236 reviews

Aeolian Islands Sailing Flotilla August

7 Days | Flotilla | Aeolian Islands

4.9

236 reviews

Aeolian Islands Sailing Flotilla August

7 Days | Flotilla | Aeolian Islands

Starting

799,00 €-11%

CHOOSE

Starting

799,00 €-11%

One week: Saturday – Saturday

CHOOSE A DATE

If you love the idea of spending a week in the company of new friends, sailing through the stunning waters of the Aeolian Islands, then our holiday is perfect for you.

You will live on board a sailboat that will become your home for a week, where you can dive into the beautiful waters of Grotta del Cavallo or Panarea and admire breathtaking sunsets with Stromboli as your backdrop all while enjoying aperitifs, music, fun, and relaxation.

Choose a date

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Watch our boats

Recommended age: Age range: 23–45

Duration: One week: Saturday – Saturday

PLEASE NOTE: you can book the ENTIRE BOAT with a skipper-instructor and choose the type of experience.

What kind of experience is it?

Social & good vibes
Relax
Photos & great moments
Sailing: basics & maneuvers
Nature & views

Teaser video

Kick off your Summer: Aeolian Flotilla 2026
Turn your holiday into a legendary experience through Sicily’s cobalt waters and active volcanoes.

From the wild cliffs of Pollara to the iconic black sands of Vulcano, this is more than just a cruise. Sail aboard our 45ft+ monohulls with professional skippers, exploring hidden gems by day and dancing to the rhythms of Panarea by night—all with the spectacular eruptions of Stromboli as your backdrop.

Whether you want to relax or pull the ropes, you’ll join a like-minded crew (ages 23–45) sharing the true Different Sailing spirit: adrenaline, fun, and teamwork.

Unplug and Join the Crew. Watch the video, pack your (soft!) bag, and dive into the heart of the Mediterranean.

What our guests say

Full Itinerary

We will board on Saturday afternoon at Marina di Portorosa and kick off our holiday with a group dinner to get to know one another.
On Sunday, we’ll set sail at dawn. Our first stop will be Vulcano, where we’ll unwind with plenty of swimming, aperitifs, and dinners.
Over the following days, we will visit the islands of Salina, Panarea, and Lipari with their stunning beaches; we’ll also admire the majesty of Stromboli, which will provide the perfect backdrop for our sunsets.
We’ll wrap up the week with a fantastic closing party and return to Marina di Portorosa by 8:00 AM.

IMBARCO

Saturday from 5:00 PM at Marina di Portorosa.
SBARCO

The following Saturday by 8:00 AM at Marina di Portorosa.

Welcome on Board

Saturday

We meet at Marina di Portorosa in the afternoon to settle into our cabins and organize the galley. We’ll kick off the holiday with a big welcome dinner and our first party to get to know the whole crew before our first night on board.
Into the Wild Vulcano

Sunday

An early departure takes us straight to the stunning Grotta del Cavallo for a dip and a group lunch rafted together. We’ll then sail toward Salinato spend the night, heading ashore at Santa Marina for a sunset aperitivo and a lively evening in the village.
Flavors & Volcano Fire

Monday

We set sail for Pollara for a swim followed by a stop at Lingua to taste the legendary Pane Cunzato at Alfredo’s. After a relaxed sail to Stromboli for a group dip, we’ll enjoy dinner on board before a magical night sail under the Sciara del Fuoco to witness the volcano’s eruptions from the sea.
Chic Vibes & Crystalline Waters

Tuesday

A quick dip at Strombolicchio starts our morning, followed by swimming between the islets of Basiluzzo and Lisca Bianca. We’ll then moor at the buoys in Panarea for a sunset drink at the famous Raja, followed by dinner and a night out with the entire flotilla.
Turquoise Dreams & Lipari Nights

Wednesday

Sailing from Panarea to Lipari, we’ll stop at the Pumice Quarries to swim in breathtakingly turquoise waters. We’ll enjoy a sunset under sail before docking at the port for a night out exploring the vibrant streets of Lipari.
Faraglioni & Hidden Coves

Thursday

We head toward the majestic Faraglioni of Lipari for a day of swimming and exploring hidden coves by dinghy. If possible, we’ll spend the night at anchor in Vulcano with a group dinner and a “rafted boat” party under the stars.
The Grand Finale

Friday

A final spectacular swim at Cala Gelso and a farewell group lunch before heading back to Marina di Portorosa around 6:00 PM. We’ll wrap up the week with a final night ashore and our Epic Closing Party to celebrate an unforgettable journey.
Farewell

Saturday

Disembarkation by 8:00 AM. Hugs, photos, and see you on the next adventure!

Pricing details

799,00 €-11%
/person

Included
- Certified Sailing Vessels: All boats are equipped with safety certifications and are fully compliant for commercial/professional use.
- Professional Skipper / Instructor: Expert guidance throughout the journey.
- On-board Accommodation: Your cabin for the entire duration of the trip.
- Insurance Coverage: Third-party liability (RCT) and individual accident insurance.
- UISP Membership Card: Official association membership included.
NOT included
- UISP Membership Card
- Transfers: To/from the boarding port.
- Fuel: Calculated at 6 L/h, to be shared among all participants.
- Mooring & Berthing Fees: Costs for marinas, harbors, buoys, or private piers.
- Security Deposit: Refundable deposit and optional damage waiver (deposit reduction).
- Starter Pack: €100 per person for monohulls or €120 for Catamarans. This covers bed linens, towels, final cleaning, and the first and last night at the marina.
- Estimated Extra Costs: Based on our extensive experience, you should plan for approximately €200–€300 per person for extra expenses (food, fuel, and moorings) during a week sailing the Aeolian Islands.

CHOOSE A DATE

How to get here

How to reach Marina di Portorosa?

FROM CATANIA (HIGHLY RECOMMENDED): The Portorosa Marina is easily accessible from Catania Fontanarossa International Airport. We organize a shuttle transfer from the airport that takes you directly to the boarding port in approximately 2 hours. Cost: €35 per person, each way.

FROM PALERMO: from Palermo-Punta Raisi Airport (PMO), we also organize private transfers with a driver (NCC) that will take you directly to the embarkation port in about 2 hours or 2 hours and 20 minutes. The cost is €250 for a 9-seater bus (€30 per person) or €200 for a 4-seater car (€50 per person).

Alternative: You can take a bus or taxi from the airport to Palermo Centrale Station. From there, take a train (changing at Barcellona-Castroreale) to the Novara-Montalbano-Furnari station.

FROM REGGIO CALABRIA
You can also reach the port via Reggio Calabria Airport. From there, head to the Villa San Giovanni station, take the ferry to Messina, and from Messina Centrale, take a train to the Novara-Montalbano-Furnari station.

Note: For further information and schedules, we recommend consulting trenitalia.it.

Our Advice: We strongly suggest reaching the Portorosa Marina via Catania Airport, as it is the least demanding and fastest route.

Is our Aeolian sailing holiday right for you?

Yes, if you are looking for a unique and unforgettable holiday experience.
Yes, if you want to meet new people and share incredible adventures together.
Yes, if you want to try something truly unique, blending sailing, fun, and the discovery of amazing new places.

The Different Sailing Aeolian Islands Flotilla is designed to help you build new friendships while living a wonderful experience of sailing, relaxation, and fun. Together, we will share exciting and adventurous moments in one of the most stunning corners of the Mediterranean.

Dates & Rates

Special Offer: 15% Early Bird Discount available for bookings made by April 1st, 2026!

August 1st – 8th | 5-Boat Flotilla

CATAMARAN: €1,299.00 (instead of €1,499.00)

Models: Lagoon 400 S2 (2017) or Lagoon 40 (2019)
ECONOMY LINE SAILBOAT: €799.00 (instead of €999.00)

Model: Beneteau Cyclades 50.5 (2008 – Refit 2023)
PRESTIGE LINE SAILBOAT: €999.00 (instead of €1,199.00)

Models: Beneteau Oceanis 51.1, Oceanis 46.1, or Dufour 52

August 8th – 15th | 8-Boat Flotilla

CATAMARAN: €1,299.00 (instead of €1,499.00)

Models: Lagoon 400 S2 (2017) or Lagoon 40 (2019)
ECONOMY LINE SAILBOAT: €799.00 (instead of €999.00)

Model: Beneteau Cyclades 50.5 (2008 – Refit 2023)
PRESTIGE LINE SAILBOAT: €999.00 (instead of €1,199.00)

Models: Beneteau Oceanis 51.1, Oceanis 46.1, or Dufour 52

August 15th – 22nd | 6-Boat Flotilla

CATAMARAN: €1,299.00 (instead of €1,499.00)

Models: Lagoon 400 S2 (2017) or Lagoon 40 (2019)
ECONOMY LINE SAILBOAT: €799.00 (instead of €999.00)

Model: Beneteau Cyclades 50.5 (2008 – Refit 2023)
PRESTIGE LINE SAILBOAT: €999.00 (instead of €1,199.00)

Models: Beneteau Oceanis 51.1, Oceanis 46.1, or Dufour 52

Our boats

Sanbosò – ELAN IMPRESSION 434

At nearly 14 meters long with a hull designed for stability, Sanbosò is a spacious, solid, and seaworthy vessel. Equipped with every comfort for life on board, she features a full range of amenities ideal for enjoying the ultimate offshore anchoring experience.

Cabins
3 doubles, 1 bunk bed cabin, 1 skipper cabin
Berths (Sleeps)
8 + Skipper
Bathrooms
2 bathrooms
Le Pleiadi – Bavaria 44

At nearly 14 meters long with a solid, seaworthy hull, Le Pleiadi is an extremely livable and comfortable vessel, ideal for sailing. Equipped with every modern amenity—including electric toilets and spacious living areas—it is the perfect choice for a cruising holiday in total relaxation.

Cabins
3 doubles, 1 bunk bed cabin, 1 skipper cabin
Berths (Sleeps)
8 + Skipper
Bathrooms
2 bathrooms
Ma Mousse – Beneteau 50

With its generous volumes and a layout that ensures maximum livability and privacy, Ma Mousse is a solid, functional boat, ideal for life on board.

Equipped with ample space and extra features—such as a double refrigerator—it is the perfect vessel for hosting large crews in total comfort.

Cabins
4 doubles + 1 crew cabin with bunk beds
Berths (Sleeps)
10+2
Bathrooms
5 bathrooms

FAQ

Our Philosophy

Those who join our Pontine Islands sailing weekends share a love for the sea, fun, and the authentic sailing lifestyle.

Our itinerary, shared by the entire fleet, balances moments of swimming in the most stunning bays of Ponza and Palmarola—exploring hidden spots accessible only by sea—with plenty of socializing both on board and ashore (including aperitivos, dinners, parties, and excursions).

Life on board is a team effort and relies on everyone’s collaboration: taking care of your personal space and keeping the equipment and common areas tidy is part of the experience.

Is our June 2nd Long Weekend for you?

Yes, if you’re looking for an alternative and exciting way to spend your weekend.
Yes, if you want to combine your passion for travel with your love for the sea.
Yes, if you want to make new friends and have fun while discovering breathtaking new spots.

With Different Sailing, you can flip the script on your June holiday. Break away from the daily routine and soak up the sun, the sea, and the great vibes with a new crew of friends. It’s all about fun on board!

How to reach Nettuno?

Nettuno is easily accessible from Rome:

By Train: Trains from Rome city center take approximately 1 hour and 10 minutes. The marina is just 300 meters from the train station.
By Car: From Rome, take the Pontina (SS148) highway.

Parking at the Marina:

Private Parking: There is a gated (unattended) private parking area inside the port for €15 per day (approx. €30 for the weekend).
Free Parking: You can also find free parking (white lines) just outside the marina area. It is a safe area, and our guests have never had any issues.

Aeolian Islands Sailing Flotilla August

Aeolian Islands Sailing Flotilla August

What kind of experience is it?

Teaser video

What our guests say

Full Itinerary

Welcome on Board

Into the Wild Vulcano

Flavors & Volcano Fire

Chic Vibes & Crystalline Waters

Turquoise Dreams & Lipari Nights

Faraglioni & Hidden Coves

The Grand Finale