Assuming that the trip starts from Athens main marina in Kalamaki, you may spend the first night in the bay of Agia Marina, in Aegina island. Distance is approximately 20 nautical miles (nm); the bay is safe with north – east wind, but exposed to south – southwest. Usually, I prefer the north side of the bay to anchor, keeping a safe distance of 50-70 meters from the small dock, as well as the rocky shore, where the hotels are. Anchoring is easy since there is plenty of space to anchor with depth up to 10 meters and the sea bed is mostly sandy, thus safe. However, always be cautious of the wind change, because of problematic protection to SSW winds.
The next day you leave Agia Marina and head toward the island of Hydra. The famous history of this small island, the wealth once held by the boat owners and traders of previous centuries, as well as it's important role in Greek Revolution (19th century), all these elements are encapsulated in the magnificent town of Hydra. It's also worth noting that no engine vehicles are allowed on the island, as well as it offers one of the most charming sunsets in the Aegean Sea. The trip from Agia Marina to Hydra is long, around 35-40 miles, so make sure you start early from Aegina to reach destination during day light. A yacht may best anchor in the bay 'Mandraki' of Hydra, only a bit to the north compared to old port. Although the old port is very beautiful and is worth anchoring at its docks, it is so small that you can rarely find a spot there.
Most of the times yachts berth in second and triple row, while the speed ferries may create turbulence inside the port. To keep on the safe side, we suggest the bay Mandraki, where the yacht may anchor few meters away from shore and use a line to keep steady and a dinghy to move to the land. As Mandraki has only a hotel and a little restaurant (taverna), you can get a sea taxi from the
Old Harbor to Mandraki to visit the town and then return to your boat. Walking (around half an hour) through the island's landscape is another alternative. Tourists in Hydra can enjoy walks through the small roads and alleys, good cuisine, historic aspects that are prevalent in the Town, as well as a busy nightlife in the cozy bars in the harbor and in the small roads around it.
Another cozy destination near Hydra is the island of Dokos, around 10 nm away from Mandraki (in the picture aside – map detail of Dokos, please note that Mandraki is at the right side of the picture). It is another wonderful sailing destination where the yacht may anchor few meters away from the shore and use a line to stay steady.
There is only one taverna in the island (I think not working regularly, so don't count on it to feed the hungry crew) but it offers very safe berth as it is protected from all possible winds (it's 'open' to the north but the land across does not allow strong winds to develop). Consider the option of visiting it and enjoy all the calmness you can find.
The following destination is Kyparissi bay, in Peloponnese (mainland Greece). It is located about 50 nm away of Hydra, so it's a long trip by sailing boat. Like most of the eastern coastline of Peloponnese is full in trees and it's a very calm place with clean waters to swim. I have been there once but I had the chance to see a sea turtle (unfortunately also a herd of jellyfish, which disappeared after a short while...).
Kyparissi bay is big (1,8 nm from one side to the other). There is a little dock at the north side that offers secure shelter and you can walk (or call for a taxi) to the south side where is the small village. I loved the calmness which that village offers. You can find supplies there (food, water, ice) but no electricity (to the best of my knowledge). There is also a small dock at the south side of the bay (at the village) but it is not recommended because it is heavily affected by silent waves coming from the open sea. When we tried to berth there it was impossible to approach the dock, exactly because of those silent waves which we could not see in the bay, but made themselves obvious near the village.
By all means, anchorage might take place within the bay (away from the shore) in order to enjoy swimming, fishing and the like in the wonderful waters of the bay. Please check carefully the weather forecast if the plan is to stay away from the shore during the night.
The next day continue for the southern destination of Monemvasia (around 25-30 nm away from Kyparissi). Sail by the wonderful green coast line of Peloponnese and after few hours the big rock of the castle will appear in front of your eyes. The spectacle is indeed impressive, as the rock looks like the top of a mountain, connected to the mainland only through a narrow bridge.
There is a lot written about the history of the place, which creates a sample of the history of Greece after medieval years (Byzantine period and Ottoman Empire); you can find a brief description at: http://www.monemvasia-online.com/history/. Berth is a bit problematic, especially in the pick season (mid July to mid August). If you are lucky, you can find a spot in the new built marina, 1-2 miles southern to the Castle. From there, walking to the Castle is easy.
Please note that provisions are rather inadequate: you can find water but not electricity, and the marina is not guarded. The village provides all the necessary shopping (supplies, food, ice) and there are many tavernas. Additionally, since the marina is rather small, if there is no spot available, yacht can also find anchorage in the old dock by the bridge. But this place is not as carefree as the marina, since it is exposed to the north wind. Always put a spring to the north side, and please check the nautical map on more advice how to anchor safely.
Walking to the castle is a mere pleasure. There is approximately two kilometers of walking, upwards the hill, keeping the Aegean sea on your right hand side. Once you enter the castle the old town is preserved in a good shape. There are some hotels, restaurants and cozy bars, all with wonderful view, as well as gift shops with traditional items to buy. The architecture of the buildings, one next to the other, is spectacular and offered a good solution to spatial restrictions as well as defense purposes. On the top of the hill lays the castle and it takes another half walking on stiff stairs to get there. But once you reach the top, you can see the remainings of the palace, the old church "Agia Sofia" and a 360o view of the surroundings, mainly the Aegean Sea.
Once the visitor has filled his or her mind with the image of Monemvasia, it is time to start the return trip. It's already day 4, and there are only three days left. A long journey of approximately 60 nm to the north is ahead, to Hinitsa, a small island inside the Spetses canal, and just by the entry of mainland port 'Porto Heli'.
Hinitsa is ideal for relaxation and care free swimming as it is protected in the canal and forms a small bay, where the yacht can anchor, sometimes using additionally a line ashore. During the peak season it is probable that Hinitsa is too busy to find a descent place to anchor. A good alternative is the bay of Zogeria that lies at the opposite side of the canal, on the northwest side of island Spetses. The bay is beautiful, has a lot of trees, clean sea and although it looks exposed to the north wind the land at the opposite side of the canal creates a good shelter. Do not visit in case of strong north winds. On the other hand, if guests prefer to spend the night in a port, you can visit Porto Heli, and berth at the dock. The port is very well protected from all winds, but the dock is not very long, and more important, the town has urban style, hence does not have the traditional look of Hydra or Monemvasia.
A special note should be made about the beautiful island of Spetses. It's very traditional and has a rich history. However, it is not the most suitable place for sailors, since anchorage by the port of Spetses is very restricted and the skipper needs to be very experienced to berth the yacht there. An alternative to visit Spetses is If time allows for a visit to Spetses I would suggest using a sea taxi from Porto Heli or the port of 'Kosta' that lies exactly opposite to the town of Spetses.
Next destination is Poros, in the Saronic Gulf. It is a beautiful island, covered with pine trees, very close to the northern Peloponnese coast. You may swim at the bays of Poros, in friendly, crystal waters. When heading to the port, cross the Poros canal with caution and berth at Poros port. Attention is needed to the big depths in the port where a lot of chain is required. By the dock, the depth reaches 3 meters.
The port of Poros is beautiful and busy, with many restaurants and bars. Because of its proximity to Athens, it is especially busy during summer weekends.
The final day (Friday morning) leave Poros island to return to Kalamaki (trip of approximately 40 nm). If you want to deliver the boat on Saturday morning (usually deadline is 9 pm but this depends on agreement) you can split the trip, visit the island Moni, near Aegina, but keep in mind that the only bay in Moni is exposed to north wind. From there you can start on sun dawn to Kalamaki, but once again my suggestion is to reach Kalamaki on Friday afternoon and enjoy the last evening in the boat, relaxing in the marina.
Note: Above data (distances, berthing information, etc.) are included merely for informational purposes and are not accurate. Please assess a nautical chart before your trip, to ensure a safe and pleasant trip.