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aeolian islands hiking sailing

Hiking & Sailing the Aeolian Islands: 8-Day Italian Adventure

8 days | Moderate | 5.00
From $2,985 ()
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The Aeolian Islands don’t look like anywhere else in the Mediterranean—seven volcanic islands off the northern tip of Sicily, each with its own character, its own terrain, its own way of stopping you in your tracks. We sail between them and hike them on foot, moving at a pace shaped by wind and weather and the group itself. Active craters, ancient ruins, lush ridgelines, and water so clear it almost looks fake—this is one of those trips that’s genuinely hard to describe until you’ve done it.

Lorenzo
Lorenzo
IFMGA/UIAGM Mountain Guide & Skipper

Adventure Highlights

  • Sailing and trekking, back to back: Each island is approached from the water and explored on foot—two ways of moving that complement each other perfectly across the week
  • A living, breathing archipelago: Seven volcanic islands, each completely different: steaming craters, ancient forests, remote islets, and Stromboli erupting after dark
  • A floating home: We’ll stay aboard a sailing boat with a full kitchen, a living area and a deck that's hard to leave once the sun goes down
Duration
8 days
Season
May through October
Group size
Up to 9 people
Accommodation
Comfort: Monohull or catamaran boat
Difficulty
Moderate: Good fitness required, hiking up to 8 km (5 mi) per day, with up to 924 m (3,031 ft) of elevation gain
What's included
Guide, boat lodging, skipper, harbor fees, boat fuel, pantry-ready service

The adventure, day by day

Come join our 8-day guided sailing and trekking adventure through the Aeolian Islands, departing from and returning to Capo d'Orlando Marina. Over the course of the week, we sail to and hike Vulcano, Lipari, Salina, Filicudi, Panarea, Basiluzzo, and Stromboli—each island explored on its own terms, connected by daily navigation. Accommodation is on board throughout, and most meals are prepared together as a crew. An experienced U.I.A.G.M.-certified mountain guide leads all treks on land, while a skipper handles everything at sea.

Day 1: Arrival in Capo d’Orlando
Capo d'Orlando Sicily

Arrive at Capo d’Orlando marina, where boarding opens from 4 pm. The afternoon is for settling in, organizing provisions, and getting a feel for the boat and the people you’ll be sharing it with all week. If conditions allow, we sail towards Vulcano in the late afternoon and anchor for the night—a quiet first evening on the water, with the week still ahead.

Accommodation: Sailing boat

Day 2: Vulcano island
Sunset Vulcano island

We anchor in a bay shaped by volcanic activity, where warm currents rise from the seabed—an unusual spot to wake up to. In the afternoon, we hike up to the Gran Cratere, moving through terrain marked by sulphur vents and fumaroles. It’s a raw, active landscape and a strong introduction to what the Aeolians are really about. Pace and timing are adjusted to conditions and the group.

Accommodation: Sailing boat

Day 3: Lipari and Salina islands
lipari town view

We sail along the dramatic sea stacks of Lipari before continuing to Salina—a greener, quieter island defined more by forest and altitude than volcanic drama. After anchoring, we hike to Monte Fossa delle Felci, the highest point in the Aeolian Islands at 962 m (3,156 ft). The trail climbs through humid forest and shaded slopes, with a silence and atmosphere that feels unexpectedly alpine for the Mediterranean. If timing and interest align, there’s a chance to visit a small local winery on the way.

Accommodation: Sailing boat

Day 4: Filicudi island
fillicudi port

A morning sail brings us to Filicudi, one of the most remote and least-visited islands in the archipelago. We explore a Bronze Age village overlooking the sea—stone walls and dry-stacked structures that speak clearly about life built around exposure and isolation. The afternoon is left open: swimming, resting, wandering. In the evening, we head into the village for an aperitif and dinner, keeping it simple and local.

Accommodation: Sailing boat

Day 5: Panarea island
panarea island

Panarea is a small island that holds two very different versions of itself: wild, exposed coastal terrain on one side and a social scene shaped by visibility on the other. A coastal trek lets us move through both, reading the landscape and understanding how they coexist on such a small piece of land. The walk isn’t about covering distance—it’s about paying attention.

Accommodation: Sailing boat

Day 6: Basiluzzo and Stromboli islands
Stromboli from Panarea

An early sail takes us to Basiluzzo, a small uninhabited islet where the day is spent swimming, resting, and slowing down before what comes next. In the afternoon, we sail to Stromboli. After an early dinner ashore, we begin the evening ascent—a guided climb to an authorized viewpoint to watch Stromboli erupt. It’s an active environment, and decisions are made in real time based on conditions and safety. The experience unfolds accordingly.

Accommodation: Sailing boat

Day 7: Lipari island
lipari views

We sail back past the former pumice quarries of Lipari, where white rock drops into some of the clearest water in the archipelago. The morning is unstructured—swimming, resting, quiet navigation. In the afternoon, we sail back to Capo d’Orlando Marina, closing out the week.

Accommodation: Sailing boat

Day 8: Departure
Capo d'Orland lighthouse

After our final night at Capo d’Orlando Marina, our journey comes to an end. Disembark by 9 am.

Important note

The daily program can be adjusted at any time for safety reasons or to better suit weather conditions and the needs of the group. While at sea, the skipper is fully in charge of navigation (a great opportunity to pick up some sailing skills along the way). On land, the mountain guide leads all treks and oversees any climbing activities, keeping safety the priority regardless of your experience level. Flexibility is part of how this trip works—and what makes it feel like a real expedition rather than a fixed tour.

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Meet your guides

Seasoned pros, local legends, and passionate adventurers—your trip is in the best hands.
Lorenzo
5.00
Lorenzo
IFMGA/UIAGM Mountain Guide & Skipper
Lorenzo has spent his life in the mountains—skiing, climbing, and chasing every form of movement the vertical world has to offer. In 2013, a new playground opened up: the Mediterranean coastline, with its sea cliffs, volcanic islands, and open water. He hasn't looked back since. A ski instructor in the winter and a certified mountain guide since 2024, Lorenzo splits his year between the slopes and the sea, leading sailing and trekking expeditions across the Aeolian Islands throughout the summer. He brings the same energy to both—precise where it counts, relaxed everywhere else. Fair warning: don't get between him and a good meal. Or a good party. There's more to life than climbing and sailing, and Lorenzo knows it better than most.
Alberto
5.00
Alberto
IFMGA/UIAGM Mountain Guide
Alberto is an experienced UIAGM/IFMGA Mountain guide and the chief guide working with Lorenzo. From the point of Cerro Torre to the wall of El Capitan, from the desert of Saudi Arabia to the picks of Mt. Blanc, he has travelled the world to climb in the most remote places. Since the beginning, he has been on board and his kind personality combined with his great expertise are the things that make the clients love him.

What others say about this adventure

5.00 (4 reviews)
L
LS Blatter

Lorenzo and Francesco are amazing humans and excellent trip guides–kind and knowledgeable and fun!

S
Sunday Purselley

The guide was very flexible and extremely helpful.

r
rhonda hughes

Guide was professional and knowledgeable. Trusted their judgement and expertise. Was a fun adventures guide

5.00(4 reviews)
L
LS Blatter

Lorenzo and Francesco are amazing humans and excellent trip guides–kind and knowledgeable and fun!

S
Sunday Purselley

The guide was very flexible and extremely helpful.

r
rhonda hughes

Guide was professional and knowledgeable. Trusted their judgement and expertise. Was a fun adventures guide

W
Wehtahnah Tucker

If you enjoy living life to its fullest, this is the adventure for you! Leave your expectations at home and enjoy the journey!

Things to know

  • Included:

      • An experienced, UIAGM-certified mountain guide with extensive knowledge of the area
      • 8-day Aeolian Islands hiking & sailing adventure
      • Accommodation on a sailing boat for 7 nights — double-sized beds or bunk beds sorted and arranged by and among guests
      • Skipper
      • Pantry-ready service (shopping for food and beverages will be done by the staff prior to your arrival)
      • All meals onboard with the exception of meals on land
      • First and last night’s harbor fee
      • Boat fuel

    Upon boarding, a €300 cash fee must be paid for all onboard food provisions, bedding, towels, and essential boat services like the outboard engine and final cleaning. If you have any questions about this, contact us and we will get back ASAP !

    Not included:

      • Travel expenses to reach/leave the harbor of departure
      • Meals on land (the cost of meals for the staff will be distributed evenly among all guests)
      • Harbor fees for any extra nights spent in the harbor (if the skipper decides to stay due to adverse weather or sea conditions)
      • Alcoholic beverages on board
      • Anything not mentioned in the “Included” section above
      • Insurance — recommended, available to add at checkout
      • Guide gratuities — optional
  • To join this Aeolian Islands hiking and sailing tour, good fitness is required. Hiking days involve sustained ascents on volcanic and Mediterranean scrub terrain—some steep and exposed—and the Stromboli evening climb is a demanding effort with a return in the dark. Strong swimming skills are also strongly recommended, as swimming is a regular part of the week. No sailing experience is necessary.

    Across the week, you’ll hike up to 8 km (5 mi) per day, with a maximum daily elevation gain of 924 m (3,031 ft). Total hiking distance is around 20 km (12.4 mi), with a total elevation of 2,000 m (6,562 ft).

    Want to see what else is there in the area? Discover more Italy hiking tours here!

  • If this is your first time on a sailing boat and you don’t know what to expect, here is what you can expect from life on board:

      • On board, everyone is responsible to clean up after themselves.
      • Teamwork makes the dreamwork! Be ready to participate in cooking, prepping food, washing the dishes, etc. Don’t worry if you don’t know how to cook or if you hate washing the dishes, you can always swap the job with another crew member.
      • When at sea, it’s important to use water and electricity conservatively. You may be asked to use water and electricity with moderation while out at the sea.
      • Don’t worry about any sailing knowledge. The skipper will be there to ensure your safety and will give you precious tips on how to live on board.
      •  If you wish to learn how to sail or if you are an experienced sailor and want to help your skipper, they will be glad to operate the sails with you and teach you anything you want to know!
  • Note that rigid suitcases are not permitted on board. Use a bag that can be folded and stored once empty—space is limited and shared.

    Here’s a list of the equipment you need to bring:

      • Day pack large enough to carry everything you might need throughout the day (around a 25-40L bag)
      • Hiking poles — optional
      • Water bottle or hydration bladder (2L capacity)
      • Lightweight hiking boots or shoes
      • Comfortable hiking clothes 
      • Spare clothes for layering
      • Waterproof rain jacket
      • Sunhat
      • Toiletries (sunscreen, hand sanitizer, bug spray, tissues, etc.)
      • Headlamp or flashlight
      • Sunglasses
      • Camera — optional (but recommended)

    Dress comfortably and for the weather in clothes you can move in. We suggest bringing clothing appropriate for the season. Layers are best and don’t wear jeans.

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  • Group sizes and pricing

      • For this Aeolian Islands hiking and sailing adventure, the usual client-to-guide ratio is 9:1. 
      • It takes a minimum of 5 people for this tour to operate. The maximum group size is set at 9 participants.

    Aeolian Islands hiking & sailing tours can be arranged for larger groups. Contact us to make arrangements.

    Min. age requirements

      • If you are older than 18, you’re good to go.
      • Minors younger than 18 may be permitted to join the Aeolian Islands hiking & sailing tour on a case-by-case basis, but must be in the presence of a parent or legal guardian.

    If your group has participants under the age of 18, contact us prior to booking to make arrangements.

  • Due to very limited availability onboard, a single occupancy cabin is not available on this Aeolian Islands hiking and sailing adventure.

  • We highly recommend that you cover all your bases with insurance. To make your booking and traveling experience as carefree as possible, you’ll be offered to simply insure your trip with Redpoint at checkout.

    Redpoint—the official 57hours insurance partner—tailors protection packages for adventure travel, offering a comprehensive travel program, even in remote locations! Trip cancellation, natural disasters, pandemic coverage, medical evacuation, primary medical expenses—regardless of the travel interruption that may happen, Redpoint will have you covered.

  • Deposits

    Secure your spot with a 30% deposit upon booking! The remaining 70% of the trip price must be paid 90 days prior to departure at the latest. If booking within 90 days of departure, the full amount is required at the time of booking.

    Cancellations

    Booking fees are non-refundable after a 48-hour grace period. During checkout, however, you can choose one of 57hours’ flexibility options—Basic, Flexible, or Super Flexible. Depending on which one you choose, a different cancellation policy will apply to your booking.

    Basic

      • If cancelled within 48 hours of booking, a full refund will be issued.
      • If cancelled 90 or more days before departure, a 70% refund of the total trip price will be issued.
      • If cancelled within 89 days of departure, no refund will be issued.

    Flexible

      • If cancelled within 48 hours of booking, a full refund will be issued.
      • If cancelled 90 or more days before departure, a full refund of the total trip price will be issued.
      • If cancelled 60-89 days before departure, a 50% refund of the total trip price will be issued.
      • If cancelled within 59 days of departure, no refund will be issued.

    Super Flexible

      • If cancelled within 48 hours of booking, a full refund will be issued.
      • If cancelled 60 or more days before departure, a full refund of the total trip price will be issued.
      • If cancelled within 59 days of departure, a 50% refund of the total trip price will be issued.
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