An amazing sailing week around Santorini

Summary: The incredible natural beauty of Santorini attracts many sailors each year, but there is no wonder because Santorini and the islands surrounding it are top destinations and on many people’s bucket list. The volcanic landscape with rugged cliffs, the unique wild nature, the beautiful beaches with crystalline azure water, combined with rich history, amazing people and traditions, will surely win a piece of everyone's heart.

An amazing sailing week around Santorini

Around 1650 BC, a severe volcanic eruption occurred and the myths say that Santorini emerged out of the sea in a miraculous way. After the eruption, half of the island disappeared, and due to it, the raised waves were so high that reached the northern coast of Crete, destroying the coast towns, including the well-known Knossos Palace.

Nowadays, Santorini is most known for the architecture of the villages, built right on top of the caldera. The sugar-cube houses, the stone paved streets and wonderful churches make Santorini a unique place that will just impress you with its natural beauty. From the top hill of Oia, you can enjoy probably one of the best sunsets you ever seen, with the orange sun at the horizon, dipping into the sea. Due to the romantic atmosphere created by this place, Santorini has become a very popular wedding destination.

Arriving in Santorini

The best and fastest way to travel to Santorini is by plane to Santorini Airport, and from there you can easily find buses or taxis to all major cities of the island.

If you plan to sail to Santorini, it can be found at these coordinates: 36°23'09.3"N 25°25'43.3"E, and if you want to charter a boat in Santorini, we recommend Vlichada Marina, where you can find good deals for renting a sailing boat or a catamaran.

Weather in Santorini

Santorini, as most of the Greek Islands, has a Mediterranean climate, and the temperatures vary across the year. From June to September the weather is hot, with July and August being the hottest months, with an average temperature of 26 °C (79 °F) and January is the coldest month with an average temperature of 12 °C (54 °F).

Summer months are ideal for sailing, relaxation, swimming and sunbathing. However, these are also the most crowded months, and if you want to enjoy a more serene side of Santorini and surrounding islands, the ideal months are April, May and October.

The winds in Santorini blow mostly from the North - North West. Since these islands are located at the southeast end of Greece, they are considered to be among the warmest sailing destinations. The Meltemi winds can be quite strong in July and August, so don’t forget to reef the sails, because weather can change rapidly.

If you are quite new to sailing, you can visit these islands in the months of early April or late November and October, because the winds are calmer and blow from South East.

Planning the itinerary

Prepare for a 7 days unforgettable sailing adventure around Santorini, one of the best sailing places in Europe and an amazing opportunity to spend the summer vacation with your family and friends. For this sailing itinerary, the starting point is located in the South part of Santorini, in Vlichada Marina and you will sail more than 90 nautical miles around a very unique landscape, amazing Mediterranean cuisine and amazing blue waters. Depending on your yacht type, course and pace, the below information may vary.

  • Leg 1 – Vilchada to Oia, Santorini – 8 NM – 1.5 hours
  • Leg 2 – Oia to Ios Island – 17 NM – 3 hours
  • Leg 3 – Ios Island to Folegandros Island – 20 NM – 3.5 hours
  • Leg 4 – Folegrados Island to Thirasia Island – 25 NM – 4.5 hours
  • Leg 5 – Thirasia Island to Vilchada, Santorini Island – 9 NM – 1.5 hours
Santorini itinerary

1. Vilchada to Oia, Santorini – Leg 1

Sailing to Oia, Santorini

Santorini worth to be visited for an entire week so maybe one week will not be enough to explore every place in this itinerary, but it will create a reason to return in this amazing place.

After provisioning the boat, you can head North to Oia city, either surrounding the island to East or West. If you choose to go West, watch out for ferries, especially in summer months when the traffic is heavy.

You should reach Oia in about one hour and a half, where you will find several anchorages from where you can enjoy the amazing sunset this place offers.

Sightseeing in Oia, Santorini

From Ammoudi Bay, you can reach the upper city by riding a donkey, which is the favoured mean of transportation for locals, and also becoming increasingly popular among tourists. If you prefer, you can hike to the top and keep yourself in a good shape.

Going up, you will notice on your right-hand side the remains of Caste of Oia, more precisely a surviving watchtower of a Renaissance-era castle, built to guard against pirates. This castle is also known as the most popular spot to watch the sunset, the main point of interest for this city. The stunning views of the windmills and the whitewashed buildings perched on the edge of the caldera, it’s an image you’ll always keep close to your heart.

Accomodation when sailing to Oia, Santorini

Good accommodation can be found in Oia and if you don’t want to spend the night at anchor, we recommend Charisma Suites**** with starting price from 541 € / night or La Perla Villas and Suites***** from 512 € / night.

Sunset in Oia, Santorini

Sunset in Oia, Santorini

2. Oia to Ios Island – Leg 2

Sailing to Ios Island

From the anchorage in Oia to Ios Island you will sail for around 17 nautical miles, and depending on your boat, you should arrive in about 3 hours. Taking a N-NW course, you can reach Chora, where you can find safe shelter and also a starting point to explore the island.

Sightseeing in Ios Island

Ios Island is well known for its crystal-clear waters, pristine beaches, dramatic crags, a mythological history and whitewashed buildings. Chora offers a great number of scenic views, as well as numerous side alleys to explore, not to mention the shops that line the streets of this whitewashed town. Chora is known for its peaceful vibe by day, but also for its lively nightlife scene with numerous bars and clubs.

As we mentioned the pristine beaches of Ios island, you can find below a list with our recommendations:

Accomodation when sailing to Ios Island

Good accommodation can be found on Ios Island, like Hotel Petradi** with starting price from 130 € / night or Ios Palace Hotel & SPA**** from 208 € / night.

Port of Ios, Ios Island

Port of Ios, Ios Island

3. Ios Island to Folegandros Island – Leg 3

Sailing to Folegandros Island

Folegadros is only 20 NM away from your departure, so take your time to admire the impressive scenery around you. After leaving the Port of Ios, take a W-SW course and after about 10 miles you will have on your starboard side the island of Sikinos, with good anchorages on the NE part of the island, in case you want to explore the island.

Sightseeing in Saint Folegandros Island

Characterised by jagged cliffs and rocky hills, the Folegandros island is a wilderness retreat for those wanting a sailing holiday steeped in tranquillity. Offering ancient history, sleepy tavernas, breath-taking landscapes and secluded beaches, there is an abundance of things to do in Folegandros. The island is a hidden gem, so it’s well worth a stop before the rest of the world catches on.

The traditional Cycladic style town of Chora is the capital city of Folegandros and will just enchant you with its narrow alleyways, whitewashed buildings adorned with blue shutters and cascading flowers. You can explore the surroundings by renting a moped, or hiking.

The best beaches on the island are the following:

Accomodation when sailing to Folegandros

Good accommodation can be found at Anemi Hotel***** with starting price from 389 € / night and Lemon Tree Houses*** from 340 € / night.

In terms of restaurants and tavernas, Chora has plenty to offer. Good wine can be tasted at Merkouri Wines Bar - Chora Folegandros and amazing food at Nicolas’ Place.

Folegardos Island

Folegardos Island

4. Folegardos to Thirasia Island – Leg 4

Sailing to Thirasia Island

Raise the anchor and head S-SE for the amazing island of Thirasia, only 25 NM away from Folegardos. In about 4 hours you can admire this impressive, virgin island, still untouched by tourism and modern lifestyle.

Sightseeing in Thirasia Island

Thirasia Island is located near Santorini. Once, the island was part of Santorini, before the volcanic eruption that happened around 1500 BC broke Santorini into many pieces.

On the island you should visit the town of Manolas with its small, picturesque houses painted in various colours, and further on, the Monastery of the Assumption of the Virgin Mary. In the surroundings, there are also another 20 churches worth visiting.

Close to Thirasia, you can also visit the hot springs of Palia Kameni, or book a paid tour, that includes also other attractions. There are many companies offering tours, like Santorini Action.

  • Volcano entrance fee 2.5 € per person

Accomodation when sailing to Thirasia Island

Good accommodation can be found on the island, like Thirassia Paradise Suites*** with starting price from 128 € / night. Try some local dishes at the restaurant Agistri Restaurant, which will amaze you with the flavours and traditional recipes.

Thirasia Island

Thirasia Island

5. Thirasia Island to Vlichada, Santorini – Leg 5

Sailing to Vlichada, Santorini

Sailing back to Vlichada is only 9 nautical miles away, so set sail when you consider best, because there are lots of things to discover on Santorini island. If you charter the boat, maybe is best to consider staying some extra days, to discover the magnificent island.

Sightseeing in Vlichada, Santorini

If you have more than one week to spend here, we strongly advise you to explore Santorini, as if has lots of amazing places to offer. One must see spot is Fira, Santorini’s capital, which will just amaze you with its famous white and blue houses, picturesque narrow streets, chic boutiques, luxury hotels with infinity pools and the magnificent views of the caldera.

It’s impossible not to mention also the best beaches on the island:

Accomodation when sailing to Vlichada, Santorini

Good accommodation can be found in Vlichada and also on the island. If you prefer to spend some time in Vlichada, we recommend Villa Michalis*** with starting price from 135 € / night. Try some local dishes at the restaurant Dimitris, close to the marina, which will amaze you with the flavours and traditional recipes.

Santorini, Greece

Santorini, Greece

Capetanos sailing and general recommendations

For an amazing sailing week around Santorini, we strongly recommend to plan in advance, consult the charts, weather conditions and choose the most suitable time and boat, according to your sailing skills.

We hope that information in this article will contribute to your decision for your next sailing holiday in Santorini, one of the top destinations in Greece and Europe.

Sailing bugdet calculator / rent boat calculator Santorini

These calculations are performed for one-week charter on a 46 feet sailing boat in mid-august and crew of 8. The total may differ depending on many factors like boat amenities and construction year, mooring fees, dinner out, etc.

1-week total 5.770 €
3 cabins sailing boat 3.000 €
Skipper (optional) 1.050 €
Food 460 €
Water 50 €
Diesel 210 €
Moorings 150 €
Food out 850 €