• 1
  • 2
  • 3
As awarded by
Top Travel Specialist since 2008
Condé Nast Traveler since 2008
Top Travel Advisor since 2009
Travel+Leisure since 2009
As awarded by
Top Travel Specialist since 2008
Condé Nast Traveler since 2008
Top Travel Advisor since 2009
Travel+Leisure since 2009

Santorini - Sikinos - Ios - Koufonisi - Mykonos Cyclades Islands

Santorini Private Yacht Charter - Greece Yacht Charter, Cyclades Sailing Trip, Santorini, Sikinos, Ios, Pano Koufonisi, Mykonos


Start your wonderful Greek islands sailing trip from the spectacular Santorini and sail past the famous Santorini caldera as you make your way to the island of Sikinos, an off the beaten path island that will definitely help you relax. After exploring Sikinos, make your way to the lively island of Ios and visit the famous beach of Manganari. Leave for Pano Koufonisi, one of the most pristine small islands in the entire Aegean, and relax in the tranquil locale. From Koufonisia, make your way to cosmopolitan Mykonos, dine in its flashy restaurants and discover the beauty of Mykonos town, not forgetting to visit the majestic ancient island of Delos.

Day 1: Santorini

Santorini, world-renowned for its widely photographed, romantic sunsets and unique, volcanic natural environment, is arguably the most striking of the Greek islands. Its dramatic red and black sand beaches, narrow white-washed alleys, exquisite traditional and international cuisine, as well as its agricultural and wine-making tradition, make Santorini a truly spectacular island.

Day 2: Sikinos

Known as the island of wine or “Oinos” in Ancient Greece, Sikinos is considerably less developed than the other islands in the Cyclades. With only a couple of roads, the island is difficult to navigate, yet offers some wonderful beaches and traditional settlements.

Day 3: Ios

Located halfway between Naxos and Santorini, this island has been featured in several movies for its crystal clear waters and magnificent beaches. Most famous of all, the “Big Blue” featured the idyllic beach at Manganari. With a rich history starting from the prehistoric era, Ios will also offer visitors a fascinating historical and cultural experience, but Ios visitors will also find a vivid night scene.

Day 4: Pano Koufonisi / Koufonisia

Koufonisia, a small group of islands, have only recently come to the attention of tourists and have seen a boom in visitors in the last few years due to their amazing natural beauty and traditional Cycladic architecture. Pano Koufonisi, the smallest of these islands, is also the most densely populated. The main attraction of this stunningly beautiful small island complex is its tranquility and amazing beaches.

Day 5: Mykonos

Cosmopolitan Mykonos, with its wonderful beaches, impressive restaurants, and energetic nightlife, offers a more adventurous yet genuinely Greek experience. In Mykonos, freedom of expression is visible in every corner, and the combination of such a tranquil setting with a vibrant social scene has elevated the island to a premier destination for travelers from around the world.

Associated Vessels


Interested in a more private experience?

True Greece can plan your ideal customized trip experience


Let us create an unsurpassed vacation just for you

Contact our Concierges

1-800-817-7098 (US)