Greece is at the top of everyone’s bucket list these days but let me tell you, as someone who has spent two weeks island hopping in the Cyclades, traveling the Greek isles is not easy!! Navigating your luggage onto and off of ferries with hundreds of other passengers is a total nightmare. If you’re considering a Greek vacation and really want to visit Mykonos and Santorini, a sailing vacation is a great way to avoid the ferry system during peak vacation months. You’ll never have to unpack! Here are a few different Greek island hopping itineraries to consider that keep you on small sailing ships, away from the big cruise ships. I’ve also included a few of my favorite islands below.

Sailing Greece: Santorini to Santorini (10 Days)

A yacht adventure is the ideal way to experience what many consider the world’s most beautiful islands in Greece. Sail aboard an18m (58 ft) yacht, with time for hiking, snorkelling, and relaxing. Explore ancient archaeological sites and taverna-lined harbours, dine on fresh seafood and don’t forget to try the Ouzo! This 10-day round trip from Santorini will give you the chance to explore some of the treasures of the Greek Islands. Sail through the pristine waters of the Greek Islands aboard a yacht, capture the ultimate Greek snapshot on Santorini, wander through whitewashed villages on Paros, enjoy the party on Mykonos, discover Venetian architecture on Naxos

Tall Ship Sailing in the Northern Cyclades (8 Days)

How about a tall ship cruise of the Cyclades? Experience and fall in love with the traditional charm of the famous Cyclades Islands on this 8-day sailing adventure. Discover the magic and mythology of the Greek Isles, one of the most storied regions of the world. Sail across the azure waters of the Aegean Sea in a tall ship. After leaving from Athens, you will not only visit Mykonos, but also more local islands like Amorgos and Spetses. Book through me for benefits such as onboard credits, massages, and free champagne.

Treasures of the Greek Isles (8 Days)

On the motorized sailing ship, you’ll visit sun-drenched places as you sail the Greek isles, discovering a world abounding with seaside scenery and ancient treasures. On such legendary islands as Santorini and Mykonos, views of azure sea and white-washed villages will take your breath away. On your small ship cruise, Greece unfolds at a leisurely pace. You'll have time to linger in magical places, to swim from powdery sand beaches, and to explore the local cuisine.

Three Greek Islands to Visit that Aren’t Mykonos or Santorini

Paros: Paros captivates visitors with its picturesque villages like Naoussa and Parikia, adorned with white-washed houses and blue-domed churches. Explore Kolymbithres beach's sculpted rocks, windsurf at Golden Beach, or visit the Panagia Ekatontapiliani, an ancient Byzantine church. Enjoy local delicacies at traditional tavernas and witness stunning sunsets over the Aegean Sea.

Spetses: Spetses, a charming Saronic Gulf island, exudes elegance and tranquility. Explore the quaint old town's narrow streets and neoclassical mansions. Admire the Bouboulina Museum, dedicated to a Greek naval heroine. Rent a bicycle or horse-drawn carriage to tour the island. Crystal-clear waters invite swimming and snorkeling, while Agia Paraskevi beach offers a serene escape.

Amorgos: Amorgos, a hidden gem in the Cyclades, allures with its rugged beauty and secluded ambiance. Explore the Byzantine Monastery of Panagia Hozoviotissa, perched dramatically on a cliffside. Embark on hiking trails, like the trek to Agia Anna beach, and visit the ancient Minoa settlement. Discover unspoiled beaches like Agia Saranta and Mouros, offering tranquil retreats.

Please reach out if I can help you plan your Greek island hopping vacation. I can do anything — cruises large and small or independent touring.

About Krista: I’m a Notre Dame grad (Go Irish!) and a Chicago Booth MBA. I spent over 11 years living and working in London, England, selling financial data. I moved to South Florida 4 years ago to be closer to my elderly mom, who has Parkinson’s Disease. Instead of selling financial data, these days, I sell travel!

After visiting more than 78 countries, I love talking travel and organizing amazing vacations for my clients. Please do not hesitate to reach out for your complimentary travel consultation.