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

Best Greek Island Hopping Vacation for Travelers Over 50

Ratings of Zicasso's Service
Customizable Itinerary

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

Countries Visited


Places Visited

Athens, Mykonos, Delos, Naxos...

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Suggested Duration

8 Days

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.

Customizable Itinerary

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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

$2,699 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.

Reviews of Zicasso's Referral Service

4.93 stars based on 1785 reviews.

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