Self-Launched Greek Island Hop: Kos to Mykonos by Ferry

Fly into Kos (or come in by ferry from Rhodes/Athens). Kos Town is walkable and flat — check into a hostel or guesthouse near the old town, then walk the harbour, the Ottoman-era Plane Tree of Hippocrates and the ancient Agora ruins scattered between the streets. Evening: first gyros and ouzo by the marina.

🚌Bus or taxi from Kos airport (~£4 bus / ~£25 taxi)

🛏Hostel or guesthouse in Kos Town, ~£20/night

• →Harbour walk and Plane Tree of Hippocrates
• →Ancient Agora and Roman Odeon (free/cheap entry)
• →Evening taverna in Kos old town

Rent a scooter or take the local bus to the Asklepion, the healing sanctuary on the hillside above town, then ride down to the south-coast beaches at Kardamena or the quieter sands at Agios Stefanos (with its basilica ruins right on the beach). Swim, sunbathe, back to town for dinner.

🚌Scooter rental ~£15/day or local bus ~£3

🛏Same Kos Town hostel/guesthouse

• →Asklepion archaeological site (~£6 entry)
• →Beach day at Agios Stefanos
• →Harbour seafood dinner

Short ferry hop to Kalymnos, the Dodecanese's rock-climbing and sponge-diving island. Base yourself in Pothia (harbour town) or the more laid-back Myrties/Masouri in the north. Visit the Nautical Museum's sponge-diving display and take an afternoon swim at Platis Gialos.

🚌Kos–Kalymnos ferry, ~1h, ~£10

🛏Family guesthouse in Myrties or Pothia, ~£28/night

• →Nautical and Folklore Museum in Pothia
• →Swim at Platis Gialos beach

Morning ferry to Leros, the most 'Greek-feeling' of the northern Dodecanese. Leros has a mix of Italian-era Art Deco architecture from the fascist occupation, a castle above the harbour at Platanos, and quiet beaches at Agia Marina and Vromolithos. Walk the harbour, eat at a family taverna.

🚌Kalymnos–Leros ferry, ~1h, ~£9

🛏Small guesthouse in Agia Marina, ~£26/night

• →Panagia Castle viewpoint
• →Walk the Agia Marina harbour strip

Keep the day loose. Leros rewards a slow pace: a morning swim at Vromolithos, a wander through Panteli's fishing-village tavernas over a long lunch, then hire a cycle to the Tunnel of Merkies (a WWII-era underground shelter). If you're the impatient type, ferry back to Kalymnos for afternoon climbing or a boat trip to tiny Telendos island.

🚌Local bus/bike hire ~£6

🛏Same Leros guesthouse

• →Vromolithos beach swim
• →Tunnel of Merkies
• →Long taverna lunch in Panteli

Long-ish transfer day: ferry back via Kos (or a direct connection if sailing) to Nisyros, the volcanic crater island. Yes, it's a detour — but standing inside the Stefanos crater is one of the Dodecanese's great unexpected experiences. Drop bags, walk the crater rim trail, and stay the night in Mandraki so you see the island after the day-trippers leave.

🚌Leros–Kos–Nisyros ferries, ~£18 total

🛏Small guesthouse in Mandraki, ~£25/night

• →Stefanos crater walk (~£4 entry)
• →Mandraki village evening

Ferry to Astypalea, the Dodecanese island closest to the Cyclades, with a whitewashed chora topped by a Venetian castle that looks like a postcard of Santorini before the crowds. Hike up to the chora's Kastro, eat at the kafeneion below Livadi beach, and swim in the turquoise bay.

🚌Nisyros–Astypalea ferry, ~2h, ~£14

🛏Guesthouse in Astypalea Chora or Livadi, ~£30/night

• →Walk up to the Chora and Kastro
• →Livadi beach

Morning swim at Vatses or Marmari, then your first proper Cyclades crossing — Astypalea to Santorini (via a connecting ferry; check Blue Star Ferries/SeaJets for seasonal direct sailings, otherwise route via Naxos). Late afternoon arrival in Santorini; check into a Fira or Karterados guesthouse and watch your first caldera sunset from the Fira cliff path.

🚌Astypalea–Santorini ferry, ~£25

🛏Guesthouse in Fira or Karterados, ~£45/night (Santorini is the priciest stop)

• →Fira cliff-path sunset walk
• →Caldera viewpoint

Do the classic 10km clifftop walk from Fira to Oia — about 3-4 hours with stops, all free, the best thing to do on the island. Recover with a swim at Amoudi Bay below Oia, eat grilled octopus on the harbour, and take the local bus back to Fira (~£2). Skip the crowded Oia sunset if you value your sanity; Fira delivers the same show.

🚌Local buses ~£4

🛏Same Santorini guesthouse

• →Fira–Oia caldera hike
• →Amoudi Bay swim
• →Seafood lunch at Amoudi

Morning at Akrotiri, the Minoan town preserved under volcanic ash (entry ~£11; book via GetYourGuide for a guided small-group version from ~£35 if you want the archaeology explained). Afternoon at Red Beach or Vlychada. Optional: a shared sunset catamaran with hot springs and dinner, ~£90-110 — this is the closest you'll get to the yachting experience, and worth it if you saved money elsewhere.

🚌Local bus ~£4

🛏Same Santorini guesthouse

• →Akrotiri archaeological site (~£11)
• →Red Beach
• →Optional shared catamaran sunset cruise (~£95)

Ferry out of Santorini's crowds to Folegandros, a small island with a spectacular clifftop chora and virtually no mass tourism. Check into a chora guesthouse, walk the zigzag path up to the Panagia church above the village, and eat at one of the dozen square-side tavernas.

🚌Santorini–Folegandros ferry, ~1-2h, ~£12

🛏Chora guesthouse, ~£30/night

• →Chora village and Kastro
• →Panagia church clifftop walk

Hop to Sifnos, a favourite of Greek island connoisseurs for its pottery, honey, chickpea stew and hiking paths connecting hill villages. Base in Apollonia or the port of Kamares. Afternoon swim at Chrysopigi beach, then dinner in Apollonia.

🚌Folegandros–Sifnos ferry, ~2h, ~£14

🛏Guesthouse in Apollonia, ~£32/night

• →Chrysopigi monastery and beach
• →Apollonia village evening

Walk part of the island's restored 'Ancient Paths' network — the Apollonia-to-Kastro trail takes about 2 hours and ends at a medieval village on the cliff. Afternoon ceramics shopping in Artemonas (Sifnos pottery is the island's signature craft) and a beach stop at Platis Gialos.

🚌Local buses ~£5

🛏Same Sifnos guesthouse

• →Ancient Paths hike to Kastro
• →Artemonas pottery workshops
• →Platis Gialos beach

Morning ferry to Paros — hop off for a few hours: wander Parikia's old town and its Byzantine Ekatontapyliani church, swim at Livadia — then take the short ferry on to Naxos. Evening on Naxos's Portara, the giant marble temple gate on its own islet, which faces due west.

🚌Sifnos–Paros ~£12, Paros–Naxos ~£7

🛏Guesthouse near Naxos Chora, ~£30/night

• →Parikia old town and Ekatontapyliani
• →Livadia beach
• →Naxos Portara at sunset

Morning bus up to the Temple of Apollo at Sangri or the Mount Zas trail if you want one last hike, then the fast ferry to Mykonos (~40 min). End the trip the way the sailing version does: wander the whitewashed lanes of Little Venice, watch the windmills at sunset, and celebrate a completed island hop. Ferries to Athens/Piraeus and Mykonos airport (£1.60 bus) are straightforward for onward travel.

🚌Naxos–Mykonos fast ferry, ~40min, ~£20

🛏Hostel or guesthouse in Mykonos Town, ~£50/night in high season

• →Little Venice sunset walk
• →Mykonos windmills
• →Final dinner by the harbour