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September 21-28, 2024

A Stunning Cruising Destination with Majestic Views and World Class Cuisine

Named after Aeolus, God of the Winds, the UNESCO-protected Aeolian islands were formed by volcanoes rising theatrically from the sea. Breathtaking views of mountain peaks and steamy volcanoes, black sand beaches, ancient architecture, huge sea caves, therapeutic hot springs, and world-famous cuisine highlight this Aeolian Islands adventure.

The Cruise Starts and Ends in Portorosa

You will board the yachts at 6:00 p.m. at the marina on September 21. You will disembark at the same marina by 9:00 a.m. on September 28.

Nestled in the northeast corner of Sicily with Mount Etna prominently in view, Portorosa has many activities and sites within walking distance of the marina or beyond. Explore Chiesa di Santa Maria Assunta featuring a 13th Century Black Madonna and Child above the main altar. Discover Tonnarella’s white sand beaches and the black pebble Fornillo Beach, flanked by picturesque towers. Take a three-hour pasta and tiramisu class in a private home in town, or head into the hills to savor home cooking at a family run vineyard.

Cruise in Comfort on 4-Cabin Catamarans!

On this Sicily cruise, Colgate Sailing Adventures® flotilla participants enjoy cruising on spacious 45’-46’ Lagoon and Leopard 4-cabin, 4-head catamarans provided by Sailitalia through our Moorings/Sunsail partners. Trip leaders assign participants as Skipper, Navigator, or crew, based on submitted Sailing Resumes, and also assign the yachts. Upon enrollment, please provide names of any other confirmed participants you wish to sail with and that will be taken into consideration.

Beyond Portorosa

Your week on a comfortable four-cabin catamaran takes you to secluded anchorages, exciting modern towns, and lovely traditional ports. As you head for Stromboli, the lava-spewing force of Europe’s second-largest active volcano comes into view. These fabled waters provide a lot of variety including beautiful beaches in quiet harbors, spectacular snorkeling, rugged cliffs formed by steaming craters, lush greenery and black rock formations. Your cruise leaders will choose the final itinerary after discussion with the base managers before you arrive. Here are some highlights.


Thought to be the former location of the “God of Fire’s” blacksmiths, Vulcano has steaming peaks, black sand beaches, and local mud and natural hot springs known for their therapeutic qualities. The smoldering crater, Fossa di Vulcano, encrusted with vivid red and yellow crystals, is a well-worth-it one-hour hike. There is also an interesting volcano museum. The south and northwest coasts are great for snorkeling and swimming.  At the Grotta del Cavallo, a unique half-submerged cave, you can explore underground lakes with hanging stalactites.


This is the wildest and most beautiful Aeolian Island, with a stunning Blue Grotto and network of hiking trails to the island’s scenic interior. A short walk from the main port of Capo Graziano takes you to the remains of a village dating back to 1800 BC. Enjoy superior snorkeling around the natural rock formation at La Canna. Explore the huge sea cave known as Grotta del Bue Marino.


Lush landscape with vast wooded areas filled with ferns, several freshwater springs and  panoramic views from Salina’s three towering peaks are nothing short of awe-inspiring. Scooter and bike rentals are available to get to the top. Along the waterfront you’ll find great shoreside restaurants serving local seafood dishes in beautiful settings. Pollara on the south side of the island was the setting for the Italian movie “Il Postino.”


Known as the “Lighthouse of the Mediterranean,” Stromboli is the second-largest volcano in Europe, with continuous eruptions for more than 80 years. No matter where you stand on the island, you can see the natural beauty of this massive lava-spewing mountain, extending 924 meters from the Tyrrhenian Sea, and plunging 2000 meters below the surface. At night the red-hot flow of lava is visible as it makes its way into the sea. The black rock of the towering volcano mixed with the island’s traditional white houses creates a magical effect. A half-hour scenic hike takes you to an observatory area where you can dine while enjoying breathtaking views. In Ginostra’s town piazza you’ll find this island’s famous, decadent cannoli desserts.


This is the largest, oldest, and most densely populated Aeolian Island. Explore its ancient Greek acropolis, exquisitely preserved 13th century cathedral, the Aeolian Museum and enjoy fine wine at one of the five vineyards located on the eastern coast. The fleet might cruise over to the small uninhabited island of Basiluzzo for spectacular snorkeling, or stop at Panarea, the smallest, but most picturesque of the islands with a glamorous port town and panoramic views from Punta del Corno.



2024 Sicily Package Costs

The Grad Discounts below apply only to those individuals who currently hold the specified certification and certificate. If you are traveling with someone who does not meet the Category 1 or Category 2 requirements below, they must pay the Category 3 package cost. Offshore Sailing School grads with US Sailing Bareboat Cruising certification designated as “skipper” or “mate” need to hold the US Sailing International Proficiency Certificate (IPC), in order to charter and skipper in Sicily.

For Qualified Offshore Sailing School Graduates


  • $4,495 single in a private cabin
  • $3,995 per person, sharing a cabin


  • $4,695 single in a private cabin
  • $4,195 per person, sharing a cabin


  • $4,995 single in a private cabin
  • $4,495 per person, sharing a cabin

Payment Schedule

If you book anytime up to May 24, 2024, a deposit of 30% of the total package cost – and your sailing resume – are required to hold your spot in the cruise. Final payment is due May 24, 2024.  If you book May 24, 2024 or later the full amount is due. Refunds are not allowed on any cancellations May 24, 2024 or later for any reason. BUY TRIP INSURANCE PLEASE!

Your Sicily Flotilla Cruise Package Includes:

  • 7 nights in a private or shared cabin on one of the flotilla catamarans, assigned in advance by your cruise leaders
  • Welcome meet and greet party and dinner first night of trip
  • Gala group dinner ashore during the cruise or at end of cruise
  • Starter pack of provisions and bottled water
  • Wi-Fi aboard your yacht
  • Full fuel and water tanks upon departure, no need to replenish and pay for fuel upon return
  • Damage waiver
  • Commemorative Colgate Sailing Adventures® Sicily Flotilla Cruise shirt and hat
  • Comprehensive e-book prepared by Offshore, to help you plan your trip
  • Guidance by expert cruise leaders Nate and Heather Atwater, with the fleet throughout the cruise

Contributing to the Boat Kitty

As with any Colgate Sailing Adventures® Flotilla Cruise, crew on each boat contribute equally to a kitty to cover shared costs during the cruise, usually starting with $100 per person. To discover Sicilian food and cuisine, and the hospitality of those who live there, plan on shopping local markets for goodies to share aboard. Most nights you will enjoy dining ashore at seaside and inland eateries.

Who Can Participate on a Colgate Sailing Adventures® Flotilla Cruise?

If you are an Offshore Sailing School graduate with Bareboat Cruising Certification (OSS 104/114) or higher, and love sharing sailing adventures with likeminded sailors, this cruise is for you!  If you took OSS 101 or OSS 102 you are also welcome, as well as experienced sailors.  All participation acceptance is based on review of the required sailing resume.


Why is a Sailing Resume Required?

All Colgate Sailing Adventures® flotilla cruises are hands-on activities that require unaided mobility on the yacht you live and sail on, and on the dinghies you must board to go ashore and back to the boat, regardless of how choppy the seas and harbor waters might be. So, you must complete a Sailing Resume before you can be confirmed on this trip. There are many questions, all of which must be answered, including information about medical or physical conditions that may hinder your full participation. Only the cruise leaders and Offshore management see these resumes.

Be a Designated Skipper or Designated Mate

Sicilian charter companies and authorities require two people on each boat have an International Proficiency Certification (IPC). A designated Skipper and Designated Mate will be assigned to each boat based on completed Resumes and possession of the IPC. It’s very easy to obtain if you have Bareboat Cruising Certification! Learn how to get it here.

Your Cruise Leaders

Heather and Nate Atwater are your guides as you discover this exciting Sicilian region under sail. They have led Colgate Sailing Adventures® Flotilla cruises for many years and they must have your completed resume in order to assign crews to each boat and choose the designated “skipper and mate” from information you provide on the resume. When you are ready to book, please print, fill out and email the form in the link provided and send it to

How to Get to Portorosa

There are three airports with various train, ferry and taxi connections to Portorosa Marina: Reggio Calabria (REG) 30 miles; Catania-Fontanaross (CTA) 45 miles; Palmero (PMO) 110 miles to the marina. To find the best flights from your home base to Sicily, and the best connections to the marina, we highly recommend you call the Moorings/Sunsail travel service (866-649-2003). They have tremendous experience helping sailors get to Sunsail/Moorings destinations. Check your passport now! It must be valid for six months after your return home.

Sign Up for this Sicily Flotilla Cruise NOW!

This cruise will fill quickly, as it is another Colgate Sailing Adventures® “first!” Only 15 cabins are available so get your reservation and resume in now!