A Glorious 7-Day Sailing Itinerary: Rhodes to Rhodes – A Dodecanese Dream

Embarking on a sailing adventure from Rhodes offers an exquisite exploration of the Dodecanese islands. This 7-day itinerary encapsulates the perfect blend of adventure, relaxation, and cultural immersion. Let’s set sail from Rhodes and discover the hidden gems of the Aegean Sea.

Embarkation Rhodes/Disembarkation Rhodes

• Day 1  : Rhodes marina-Simi   23 miles
• Day 2  : Simi-Nisiros(Palos)   32 miles
• Day 3  : Nisiros-Kos   14 miles
• Day 4  : Kos-Tilos   35 miles
• Day 5  : Tilos-Chalki   17 miles
• Day 6  : Chalki-Rhodes marina   37 miles
• Day 7  : Check-out

Day 1: From Rhodes Marina to Simi – A Picturesque Beginning (23 miles)

Setting Sail from Rhodes

Your journey begins at the historic Mandraki Marina in Rhodes. As you depart, embrace the views of the medieval city and the famous Colossus of Rhodes site.

First Stop: Simi

Your first destination is the charming island of Simi. This leg of your journey, covering 23 miles, offers a delightful introduction to the Aegean’s turquoise waters.

Exploring Simi

• Stunning Harbors: Simi is renowned for its picturesque harbor, painted with a palette of neoclassical pastels.
• Local Delicacies: Savor the local cuisine, especially their seafood, in one of the waterfront tavernas.

Day 2: Simi to Nisiros (Palos) – A Voyage to the Volcano (32 miles)

Journey to Nisiros

Today’s 32-mile sail takes you to Nisiros, a volcanic island known for its dramatic landscapes.

Experiencing Nisiros

• Volcanic Crater Visit: Explore the island’s famous volcano and its lunar-like craters.
• Palos Beach: Anchor near Palos, a serene spot ideal for an evening swim.

Day 3: Nisiros to Kos – Unveiling Historic Charm (14 miles)

Short Sail to Kos

A relatively short journey of 14 miles brings you to Kos, an island rich in history and beauty.

Discovering Kos

• Ancient Ruins: Visit the ancient Agora and the Tree of Hippocrates.
• Vibrant Nightlife: Kos Town offers a lively nightlife scene, well-suited for those looking to dance the night away.

Day 4: Kos to Tilos – Embracing Tranquility (35 miles)

Sailing to Secluded Tilos

Your fourth day involves a 35-mile sail to the tranquil and less-traveled island of Tilos. This journey promises serene landscapes and an escape from the hustle of more frequented islands.

Tilos: A Haven of Peace

• Natural Splendors: Explore Tilos’s lush landscapes, home to numerous bird species and natural trails.
• Livadia Beach: Relax on the pristine beaches of Livadia, well-suited for a quiet day under the sun.

Day 5: Tilos to Chalki – Navigating to Nostalgia (17 miles)

A Short Trip to Charming Chalki

On day five, a shorter 17-mile sail brings you to Chalki, an island that exudes a sense of timelessness and nostalgia.

Exploring Chalki

• Traditional Architecture: Stroll through the streets of Nimporio, the only village, adorned with neoclassical houses.
• Crystal-Clear Waters: Swim in the crystal-clear waters of Chalki’s secluded bays, offering perfect snorkeling spots.

Day 6: Chalki to Mandraki Marina (Rhodes) – The Return Journey (37 miles)

The Last Leg: Returning to Rhodes

Your sailing adventure culminates with a 37-mile journey back to Mandraki Marina in Rhodes. It’s a day to reflect on the amazing experiences and sights of the past week.

Last Day at Sea

• Sailing Bliss: Enjoy the final hours on the Aegean Sea, embracing the freedom and tranquility of sailing.
• Rhodes Old Town: On arrival, consider a visit to Rhodes Old Town, a UNESCO World Heritage Site, to conclude your journey with historical exploration.

Day 7: Cherishing Memories and Check-out

Reflections and Farewells

Your final day is not just about check-out procedures but about reflecting on a week filled with incredible sights, sounds, and experiences. It’s a time to cherish the memories made and the bonds strengthened during your sailing adventure in the Dodecanese.

Preparing for Departure

• Check-out Process: Ensure all belongings are packed, and the boat is left in good condition as you prepare to disembark.
• Last Goodbyes: Say your farewells to the crew and fellow travelers who have shared this remarkable journey with you.

Post-Charter Recommendations

Before you leave Rhodes, consider spending some extra time exploring this historically rich island.

Exploring Rhodes

• Medieval Wonders: Wander through the streets of Rhodes Old Town, where history is etched in every stone.
• Beach Relaxation: If time allows, relax on one of Rhodes’ beautiful beaches, a ideal way to end your vacation.

Your sailing holiday from Rhodes to Rhodes is more than just a vacation; it’s an expedition that acquaints you with the diverse beauty and culture of the Dodecanese islands. From the volcanic vistas of Nisiros to the serene shores of Tilos, every stop has offered something unique. As you leave, you carry not only souvenirs but also tales of the sea and the timeless allure of these Greek islands.

Related reading

Planning your trip? Explore greece’s catamaran destinations or check our charter FAQ and request a personalized quote for your dates.

Other guides you might find useful:

• Aegean Islands – Dodecanese
• Rhodes
• Zakynthos – 10 Things to Do

Frequently asked questions

How do I book a yacht charter on Catamaran Charter Greece?

Choose your dates and destination, browse our fleet, and use request a quote to lock in pricing. Our team confirms availability with the agency and emails the booking summary within 24 hours.

Do I need a sailing license?

For most bareboat charters in Greece you need a recognised skipper certificate (RYA Day Skipper, ICC, or equivalent) plus a VHF licence. If you don’t hold one, we book a professional skipper alongside the boat for the week.

What’s included in the price?

The base charter fee covers the boat, standard equipment, insurance, and final cleaning fee in most cases. Extras such as fuel, port fees, transit log, tourist tax and skipper service are billed separately and explained in the booking summary.

How far in advance should I book?

For peak weeks (mid-July to late August) we recommend booking 6–9 months ahead to lock in the boat and the early-bird discount. Shoulder seasons (May, June, September) usually have availability up to a month before departure.

About this guide

This guide was prepared by the Catamaran Charter Greece editorial team — a group of charter brokers and sailors who have been organizing yacht charters in Greece since 2007. Every itinerary, marina, and pricing range described here reflects current first-hand fleet experience and direct partnership with licensed charter agencies. Last reviewed: May 2026.

If a detail looks out of date, write us at www.catamaran-charter-greece.com/contact — we update guides quarterly.