Flotilla sailing travel guide

Sailing in a flotilla is a fantastic way to devote a vacation to the pleasures of cruising in sunny climes, with minimal organisation on your part. Potter between lunch spots, or keep the sails hoisted: You’ve got the freedom to decide how much you want to sail, and how much you want to relax.
Ever sat on the shore on vacation and wondered how that family managed to afford that fancy sailing boat? Chances are, they’ve probably rented it for the week as part of a flotilla vacation.
In flotilla sailing you get your own boat, but are part of a small fleet. One big misconception about this set-up is that it’s really boring and controlled – people think you’ll follow the lead boat like it’s a mother goose and you’re some helpless gosling. Wrong: on flotilla, you can sail wherever you wish, just as long as you make it to the agreed meeting point by the end of the day. No, flotilla is anything but vanilla. And there’s nothing quite as thrilling as the moment the wind hits and the boat heels towards the water. The lines vibrate, the spray flies in your face, and you’ll bear down on the horizon with your heart racing.
Read on in our flotilla sailing guide for more details.

Flotilla sailing is…

great for close knit friends and family, who don’t mind an active vacation, nor being in close quarters with each other for days on end.

Flotilla sailing isn’t…

for those who like to stay put, or who get seasick – you’ll always be on the move.

When is the best time to go on a flotilla sailing vacation?

It’s always flotilla season somewhere. If you’re flotilla sailing in Europe, the season runs from May to October. Caribbean trips run all year around, except for September, and are most popular from December to March – when its tropical climes chime well with visitors from chilly Europe. The best time to flotilla sail in Europe is probably just outside summer, in May or September, to avoid the worst of the heat and crowds – though both are less problematic if you’re in command of your own floating breeze machine. Whilst the Greek Ionian Islands are calm all summer, the Greek Aegean can get strong winds on summer afternoons, when a wind called the Meltemi rises, and hurricane season in the Caribbean is technically from June until October. Sailors are weather-obsessed and flotilla leaders are no different; they’ll keep an eagle eye on the forecast and keep you safe.
Travel Team
If you'd like to chat about Flotilla sailing or need help finding a vacation to suit you we're very happy to help.

Flotilla sailing, month by month

From December to March, Caribbean sailing is at its peak popularity. There are lots of regattas around this time which attract competitive sailors and their performance vessels. The British Virgin Islands (BVI) Spring Regatta occurs from late March to early April in Tortola. In late April and May, the BVIs are quieter for sailing – you won’t have to play chicken with other boats over the last mooring buoy in the bay, and there’s less traffic to watch out for when you’re underway. May is the start of Europe’s flotilla season, and the big fleets of flotilla boats get their first outings out of the marinas. June is the start of hurricane season in the Caribbean and it’s very hot, but this doesn’t stop trips running. In the Ionian islands a lovely fresh breeze is blowing. From June to September, the maistros, a north-westerly wind, builds power throughout the day and is at its strongest in the afternoon, offering exciting sailing. July and August is peak time for cruise ships in Europe – especially in cities like Dubrovnik in Croatia and Sorrento on the Amalfi Coast. Your lead boat will time your visit to places like this so you don’t clash with the big ships and their enormous crowds. September is a quieter time to sail in Europe, as the beaches are less crowded. October marks the end of the flotilla season in Europe, and the start of more unsettled weather in the region. Autumn storms can bring strong winds – but there’s still enough good weather about to have a pleasant and safe trip. From November to April there is no flotilla sailing running in Europe, as there are winter storms and winds like the ‘bura’ in Croatia can whip the sea into a frenzy. Caribbean sailing runs all year round.
Written by Eloise Barker
Photo credits: [Page banner: Karla Car] [Is/isn't: Val Vesa] [When to go: _dChris]