picturesque journey to Mykonos. The soft breeze from the Aegean Sea will guide your boat to this fantastic destination, and your afternoon will feature an exclusive tour of the island. Your expert guide will lead you to some of the best spots on Mykonos, including the Kato Milli area, to see the island’s ancient windmills and the village of Ano Mera. The majority of the day will be spent at your leisure as you continue to explore all Mykonos has to offer.

Day four will provide you with another immersive experience in the form of a private catamaran cruise and visit to the nearby island of Delos. Your surroundings will be breathtaking as you cruise over the peaceful waters, and upon your arrival in Delos, your expert guide will lead you on a private tour of the island. The luxurious ride back to Mykonos on your private catamaran will feature tasty snacks and a glass of champagne, which will set the tone for another wonderful evening on the island of Mykonos.

The following morning, you will set off in a private boat for your next amazing destination of Santorini. Along the way, Naxos will prove to be an ideal place to stop for a visit. From ancient attractions to a restored olive mill and a pottery workshop, you will explore much that Naxos has to offer during your excursion. Afterward, you will continue to the spectacular island of Santorini. The next two days will allow you to discover the best of the island through private tours, time at the beach, and exclusive experiences.

Your private tour of Santorini will lead you to the ancient settlement of Akrotiri and the premier village of Fira. Your time at the outstanding Perivolos Beach will be pure luxury, and a dip in the hot springs of the volcanic island of Nea Kameni and a private wine tour will culminate your stay on the island of Santorini. Private transfers will lead you back to Athens International Airport for the return flight on the final day of your vacation. You will return home from this trip with incredible memories, yearning for a return to Greece and its luxurious islands.

Starting Price

$2,800 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.

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Verified Traveler Reviews

Based on 940 reviews

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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Greece Tour Review: Athens, Santorini, Mykonos, History, Culture, Tradition, Local Cuisine, Shopping, 8 Nights

If you're considering a trip to Greece, look no further than Zicasso. Our travel expert planned an unforgettable journey for our family; Athens, Mykonos, and Santorini, and every detail was executed with care, expertise, and passion. 

From the moment we arrived in Athens, we were immersed in the country’s warm hospitality. Our agent made sure we had the perfect balance of sightseeing and relaxation. The historical sites in Athens, like the Acropolis and the ancient Agora, were must-sees.

Mykonos is vibrant yet relaxed. The beaches were beautiful. Every meal on this trip was a highlight. Fresh seafood, local cheeses, olive oil, and delicious pastries—each bite told a story of Greece’s deep culinary heritage.

In Santorini, we were captivated by the island’s charm—whitewashed buildings, breathtaking sunsets, and the deep blue Aegean Sea. We visited traditional villages, giving us a glimpse into the rich cultural traditions that are still very much alive.

Throughout the trip, what stood out most—beyond the stunning landscapes and ancient history—was the friendliness of the Greek people. Their warmth and pride in their culture made every moment feel welcoming and genuine.

Our agent didn’t just plan a vacation—he created an experience rooted in history, tradition, and hospitality. I can’t recommend him and Zicasso highly enough.

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Greece Travel Review: Naxos, Santorini, Crete, Athens, 2-Week Trip

Zicasso's travel planner and her company gave me one of the most phenomenal vacations I have ever had. This trip can be labelled as the trip of a lifetime. She had every detail completed.

Our flights, our transfers, and our ferry tickets were waiting for us at the hotel front desk on every island. We had incredible tours set up, with the most incredible tour guides. We laughed, drank, ate, and celebrated in the most decadent locations in Naxos, Santorini, Crete, and Athens.

We encountered only one hiccup and she was on it within minutes of receiving my email. She stood by her word and solved my issue with professionalism and expedited the correction. I cannot emphasize enough how awesome she is. I cannot wait to plan my trip for next year. I highly recommend her and her company. Thank you for the lifelong memories!!!! You're the best!!

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Greece Tour Review: Athens, Naxos, Santorini, Akrotiri, Winery, Volcano, Walking Food Tour, 8 Nights

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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Greece Vacation Review: Athens, Mykonos, Santorini, Beaches, Scenery, Shopping, History, 9 Nights

Zicasso's travel specialist went above and beyond to curate a fantastic, scenic, exciting, and restful vacation for us and was sure to provide us the best possible accommodations at each destination (Athens, Mykonos, Santorini). We didn't have to worry about one single detail for the entire trip as all of our transport was covered, we had a local contact in each location, and all hotels were pre-paid and perfect. We loved every single second of the trip and would absolutely recommend our specialist for anyone seeking a wonderful visit to Greece!

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Greece Honeymoon Review: Athens, Crete, Santorini, Naxos, 10 Nights

My husband and I had the most amazing honeymoon and owe it all to Zicasso’s travel specialists. We visited Athens, Crete, Santorini, and Naxos. We had an amazing experience in each location and were constantly in awe of the hotels and experiences that had been booked for us. Zicasso’s travel specialist responded to messages almost immediately and sent us our ferry/plane boarding passes before we had even thought of them. We only got home a few days ago and are already looking forward to planning another trip with Zicasso.

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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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