Why This Is the Perfect Year to Experience a Sunsail Flotilla

April 7, 2025 5 min

Sunsail pioneered the concept of flotilla sailing in the 1970s and has spent more than five decades refining it into the perfect sailing holiday. With new itineraries, carefully curated routes and a host of specialist activities – ideal for both seasoned skippers and complete beginners – Sunsail flotillas offer a unique blend of independence, camaraderie and support.

Yet even after all these years, there is still a sense of trepidation and a fair few misconceptions about what a flotilla holiday actually involves. Some imagine joining a flotilla means being herded from bay to bay like a school of fish by an over‑keen leader – no room to explore under your own steam and expected to socialise at every stop.

Admittedly, that does sound awful – but it couldn’t be further from the truth. In reality, flotilla sailing with Sunsail can be as structured or as laid‑back as you want it to be. Whether you’re a newer sailor looking for reassurance on your first Mediterranean adventure, an experienced owner keen to see a favourite cruising ground with fresh eyes, or you simply want a stress‑free sailing holiday without planning routes, choosing destinations or juggling mooring bookings, a flotilla could be exactly what you’re after.

With new routes and family‑friendly itineraries for 2025, we’re here to set the record straight on what flotilla sailing is really about – and to show you why this is an ideal year to experience the freedom and flexibility of a Sunsail flotilla.

Debunking the Myth: What Flotilla Sailing Really Is

Flotilla sailing is often misunderstood. Many sailors assume it means rigid group sailing, sticking to a strict timetable and set route, with limited freedom to do your own thing. The reality? A Sunsail flotilla is as structured or as flexible as you choose – with absolutely no forced socialising.

You’re in control of your own adventure, with the added benefit of support from a lead skipper and engineer, and none of the day‑to‑day worries about where to go, what to see, booking moorings or wondering whether your anchor will hold.

In essence, a Sunsail flotilla sits neatly between bareboat and skippered charter. You have all the knowledge and back‑up of an experienced skipper and engineer on the lead boat, but still enjoy the privacy and comfort of having your own yacht to yourselves.

A typical day starts with a morning briefing from the lead crew, covering the weather, navigation notes and recommended swim stops or lunch spots. After that, the day is yours. Sail at your own pace, drop the hook in a quiet bay for a swim or head ashore to wander through a harbour village before meeting the rest of the flotilla at the agreed evening stop.

Joining in socially is entirely optional. Flotilla events – from beach barbecues and themed evenings to group dinners – are a great way to meet other crews, but there’s no obligation to take part. If you’d prefer a quiet dinner aboard or a low‑key night ashore, that’s absolutely fine.

Flotilla sailing isn’t just for beginners either. While it’s an excellent choice if you’d like extra support – especially with trickier stern‑to Med moorings – it also appeals to experienced sailors who want to explore new cruising grounds without the admin, or revisit familiar waters with local insight and fresh ideas. It’s also a great option if you simply enjoy the social side of sailing and like the idea of meeting like‑minded crews from around the world.

What Is Included in Your Sunsail Flotilla?

When you book a Sunsail flotilla you get much more than just a yacht. You step into a low‑stress sailing holiday with built‑in support, optional social activities and tried‑and‑tested itineraries in some of the world’s most attractive cruising grounds.

The Lead Crew Experience: Expert Guidance

Every Sunsail flotilla is supported by an experienced lead crew – typically a skipper, an engineer and a host – whose job is to keep things running smoothly. The skipper looks after navigation, weather updates and daily briefings, the engineer focuses on keeping yachts running well, and the host organises social events such as beach barbecues, group meals and local excursions, helping you discover the best of each stop.

Mooring Assistance: Stress-Free Docking at Every Destination

Mooring support is one of the stand‑out benefits of a Sunsail flotilla, especially if you’re tempted by the Med but a little daunted by Med‑style stern‑to berthing. Each evening, the lead skipper is on hand to help you onto the quay or mooring buoy, often stepping aboard to guide you through the process.

It’s not only reassuring in the moment; it’s also a brilliant way to build your own skills and confidence ready for future trips.

Planned Activities: Fun, Social, and Flexible

Most flotillas include a programme of optional activities – from barbecues and themed nights to an end‑of‑week fun regatta – creating a relaxed, sociable atmosphere. The shared itinerary covers recommended anchorages and pre‑booked moorings, saving you time and ensuring a smooth, joined‑up route.

24/7 Support: You’re Never on Your Own

On a Sunsail flotilla you’re never truly alone on the water. The lead crew are available around the clock for questions, advice or emergencies. If you need help with navigation, a steer on conditions or support with an unexpected issue, you can call on them via VHF and they’ll be there to assist.

Top Sunsail Flotilla Routes to Explore in 2025

Sunsail runs flotillas in some of the most scenic sailing areas on the planet, and the 2025 line‑up mixes much‑loved classics with new itineraries, each designed to showcase the best of its region.

1. Adrenaline and Watersports: Lefkas, Greece

Perfect if you like your flotilla with a side of action. This route takes in dramatic cliffs, sheltered bays and a vibrant watersports scene – from windsurfing in Vasiliki (one of Europe’s top spots) to paddleboarding in tucked‑away coves and ticking off must‑see stops like Meganisi and Porto Katsiki beach.

Discover what an unforgettable flotilla sailing adventure in Lefkas, Greece has to offer

2. Family-FriendlySailing: Marina Agana, Croatia

Based out of Marina Agana on the Dalmatian coast, this flotilla is ideal for families. Expect gentle winds, calm seas and short hops between islands – just right for younger crew. The route takes in pretty coastal towns, national parks and clear‑water anchorages where children can swim, snorkel and explore, with stops at family‑favourites such as Šolta, Drvenik and the Blue Lagoon.

3. Discover the New Libertas Flotilla: Sailing from Dubrovnik

Launching in summer 2025, the Libertas flotilla offers a fresh way to discover Croatia’s southern Dalmatian coast. Setting off from historic Dubrovnik, it blends easy sailing with culture, scenery and crystal‑clear water, calling at the Elaphiti Islands, the village of Ston and the coves of Mljet National Park, among others.

Discover the Freedom of Flotilla Sailing as a Sunsail Owner

Whether you’re an existing owner looking for a new way to enjoy your time afloat, or you’re just starting out with Sunsail yacht ownership, a flotilla offers an appealing mix of relaxation, independence and sociable moments – ideal for families, couples and groups alike.

Say goodbye to route‑planning and marina admin; simply step aboard, cast off and enjoy the experience, knowing expert support is never far away.

Ready to start planning? Contact us to find out more and begin plotting your next flotilla adventure.