Just after sunset on the first day of the Rolex Middle Sea Race, George David's Rambler (USA), the first yacht on the water, passed Capo Passero on the southwest corner of Sicily. During the night, all of the remaining teams racing joined Rambler, with the majority of the fleet enjoying sufficient breeze to make progress hugging the Sicilian Coast. At 11:00 CEST on Sunday, 20 October, Rambler was just 8 miles from exiting the Messina Strait.

Showing in second overall on the race traceker, under IRC, is Gerard Logel's IRC52 Arobas² (FRA), positioned just south of the entrance to the narrow strait, and approaching from the southeast. Logel is in close company with a number of other yachts, including Wild Joe (HUN), Kuka 3(SUI) (estimated to be in third place overall), Aragon (POL) and R’92 Pendragon (HUN).

Overall leader under IRC, according to the tracker, is BeWild (ITA), the ClubSwan 42 having made remarkable headway overnight, and is the next, small chasing pack, roughly in line with Etna.

Bruno Cardile's ORMA 60 Ad Maiora (ITA) has opened up an 80-mile lead in the multihull fleet and should exit the Strait of Messina shortly after Rambler.

Overnight, the southerly appears to have kept the fleet moving through the hours of darkness. At Capo Passero, the wind bent to the southwest for the passage north to Messina. According to the boats further south of the leaders, it shut off at daybreak, particularly close to land. Etna looks to be creating quite a shadow in the mid-point of the leg, causing the leaders to head offshore on the approach to Messina. Further north in the strait, the wind looks very light throughout the day. Once through the strait, there is light easterly funneling across the northern coast of Sicily. At Favignana, there is currently a solid southerly flow, forecast to dip on Monday, and then build again steadily from the southeast on Tuesday.