Dodecanese Islands 7 Day Yacht Charter Itinerary Greece: Rhodes, Tilos, Astypalea, Kalymnos, Kos, Nisyros, Symi

Dodecanese Yacht Charter Itinerary

Yacht Charter Day 0 – Arrive in Rhodes, Greece

Yacht Charter Day 1 – Rhodes to Tilos

Yacht Charter Day 2 – Tilos to Astypalea

Yacht Charter Day 3 – Astypalea to Kalymnos

Yacht Charter Day 4 – Kalymnos to Kos

Yacht Charter Day 5 – Kos to Nisyros

Yacht Charter Day 6 – Nisyros to Symi

Yacht Charter Day 7 – Symi to Rhodes

Note that the video, text, and images are only a suggestion, your broker and captain will advise on the feasibility of this itinerary for your season and yacht. The video and the images were not taken on the charter.

Yacht Charter Day 0 – Arrive in Rhodes, Greece

This Greek adventure begins on the island of Rhodes, but this is much more than just a starting point. Rhodes is one of the biggest islands in Greece and by far the biggest of the Dodecanese islands (the region that this charter covers) so we recommend getting here early and spending some time on the island.

It is home to one of the biggest airports in Greece as well as five ports, and there are connections to the Greek mainland as well as many other major European cities, so finding a route into the island to begin this journey should not be an issue.

Once you’re there then it’s time to explore and to immerse yourself in some Ancient Greek history as well as some modern Greek culture.

Rhodes has been inhabited since the neolithic age and over 3,000 years ago it became home to the Minoan and then the Mycenaean civilizations, before participating in the famous Trojan war. Some traces of this ancient history remain on the island today, but mostly in its museums, with the oldest history you can actually explore dating back to around the 4th century BC.

One such historical site is the Acropolis of Rhodes, which is a short journey from the centre of the city of Rhodes and consists of a temple, theater and stadium. Most of it is in a state of ruin, but it’ll still give you some insight into the ancient history of this island and it’s a great appetizer to begin this cultural feast.

We’d also recommend taking a walk down the Street of the Knights for a piece of medieval Greek history and, if your schedule allows it, paying a visit to the Fort of St. Nicholas. There is also a lot of history outside of the city, including the ruins in Kamiros and the monastery in Lindos, but there’s a lot of traveling to come and a lot of things to see, so feel free to keep it local and within walking distance for this first day.

Rhodes is a very tourist-centric island, so there are also plenty of beaches, bars, and fun activities for you to enjoy if you’re not in the mood for a history lesson. Just make sure you have an early night and are up bright and early for your adventure the next day!

Yacht Charter Day 1 – Rhodes to Tilos

The following morning you can make your way down to the harbor to meet the captain and crew and to acquaint yourself with the yacht that will take you on this island adventure. You’ll have your own private chef onboard, so they can cook you a hearty breakfast that you can toast with a glass of Champagne.

Yamas (cheers!), as the locals say.

The first leg of your adventure will take you to the neighboring island of Tilos. This island has a population of less than 1,000 at last count, and while it’s popular with tourists from Rhodes and other islands, it’s far from a tourist hotspot.

It’s perfect for the first leg of your journey though as it will allow you to shake off a busy day of sightseeing in Rhodes and to become aquatinted with the boat and the beautiful Dodecanese region.

We recommend taking a walk through the ancient streets, snapping pictures in and around the ancient buildings, and enjoying a level of freedom and solitude that you rarely find on Greek islands.

Tilos is very much an undiscovered gem, and as you step off the boat you’ll get a feeling that you have the whole island to yourself.

And what a beautiful island it is.

Yacht Charter Day 2 – Tilos to Astypalea

After a peaceful day on the island of Tilos and a night spent drinking wine underneath a clear sky, it’s time to head for Astypalea. This island also has a relatively small population, but it’s bigger and considerably more popular with tourists, so you won’t have it all to yourself.

For your first stop we recommended visiting Astypalea castle, which sits atop this steep mountainous island and can be seen for miles around. It’s a bit of a climb, but there is a lot to see once you’re up there and it also provides you with some of the best views in the region. If you time it right, visiting around 6 or 7 in the evening, then you can see the sun go down and watch as these beautifully white buildings are bathed in a sea of gold.

After a day spent climbing and sightseeing, you’ll want nothing more than to kick-back and relax, and that’s perfect, as there are several pristine beaches on this island. Kaminakia Beach is the most pure and the most beautiful, and while it’s too long and treacherous to walk there, there are taxi services and you can also rent a car.

There are other beaches within walking distance as well, just make you you’re back by nightfall to enjoy a specially prepared supper on your yacht.

Yacht Charter Day 3 – Astypalea to Kalymnos

After a peaceful day on the island of Tilos and a night spent drinking wine underneath a clear sky, it’s time to head for Astypalea. This island also has a relatively small population, but it’s bigger and considerably more popular with tourists, so you won’t have it all to yourself.

For your first stop we recommended visiting Astypalea castle, which sits atop this steep mountainous island and can be seen for miles around. It’s a bit of a climb, but there is a lot to see once you’re up there and it also provides you with some of the best views in the region. If you time it right, visiting around 6 or 7 in the evening, then you can see the sun go down and watch as these beautifully white buildings are bathed in a sea of gold.

After a day spent climbing and sightseeing, you’ll want nothing more than to kick-back and relax, and that’s perfect, as there are several pristine beaches on this island. Kaminakia Beach is the most pure and the most beautiful, and while it’s too long and treacherous to walk there, there are taxi services and you can also rent a car.

There are other beaches within walking distance as well, just make you you’re back by nightfall to enjoy a specially prepared supper on your yacht.

Yacht Charter Day 4 – Kalymnos to Kos

A good early start is needed in Kos, so set sail at dawn, grab a hearty breakfast onboard, and prepare for a day on one of the busiest islands in Greece.

You’ve immersed yourself in ancient Greek history, you’ve taken walking tours and you’ve enjoyed some time on the beach—it’s time to do something different in Kos. And there are a lot of things to choose from, so you might want to plan ahead to fit them all in.

Kos Divers is a great way to acquaint yourself with the beautiful blue waters of the Greek islands, and when you emerge and dry off you can jump one of the horses from Salt Lake Stables to take a ride on the beach and even into the sea itself. After a morning keeping yourself busy on the beach you can stop for a drink at one of the many beach bars, where everything from delicious cocktails to games of pool are available.

If you journey to the middle of the island you can visit Plaka Forest, where you can spend the evening fraternizing with free-roaming peacocks, before heading back to Kos Town to spend the evening in Eleftherias Square, a classic Greek town square where you can enjoy drinks with locals and tourists and watch the sun go down over Kos.

You’ll be glad to hit the sheets at the end of day 4, but your journey through the Dodecanese isn’t over yet.

Yacht Charter Day 5 – Kos to Nisyros

Feel free to sleep-in on day 5 and spend some more time in Kos, before heading off in the afternoon to visit Nisyros, the fifth step of your island journey. This is another small island, with only around 1,000 residents spread across just a few thousand square miles.

According to Greek mythology, Nisyros was created when the sea-god Poseidon tore off a piece of Kos and threw it at an escaping giant to block his path. It was mentioned by Homer in some of his writings and over the centuries it was inhabited by both Greek and Roman conquerors, before the Knights Hospitaller settled here in 1315.

This volcanic island has some of the best views in all of Greece, perfect for watching the sun rise and fall over mountainous terrain, and it’s very popular with day-trippers from Kos. We recommend renting a car and taking a trip around the island, enjoying as much of the scenery as you can and making regular stops to snap some Instagrammable pictures.

It’s a great place for hikers, if you’re into that sort of thing, but you don’t need to do a lot of climbing to see some breathtaking views and snap some equally breathtaking pictures. Just ask the chef to prepare you a packed lunch, grab a few bottles of water, and enjoy your escapade.

It’s small enough that you won’t get lost, but big enough to sate your appetite for adventure.

Yacht Charter Day 6 – Nisyros to Symi

The final island on your journey is Symi, an affluent, charming island that offers a little something for everyone.

If you still have some energy in your legs then we recommend climbing the several hundred steps of Kali Strata that will take you to the old town of Chora. It’s a trek, but the destination is well worth it. It’s a similar story with the Panormitis Monastery in that it’s a bit of a journey and one that is somewhat out of the way, but worth it when you get there.

You can rent a scooter in the town if you want to make this journey easier, but there’s plenty to see on foot if you’d rather walk. Whatever you do, make sure you’re back in town for lunch or an evening meal. The onboard chef will of course provide you with whatever you need, but we also recommend trying the local shrimps. Known as “Symi’s Shrimps”, these pan-fried bites are famous in this area and are a delicacy you won’t want to miss.

There are plenty of tavernas and bars on the island as well, including ones that offer a view of the Aegean sea. We recommend grabbing a seat outside one of these bars or restaurants in the evening, just in time to watch the sun go down on the island, and on your Greek adventure, as you sip an evening cocktail or a chilled ouzo.

If you’re in the town during the summer months then you may also catch the Symi festival. This festival has become a hotspot for Greek musicians since it was first founded in 1995. It could provide you with an opportunity to hear some local music and maybe even partake in some events yourself.

Yacht Charter Day 7 – Symi to Rhodes

Day 7 is the final day of your charter and the end of your Greek adventure, but there is still more to see. If you only spent a few hours or a day in Rhodes before you began your trip, then we recommend booking yourself into a hotel when you return to the island and spending a couple more days there.

The Mitsis, Lindos Blu, and Boutique Hotel will all provide you with a top-of-the-line 5-star experience as you spend more time on the island. Try some of the fine dining restaurants like Alter Ego, Shark Fish or Mageirotechneio Paraga, visit the museums and sites that you didn’t see the first time around, purchase gifts and goodies at the local stores, and take some more pictures.

And if you like what you see and want to see even more, why not book another charter? There are many more glorious Greek islands to see, with a wealth of history, culture and great food to experience.

Would you like a Greek yacht charter in the Dodecanese? Inquire now!