country flag

Greek Island Hopping Itineraries

Ratings of Zicasso's Service

The Aegean Sea holds a wealth of treasures. Enjoy serene beaches that look out upon azure waters, an ancient history that harkens back to the roots of Western Civilization, and unforgettable cuisine full of tantalizing flavors. From the most popular destinations to lesser-known gems, an island-hopping itinerary from Zicasso will provide you with the perfect Greece vacation.

How Zicasso Works

  1. Describe your dream Greece island hopping itinerary.

  2. We match you with up to 3 top travel specialists. They compete to plan your tour.

  3. Book the trip when you are satisfied.

Ratings of Zicasso's Service

Sample Itineraries

Get inspired with our sample trips below. You can have any trip tailor made for your private travelAny number of days.
Any departure date. Any experience you want.

Potara Gates overlooks Naxos.

Spectacular Island Tour of Greece's Charm

9 Day Custom Tour

From $2,380

The Greek Islands are breathtaking and boast beautiful beaches as well as luxuriant landscapes for you to discover on this 9-day self-drive exploration from Crete to Naxos. Along the way, scenes of the spectacular seascape and moments of indulging in Ancient Greek heritage will fill you with an appreciation of the picturesque encounters and fascinating historical discoveries that await you.

This is a customizable tour. It’s simply a starting point for inspiration and ideas. Each trip is personalized uniquely for you, based on what you want, for your private travel.

Customize

Dome of a church surrounded by flowers in Santorini, Greece.

Greek Island Itinerary for the Ages

13 Day Custom Tour

From $3,505

Discover the fascinating history and explore the breathtaking scenery of Greece on this spellbinding 13-day tour that takes you from Athens to Milos. Your adventures will take you back in time as you visit Ancient Greek monuments, expand your culinary horizons, and spend moments under the Mediterranean sun on the beautiful shores of idyllic islands.

This is a customizable tour. It’s simply a starting point for inspiration and ideas. Each trip is personalized uniquely for you, based on what you want, for your private travel.

Customize

Village of Oia at sunnset.

Island-Hopping Tour of Mykonos, Naxos, Santorini

8 Day Custom Tour

From $2,075

The Greek Islands will awaken your senses on this bewitching 8-day tour, starting in Naxos and ending in Athens. Delight in the sumptuous flavors of authentic Greek cuisine, spend time luxuriating on the white-sand beaches that hug the coastline of Naxos, escape to the secluded beaches of Koufonisia, bask in Santorini's serenity, and satiate your hunger for all ancient history in Athens.

This is a customizable tour. It’s simply a starting point for inspiration and ideas. Each trip is personalized uniquely for you, based on what you want, for your private travel.

Customize

Enjoy a delightful sunset on a boat cruise around Santorini

Family Friendly Greek Island Hopping Vacation

9 Day Custom Tour

From $2,245

The gorgeous Greek Islands are the perfect destination for a memorable and luxurious family vacation. Begin with a stay in Athens to discover the ancient sites of Greece’s capital city. The amazing Acropolis and sight of the Parthenon will leave you in awe before you depart via a private, high-speed boat for the exotic islands of Mykonos, Naxos, and Santorini. Pristine beaches, historical sites, and engaging family activities will be found on every island, and you can discover the best of the Greek Islands during this immersive and unforgettable, 9-day family vacation.

This is a customizable tour. It’s simply a starting point for inspiration and ideas. Each trip is personalized uniquely for you, based on what you want, for your private travel.

Customize

Admire the Theater of Dionysus, the first theater in the world, on your Acropolis tour in Athens.

Romantic Greece Island Hopping Tour

7 Day Custom Tour

From $1,745

When one thinks of beautiful and romantic locations, the stunning Greek islands most likely come to the forefront of your mind. This luxurious, 7-day excursion to Greece’s premier islands is designed especially for couples. A brief stay in Athens begins your trip before you travel in luxury to the gorgeous islands of Mykonos, Paros, and Santorini. Exclusive tours, dinners for two, and spectacular sea views will be found on every island. Add in the delicious food and idyllic beaches, and you have a true paradise on your hands. During this luxurious and memorable adventure for two, experience some of the best that the Greek islands have to offer.

This is a customizable tour. It’s simply a starting point for inspiration and ideas. Each trip is personalized uniquely for you, based on what you want, for your private travel.

Customize

The island of Ios is one of the most beautiful islands in Greece.

Best of Greece Island Hopping Itinerary

8 Day Custom Tour

From $1,995

Amazing views, beautiful waters, and delicious cuisine are just a few things that you should expect during your 8-day, highlights tour through Greece. The islands of Greece are renowned for their beauty and remarkable location, and you will discover the best of these islands. Begin in the capital city of Athens, which is full of history and culture, before embarking via private boat for the islands of Mykonos, Santorini, and Ios. From golden beaches with sparkling waters to historic attractions and mouthwatering restaurants, your stay on each Greek island will be unforgettable. Experience the essential and breathtaking highlights of these islands during this luxurious and memorable 8-day trip through Greece.

This is a customizable tour. It’s simply a starting point for inspiration and ideas. Each trip is personalized uniquely for you, based on what you want, for your private travel.

Customize

Why Travelers Choose Us

Benefits of Using Zicasso

Plan Your Trip with
Top Travel Specialists
We connect you with the best boutique tour companies to plan your dream trip.
Your Itinerary Tailor-Made
Just for You
Travel with a personalized itinerary and experiences designed for you.
Travel Worry-Free
Every Time
24/7 support and local assistance for every moment of your vacation.

Island Hop Through History: Unique Greek Island Hopping Itinerary

9 Day Custom Tour

From $2,335

During this luxurious 9-day excursion to Delos, Tinos, and Nea Kameni have been arranged for you to uncover the beauty, history, and culture of the remarkable Greek Islands. This vacation immerses you in the history and culture of each destination. Explore the iconic sites of the Acropolis, traverse the ruins of Akrotiri, venture to the charming island of Tinos, and uncover the diverse ancient history of Greece.

This is a customizable tour. It’s simply a starting point for inspiration and ideas. Each trip is personalized uniquely for you, based on what you want, for your private travel.

Customize

Indulge in the islands’ savory food and wine.

Greek Island Paradise and Gourmet Gastronomy Tour

7 Day Custom Tour

From $1,815

This immersive 7-day vacation will allow you to explore the gorgeous islands of Mykonos, Naxos, and Santorini. Indulge in the islands’ savory food and wine. The cuisine of Greece has been perfected over thousands of years, and the delicious flavors of the country can be experienced with a trip to its premier islands. Indulge in the flavors of Greece and its celebrated islands, learn the techniques of traditional Greek cooking, and savor the delicious wines of Santorini.

This is a customizable tour. It’s simply a starting point for inspiration and ideas. Each trip is personalized uniquely for you, based on what you want, for your private travel.

Customize

View of old town Agora in Athens Greece.

Essential Aegean Gems: Perfect Greece Tour

12 Day Custom Tour

From $3,115

Submerge yourself in the cradle of Western Civilization on this 12-day tour of Greece. Visits to Athens, Santorini, Naxos, and Crete ensure that nothing is missed in each of these attractive locations. Witness the abundance of history on display, appreciate the culture of modern Greece, and enjoy this distinct corner of the Mediterranean world.

This is a customizable tour. It’s simply a starting point for inspiration and ideas. Each trip is personalized uniquely for you, based on what you want, for your private travel.

Customize

Romantic Greece Vacation: Athens & Island Hopping

8 Day Custom Tour

From $1,995

Romance overtakes you and wonders enrapture you on this custom tailored tour that will take you through the fantastic Greek Isles. From the glassy waters of a Mykonos beach to the immaculate whitewashed walls of a Santorini village, the rising pillars of the Parthenon to the birthplace of Apollo, there is no end to the beauty that has captivated the world for thousands of years. Come see the passion. Come see the grandeur. Come see Greece.

This is a customizable tour. It’s simply a starting point for inspiration and ideas. Each trip is personalized uniquely for you, based on what you want, for your private travel.

Customize

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

Best Greek Island Hopping Vacation for Travelers Over 50

8 Day Custom Tour

From $2,075

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.

This is a customizable tour. It’s simply a starting point for inspiration and ideas. Each trip is personalized uniquely for you, based on what you want, for your private travel.

Customize

Naxos island in the Aegean Sea, Greece

History and Culture of Greece: 10-Day Island Hopping Tour

10 Day Custom Tour

From $2,595

This luxurious 10-day journey of Greece and its islands is designed to uncover the best historical and cultural attractions. The islands of Greece are the ideal combination of beauty and history. Steeped in centuries of culture, they are the ultimate destination for an immersive vacation. Sail across the Aegean Sea, explore the Acropolis, and bask in the tranquility of Greece’s hot springs.

This is a customizable tour. It’s simply a starting point for inspiration and ideas. Each trip is personalized uniquely for you, based on what you want, for your private travel.

Customize

See More(1 itineraries)

Helpful Content

Reviews of Zicasso's Referral Service

4.9 stars based on 1551 reviews. See all our reviews.

Review photo submitted by Ruth L.
Greece Vacation: Luxury 10-Day Family Tour, Naxos, Santorini,...

"Having everything booked (including most restaurants) and...

Reviewed By Ruth L.

Review photo submitted by Roy H.
Travel Review: Luxury Greece Vacation, Athens, Paros, Mykonos,...

"Having a local travel expert is paramount to having the...

Reviewed By Roy H.

Review photo submitted by Joshua L.
Vacation Review: Luxury Greece Family Trip, Greek Mythology...

"The accommodations were perfect and centrally located."

Reviewed By Joshua L.

Review photo submitted by Donald M.
Greece Luxury Vacation Review: Greek Islands, Athens, Chania,...

"All were extremely knowledgeable, professional, and friendly."

Reviewed By Donald M.

Review photo submitted by Deveny M.
Greece Travel Agent Review: 10-Day Honeymoon Trip, Athens,...

"They listened to exactly what we wanted and the trip was...

Reviewed By Deveny M.

Review photo submitted by Yvonne K.
Travel Review: Luxury Greece Family Tour, Naxos Island,...

"Each day was wonderfully planned with each of our kids...

Reviewed By Yvonne K.