7 Days Sicily Sailing Itinerary – Best Spots & Activities

Sicily is an island in Italy that sits at the center of the Mediterranean Sea. The island is separated from the South of Italy by the strait of Messina. Its vast waterways are perfect for sailing. 

The country has withstood different colonizers from the Greek Colonies and the Roman Empire in the 5th century AD to the Germans, Arab and Normans created a hodgepodge of architectural design and culture.
From the grandiosity of its structures to the active volcano to the turquoise water next to the pebbly beach, that is Sicily’s unique charm. Here is 7 days Sicily sailing itinerary prepared just for you so you can plan your sailing trip easily!

Sailing Itinerary Sicily
Weather All Year

The country has a Mediterranean climate which consists of hot and dry summer and mild and wet winters. The best time to sail in Sicily enjoying the rhythm of nature is from April to October. A great time to enjoy the country which is home to seven UNESCO World Heritage Sites.

7 Days Itinerary in Sicily


Day 1 – Palermo

Anchor in Marina di Villa Igiea in Palermo, the 2700-year-old capital of Sicily. A vibrant city full of rich history, culture and architecture right by the Gulf of Palermo. The grandiose architecture against the mountains is an amazing contrast in itself, organized chaos. Every nook and cranny of the island will leave you in awe and a delight to the senses.


Conquer your taste buds as you savor Sicilian cuisine that is better than anywhere else. From the Sicilian rice balls called arancini to the mouthwatering gelato and the infamous cannoli. A gastronomic experience you will never forget.
Spend a day admiring Palermo’s architecture and be amazed at how different foreign countries shaped the architecture of Palermo as we see it today. Be amazed at the Byzantine architecture of Palantine Chapel to the multi-architectural style of Palermo Cathedral to the Norman architecture of San Cataldo. Church of San Cataldo is listed as a UNESCO World Heritage site.


Palermo is a city that never sleeps so an overnight stay is recommended to see its beauty at night. Palermo may not have the famous clubs like the huge cities but who needs one when you can go down the town alley for some dance party.

Palermo Sicily Sailing Itinerary

Day 2 – Stromboli

After having a sumptuous breakfast in Palermo, sail away to the island of Stromboli. Watch nature in action as you see the 2nd most active volcano in Europe. Thus, the name “Lighthouse of the Mediterranean.”


Have your lunch at one of the restaurants that offer great food and an amazing view of the sea. Lounge by the beachside and be enthralled by its breathtaking sunset.

If you are at the adventurous side, explore Stromboli’s crate as the sun sets to watch the crater glow red and magma flows slowly down the mountain to the sea. Experience the eruptions up close and personal.

Stromboli Sicily Sailing Itinerary

Day 3 Lipari

Anchor in Porto di Pignataro the following morning in Lipari. The island is the largest of the Aeolian Islands. Have a quick breakfast in your before hiking the 16th century Lipari castle. The Lipari Town centers have several cafes and restaurants lined up to choose from. Stroll along the picturesque Marina Lunga and drop by the Church of Anime del Purgatorioto and the sea. 

At the opposite side of the town are the 16th-century castle, the Cathedral of San Bartolome and some ancient Greek ruins. The town is small enough to wander around on foot. Never let the day pass without swimming in the clear water and sunbathing on the pebbly beach of Acquacalda. Stay for the night at Lipari before sailing to Vulcano, which is just within sight.

Lipari Sicily Sailing Itinerary

Day 4 Vulcano

It is a small volcanic island at the southern end most of Aeolian Islands. Vulcano has been quiet since 1888 so it is safe to hike on top of the ashes and pumice stone.
Dock your yacht at Porto de Levante. Immerse in the splendid view of the island. On a clear day, you can see the other islands in the distance – Alicudi, Salina, Stromboli, and Lipari.


Mud baths are a must on the island of Vulcano. It is known to have beneficial properties such as curing asthma. If you are a fan of hot springs, then Vulcano is heaven for you. Swim in their famous “acque calde” or warm waters for that soothing experience. Last but not least, hike the Gran Cratere. 

Vulcano Sicily Sailing Itinerary

Day 5 Taormina

Depart in the morning to Taormina, the tourist capital of Sicily. Relish a one of kind panoramic view at the top of the Ancient Theatre, Teatro Greco. Stroll along Palazzo Corvaja (Corvaja Palace) built in the 14th century to see its hidden gem Naumachia, remains of a spacious edifice. 


The town perched on top of the hill is charming with its old churches, bars, Michelin star restaurants, and shops. In the evening, anchor in Isola Bella as you enjoy its magnificent beauty. 

Taormina Sicily Sailing Itinerary

Day 6 Syracuse

Arrive in Syracuse early as the stunning city is one you should never miss. It is considered as the Greek Sicily and described as “the greatest Greek city and the most beautiful of them all” by Cicero. The whole city is listed as a UNESCO World Heritage Site.


Syracuse houses some of the infrastructures built for the gods such as the Temple of Apollo, Fountain of Arethusa, Greek Theatre, Roman Amphitheatre, and the Temple of Olympian Zeus. Notable churches in the Christian period like Cathedral of Syracuse, Basilica of Santa Lucia and Our Lady of tears can be found in the island.

Syracuse Sicily Sailing Itinerary

Day 7 Back to Palermo

On the last day of a, it is always great to go back to where you started. What is an Italian city without its opera? Admire the grandiosity of the opera houses in Palermo such as Teatro Massimo and Teatro Politeama.
Another of Palermo’s landmark is Quadro Canti, which means four corners. It is an intersection that divides the city into its four historic neighborhoods. For the brave souls, drop by Capuchin Catacombs which has mummified corpses that can send shivers to your bones.


For the rest of the trip in Palermo, drop by their boisterous market to shop for some food and souvenir that’s truly Sicilian. Be entertained by the singing salesman trying to lure their customers. The Palermo market is one of the best in Europe.

Palermo Sailing Itinerary in Sicily


The week that has passed brought you back to the ancient civilization in an experience like never before. As you lay back on your yacht, a sudden realization came into view: sailing and Sicily share the same charm. Both exude beauty in the mishap. Sicily’s cultural diversity brought about by its long list of colonizers is like sailing amidst rough waves, giving you a sense of tranquility and accomplishment. 

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10 thoughts on “7 Days Sicily Sailing Itinerary – Best Spots & Activities”

  1. Hello Daniella! Well, if I needed to be convinced to go on cruise in Sicily, it’s done! Thank you so much for such a precise description of the trip and for the choice of locations during these 7 days. 

    Reading your article reminded me of Luc Besson’s movie ‘The Big Blue’, one of my cult movies. 

    I would love to swim in the acque calde of Vulcano and to take a tour of Taormina. I suppose lying a few hours on a yacht between trips is quite heavenly! Cheers, Anso

    • Hi Anne,

      Oh, yes! Sailing through beautiful islands on a yacht is definitely a dream!

      I am glad this article has inspired you!

      If you need help, let me know, I am always happy to help! Thank you for the comment and wish you a nice day!

  2. This is possibly the best itinerary I have ever seen, it even has an active volcano! Being a musician myself, I would love to visit an Italian opera in Italy. These opera houses that you have mentioned are worth checking out. And if I ever want to plan a trip to Sicily, I will definitely contact you.

    • Hi Mikhail,

      Thank you for the kind comment!

      If you are a musician, I am sure you’ll not only enjoy opera houses there but everything that Sicily has to offer! Food, arts, music, views, and much more!

      You can contact me whenever you want. I’ll be more than happy to assist!

      Thank you for passing by and wish you a lovely day!

  3. OK.  Italy has always been a dream destination for me and after reading your article, I know there is no way I can ever leave this earth without visiting there at least once!

    Your descriptions of the various locations created amazing images in my mind and really brought the history of them all to life.

    Hmmmmm I even found myself speaking in an italian accent – Fabulous job and well-written!

    • Hi there,

      Yes, I understand, Italy is the dream destination of many people around the world:)

      That’s wonderful! That way you’ll be ready to speak when you get there:)

      I am glad this article has inspired you.

      Let me know if you need help. I’ll be more than happy to assist!

  4. I think Sicily is the best place to visit in Italia. And I always wanted to visit stromboli. So, how do I sail in Sicily? I would like it to be a cruise with many people, it’s always great to share such awesome moment with friends. Is the fee an whole inclusive? Or the food and other things will be on me.


    • Hi Adyn,

      Sicily is beautiful and so unique.

      If you want to sail with other people, then you should rent the boat with a group of friends. You can definitely rent a boat that included food, drinks, and services.

      The best thing to do is to either choose a boat or send an inquiry, so you can receive a sailing holiday charter quote:)

      I hope it helped. Please don’t hesitate to contact me with any question. I’ll be more than happy to assist.

      Thank you for the comment and wish you a nice day!

  5. I have to say, I’ve never had Sicily on my list of “must go” travel destinations, but after reading this article that has changed.  Based on your descriptions and the pictures it seems amazing!

    You mentioned the possibility of hiking on Vulcano.  Are there other hiking spots that you would recommend in or near the locations?  For Vulcano (and/or any other suggested hikes), do you think true hiking boots are necessary, or would it be possible to do the hike in sneakers since that would be more comfortable when walking around town before or after hiking?  Thanks in advance!

    • Hi Jordan,

      Yes, sure, there are many great hiking trails around the Vulcano where you can enjoy hiking such as Valle Roia, Stromboli, Vulcano sull’isola di Vulcano, Gran Cratere, Subida al Gran Cráter de la isla, etc..

      There are other islands for hiking too such as Lipari, Palmarola, Caprera, and many others. I highly recommend wearing decent hiking boots for hiking on the Vulcano as it is rocky terrain. Anyway, at the entree, they won’t let you hike without hiking boots. There is a store near the Vulcano that rent boots and other equipment. Bring with you some snacks, water, and a headlamp because it’s dark too:)

      I hope it helped. Let me know if you need more info. I’ll be more than happy to assist.

      Thank you for the comment and wish you a lovely day!


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