16 Day Islands Hopping, Milos, Santorini, Koufonisia, Naxos, Paros, Mykonos

Over 16 days, this Cyclades itinerary takes you through a carefully selected mix of well-known islands and more peaceful destinations, creating a journey that feels both complete and distinctive. Milos and Santorini offer dramatic scenery, Koufonisia adds a slower rhythm, Naxos and Paros bring authentic island charm, and Mykonos closes the trip with energy and style.

Day 1: Meet & Greet at Athens Airprot

• Our driver will meet and assist you at Athens airport El. Venizelos, and then he will transfer you at your hotel. Overnight in Athens.

Day 2: Private Tour Acropolis & Parthenon & Food tasting in Monastiraki

• Start your journey with a licensed private guide who brings the legends of Athens to life, exploring the Acropolis, Parthenon, Erechtheion, and Temple of Athena Nike. With skip-the-line tickets, you’ll maximize your time at these iconic sites while learning stories of gods, heroes, and the birth of democracy. Wander through the vibrant streets of Monastiraki, discovering hidden corners, lively markets, and historic architecture. Enjoy a curated tasting of traditional Greek foods, including souvlaki with tzatziki, olives, loukoumades, and pastries. Each tasting is paired with expert commentary, giving you a rich understanding of Athens’ culinary heritage and local traditions. Overnight Athens. Overnight stay in Athens.

Day 3: Athens to Milos

• Our driver will meet you at your hotel to transfer you to Piraeus Port to take the Ferry for the Island of Milos.Our driver will meet you at the Milos port and transfer you at your hotel. You will have free time for yourself. The island of Milos is known all over the world for the Marble Statue of The Aphrodite of Milos, the Greek goddess of Love and Beauty. Overnight in Milos.

Day 4: Milos - Semi Private Sunset Cruise with buffet on board

• Optional: Do not miss the chance to discover Milos' artistic and architectural Aegean icons and the majestic rocky formations of the volcanic lava! This cruise tour is ideal for travelers who wish to explore the must-sees of Milos and also to admire a unique sunset from the exceptional rock formations which look like the lunar landscape. Get a half-day cruise in Milos to feel the magic, just like the pirates once did. We will visit the wonderful beaches with white rocks and deep blue & turquoise waters such as “Kleftiko beach”, “Arkoudes” “Kalogries beach”. Most of these beaches are accessible only by boat. Overnight in Milos.

Day 5: Milos to Santorini

• Our driver will meet you at your hotel to transfer you to Milos Port to take the ferry for the famous Santorini Island. Our local driver will meet you at the Santorini port and transfer you to your hotel. You will have free time for yourself. The Cycladic island of Santorini will excite your senses. The volcano's black lava greets the whitewashed villages of the caldera. Walk in Thira's narrow alleys and indulge in gastronomical creations by tasting Santorini's local produce - the tomato, fava, capers, and the white eggplant. Above all, you cannot miss Oia's magnificent sunset, that magical hour of the day when the light makes everything look more beautiful. Overnight in Santorini.

Day 6: Santorini - Sunset Cruise to the Volcano with buffet on board

• Pick you up from your hotel around noon to have our first stop at the famous volcano of Santorini! The next stop is at the island of Palea Kameni where the famous hot springs are located on the west side. Dinner on Board: Sailing above the underwater craters from Palea Kameni to Thirasia Island, the boat will anchor close to the island to enjoy your dinner. The end of the excursion comes at sunset time. Our boat will stop close to Oia village where you will have the chance to watch the warm light of the setting sun under the violet sky before the night falls. This is the most unforgettable experience as the Caldera and the village of Oia will turn into a gold color. Overnight in Santorini.

Day 7: Santorini to Koufonisia

• Enjoy the morning until our driver meets you at your hotel to transfer you to Santorini port to take the ferry to Koufonisia. In walking distances, you will reach your hotel. Overnight in Koufonisia.

Day 8: Koufonisia - Day at leisure at "Jamaica of Europe"

• Koufonisia is considered to be the hidden gem of the Cyclades. This spectacular island is a secluded destination with a very tranquil way of life, naturist sandy beaches with turquoise sea-through waters, and delicious traditional cuisine. Koufonisia, which has also been described as the "Jamaica of Europe", is the idyllic place for the ultimate relaxation of body and mind. The real uniqueness of the island is that there are no motor vehicles as the only 400 inhabitants of the islands use bicycles or travel on foot, which means that you can reach the beaches either on foot, renting a bicycle, or by boat which drops you off at a beach and picks you up again in the afternoon! Koufonisia a great opportunity to get away from the cosmopolitan way of life and truly “live like a local”. Overnight in Koufonisia.

Day 9: Koufonisia to Naxos

• Today you will leave Koufonisia and take the ferry to the Island of Naxos. Our local driver will meet you at the Naxos port to transfer you to your hotel. You will have free time for yourself. The first thing you will notice visiting Naxos is the famous and formidable Portara - the supernatural marble statue and the medieval Venetian castle which can be found in the old city. Naxos is a unique island that combines both the ancient ruins, the primitive structures, and the long sandy beaches! Overnight in Naxos.

Day 10:  Naxos, Olive Oil, Kitron Tasting, & Apeiranthos Village

• Optional: Discover the heart of Naxos as you explore its charming traditional villages and stunning countryside. Visit a family olive press to learn the secrets of olive oil production and enjoy a premium tasting experience. Continue to Chalki for a guided tour of the historic Kitron distillery and sample this famous local spirit. Wander the marble-paved alleys of Apeiranthos, one of the island’s most authentic and culturally rich villages. A perfect journey blending history, flavor, and the true soul of Naxos. Overnight in Naxos.

Day 11: Naxos to Paros

• Our driver will meet you at your hotel to transfer you to Naxos Port to take the ferry to Paros. Transfer you to your hotel. Then, you will have free time for yourself. On this Cycladic Island, natural beauty encounters history and pleasure. Paros gives you the opportunity to enjoy your dream holidays: If you are a sea enthusiast, you will be enthralled by the many small, big, uncrowded or famous beaches or to explore the traditional town with the narrow streets. Overnight in Paros

Day 12: Paros - Private tour to Villages Tour & Pie Tasting at Kafeneio

• Optional: Embark on a culinary and cultural journey through Lefkes, Naoussa, and a traditional fishing village. Taste homemade Greek pies, meet local artisans, and wander historic alleys and charming churches. Learn about local traditions and artisan crafts, discovering hidden gems off the beaten path. Enjoy a leisurely coffee at a traditional "kafeneio" one of the village squares, soaking in the authentic Cycladic atmosphere. Overnight in Paros.

Day 13: Paros to Mykonos -  Wine, Olive Oil and Food Tasting with Music

• Today you will take the ferry to Mykonos. Our local driver will meet you at Mykonos port and transfer you to your hotel. Mykonos is the most famous island in the world for its beaches, its fun, its exciting nightlife, its picturesque Cycladic houses, the luxury hotels, also known as the island of winds. Our driver will transfer you to your hotel. The stroll in ‘’Little Venice’’ of the island, or the walk through the narrow streets of "Matogiania" will be memorable for your vacations, where you can shop for clothes and other local items. We propose you relax at your hotel and enjoy the amazing nightlife of Mykonos! In the afternoon, enjoy a romantic visit to a local Mykonos farm with a guided walk through vineyards and olive groves. Taste premium extra virgin olive oil, Kalamon olives, and a selection of local sweet and savory delicacies, including louza, kopanisti, and traditional pastries. The experience is beautifully complemented by live Cycladic music, offering an authentic taste of Mykonian culture. Overnight in Mykonos.

Day 14: Mykonos - Delos & Rhenia Beach Cruise with BBQ on Board

• Optional: Start a stunning cruise to the sacred island of Delos, where history comes alive amidst ancient ruins and archaeological wonders. Explore the birthplace of Apollo and Artemis, a UNESCO World Heritage site rich in cultural heritage. Passengers can either disembark to visit the archaeological area of Delos for 1.5 hours or enjoy swimming in a nearby gulf.In continue, savor a delicious BBQ lunch freshly prepared onboard as you cruise towards the paradise of Rhenia Island, where crystal-clear waters and serene beaches await. Dive into the turquoise sea, soak up the sun, and experience ultimate relaxation for two hours. The duration of the cruise is around 6 hours. Overnight in Mykonos.

Day 15: Mykonos to Athens

• Our local driver will meet you at your hotel to transfer you to Mykonos Port to take the ferry for Piraeus port. Our driver will be waiting for you at the Piraeus port to transfer you to your hotel. Then, you will have free time for yourself. Overnight in Athens.

Day 16: Departure Day

• Our driver will meet you at your hotel to transfer you to Athens airport according to your flight details.

Aditional Optional Local Tours in ecah Island

• Tours in Santorini
• Tours in Mykonos 
• Tours in Milos
• Tours in Paros
• Tours in Naxos