20 Days Exploring the Greek Islands Itinerary

Begin your second day with a visit to Fira, Santorini's bustling capital. Explore its vibrant markets, quaint shops, and historic sites. Make sure to visit the Archaeological Museum of Thera for a deep dive into Santorini's ancient history.

After exploring Fira, take a short trip to Akrotiri Archaeological Site. This well-preserved ancient Minoan city offers fascinating insights into prehistoric life on Santorini. For lunch, head over to The Good Heart for some authentic local dishes.

In the evening, join a wine-tasting tour at Santo Wines Winery. Enjoy sampling some of Santorini's finest wines while taking in panoramic views of the island. For dinner, dine at Selene, known for its exquisite Greek cuisine and elegant ambiance.

Take an early ferry from Santorini to Mykonos (approximately 2 hours). Start your day by exploring Mykonos Town (Chora), known for its charming narrow streets, whitewashed houses, and iconic windmills. Visit landmarks like Little Venice and Paraportiani Church.

In the afternoon, relax on one of Mykonos' famous beaches such as Paradise Beach or Super Paradise Beach. Enjoy sunbathing or partake in water sports activities available on-site. For lunch, try out Kiki's Tavern, renowned for its fresh seafood dishes.

As evening falls, experience Mykonos' vibrant nightlife starting with dinner at Interni Restaurant. Afterward, head over to Scandinavian Bar for cocktails and dancing till late night.

Start your day with a visit to the Archaeological Museum of Mykonos. This museum houses a fascinating collection of artifacts from the island's ancient past, including pottery, sculptures, and jewelry. It's a great way to learn about the rich history of Mykonos.

After the museum, head over to Ano Mera village, one of the oldest villages on the island. Here you can visit the Monastery of Panagia Tourliani, which dates back to the 16th century. For lunch, stop by Veneti Bakery for some delicious local pastries and coffee.

In the evening, take a sunset cruise around Mykonos. This tour offers stunning views of the island from the sea and is a perfect way to end your day. For dinner, dine at M-Eating, known for its modern take on traditional Greek cuisine.

Take an early ferry from Mykonos to Naxos (approximately 1 hour). Start your day by exploring Naxos Town (Chora), with its charming old town and impressive Venetian Castle. Don't miss visiting Portara, the massive marble gate that is all that remains of an unfinished temple dedicated to Apollo.

Monemvasia:CoupleAdventure:fun game,challenges and city walk will be an exciting addition to your afternoon as you engage in fun games and challenges while exploring Monemvasia's historic sites. For lunch, try out To Elliniko, known for its authentic Greek dishes.

In the evening, relax at Agios Prokopios Beach, one of Naxos' most beautiful beaches. Enjoy swimming in its crystal-clear waters or simply unwind on the sandy shore. For dinner, head over to Nostimon Hellas, which offers a delightful mix of traditional and contemporary Greek cuisine.

Monemvasia:CoupleAdventure:fun game,challenges and city walk will kick off your day with engaging activities as you explore Parikia's historic sites in Paros.

Monemvasia:CoupleAdventure:fun game,challenges and city walk continues into your afternoon as you delve deeper into Parikia's charming streets and landmarks like Panagia Ekatontapiliani Church. For lunch, stop by Taverna Glafkos for some fresh seafood right by the sea.

In the evening join a sunset tour at Kolymbithres Beach where unique rock formations create picturesque views perfect for photography enthusiasts! End your day dining at Barbarossa known not only for their exquisite food but also stunning harbor views.

Begin your day with a visit to Naoussa, a picturesque fishing village known for its charming harbor and traditional whitewashed houses. Stroll through the narrow streets, explore local shops, and enjoy the serene atmosphere. Don't miss visiting the Venetian Castle, which offers stunning views of the harbor.

After exploring Naoussa, head to Lefkes village, located in the heart of Paros. This quaint village is known for its beautiful architecture and scenic views. Wander through its cobblestone streets and visit the Church of Agia Triada. For lunch, stop by Clara's Restaurant for some delicious local cuisine.

In the evening, take a sunset cruise around Paros. This tour offers breathtaking views of the island from the sea and is a perfect way to end your day. For dinner, dine at Soso, known for its creative Greek dishes and cozy ambiance.

Take a short ferry ride from Paros to Antiparos (approximately 30 minutes). Start your day by exploring Antiparos Town with its charming streets and traditional Cycladic architecture. Visit the Cave of Antiparos, one of the most impressive caves in Greece with stunning stalactites and stalagmites.

Monemvasia:CoupleAdventure:fun game,challenges and city walk will add excitement to your afternoon as you engage in fun games and challenges while exploring Antiparos' historic sites. For lunch, try out Yam which offers delicious Mediterranean dishes.

In the evening relax at Soros Beach where you can enjoy swimming in crystal-clear waters or simply unwind on sandy shores before heading back to Paros for dinner at Dionysos, known not only for their exquisite food but also stunning harbor views.

Take an early ferry from Paros to Ios (approximately 1 hour). Start your day by exploring Chora (Ios Town), known for its vibrant nightlife but equally charming during daytime with narrow alleys filled with shops cafes bars churches like Panagia Gremiotissa offering panoramic island views.

Monemvasia:CoupleAdventure:fun game,challenges and city walk will be an exciting addition as you engage in fun games challenges while discovering Ios' historical landmarks such as Skarkos Archaeological Site showcasing ancient settlement remains dating back Bronze Age! For lunch head over The Nest renowned their authentic Greek dishes warm hospitality.

As evening falls experience famous Mylopotas Beach where golden sands meet turquoise waters perfect relaxation water sports enthusiasts alike! End day dining at Karma Beach Bar Restaurant offering delightful mix international cuisines vibrant beachside atmosphere.

Start your day with a visit to the Tomb of Homer, one of the most significant historical sites on Ios. This ancient tomb is believed to be the final resting place of the legendary poet Homer. The site offers not only historical insights but also stunning views of the surrounding landscape.

After visiting the Tomb of Homer, head to Agia Theodoti Beach. This serene and less crowded beach is perfect for relaxation and swimming in its crystal-clear waters. For lunch, stop by Drakos Tavern, known for its fresh seafood and traditional Greek dishes.

In the evening, take a sunset cruise around Ios. This tour offers breathtaking views of the island from the sea and is a perfect way to end your day. For dinner, dine at Grandma's Restaurant, renowned for its exquisite Greek cuisine and warm ambiance.

Take an early ferry from Ios to Folegandros (approximately 1 hour). Start your day by exploring Chora, Folegandros' main town, known for its picturesque streets and traditional Cycladic architecture. Visit landmarks like Panagia Church which offers panoramic views of the island.

Monemvasia:CoupleAdventure:fun game,challenges and city walk will add excitement as you engage in fun games challenges while exploring Chora's historic sites! For lunch try out Pounta offering delicious local dishes stunning sea views.

In evening relax at Katergo Beach accessible only by boat or hiking trail providing secluded spot perfect swimming sunbathing! End day dining at Captain Nikolas known their fresh seafood friendly atmosphere.

Take an early ferry from Folegandros to Sikinos (approximately 1 hour). Start your day by exploring Hora (Sikinos Town), a charming village with narrow streets whitewashed houses offering glimpse into traditional island life! Visit Episkopi Temple ancient Roman mausoleum converted into Byzantine church.

Monemvasia:CoupleAdventure:fun game,challenges and city walk continues as you delve deeper into Hora's historic sites engaging fun activities along way! For lunch head over Manalis Winery not only great food but also spectacular vineyard views.

In evening unwind at Alopronia Beach where golden sands meet azure waters creating idyllic setting relaxation before heading back Hora dinner at Steki Tou Garmpi renowned their authentic Greek cuisine warm hospitality.

Begin your day with a visit to the Monastery of Zoodochos Pigi, perched on a hill offering panoramic views of the island and the Aegean Sea. This serene monastery is a perfect spot for some peaceful reflection and photography.

Monemvasia:CoupleAdventure:fun game,challenges and city walk will add excitement to your afternoon as you engage in fun games and challenges while exploring Sikinos' historic sites. For lunch, stop by To Kastro for some delicious local dishes.

In the evening, take a leisurely stroll along the scenic paths of Sikinos, enjoying the tranquil atmosphere. For dinner, dine at Anemelo, known for its traditional Greek cuisine and warm hospitality.

Take an early ferry from Sikinos to Amorgos (approximately 1 hour). Start your day by visiting the Monastery of Panagia Hozoviotissa, an iconic landmark built into a cliffside offering breathtaking views of the sea.

Monemvasia:CoupleAdventure:fun game,challenges and city walk will be an exciting addition as you engage in fun games and challenges while exploring Amorgos' historic sites. For lunch, try out Taverna Nikos, known for its authentic Greek dishes.

In the evening, relax at Agia Anna Beach, famous for its crystal-clear waters and stunning surroundings. End your day dining at Aegiali Restaurant, which offers exquisite food with beautiful sea views.

Monemvasia:CoupleAdventure:fun game,challenges and city walk will kick off your day with engaging activities as you explore Koufonisia's charming streets and landmarks.

Monemvasia:CoupleAdventure:fun game,challenges and city walk continues into your afternoon as you delve deeper into Koufonisia's scenic beauty. For lunch, stop by Kalamia for some fresh seafood right by the sea.

In the evening join a sunset tour at Pori Beach where unique rock formations create picturesque views perfect for photography enthusiasts! End your day dining at Souvlaki Sti Strofi known not only for their exquisite food but also stunning harbor views.

Start your day with a visit to Finikas Beach, known for its golden sands and crystal-clear waters. This serene beach is perfect for a morning swim or simply relaxing under the sun.

Monemvasia:CoupleAdventure:fun game,challenges and city walk will add excitement to your afternoon as you engage in fun games and challenges while exploring Koufonisia's scenic beauty. For lunch, stop by Captain Dimitris for some delicious local dishes.

In the evening, take a leisurely stroll along the coastal paths of Koufonisia, enjoying the tranquil atmosphere. For dinner, dine at To Steki Tis Marias, known for its traditional Greek cuisine and warm hospitality.

Take an early ferry from Koufonisia to Naxos (approximately 1 hour). Start your day by visiting the Temple of Demeter, an ancient sanctuary dedicated to the goddess Demeter. The site offers fascinating insights into ancient Greek religion and architecture.

Monemvasia:CoupleAdventure:fun game,challenges and city walk will be an exciting addition as you engage in fun games and challenges while exploring Naxos' historic sites. For lunch, try out Axiotissa, known for its authentic Greek dishes.

In the evening, relax at Plaka Beach, one of Naxos' most beautiful beaches. Enjoy swimming in its crystal-clear waters or simply unwind on the sandy shore. End your day dining at Ocean Club, which offers exquisite food with beautiful sea views.

Take an early ferry from Naxos to Syros (approximately 1 hour). Start your day by exploring Ermoupoli, Syros' capital city known for its neoclassical architecture and vibrant cultural scene. Visit landmarks like Miaouli Square and Apollo Theater.

Monemvasia:CoupleAdventure:fun game,challenges and city walk will add excitement as you engage in fun games challenges while exploring Ermoupoli's historic sites! For lunch try out Kouzina offering delicious local dishes stunning sea views.

In evening relax at Galissas Beach where golden sands meet azure waters creating idyllic setting relaxation before heading back Ermoupoli dinner at Allou Yialou renowned their fresh seafood friendly atmosphere.

Start your day with a visit to Ano Syros, a medieval settlement perched on a hill offering panoramic views of the island and the Aegean Sea. Wander through its narrow streets, explore local shops, and visit the Catholic Cathedral of Saint George.

Monemvasia:CoupleAdventure:fun game,challenges and city walk will add excitement to your afternoon as you engage in fun games and challenges while exploring Ano Syros' historic sites. For lunch, stop by Syrianon Kafepoteio for some delicious local dishes.

In the evening, take a leisurely stroll along the waterfront promenade in Ermoupoli, enjoying the vibrant atmosphere. For dinner, dine at Mazi, known for its exquisite Greek cuisine and warm hospitality.

Monemvasia:CoupleAdventure:fun game,challenges and city walk will kick off your final day with engaging activities as you explore Syros' charming streets and landmarks.

Monemvasia:CoupleAdventure:fun game,challenges and city walk continues into your afternoon as you delve deeper into Syros' scenic beauty. For lunch, stop by Ousyra for some fresh seafood right by the sea.

In the evening join a sunset tour at Kini Beach where unique rock formations create picturesque views perfect for photography enthusiasts! End your day dining at Allou Yialou known not only for their exquisite food but also stunning harbor views.