Sailboat charter Portorosa with or without a skipper

Sailboat charters in Portorosa, Sicily, start at $1,350 per week bareboat, with more than 150 boats available within 31 miles (50 km). A sailboat charter in Portorosa puts you 20 nautical miles from Vulcano: half a day of sailing is all it takes to reach the Aeolian Islands. You join the boat in Sicily, stock up on provisions at the marina and set course for seven volcanic islands listed as a UNESCO World Heritage Site.

Why charter a sailboat in Portorosa?

Marina di Portorosa, in Furnari (Messina) between Capo Tindari and the Milazzo peninsula, is one of the main yacht charter bases for the Aeolian Islands, with a sheltered marina and free parking. It is built on a network of canals and protected by two breakwaters. Several charter companies have set up their base there: the fleet consists mainly of sailboats built between 2017 and 2026.

• A convenient base for boarding: free parking at the marina, shops and restaurants on site, mooring assistance by VHF (channel 9). Boarding here is easier than in Lipari or Vulcano in the height of summer.
• Close to the Aeolian Islands: Lipari is just 5 nautical miles from Vulcano. A week of sailing covers 100 to 130 nautical miles to tour Vulcano, Lipari, Salina, Panarea and Stromboli.
• The Sicilian coast right off your bow: a few miles to the west, Capo Tindari, its sanctuary and the Marinello lagoons can be visited on the first or last evening of your cruise.

How much does a sailboat charter in Portorosa cost?

The budget for a week departing from Portorosa depends above all on the type of charter you choose. Prices are shown in US dollars, converted from euros at the rate used on our boat listings in October 2026; the amount you pay may vary with the exchange rate. The table below gives entry-level prices; they then increase depending on the season, the size, the model and the year the boat was built.

Source: Filovent, prices observed for departures from Portorosa in October 2026, average skipper rate in the Mediterranean.

For a skippered charter, also plan for the skipper's meals: they share your meals on board or receive an allowance of about $22 per meal.

The price includes: the boat charter and its basic equipment (sails, dinghy, dishes, safety equipment).

The price does not include: the skipper and hostess, insurance, the mandatory end-of-charter fee (final cleaning, gas and bed linen, $200 to $340 depending on the boat), fuel, port fees in the Aeolian Islands, extras (outboard motor, paddleboard, Wi-Fi) and provisioning.

You receive the boat with a full tank and return it full, or pay for the fuel used at the marina price.

We recommend taking out our trip cancellation insurance: it covers the entire crew, whereas individual insurance or your credit card insurance only protects the cardholder. A damage waiver is mandatory if you charter with a skipper and recommended if you sail without one: it allows you to recover most of your security deposit in the event of damage while sailing.

Which sailboat should you charter in Portorosa?

The fleet in Portorosa and the neighboring ports (Capo d'Orlando, Milazzo) consists mostly of monohulls from 31 to 54 feet (9.5 to 16.5 meters). Your choice of boat depends mainly on the size of your crew:

• 2-cabin sailboat: 31 to 36 feet (9.5 to 11 meters), 4 to 6 berths. For a couple or two couples traveling together, it slips more easily into the small ports of the Aeolian Islands in summer.
• 3-cabin sailboat: 34 to 43 feet (10.5 to 13 meters), 6 to 8 berths. This is the most common size in Portorosa, suited to a family or a group of 4 to 6 people.
• 4-cabin sailboat: 43 to 49 feet (13 to 15 meters), 10 berths. It lets 8 people sail together while keeping one double cabin per couple.
• 5- or 6-cabin sailboat: 48 to 54 feet (14.5 to 16.5 meters), 11 to 13 berths, for groups of 10 to 12 people.

Charter a catamaran in Portorosa

A catamaran charter in Sicily is available in Portorosa and Capo d'Orlando, on models from 38 to 55 feet (11.5 to 17 meters), starting at $3,900 per week. Wider and more stable at anchor than a monohull, a catamaran offers more space on board for families and large crews.

Sailboat charter with or without a skipper in Portorosa

In Portorosa, you can charter a sailboat without a skipper if a crew member holds a license, or with a professional skipper:

• Bareboat yacht charter: a member of your crew acts as skipper and holds the required license. You are free to plan your own itinerary between the islands.
• Skippered yacht charter: a professional skipper handles the sailing and chooses the anchorages and stopovers based on the day's weather. Charter companies in Portorosa generally do not provide a skipper: our concierge team finds you an independent professional skipper and sends you their sailing résumé before you book. A hostess can also be requested, subject to availability.

What license do you need for a bareboat sailboat charter in Sicily?

To charter a sailboat without a skipper in Italy, the skipper must hold a recognized certification such as an ICC (International Certificate of Competence) or an IPC (International Proficiency Certificate), or an ASA 104 or US Sailing Bareboat Cruising certification. The US Coast Guard license is not accepted in the Mediterranean. Charter companies generally also ask for a sailing résumé showing your experience and, depending on the company, a VHF radio certificate. Your Filovent advisor checks with you that your certification covers the planned itinerary before you book.

Where to sail from Portorosa?

From Portorosa, the seven Aeolian Islands lie 5 to 30 nautical miles apart:

6-day itinerary example from Portorosa

Itinerary followed by two Filovent clients on a sailboat, about 110 nautical miles in total:

• Day 1: Portorosa → Vulcano (22 nautical miles, 5 h 30 min).
• Day 2: Vulcano → Stromboli (27 nautical miles, 6 h).
• Day 3: Stromboli → Panarea → Vulcano (32 nautical miles, 8 h).
• Day 4: stopover in Vulcano.
• Day 5: Vulcano → Lipari (5 nautical miles, 1 h 30 min).
• Day 6: Lipari → Portorosa (25 nautical miles, 6 h 30 min).

For a more relaxed week, the north coast of Sicily also offers stopovers to the west, as far as Capo d'Orlando (about 17 nautical miles from Portorosa). Other departure ports are available with a sailboat charter in Sicily.

When to charter a sailboat in Portorosa?

The sailing season runs from April to October. The best months are June and September: the water reaches around 23 °C in June and 25 °C in September, and the ports of the Aeolian Islands are much less crowded than in July and August.

What is sailing like in the Aeolian Islands?

In summer, the prevailing wind is the mistral (maestrale), a northwesterly wind that often picks up in the afternoon and can kick up a steep chop in the channel between Sicily and the archipelago. The sirocco, hot and humid, blows from the southeast and makes some anchorages uncomfortable. Crossings to the islands should therefore be planned according to the day's weather, preferably in the morning.

Since the Aeolian Islands are volcanic in origin, the seabed drops off very quickly near the coast: carry enough chain and choose your anchorage carefully. In July and August, berths in the ports of Lipari, Salina or Vulcano are in high demand: it is best to book them in advance.

At Stromboli, sailing is prohibited within 2 nautical miles of the Sciara del Fuoco, the slope where the lava flows run down. The rules for approaching and accessing the volcano may change depending on its activity: check the notices issued by the Milazzo Harbormaster's Office (Capitaneria di Porto) before heading there.

Frequently asked questions about sailboat charters in Portorosa

What day does the charter start in Portorosa?

Sailboat charters in Portorosa generally run from Saturday to Saturday, for a minimum of one week. Check-in usually takes place in the afternoon, between 3 p.m. and 6 p.m. depending on the charter company. The evening before disembarkation, the boat must be back in the marina by 5 p.m., and check-out is the next morning around 9 a.m. The exact times are specified in your contract.

How much is the security deposit?

Expect a security deposit of between $2,250 and $3,350 for a 33- to 46-foot (10- to 14-meter) sailboat in Portorosa. It is paid to the charter company on boarding day and refunded no later than one month after the boat is returned, if it is returned in good condition.

What documents do you need to present at boarding?

Each crew member needs a valid passport or national ID card. The skipper presents their sailing certification or ICC and their sailing résumé. The crew list is completed in your customer account within 48 hours of booking. Also bring a Visa or Mastercard credit card in the skipper's name for the security deposit, as well as proof of your insurance.

How do you get to Portorosa?

The most convenient airports are Catania (about 93 miles, 150 km) and Palermo (about 130 miles, 210 km), both reached from the United States via connecting flights through Rome or another European hub. Allow about 2 hours by road from Catania and about 3 hours from Palermo. By train, get off at Barcellona-Castroreale station, then take a taxi to Portorosa (about $45). Reggio Calabria airport is closer (37 miles, 60 km), but it requires crossing the Strait of Messina by ferry.

Can you see Stromboli's eruptions from the boat?

Yes, from the boat, at nightfall, off the Sciara del Fuoco on the northwest coast of Stromboli, keeping the safety distance given above.

How do I book my sailboat in Portorosa?

Once we receive your request, a Filovent advisor calls you to understand your sailing plans, then emails you a selection of sailboats. Once you have chosen your boat, you confirm the charter from your customer account:

• Down payment: 50% of the price at booking, according to the charter company's terms.
• Balance: due between 12 and 6 weeks before boarding.
• Cancellation: more than 90 days before departure, you forfeit the down payment; less than 90 days before, the full price is due. Trip cancellation insurance reimburses you in the event of a covered unforeseen circumstance.

If you are still undecided about the departure port, compare our boat rental offers for a sailboat charter in Italy or set sail directly from the archipelago with a sailboat charter in the Aeolian Islands.

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