Sailing is something that everyone should aspire to do at least once in their lives - as Mark Twain declared, "Throw off the bowlines, sail away from the safe harbour... Explore. Dream. Discover." Some trips are very hands on, and you'll be acting as a junior crew member, literally learning the ropes. On others, you're free to relax on deck, snorkel and spot wildlife while your skipper takes care of everything.
Flotilla holiday map and highlights
Cruise through Croatia, idle in the Ionian Islands and navigate the Bay of Naples – even familiar places look different from the water, and flotilla sailing gives you access all areas.
Most of our flotilla sailing holidays run in southern Europe, where the weather is fine, the water so warm you’ll want to keep jumping in off the boat, and the ports of call historic. There are also a few flotilla holidays that run in the Caribbean, but because of the strong trade winds, Caribbean sailing can be more challenging, and better suited to more experienced bare boaters. The exception in the Caribbean is the British Virgin Islands. Though breezy, these piratical islands are like a playground for sailors, with short, sheltered passages, calm seas, and little open water.
Our Flotilla sailing Holidays
Amalfi Coast, Italy
1. Amalfi Coast, Italy
The chic towns along the Amalfi Coast get snarled up with road traffic in summer – so you’ll feel smug sailing free from it all on your own boat. Flotilla holidays are based out of Procida, a little island in the Bay of Naples with a charming tumble of pastel-hued houses above its main harbour. The bay is great place to try the kind of local delicacies that deserve worldwide fame.
British Virgin Islands
2. British Virgin Islands
The BVIs have some of the safest and most enjoyable sailing in the Caribbean. Four large islands and dozens of little ones – some inhabited, some deserted, form a landscape that looks like a treasure map. Plunder the underwater caves off Norman Island, and eat locally caught lobster on remote Anegada. Following Hurricane Irma in 2017, the islands need visitors to return now more than ever.
If there’s a better way to explore 1000+ islands, we’d like to hear of it. Sailing is one of the best ways to discover Croatia’s long coast and its lacy mantle of islands. Start in Dubrovnik and reach out towards Vis Island and Korkula, or begin in the north and slide towards the Krka Falls National Park. The water here is astounding: crystal-cut waves and glass-clear bays wherever you wander.
Ionian Islands, Greece
4. Ionian Islands, Greece
Sheltered, calm, and full of legends that make good bedtime stories, the seven Ionian Islands are a popular base for flotilla sailing. Lefkada is the starting point for many sailors – from here you can reach Kefalonia, the sixth-largest island in Greece, where events in World War II inspired Louis de Bernieres to write Captain Corelli’s Mandolin. Nearby is little Ithaca where, according to Homer’s Odyssey, Penelope waited for her beloved Odysseus.
If you'd like to chat about Flotilla sailing or need help finding a holiday to suit you we're very happy to help.
Flotilla holiday travel advice
Lucy Wade from our specialist sailing holiday company Sunsail, says:
Flotilla sailing in the Caribbean
“December through to March is the most popular time to go sailing in the Caribbean due to glorious weather and light winds. I would however always recommend customers to travel slightly later around April/May time to avoid the crowds and having those breathtaking beaches all to yourselves!”
Learning to sail on flotilla
“The ‘learn to sail on a flotilla’ (also known as the flotilla starter/hero) is booked by the whole yacht rather than just the cabin, so more suitable for families. They are part of a flotilla on a set route with up to 11 other yachts doing the same itinerary however they will have an instructor on their yacht teaching them how to sail.”
More about Flotilla sailing
Get a group of your best friends together, or bring the family. Pack a crate of beer and a sunhat – and build your best yacht rock playlist. Ready to clamber aboard? Read on for our flotilla sailing holiday guide.
The concept is simple: a flotilla is a group of boats under the instruction of a lead vessel. For experienced sailors who don’t want to organise all the ins and outs of their trip for themselves, a flotilla makes water-based holidays plain sailing.