What's on

Festivals, races, and cultural moments worth planning a trip around, by month. Dates read confirmed where the organizer has published them, and expected where we've projected the recurrence. Always verify before booking.

6 events upcoming for Sailing.

October 2026

Oct 17–24Confirmed47th Rolex Middle Sea Race

Rolex Middle Sea Race

Valletta · Malta

Sailing

Starts from Grand Harbour, Valletta on a Saturday in mid-to-late October each year. Upcoming: the 47th edition starts on 17 October 2026; a 2027 edition is expected in mid-to-late October.

Dates & details →

March 2027

Mar 25–29ExpectedBequia Easter Regatta 2027

Bequia Easter Regatta

Bequia · Saint Vincent and the Grenadines

Sailing

A four-day regatta held each year over the Easter weekend, dates set off the movable feast by the Bequia Sailing Club. Upcoming: around 2 to 6 April 2026 (expected, Easter Sunday 5 April); around 25 to 29 March 2027 (expected, Easter Sunday 28 March).

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April 2027

Apr 20–24ExpectedNational Family Island Regatta 2027 (expected, late April)

National Family Island Regatta

George Town, Exuma · Bahamas

Sailing

Held each April in Elizabeth Harbour off George Town, Great Exuma, staged by the National Family Island Regatta Committee since 1954, racing traditional Bahamian Class A, B and C working sloops over about five days. Dates fall in the last full week of April and are confirmed by the committee nearer the time. The 2026 edition (the 70th) ran 21 to 25 April 2026; 2027 is expected in late April.

Dates & details →

Apr 21–25ConfirmedAntigua Sailing Week 2027

Antigua Sailing Week

English Harbour · Antigua and Barbuda

Sailing

Held annually over five days in late April, out of English and Falmouth Harbours. The 58th edition runs 21 to 25 April 2027; a further edition is expected in late April 2028.

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October 2027

Oct 16–23Expected48th Rolex Middle Sea Race

Rolex Middle Sea Race

Valletta · Malta

Sailing

Starts from Grand Harbour, Valletta on a Saturday in mid-to-late October each year. Upcoming: the 47th edition starts on 17 October 2026; a 2027 edition is expected in mid-to-late October.

Dates & details →

April 2028

Apr 26–30ExpectedAntigua Sailing Week 2028

Antigua Sailing Week

English Harbour · Antigua and Barbuda

Sailing

Held annually over five days in late April, out of English and Falmouth Harbours. The 58th edition runs 21 to 25 April 2027; a further edition is expected in late April 2028.

Dates & details →