The Peloponnese – Greece’s Cradle of History and Adventure
Greece is a top sailing destination with a vast coastline offering diverse experiences. While many areas are crowded with tourists, hidden gems remain. Explore beyond the popular spots to discover regions where the traditional Greek way of life endures, and locals warmly welcome visitors. Here we feature one such locality, where you'll find the same captivating culture, history, and cuisine that make Greece famous, with a more authentic and intimate experience.
This most southern region of the Greek mainland boasts miles of stunning coastline waiting to be explored. Delightfully off the beaten track from Greece's typical tourist circuit, well known for their crowded anchorages and bustling small towns during peak season. The southern Peloponnese offers a more tranquil escape that's easily accessible from main travel hubs. The region's breathtaking coastline has a thriving charter boating scene of its own.
Steeped in Greek history and once home to the Spartans, the Peloponnese Peninsula is connected to central Greece by a land bridge that separates the Gulf of Corinth from the Saronic Gulf. Your charter sails the southern peninsula’s three southward-pointing arms: Messenia, Mani, and Malea, as well as the nearby island of Kythira. This is a region defined by rugged coastlines punctuated with picturesque bays and charming traditional Greek towns and villages: a perfect setting for your leisurely sailing holiday.
Your adventure begins in Kalamata, the region’s home base for charters. From here, most charters go south and east along the deeply indented coast with a short hop to Kythira providing a convenient turn-around point for your return.
Overnight there are numerous sheltered bays to choose from, either for anchoring or picking up a mooring. Play in the emerald waters, hike the surrounding hinterland or shop in a fishing village. Enjoy magical Mediterranean evenings aboard your floating hotel or dine ashore in a colourful Greek taverna, soaking in the vibrant local atmosphere.
Getting there
As there are no direct flights between Athens and Kalamata, the quickest - and cheapest - way to get there is by road. The daily bus service takes 3 hours 15 minutes and is a convenient way to see more of the Pelopennese countryside, starting with a crossing of the famous Corinth Canal. The car ride takes 2.5 hours, and private transport can be arranged as part of your charter. During the high season, some European airlines have direct flights to Kalamata.
Kalamata
Spend some time in this city of 70,000 people, and see a part of Greece far removed from the picture the travel brochures present of the sun-baked islands others wil be gravitating to. Here the groves of the kalamara olives give you a first impression of a city packed with cultural and historical sites. The Old Town is one of the best you will see, with its narrow alleys, neoclassical mansions, centuries-old churches, cute abodes and of course numerous small shops and stalls selling all manner of local products.
Your charter base is in the heart of Kalamata Port, close by to convenience stores and coffee shops and all the facilities if travelling there on your day of embarkment. Full provisioing can be arranged in advance as part of your charter, or if time you can visit one of several nearby supermarkets.
If spending a day or two in Kalamata, take a ride to the mountain villages on the western slope of Mt. Taygetos, on the road through Sparta considered one of the most beautiful in Greece. Also nearby is the ancient city of Messini with its extensive ruins dating back to 371 BC.
Suggested Sailing Charter Itinerary
This suggested itinerary requires an 8-day charter to achieve it at a leisurely pace, easily done with a hired skipper or crew and also possible bareboat. The large number of options for overnighting along the route makes it easy to amend this plan to visit most if not all places mentioned on a standard week-long charter.
Day 1: Kalamata to Kardamili
Your first night may be spent in port, or if time is on your side at nearby Kardamili, 14 nautical miles and about 2 hours away. This former sleepy seaside village is now quite upmarket, a far cry from when accoring to Homer's Iliad it was promised to Achilles to convince him to return to the Trojan War. An ideal spot to get acquainted with your boat and prepare for the journey ahead.
Day 2. Kardamili to the Diros Caves
As your boat lays at anchor in the tranquil waters of the Diros Caves region, you find yourself pausing to soak in the breathtaking beauty and reflect on the uniqueness of this unforgettable destination.
Day 3: Diros Caves to Porto Kagio and Elafonisos
Set against a backdrop of rugged mountains and nestled in a remote location, the tiny village of Porto Kagio offers the experience of serenity that comes with being far removed from civilization for a while.
The tiny island of Elafonisos, often referred to as the Greek Caribbean,' is renowned for its stunning beaches and crystal-clear waters, making it a paradise to explore and enjoy.
Day 4: Alafonisos to Kythera
Kythera is an island filled with traditional tavernas, charming churches, and ancient ruins. It’s the perfect place to stretch your legs after time aboard—whether by hiking scenic trails, swimming, or snorkelling—before unwinding, soaking up the sun, then enjoyin the local night life.
Day 5: Kythera to Gythio
Featuring excellent beaches, historic monuments such as the Temple of Apollo and the ruins of an ancient castle, Gythio has one of the few marinas along this coast.
Day 6: Gythio to Kotronas and Gerolimenas
With its sheltered harbour and nearby white-sand beaches, Kotronas lies at the heart of a coastline dotted with hidden coves to explore and numerous trails offering spectacular views.
Gerolimenas is a rustic and remote destination, with crumbling buildings and ancient towers set against a wild backdrop and the azure sea. Its history of pirates, Turkish rule and fishing has left a fascinating imprint on the place, which can feel like it’s at the edge of the world.
Day 7: Gerolimenas to Limini
At Limini, drop anchor and explore the alleyways, climb the Petrobeys Mavromichalis, admire the Byzantine chapels and enjoy delicious fresh mezze plates from land and sea, before your adventure ends back at home port next day.
Day 8: Limini to Kalamata
Sail the four- to 5-hour journey back to Kalamata, disembark and make your way home, or continue your fabulous Greek vacation adventure.
Our client reviews about charter sailing in Greece
Rating: 5 / 5Boat had plenty of space for the 7 of us. The sleeping cabins were well appointed and clean as were the communal areas.
The skipper Socarates took us to pristine beaches and bays that were not overrun with other boats. Loved being able to sail during the day and then visit the local towns at night. The skipper always gave us recommendations and asked what we would like to do each day. Crew were totally there to make our trip comfortable and to experience the beautiful Greek islands
The booking experience with Sail Connection was good would recommend to friends wanting to charter a boat. Anna, Australia, Oct 2nd, 2024
Rating: 5 / 5Boat was fantastic - was it's first charter so perfect condition. We sailed around Ithica and Kefalonia - both islands were beautiful. Sail connections was easy to deal with. Kurt, Australia, Jul 12th, 2024
Rating: 5 / 5(The boat was) perfect for our family of four. Only slight negative is that the helm position has a fairly large blind spot and there is no shade.
Favourite spot ... Sarakiniko Beach, Ithaka. This beautiful spot offered good anchorage, a local taverna and easy access over the hill to Vathy.
(Your service was) excellent. Dimitri in particular was very accommodating and nothing seemed to be a problem.
Stephen, Australia, Jul 8th, 2024
Rating: 5 / 5The Lagoon 46 was the best catamaran we have chartered. There was plenty of deck and seating space and all the bedrooms/ensuites were a good size.
Preveza was a great starting point and we enjoyed travelling south to Ithaki and north to Paxi. Kalamos was a highlight we tied up to a pier next to a taverna for the night and it was a lovely spot.
We had very good service from Robert and Sue at Yachting Holidays and dealing with an NZ company gave us peace of mind. The service from Fyly in Greece was also excellent. We really appreciated being able to board the boat early and our skipper was also very friendly and easy to get along with.
Our skipper Adrian Dimitru was keen to get away on Saturday afternoon so we headed south and got a day ahead which was great. .he cruise was excellent and Adrian got us to some of his favourite spots so we were very lucky.
Ithaki not to be missed. Craig, New Zealand, Oct 18th, 2023
Rating: 5 / 5Dear Sue, we would like to thank you and Robert for all the work you put in to make our charter run so smoothly from your end. We absolutely loved the Greek Islands, they were everything we had ever imagined. Jill and Pip, New Zealand , Oct 9th, 2019
Good breezes that provided just the right level of challenge. Not super crowded - no troubles berthing / mooring / eating / etc. Fairly chilled - at least compared to Croatia. Patmos was very good. John, Australia, Aug 17th, 2019
Had a great time. The wind was terrific - good fun, but nothing too hairy - exactly what we were looking for to take it up a notch or two from Croatia last year. And the Dodecanese were really good - nice ports, not too crowded (esp compared to Croatia) - just felt a bit more out of the way. DYC were fine - a little bit more on the 'smell of an oily rag' end of things compared to the very efficient German-run scene at Trogir, but it all worked and no real issues. Excellent recommendation Robert - boat and destination - you nailed it!
John, Australia, Jul 31st, 2019
The Lucky Clover was fantastic. We travelled around the Saronic Islands which were beautiful. A new adventure every day. One day we hired scooters and explored the islands. Great service thank you. 10 out of 10, a trip of a lifetime! Deborah, New Zealand, Aug 1st, 2017
Browse our yachts for charter in Greece
For a personal proposal structured to meet your needs, with advice on all aspects of your sailing charter ...
Related Blog Posts
-
Barcelona gets ready for the America’s Cup
As well as the competition for the Auld Mug itself, the 37th America’s Cup in Barcelona will incorporate the first ever Women’s and Youth America’s Cup regattas. Chartering Barcelona 2024 will be in demand!
-
Charter Sailing in Greece: It’s not just about the Islands
Charter sailing tourism started in Greece. It’s still the place where first-time charterers want to go sailing, the place seasoned sailors return to year after year. And there’s plenty of Greece to go around
-
The Sun Loft 47 Monocat: a Game Changer for Yacht Chartering
A peak season cabin-share sailing holiday with skipper in glorious Croatia in August. Chartering a 2020-model 47 foot sailboat for just 175€ per person per day! This is the reality aboard the Sun Loft Monocat 47: a whole new concept in group charter with friends or extended family.
-
Charter a Gulet: Luxury Cruising in Classical Style
For your next sailing holiday, particularly in the eastern Mediterranean but in some other surprising places as well, consider chartering a gulet. Today's gulet is now a modern charter boat built for a unique vacation experience enjoyed in complete passenger comfort and luxury living aboard.
-
Lefkas to Athens: Boat Delivery on a Busman’s Holiday
The Ionian Islands lie off the west coast of Greece. Reaching them is a little more complicated than getting to Greece's Aegean sailing holiday destinations that are accessible by ferry or charter directly out of Athens. The Ionians are worth the effort however, with the bonus Gulf of Corinth experience if time allows.
The Sail Connections Guarantee
One contact - every option - advice you can trust.
- Matching any competitive offer
- Sourcing boats with discounts available
- Personalising our proposal just for you
- Qualifying the operator as well as the boat
- Advising without bias based on 25+ years of experience
- We do more than just book yachts!
We will match any discount website offer on charter boat price, and still provide our customary high level of service.
Get in Touch