Departed Piraeus on 19.05.1941
Destined for Mαleme, Crete
About 25 small coastal vessels 
Initially by the Italian torpedo boat (Torpediniera) 'Sirio', which broke down. It was replaced by the torpedo boat 'Lupo'.
(At the disposal of 7. Flieger-Division)
2331 troops (another source indicates 2250 men) including
reinforced III./100th Gebirgsjäger-Regiment.
(without heavy equipment)
two batteries of the I./Flak-Lehr-Abteilung.
rest of the staff, 7. Flieger-Division
motorcycles During the night of 21/22.05.41, the convoy (by now only 16 ships) was intercepted and badly mauled by the British Force D (RAdm I.G. Glennie, commanding). During the attack at least 10 caiques was sunk notwithstanding the brave defense by the 'Lupo'. Losses in personnel were 297 men. That the losses were so small was owing to the very efficient German Seenotdienst (Air Sea Rescue Service) cooperating with Italian torpedo boats immediately despatched to the scene. None of the convoy arrived at Crete.
Departed Chalkis on 21.05.1941
Destined for Heraklion, Crete
About 38 small coastal vessels 
Italian torpedo boat 'Sagittario'
(At the disposal of 5. Gebirgs-Division)
4000 troops, including
further elements 5. Gebirgs-Division
(without heavy equipment)
rest of the Fallschirm-Regiment 1
one battery of the I./Flak-Lehr-Abteilung
supplies Intercepted by the British Force C (RAdm E.L.S. King, commanding) on 22.05.1941. The convoy escaped unscathed owing to two fortunate events: the 'Sagittario' fogged in the convoy hiding the small ships; and Admiral King decided to withdraw as he had insufficient antiaircraft ammunition to protect his ships from air attacks. Nevertheless, the convoy turned back to avoid the same fate as the first convoy.
Departed Rhodes on 27.05.1941 at 17:00
Disembarked Sitia Bay, Crete on 28.05.1941 between 16:50 and 17:20
- motor fishing boat S. Antonio
- motor fishing boat Navigatore
- motor fishing boat S.Giorgio
- motor fishing boat Plutone
- refrigerator ship Assab (525 tons)
- refrigerator ship Addis Abeba (514 tons)
- steamship Giorgio Orsini (470 tons)
- steamship Tarquinia (749 tons)
- riverboat Porto di Roma (470 tons)
- lagoon steamer Giampaolo (358 tons)
- tanker Nera
- 2 harbor gasoline lighters
- tug boat Impero
- tug boat Aguglia
- fleet destroyer Crispi (Flagship)
- torpedo boat Libra
- torpedo boat Lince
- torpedo boat Lira
- submarine chaser MAS 520
- submarine chaser MAS 523
- submarine chaser MAS 536
- submarine chaser MAS 540
- submarine chaser MAS 542
- submarine chaser MAS 546
Task Force, Divisione Fanteria Regina .
No interference by the Royal Navy.
 Typical Greek wood motor cutters, known as "caiques"; these ships not equipped for landing operations, but the Italian and German engineers modified the ships to enable them to function like landing ships (with wooden ladders, landing ramps made with iron and wood, etc.). One German described the caiques as; ". . . an assortment of scarcely seaworthy Greek coasting tramps and some larger rusty 'death traps' . . . "  The 50.a Regina Infantry Division had been in the Italian Deodecannese since the beginning of the war.