Number 1 Sailing Vacation Spot in the World

Sicily Rated As Number 1 Sailing Vacation Destination

Sailing in Sicily

Sailing in Sicily

If you’ve been following us on facebook, you’ll know that we went sailing in the Aeolian Islands, Sicily last week with Spartivento Yacht Charter Company. We’ve been fortunate to sail in just about every sailing vacation destination in the world and so people always ask me where is the best place. Until now, I have always responded with “each one is a 10”. But after visiting Sicily last week, I have to say: hands down, without a doubt, we are now rating the Aeolian Islands in Sicily as the number one best place on planet earth to take a sailing vacation.


  • Very inexpensive
  • Easy to get to
  • Fantastic sailing ground
  • Plenty of off-the-boat adventures
  • Excellent food
  • Fantastically tasty wine
  • Friendly people
  • Good charter companies
  • Warm water (for the Med)
  • Rife with history
  • Deep water with little hazards
  • Line of sight navigation
  • Not crowded
  • Palermo is an excellent pre or post city for a stayover

Note that we are agents for all yacht charter companies and so if you want to go to Sicily (or any other location), we can arrange that for you with no fee to you. You get the same price as going direct but you get our expertise and ability to search for best prices and boats.

Contact us here for your sailing vacation

Read on for a series of articles on our Sicilian adventure. We’ll discuss the area, what we did, logistics of getting around and give you a full guide of the Aeolian islands including best restaurants and a great weeklong sailing itinerary. Bookmark this article now.

BUT FIRST: With any Mediterranean sailing vacation, you have a great opportunity to stay on land and visit the local area. For this trip, we elected to experience Sicily on land a little before:

Palermo is the capital city of Sicily and is about an hour and a half flight from Rome. This was the launching point of our Sicilian sailing vacation. At the airport, there is a bus that will take you right into the center of town for E6 ea.

If you’re going to go sailing in Sicily you must must must spend at least a few days (more is better) in Palermo. Stay right downtown, as close to the action as possible. Palermo is a metropolitan melting pot with a vast range of food influences, street markets and architectural styles inspired by Moor, Spanish, Greek and Italian. Just like Starbucks in the USA, there is a 500 to 1000-year-old giant church on every corner.

Even with only two days, you won’t have time to experience all the markets and back street alleys. So plan on 4-5 days there.

We Airbnb’d it in the center of the old city near Piazza San Dominico which is walking distance to about everything. We stayed at Chiara’s place on Airbnb which was a fantastic apartment on the 4th story down a back alley.

What we did in Palermo

Architecture: The Architecture is ornate, old and impressive with a mishmash of ancient cultures. View this 360-degree photo by clicking on it first.


Other markets feature an interesting selection of trinkets, clothing, leather bags, fidget spinners and the like. Some cheap and some quality, but all very inexpensive.

Mafia: Sicily is the birthplace of the mafia. But for most of us, we feel like we are never really touched by this bullish tyranny. We did a walking anti-mafia tour of Sicily where our guide led us through the streets talking about how the Mafia touches everyone every day. Shopkeepers are extorted into paying the Pizzo, the “protection money,” and so, built into the price of every good or service is a portion that goes to fund the Mafia. 15 years ago, however, a group of graduating students were designing a business plan for a restaurant. They listed out all the costs of operations. At the end, one student said oh we must include the Pizzo. With disgust at the thought, the group changed gears and started an anti-mafia movement. Convincing shop owners that they could stand together and not pay. Today, there is still a large percentage of the shopkeepers paying the Pizzo out of fear but also a large percentage not paying.

Wines: Wines in Sicily are really REALLY delicious. Early one evening at a very unassuming restaurant on a back alley street, we organized a wine Sommelier to give us a wine tasting of the best wines of Sicily so that we’d not waste our time on dish water for the rest of the trip. We narrowed down the Catorratto whites as the best. With that set, we now knew what to stock for the upcoming sailing trip. Personally, I’m mostly a red drinker but for some reason on this trip, the Sicilian Catorratto white was hitting my favor. If you end up at a grocery store, it is hard to find wines over E5 and some delicious ones at E2.

Walking street food tour: Another evening, we hooked up with Giorgio a street food guide via trip advisor and he lead us around the central area taking us into the little-known street food joints so we could get a taste of typical Sicily. Personally, I passed on the classic spleen sandwich albeit others in the tour liked it.

Late night bars: We found our favorite down a little alley called Fuoriluogo. Each night we’d go there and finish off the evening with what we coined as a nighto cappo. One of the locals there even said to us “Hey Keep Austin Weird” which is the Austin informal slogan – so we made good friends with him. Some other bars we went were really hopping with lots of young locals and tourists all having a great time.

Brioche Con Gelato for Breakfast: Ice cream burger for breakfast!!! Weird right? Don’t knock it till you’ve tried it. OMG sooooo good.

Brioche Con Gelato

Brioche Con Gelato

Here is an interactive map of Palermo of some of the fun bars, restaurants, and sights seeing that we did and that we recommend.

Here is a Google maps video of Palermo of the same.

After staying in Palermo for 4 days, we took the train to the Spartivento Charter Company in Porto Rosa. The train leaves from downtown Palermo so it very convenient. The charter company will provide transport from the station near Porto Rosa to the base or to your hotel. Specifically, we took the train (Trenitalia) from Palermo Central station to Novara-Montalbano-Furnari Station which is about 4 km (3 mi) from the Porto Rosa Marina.  The cost was about E15 ea. Some of our crew flew into Catania which is a slightly closer airport (2hr drive) to Porto Rosa. Some then rented a car in Catania for a week and drove to the marina. Some hired a driver. We found the trains to be easy and inexpensive and an enjoyable ride along the coastline. TIP: when on a train use your phone with google maps so that you get off at the correct station.

See Day 1 and 2 of Sailing in Sicily; The NauticEd recommended number 1 sailing vacation destination in the world.



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