Guided Sailing Week
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Sicily Sailing – Wellness, Italian Cuisine & Aeolian Islands

(44 Reviews)
  • 7 Days 7 Nights
  • Max People: 8
  • Wifi Available
  • Aug 01 - 15, '26
  • Catamaran 46 ft (14 m)
  • Sailing Level : Beginner
  • Wellness Activities
  • Luxury Cabin Beds
  • Sicilian Cuisine

Testimonials

Schedule Your Captain’s Consultation

Discuss your private wellness sailing experience in Sicily. Ask questions, share your preferences, and let us help craft the perfect sailing adventure for your group.

What to Expect

Discover the Aeolian Islands — a volcanic archipelago off northern Sicily — on a carefully curated sailing journey designed for travellers who seek adventure, wellness, and authentic island experiences. Over seven nights, you’ll sail from island to island, exploring turquoise coves, dramatic volcanic cliffs, and hidden sea caves that few get to see.

Each day offers a balance of exploration and relaxation: start with yoga sessions on shore, hike volcanic landscapes, swim or snorkel in crystal-clear bays, and wander through charming villages full of local culture and history. Sunset swims, cliffside views, and the occasional vineyard visit bring moments of calm and discovery.

With a focus on immersive experiences and small-group connections, this journey combines adventure, culture, and wellness in a way that’s active yet restorative. Whether hiking Stromboli, discovering secret beaches, or enjoying a local wine tasting on Salina, this Aeolian Islands sailing trip offers a thoughtfully designed adventure at a relaxed pace.

Activities offered during our Aeolian Islands wellness sailing journey:

Our Yacht & Cabin Prices

The Lagoon 46 ft catamaran (14 m long x 7.9 m wide) is the ideal yacht for your Mediterranean wellness retreat. It offers generous space, comfort, and smooth sailing throughout the Ionian. Thanks to its dual-hull design, the yacht remains stable in the water, helping reduce the chance of seasickness.

All four cabins are practically identical and designed to comfortably accommodate two guests. Each cabin includes its own private ensuite bathroom, providing comfort and privacy during your journey.

Yacht Features:

  • Large dining area and bright indoor lounge
  • Spacious outdoor lounge and relaxation areas
  • Fully equipped kitchen with large fridge and freezer
  • Onboard 360° sound-system
  • 4 double cabins
  • Private Bathroom Ensuite
  • USB Charging Ports
  • Large Swimming Platform for easy water access
Aerial view of a Lagoon 46 sailing catamaran underway on bright blue water, with sails up. Represents luxury sailing and comfort for a wellness retreat. Aerial view of a Lagoon 46 sailing catamaran underway on bright blue water, with sails up. Represents luxury sailing and comfort for a wellness retreat.
Flybridge lounge of a Lagoon 46 catamaran at sunset during a Sailing2Wellness charter in calm Mediterranean waters. Flybridge lounge of a Lagoon 46 catamaran at sunset during a Sailing2Wellness charter in calm Mediterranean waters.
Spacious bow lounge on the Lagoon 46 catamaran. Features sun pads and seating area, ideal for sunbathing, relaxation, and wellness activities during a sailing retreat. Spacious bow lounge on the Lagoon 46 catamaran. Features sun pads and seating area, ideal for sunbathing, relaxation, and wellness activities during a sailing retreat.
Spacious aft cockpit and outdoor dining area on the Lagoon 46 catamaran. Features teak decking, large table, and cushioned seating for family and guest comfort on a sailing wellness retreat. Spacious aft cockpit and outdoor dining area on the Lagoon 46 catamaran. Features teak decking, large table, and cushioned seating for family and guest comfort on a sailing wellness retreat.
Bright and luxurious interior saloon of the Lagoon 46 catamaran, featuring large windows, dining table, and galley. Ideal comfortable living space for a sailing wellness retreat. Bright and luxurious interior saloon of the Lagoon 46 catamaran, featuring large windows, dining table, and galley. Ideal comfortable living space for a sailing wellness retreat.
Modern fully equipped kitchen and galley of a Lagoon 46 catamaran with ocean views during a charter. Modern fully equipped kitchen and galley of a Lagoon 46 catamaran with ocean views during a charter.
Spacious and luxurious double cabin on the Lagoon 46 catamaran, featuring a queen-size bed, seating area, ample storage, and large hull windows for natural light and comfort. Spacious and luxurious double cabin on the Lagoon 46 catamaran, featuring a queen-size bed, seating area, ample storage, and large hull windows for natural light and comfort.
Close-up of the queen-sized bed in a private cabin of the Lagoon 46 catamaran, showing reading lamps, plush pillows, and modern wood finishes. Comfort for sailing wellness. Close-up of the queen-sized bed in a private cabin of the Lagoon 46 catamaran, showing reading lamps, plush pillows, and modern wood finishes. Comfort for sailing wellness.
Bright and spacious en-suite bathroom in a Lagoon 46 cabin. Features include a marble-look vanity with double sinks and a clean glass walk-in shower. Essential comfort for a luxurious sailing and wellness vacation. Bright and spacious en-suite bathroom in a Lagoon 46 cabin. Features include a marble-look vanity with double sinks and a clean glass walk-in shower. Essential comfort for a luxurious sailing and wellness vacation.
11Technical deck plan and layout of the Lagoon 46 catamaran, showing four private cabins and four en-suite heads, ideal for sailing wellness group charters.

*All cabins have 1 double bed to share, Single bookings have shared cabins, Price incl. VAT

11Technical deck plan and layout of the Lagoon 46 catamaran, showing four private cabins and four en-suite heads, ideal for sailing wellness group charters.

*All cabins have 1 double bed to share, Single bookings have shared cabins, Price incl. VAT

Want to book your own yacht for your friends & family or a private wellness sailing retreat?

 

Charter your own luxury yacht for an exclusive Sicily adventure.

Including

  • 7-night Spacious Catamaran Accommodation
  • Expert skipper & Gourmet Chef
  • Blue Zone-inspired Mediterranean Breakfast & Lunch
  • Guided Wellness Activities
  • Fuel & Port fees
  • Wi-Fi Onboard Connectivity
  • Plush Bedding and Towels
  • Evening Vulcano Eruption Hike
  • Unforgettable Sailing Experience
  • Hassle-Free Yacht End Cleaning
  • Cabin with Air Conditioning

Extra's

  • Sicilian Wine Tasting Experience
  • Spa Visit Salina
  • Paddle Board Gear
  • Snorkel Equipment

Excluding

  • Flight Arrangements
  • Flight and Airport Transfers
  • Evening Dinners
  • BYO Alcohol or Mixes
  • Personal Travel Insurance

Our Wellness Journey

Day 1Sailing Into the Aeolian Islands: Capo d’Orlando → Vulcano

Your Sicilian voyage begins as you board the yacht in Capo d’Orlando and set out across open water toward the volcanic island of Vulcano. The sail is one of the longer passages of the week, giving you time to settle into life onboard and watch the distant islands rise above the horizon.

As you arrive, the island’s volcanic cliffs, black-sand beaches, and warm natural pools create an unmistakably wild landscape. Once moored, enjoy a relaxed evening swim or explore the small waterfront before dinner ashore. The adventure has officially begun.

Dramatic panoramic view of Vulcano Island in Sicily, showing the large volcanic cone (Grand Cratere) and rugged coastline. Essential destination on a Sailing2Wellness trip.

Day 2Morning Crater Views & the Spirit of Lipari: Vulcano → Lipari

The day starts early with a rewarding hike toward the rim of Vulcano’s Gran Cratere. The views across the entire island chain are stunning — a perfect way to begin the week. Back on the yacht, enjoy a fresh Sicilian breakfast before the short sail to Lipari, the cultural heart of the Aeolian Islands.

Lipari’s town is one of the most memorable stops of the journey: lively streets, pastel buildings, boutique shops, and a warm, unmistakable Sicilian vibe. Wander the lanes up to the castle, explore the archaeological museum, or simply enjoy the energy of the waterfront.

Don’t miss trying the island’s famous flavored cannoli, known for their creative twists on a classic. You also have the option to visit a renowned Sicilian vineyard for a taste of local wines and island hospitality.

Panoramic view of Lipari Island town and harbor, showing colorful buildings leading up to the historic citadel (Castello di Lipari). Second destination of a Sailing2Wellness Sicily trip.

Day 3Crystal Coves & Quiet Luxury: Lipari → Panarea

A gentle sail brings you to Panarea, an island that blends simplicity with understated style. Clear bays, whitewashed houses, and laid-back island energy make this one of the most charming days of the route.

Swim in the turquoise water of Cala Junco or wander to the prehistoric site at Capo Milazzese. Before lunch, we take a short moment for a simple, grounding meditation — a natural fit for Panarea’s slower rhythm. The afternoon is yours to enjoy the beaches, the water, or the relaxed vibe of this unique island.

Scenic view of Panarea Island in Sicily, showing the exclusive whitewashed village and clear turquoise harbor waters. Third destination of a Sailing2Wellness trip.

Day 4Island of Fire: Panarea → Stromboli

Today brings you to Stromboli — dramatic, raw, and unforgettable. Begin your morning with yoga on shore, followed by breakfast as the yacht makes its approach toward the island’s dark cliffs and smoking summit.

Stromboli’s villages, San Vincenzo and Ginostra, offer a surprising charm with narrow alleys, white houses, and striking coastal views. You have the option to join an evening guided hike toward the volcano’s crater. Watching lava bursts against the night sky is a rare, powerful experience and a highlight for many travelers.

Dramatic view of Stromboli Island in Sicily, showing the active conical volcano rising steeply from the sea. Fourth day destination of a Sailing2Wellness trip.

Day 5Untouched Beauty: Stromboli → Filicudi

The sail toward Filicudi leads you into one of the most peaceful islands of the Aeolian chain. Rugged landscapes, hidden caves, and pristine water give Filicudi a remote, timeless feel.

Swim in crystal-clear coves, visit the prehistoric settlement overlooking the sea, or simply enjoy the quiet that makes this island so special.

Scenic view of Filicudi Island in Sicily, showing the dramatic, rocky coastline and deep blue sea. A remote, tranquil destination for a Sailing2Wellness trip.

Day 6Green Slopes & Island Traditions: Filicudi → Salina

Start the day with yoga on the island of Filicudi, taking in the morning stillness before setting sail.

The journey continues to Salina, instantly recognizable for its terraced vineyards, green mountains, and relaxed coastal villages. Swim at Pollara Bay, explore Santa Marina, or paddle along dramatic cliffs shaped by ancient lava flow. In the evening, you can enjoy a local wine experience, tasting Salina’s celebrated Malvasia dessert wine at a family-run vineyard.

Lush green landscape of Salina Island in Sicily, known for its fertile soil and Malvasia wine. Destination for a wine tasting excursion on a Sailing2Wellness trip.

Day 7Final Sail Along the Sicilian Coast: Salina → Capo d’Orlando

Your final morning offers one last swim or a peaceful coffee with a view before raising the sails for the return to mainland Sicily.

The coastline of Capo d’Orlando comes back into view as the week’s journey settles in — a blend of adventure, culture, great food, and moments of pure island calm. By late afternoon, the yacht returns to the marina. As evening arrives, we share our final goodbyes, closing a week of memorable Sicilian exploration.

Aerial view of the modern Capo d'Orlando Marina in Sicily, surrounded by the town and scenic headland. The starting and ending port for the Sailing2Wellness trip.

Explore the Route

Interactive map of your luxury sailing itinerary in Sicily.

Impressions

FAQ

Answers to Frequently Asked Questions about our luxury wellness sailing trips in the Mediterranean.

Are you sailing with us this summer?

Don’t miss your chance to experience the ultimate wellness sailing retreat in Sicily.
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