Discover flotilla sailing holidays with Sunsail

Explore the Mediterranean from a unique perspective with experts Sunsail as they turn 50 years old…

Ever dreamed about learning to sail or chartering a yacht? Planning an extraordinary sailing holiday with Sunsail is the way to go.

Sailing holiday expert Sunsail is celebrating a very special anniversary this year: 50 years of arranging exceptional sailing holidays worldwide, tailored for everyone. With a fleet of over 500 boats in more than 20 sunny destinations, from the Mediterranean to the Caribbean and Southeast Asia to the Seychelles, Sunsail is committed to creating unforgettable memories at sea.

Following Sunsail’s 1974 launch on the Greek island of Aegina with seven 25ft Snapdragon yachts, the company swiftly doubled its fleet, giving birth to the flotilla concept. This formula soon spread to shores far and wide.

Sunsail flotilla holidays entail up to 12 yachts sailing a set route. With a Sunsail lead crew providing guidance every step of the way, they are a popular option for families, couples, friends, and solo travellers.

Take it slow with an island-hopping holiday in the Mediterranean, lapping up the sunshine and cooling off in the crystalline seas. If you're new to sailing, rise to the challenge of learning the ropes at Sunsail’s sailing school in Agana or Lefkas, or opt for a skippered yacht charter so you can completely relax.

Why is a flotilla holiday so great?

Flotilla holidays are suited to everyone, from non-sailors and first-timer charterers to the saltiest yachties, with cruising grounds catering to all experience levels. The beauty of a flotilla is that it couples the support of a lead crew, including a skipper, technician, and a host, with the freedom and flexibility of a private holiday at sea.

Each day, your lead crew briefs you on the destination, weather forecast, and what not to miss on the way. While there is a set route to follow, you decide how you wish to explore each cruising area before reaching the next stop. Drop anchor in a secluded cove for a dip or take advantage of wind conditions and head straight to the next destination to maximise time ashore. Just a VHF call away, your lead crew serves as an ever-present backup team. If you need help with mooring, they will be there to lend a hand.

With such formidable support, even those with little experience can build up confidence and practise sailing skills. Even if you have logged hundreds of nautical miles, a flotilla allows you to connect with like-minded lovers of life at sea.

Socialising is not compulsory, but there are plenty of opportunities to get to know your fellow sailors. Your flotilla host arranges events like beach barbecues, punch parties, and regattas. Alternatively, you can gather with your crew for a quiet dinner or drinks on board. Whatever floats your boat.

Families may choose to book a flotilla in Lefkas or Meganisi during July and August which includes a kids’ coordinator who can keep youngsters busy with fun activities.

Why learning to sail isn't all that hard...

While it might initially look intimidating, sailing is not rocket science. Sailing is one of the most thrilling ways to navigate our world and appreciate nature. Relying on the wind to carry you to your destination is also one of the most sustainable forms of travel.

While sailing knowledge is not required to book a Sunsail flotilla holiday, there are plenty of good reasons to learn the basics. Sailing teaches you to be open-minded, flexible, and fully present. It boosts self-confidence and conveys a sense of freedom not found on land. Sailing requires you to be a team player. You will be taught how to monitor the weather, chart a course, and trim sails. And there is truly no better feeling than helming a yacht.

With its relaxed atmosphere, warm seas, and easily navigable coastline, the Mediterranean is the perfect location to take up sailing. Flotilla Starter courses in Greece and Croatia offer an easy, fun introduction to coastal sailing. An RYA (Royal Yacht Association)-accredited skipper provides one to two hours’ tuition per day for up to five people while you savour your flotilla holiday. Sunsail’s Flotilla Hero course is geared towards those with some experience who wish to gain RYA certification while on holiday. Once qualified, you can charter a yacht at any Sunsail destination.

If you would rather leave the sailing to a professional, book a Sunsail skippered charter. This is also a great option for first-timers who want to test their sea legs.

Where to go on a flotilla holiday with Sunsail

Sunsail offers flotilla holidays in Greece, Croatia, and Italy. Brimming with history, culture, and tradition, the Mediterranean is rightly considered one of the world’s premier sailing grounds.

Exploring the region by yacht allows you to reach otherwise inaccessible mainland coastal locations and remote islands.

With ancient sites, homely beachfront tavernas, and 2,000-plus islands, Greece has long perfected its irresistible siren song. Croatia’s Dalmatian Coast, postcard-perfect villages, and Game of Thrones locations make it an equally tempting proposition. Italy, meanwhile, is in a class of its own with a plethora of sophisticated harbours, divine culinary offerings, and volcanic vistas.

Croatia

Many a sailor daydreams about navigating the blue-green waters of Croatia’s captivating Dalmatian Coast. But where do you start when there are more than 1,200 islands to choose from, let alone cobble together an Adriatic Sea itinerary on your own? With two bases, Dubrovnik and Marina Agana, Sunsail offers a wealth of local expertise for both newbies and seasoned sailors when planning a flotilla holiday.

Soaring cliffs, pebbled beaches, and centuries-old walled cities have contributed to Croatia’s evolution as one of the world’s most enticing sailing grounds. But when cruising these scintillating seas, there is no need to rush. Croatians call it pomalo, which means ‘take it easy’. So, be prepared to go with the flow.

In Croatia, you can pick from a wide range of Sunsail flotilla itineraries. A new Elafiti one-week itinerary begins in Dubrovnik, close to the historic Old Town. Inspect the city’s mediaeval fortresses, Renaissance palaces, and winding streets before stepping aboard your yacht. Ports of call include Slano village, Mljet island and its saltwater lakes, and fertile Šipan island, where figs, grapes, and almond trees grow in abundance. Short hops ensure your crew will not have to wait long between land adventures.

Marina Agana, near Split, is also an excellent jump-off point if you wish to explore Hvar and other nearby islands on a one-week flotilla trip. See the UNESCO World Heritage-listed harbour town of Trogir and the remains of Emperor Diocletian’s Palace in Split before throwing off the bowlines.

Among your stops is Brač, whose small town of Milna is filled with shops and dining spots. You will spend two days on Hvar, which is framed by undulating slopes and thick woodlands. The enchanting seaside town of Jelsa draws foodies to its konoba restaurants, which specialise in traditional Dalmatian cuisine, including lashings of seafood.

Greece

In Nikos Kazantzakis’ 1946 novel Zorba the Greek, he wrote: “Happy is the man, I thought, who, before dying, has the good fortune to sail the Aegean Sea.” If island-hopping in Greece on a yacht has long been on your bucket list, Sunsail can make it happen. And even if you have cruised there multiple times, there is always somewhere new to discover. Expert holiday planners are on hand to assist you in choosing a destination and creating a flotilla holiday experience tailored to your interests and sailing experience.

The very nature of a sailing yacht brings you closer to Greece’s millennia-spanning history and culture, its vast island archipelago, and its famously hospitable people. Conversation and laughter flow easily, regardless of language barriers, from the moment you step ashore. Keep a keen eye out for the tavernas where locals dine; they are very often hidden down an alley or in an inland village rather than on the waterfront.

Setting off from Sunsail’s Lefkas base, relish easy sailing in the relatively calm Ionian Sea between the Heptanese islands. Here, forested hillsides spill down pebble beaches washed by turquoise waters. Drop anchor in sheltered coves and small towns off Kefalonia, like Assos and Antisamos, seen in Captain Corelli’s Mandolin. Don’t miss spectacular Myrtos, the island’s best-known beach, and Melissani Caves. On Greece’s western coast, the colourful, small towns of Parga and Preveza feature Roman-era ruins, castles, and sandy shores.

Sail across cobalt blue seas to Homer’s Ithaca, where you can hike through hills studded with cypress, pine, and oak trees. In the capital, Vathy, named for its deep natural harbour, visit maritime and archaeological museums and admire a monument dedicated to seafarers.

Lefkas, Greece

Among Sunsail’s 50th anniversary celebrations this year is a special one-week Lefkas flotilla. Be quick to secure a yacht for this unique journey through the emerald waters of the Ionian and its lush islands. Before departing from the island of Lefkas, don’t miss out on swimming at Egremni beach or windsurfing at Vassiliki beach.

Next is Meganisi, where a sunken plane and glittering sea caves await snorkellers. From there, the flotilla heads to Kastos islet, whose evening highlight is a beach party in a secret bay. On the way, Kalamos’ pristine beaches are worth a stop.

Venturing south, the next port of call is Ithaca, Odysseus’ birthplace. A short walk from Kioni village are the pebbled beaches of Sarakinari and Plakoutses. Before returning to Lefkas, your final destination is the peaceful mainland coastal town of Paleros. Drop the hook at Varko Bay or off idyllic Vathiavali beach.