Tailor-made Vacation · Italy
Sailing Sicily and the Aeolian Islands
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At a glance
If you're looking for a yacht for a family or group of friends, then this itinerary is ideal for you. Set sail on a luxurious journey around Sicily and the Aeolian Islands on this exclusive sailing experience.
Your voyage begins as you board a state-of-the-art yacht, selected from a fleet of luxurious options like the Lagoon 400, Lagoon 500, and the exceptional Lagoon 520. For those seeking the pinnacle of luxury, the Catamaran 500 and Lagoon 620 provide an unmatched sailing experience. As you glide through the crystal-clear waters of the Mediterranean, each day brings a new island to explore, each with its unique charm and beauty.
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The Aeolian Islands, a volcanic archipelago off Sicily's northern coastline, are renowned for their rugged landscapes, rich history, and vibrant culture. Your journey includes visits to enchanting islands such as Stromboli, known for its active volcano; Salina, with its lush greenery; Filicudi, a haven of tranquility; Vulcano, famous for its therapeutic mud baths; and the picturesque port of Milazzo.
With the expertise of a skilled skipper and the attentive service of a hostess, your sailing adventure around Sicily and the Aeolian Islands is as relaxing as it is exciting. Customize your itinerary to include thrilling activities like snorkeling among vibrant coral reefs, diving into the depths of the Mediterranean, or trekking through scenic landscapes.
This luxury sailing trip is an ideal way to experience the Aeolian Islands' majestic beauty, offering a unique perspective on this stunning part of Italy. Whether you're soaking in the sun on the deck, enjoying the gourmet cuisine, or discovering hidden coves and beaches, each moment of this journey is a celebration of the Mediterranean's enchanting allure.
Day by day
This is a sample plan, not a fixed departure. Days can be added, removed or reordered, and almost every client changes something. Prices are an entry-level guide; your quote will be exact.
Day 1: Milazzo
Your sailing journey begins in the vibrant town of Milazzo. As you embark on your luxurious yacht, take in the bustling atmosphere of this historic port.
Settle into your sea-bound home and prepare for a voyage across the stunning waters of the Tyrrhenian Sea, with the picturesque coastline of Sicily as your backdrop.
You’ll receive a welcome drink onboard followed by a safety briefing. You’ll also enjoy dinner on board the vessel in Milazzo.
Milazzo is the best starting point for discovering the Aeolian Islands. It is the birthplace of ancient cultures and the Aeolian Islands have always attracted sailors and travellers from all over the world.
Day 2: Milazzo to Panarea
Enjoy breakfast on board before you depart from Milazzo. Continue to the smallest of the Aeolian Islands, Panarea.
We suggest lunch at uninhabited islets Lisca Bianca and Bottaro. In the late afternoon, you’ll arrive in Panarea. evel in the tranquil beauty of this chic destination, with its whitewashed houses and beautiful coves.
Panarea offers a serene escape, perfect for swimming in crystal-clear waters and enjoying the laid-back island lifestyle.
We recommend dinner at “Da Pina” Restaurant (a masterpiece of Panarea nightlife) before staying overnight in Panarea.
Day 3: Panarea to Stromboli
Enjoy breakfast on board before the departure for Stromboli. Sailing along the little islet of Basiluzzo, you will arrive in the late morning in Stromboli.
Enjoy lunch on board before having some free time to visit the village. Enjoy the unique landscape sculpted by volcanic activity. We suggest a guided trek to the Stromboli Volcano in the late afternoon.
You’ll then have dinner on board in the evening.
Day 4: Stromboli to Salina
Breakfast on board followed by a sailing tour of the island of Stromboli, which has been continuously erupting for the past 2,000 years. This beautiful island is known for its lush greenery and sweet Malvasia wine.
Continue your day swimming and snorkeling at Stromboli Ginostra before heading to Salina.
Salina’s natural beauty, from its verdant landscapes to its inviting beaches, makes it a perfect spot for relaxation and exploration. Delight in the island’s authentic charm and savor the local gastronomy.
We suggest a private wine tasting and dinner at Tasca Conti d’Almerita Winery at the Capofaro Malvasia & Resort.
Day 5: Salina to Filicudi
You’ll savor breakfast on board before you sail from Salina to Filicudi arriving in time for lunch.
Relax and swim in the waters of this isolated and beautiful Island. Filicudi is one of the most untapped retreats, with its off-the-beaten-track feel a favorite for people who are looking for the ultimate bohemian experience. Explore its rugged terrain, relax in secluded bays, and soak up the peaceful ambiance.
Today we suggest a special dinner at Pecorini Bay Restaurant, the ultimate for Southern Italian food. Stay onboard overnight at Perorini Bay in Filicudi.
Day 6: Filicudi to Lipari
Sail to Lipari, the largest of the Aeolian Islands. Lipari’s lively streets, rich history, and archaeological sites provide a contrast to the quieter islands.
Wander through the bustling town, visit the archaeological museum, and enjoy the vibrant energy of this captivating island.
Swim at Canneto and visit the famous pumice quarries.
Day 7 and 8: Lipari to Vulcano
Conclude your sailing voyage at Vulcano, an island famed for its volcanic landscapes. Take a tour of the island by boat before stopping at the Venus swimming pool Venus and the Horses’ Cave.
Sail along the west coast to the small port of Vulcano Gelso. Swim at Gelso and relax in the afternoon before having dinner on board.
Early in the morning, the crew will sail from Vulcano to the boat’s home port, Milazzo, before you set off on your onward journey.
About Your Boat and Crew
Each boat comes with a skipper who will navigate the yacht between islands and a hostess who will cook and clean the boat for you.
Each day you will need to allow around £50 per person which allows for food, gasoline, harbor fees and mooring fees.
The boat rental includes insurance, cleaning and fresh linen and towels.
All boats are equipped with fans in all areas, TV, USB sockets in all cabins, MP3 player, bimini and sprayhood as well as a canvas sunshade for the side and back. Luxury yachts come with air conditioning.
Some boats are equipped with further amenities too such as: snorkeling equipment, Submarine Dolphin SeaDoo Watercraft and fishing and diving equipment.
Our Experts
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Frequently asked questions
What does Out Of Office do?
Out Of Office is a luxury LGBTQ+ travel company specializing in tailor-made vacations and extraordinary journeys around the world. We create bespoke luxury vacations, LGBTQ+ honeymoons, safaris, cruises, beach escapes, private tours and group trips, with every itinerary designed around you. Our travel specialists combine global expertise, first-hand destination knowledge and trusted local partners to create seamless, highly personalized experiences.
Is Out Of Office a gay travel agency?
Out Of Office is an LGBTQ+ owned and run luxury travel specialist, with particular expertise in gay and LGBTQ+ travel. We understand the additional considerations that can come with traveling as an LGBTQ+ person or couple, from local laws and customs to finding genuinely welcoming hotels and experiences.
We welcome every traveler, including friends, families and allies. Many of our clients are not members of the LGBTQ+ community, but choose Out Of Office for our luxury travel expertise, personalized service and discretion.
Do you create tailor-made LGBTQ+ vacations?
Yes. Every tailor-made trip with Out Of Office is designed from scratch around your interests, travel style, budget and the way you want to experience a destination. We can arrange luxury hotels, private transfers, flights, guides, excursions, cruises and special experiences as part of one personalized itinerary. The journeys shown on our website are there to inspire you rather than restrict you; only clearly identified group departures operate as fixed itineraries.
How do you choose LGBTQ+ friendly hotels and destinations?
We combine first-hand destination knowledge with trusted local expertise to recommend luxury hotels, resorts and experiences where LGBTQ+ travelers can feel informed and welcome. We also consider the laws, customs and attitudes of each destination, because LGBTQ+ rights and experiences differ around the world. Our team regularly visit many of the properties we work with and where a destination requires greater awareness, we give you clear and considered advice so that you can make an informed decision about where and how you travel.
We plant trees for every booking
For every booking made with Out Of Office we commit to planting trees in your name to help reduce the impact of travel on future generations. You'll even get a link to see where your trees are planted in the world via our partner Ecologi.
We donate to Rainbow Railroad with every booking
Rainbow Railroad helps LGBTQ+ people escape state-sponsored violence and persecution. A donation goes with every trip we sell, funded by us and never added to your price.
Start Planning Your Trip
Tell us where you would love to go, when you are thinking of traveling and what kind of trip you have in mind. One of our LGBTQ+ travel specialists will create a tailor-made itinerary designed around your destination, style and preferences.
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