Festival Highlights of the Leeward Islands

Leeward Islands

From Antigua to Anguilla, St Barts to St Kitts & Nevis, a yacht charter in the Leeward Islands opens up some of the Caribbean’s most popular and glamorous destinations. The islands in this archipelago also home to some of the seasons most sought after festivals and sailing trophies. Here are our favourites:

St Barths Bucket

One of the world’s premier yachting regattas in one of the world’s most glamorous destinations, the St Barth’s bucket is held every March and is one of the highlights of the Caribbean yacht charter season. A series of competitive races take place during the day, which sees the most renowned sailing yacht builders in the world pitted against each other, with yachts from Perini Navi, Dubois and Alloy Yachts, to name a few. By night the port of Gustavia is lit up and ready for evenings full of entertainment and festivities. The St Barths Bucket is the sister race to Rhode Island’s Newport Bucket.


Heineken Regatta, St Maarten

One of the Caribbean’s most developed islands, full of high rise resorts and casinos, St Maarten is not known for being the relaxing retreat some of its neighbours are. Yet, come Heineken Regatta time, the popular party island creates a buzzing atmosphere unlike anywhere else in the Caribbean, where the world’s finest yachts congregate for four days of intense sailing, followed by four nights of serious partying. Acts like the Marley Brothers and the Black Eyed Peas have graced the beach front festival stage over the years. The 2015 regatta will be held from March 5th to 8th.

Moonsplash, Anguilla

The quintessential Caribbean tropical paradise, Anguilla may be small (91 kilometres square), but it boasts some of the best beaches in the world and some of the finest restaurants in the whole of the Caribbean. Come the first full moon before Easter, it’s also host to one of the Caribbean’s hippest music festival, Moonsplash. Now in its 25th year, the 2015 edition will take place in March and is the brainchild of world famous reggae singer (and Anguillan born and bred) Bankie Banx.

Antigua Sailing Week

The Caribbean’s largest regatta, the Antigua Sailing Week takes place late in the traditional Caribbean yacht charter season. The event will be held from April 25th – May 1st in 2015 and sees over 100 yachts compete in a series of races over five days. Both English and Falmouth Harbour become a hive of post-race activity, as the yachts return to anchor and prepare for the next day’s racing. The formal Lord Nelson’s Ball, held at the end of the week in Nelsons Dockyard, marks the end of the regatta for another year and recognises the best in competition over the course of the week.