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Greek Travel Desires | Skiathos to Skiathos 14-day Itinerary

The Greek islands are so beautiful it is difficult to choose just one itinerary. Your Captain will help you decide where to travel based on your interests and desires. The following is one sample Skiathos to Skiathos 14-day itinerary.

Skiathos to Skiathos 14-day Itinerary

Day 1 | Skiathos

Your yacht charter adventure begins in Skiathos, the green jewel of the Sporades. This island has over 60 stunning beaches. Koukounaries Beach is one of the most famous on the island.

A pine forest reserve surrounds this large sandy beach, offering a unique natural beauty and relaxation blend. You can swim in the crystal-clear waters, sunbathe on the soft sand, or explore the nearby nature trails.

Meet your Captain and crew at the marina. Board your yacht, then set sail for your first destination, Pithos. Enjoy lunch onboard as you cruise. Overnight in Pithos.

Day 2 | Pithos (Palaio Trikeri)

Wake at your leisure and enjoy breakfast on the deck of your yacht. You have the whole day ahead to swim, explore, and dine.

Pithos is an unchanged gem with car-free streets and the historic Church of Evangelistrias. Stroll across the island and later enjoy a peaceful evening under the stars.

Day 3 | Volos

On day 3 of your Skiathos to Skiathos 14-day Itinerary, arrive at Volos.

Volos is one of the largest cities in Greece and is home to numerous halls, churches, and mansions. You can see Mount Pelion to the north and the Pagasetic Gulf to the south. The waterfront is an excellent place to find seafood restaurants and bars.

Day 4 | Milina

Milina is a lovely fishing village home to sponge divers, shipbuilders, and fishermen. There are several things to see and do here, such as:

  • Exploring the Village: Wander through the picturesque village of Milina and immerse yourself in its traditional Greek atmosphere. Stroll along its charming streets, admire the quaint architecture and discover local shops and cafes.
  • Watching the Sunset: Milina is famous for its breathtaking sunsets. Find a cozy spot by the waterfront or on the deck of your yacht. Then, enjoy a mesmerizing sunset over the tranquil Aegean Sea.
  • Visiting Byzantine and Post-Byzantine Churches: Milina and its surroundings are home to several Byzantine and Post-Byzantine churches.
  • Swim and Relax: Milina offers access to lovely sandy beaches along its coastline. Spend some time swimming and sunbathing in the crystal-clear waters of the Aegean Sea.
  • Dining by the Sea: Indulge in delicious Greek cuisine at local tavernas and seafood restaurants that line the harbor. Try fresh catches of the day, traditional Greek dishes, and locally sourced ingredients.

Day 5 | Orei

Orei is a resort town dating from 5000 BC. It’s in the middle of a lush green area with beautiful sandy beaches, hills, and plains. Visit the Bull of Orei in the village square.

The picturesque harbor of Orei is a focal point of the town’s activity. It features several waterfront restaurants, cafes, ouzeries, and bars. You can savor fresh seafood dishes and traditional Greek cuisine while enjoying views of the harbor and the sea.

Day 6 | Koukounaries (Skiathos Island)

Koukounaries lies at the southwest end of Skiathos and is a large sandy beach. There’s a forest reserve behind the beach. Take the tender into this lovely spot and spend the day exploring or swimming in the warm, clear water.

This is also a great place to use your yacht’s water toys.

Day 7 | Loutraki (Skopelos Island)

Loutraki is a small traditional village located on the island’s northwest coast. The town is home to vast natural springs and its therapeutic spas. Rejuvenate with a massage or thermal bath at Loutraki Thermal Spa.

Day 8 | Kyra Panagia

This small island is part of the NMPANS nature reserve and is another place to spot the Mediterranean Monk Seal. The idyllic Kyra Panagia Beach is well worth visiting.

It is a semi-circular beach surrounded by white rocky cliffs and a brilliant blue sea. It is a perfect setting for Instagram-worthy photos. The beach offers sunbed rentals, snack bars, and restrooms.

Day 9 | Patitiri (Alonnisos Island)

The largest town on Alonnisos, Patitiri, is also home to the largest harbor on the island. The town’s calm and peaceful atmosphere invites you to explore its small taverns, shops, and beach. There’s excellent diving in the nearby Alonissos National Marine Park.

Day 10 | Skantzoura

Skantzoura is a small uninhabited island, and its only structure is an old hermitage. The island is within the Marine Park, which protects marine life and the endangered Mediterranean seal. All fishing is strictly forbidden.

Day 11 | Skyros (Skyros Island)

The largest town on the island (Skyros Town) has some fantastic traditional architecture. The island is green and fertile in the north and barren in the south. Visit Mouries Farm and see endangered Skyrian horses. There’s also a Taverna that serves authentic Greek food.

Day 12 | Skopelos (Skopelos Island)

Skopelos is the largest of the four main islands in the Sporades. This beautiful island is home to many natural springs, so it has many large olive groves, plum trees, almonds, and orange trees. The island is famous for the quality of its wine.

Visit Skopelos Town and immerse yourself in the laid-back atmosphere.

Day 13 | Glossa (Skopelos Island)

On day 13 of your Skiathos to Skiathos 14-day itinerary, arrive at Glossa.

Glossa Village is a working village that reflects authentic Greece. Glossa is lush with olive, almond, and plum trees. You will also find many springs with running fresh water. Kayak, hike or explore the town.

Day 14 | Skiathos Town (Skiathos Island)

Return to Skiathos and end your Skiathos to Skiathos 14-day itinerary.