| Day 1 | Sat | 11 nm | Kos, leaving kos marina for Pserimos anchorage (or Kalymos/Vathi port on Kalymnos). |
| Day 2 | Sun | 21 nm | Leros, Leros Lakki or Ay marina. |
| Day 3 | Mon | 43 nm | Cross towards Astypalea, long day sailing. |
| Day 4 | Tue | 38 nm | Palon or Mandraki port on Nisyros (visit the fumaroles) - another real crossing. |
| Day 5 | Wed | 18 nm | Tilos, off the beaten track. |
| Day 6 | Thu | 35 nm | Symi, visit Symi port as well as the anchorages south of Pethi. |
| Day 7 | Fri | 56 nm | Kos, explore town and castle. |
A similar idea is to sail Kos - Leros - Astypalaia - Tilos - Symi - Nisyros - Kos (11, 21, 43, 53, 35, 38, 23 = 224 nm).
| Day 1 | Sat | 23 nm | Leaving Rhodes for Symi - the three southernmost anchorages along the east coast and Simi port |
| Day 2 | Sun | 38 nm | Nisyros - Palon (more shelter) & Mandraki ports, a visit to the caldera and try to anchor at the many volcanic beaches. |
| Day 3 | Mon | 31 nm | Kalymnos - The main port of Pothia, with its Italianate style of architecture. Anchor at Telendos or much more secluded in Emborios. |
| Day 4 | Tue | 34 nm | Lipsi (Leipsoi) - Churches of Panagia/Virgin Mary and the nearest blue cupola Ioannis Theologos/John Evangelist. Anchorages at the northwest and south - lots of reefs! |
| Day 5 | Wed | 11 nm | Patmos - Rent bikes/scooters from Skala. |
| Day 6 | Thu | 10 nm | Arki - Port Augusta and Marathos islet (Marathi) |
| Day 7 | Fri | 31 nm | Samos - Marathakambos (27 nm) or Pythagorion (31 nm) ports, Pythagorio fortress and the tunnel of Eupalinos. |
| Day 8 | Sat | 17 nm | Agathonisi (Gaidaros) - Ay. Georgiou port and the narrow anchorage 1.3 nm to the east. |
| Day 9 | Sun | 19 nm | Leros - Alindas bay and the Venetian castle, or the more peaceful and lush Pandeli bay further south. |
| Day 10 | Mon | 23 nm | Pserimos - The small hamlet of Pserimos is delightful after the tripperboats have returned elsewhere in the end of the afternoon. |
| Day 11 | Tue | 11 nm | Kos - Kardamena has one of the best beaches in Greece, yet only visit well after the season due to the overwhelming amount of tourists. Normally just visit Kos port and discover the wonderful town. |
| Day 12 | Wed | 34 nm | Tilos - Lidavia port |
| Day 13 | Thu | 20 nm | Chalki (Halki)- The main port Emborio, and the castle on the adjacent island of Alimia (Alimnia). |
| Day 14 | Fri | 37 nm | Rhodes |