4-Day Symi, Tilos & Chalki Sailing Cruise from Rhodes

The 4-Day Symi, Tilos & Chalki Sailing Cruise from Rhodes is a private island-hopping yacht journey for up to six guests, departing from Rhodes New Marina and visiting three distinctive Dodecanese islands.

Aboard Sailing Edisa, the four-day route balances time under sail with harbour visits, quiet swimming stops and personalised hospitality. Meals blend Mediterranean and Asian influences, accompanied by selected wines, Champagne and signature cocktails. With a maximum of six guests, the experience suits couples, families or friends seeking a more intimate alternative to a day cruise.

The first island is Symi, known for the pastel neoclassical houses lining its harbour and a maritime heritage shaped by shipbuilding and sponge diving. You can step ashore to enjoy the waterfront before continuing through the Aegean Sea.

Tilos brings a slower, nature-focused character. Livadia is the island’s main harbour village, while the surrounding landscape offers walking trails, peaceful beaches and seasonal wildflowers. It is an appealing stop for travellers who value uncrowded coastlines and authentic island life.

Chalki, also written Halki, completes the route. The yacht approaches Nimporio, where colourful mansions, a stone clock tower and the bell tower of Saint Nicolas Church frame the waterfront. Clear bays around this small island invite relaxed swimming away from Rhodes’ busier beaches.

Departure is from New Marina in Rhodes Town. Travellers comparing Rhodes boat trips can use the wider collection to find shorter alternatives, while the 7-day private sailing cruise from Rhodes extends the itinerary to five islands. If you would rather stay close to Rhodes, the late afternoon Lindos sailing cruise offers a compact swim-and-sail experience.

This is a weather-dependent voyage, so the skipper may adjust the order, anchorages or timing for comfort and safety. Confirm the final itinerary, cabin arrangement, meal requirements and exact meeting instructions before booking, especially if anyone in your party has mobility needs or dietary allergies.