Self-Launched Cyclades Island-Hopping Adventure: Santorini Loop

Fly into Santorini (JTR) and take the local KTEL bus to Fira (~£2). Check into a budget guesthouse or hostel in Karterados or Fira, which is far cheaper than the caldera rim. Settle in, then walk the caldera path toward Imerovigli and take the bus to Oia for sunset (go early — it's mobbed). Dinner at a taverna off the main strip in Fira: gyros or grilled octopus with a half-litre of house white for £12–15.

🚌Airport bus to Fira ~£2; local buses £1.80 per ride

🛏Budget guesthouse/hostel in Karterados or Fira (~£32/night)

• →Self-guided caldera rim walk Fira to Imerovigli
• →Oia sunset viewpoint (free)
• →Taverna dinner in Fira

Take the morning Blue Star or SeaJets ferry from Santorini (Athinios port) to Ios, roughly 45–70 minutes, £15–25 depending on operator. Drop bags at a hostel in Ios Chora. In the afternoon take the local bus to Magganari Beach on the south coast (£3) — the wild, unspoilt sweep of sand the sailing tour swims at. Walk up to Homer's Tomb above Plakoto for sunset views. Evening back in Chora: cheap, lively tavernas and bars.

🚌Ferry Santorini–Ios £15–25; local bus to Magganari £3 each way

🛏Hostel or simple rooms in Ios Chora (~£28/night)

• →Magganari Beach swim
• →Homer's Tomb sunset walk
• →Ios Chora evening wander

Morning ferry to Naxos (~1hr, £10–18). Check into a guesthouse in Naxos Chora or Agios Georgios beach. Spend the afternoon exploring the old town's Venetian kastro and the unfinished Temple of Apollo gate (Portara) on the islet — free and best at sunset. Pick up supplies at the local bakery and greengrocer for beach days ahead. Optional: hire a bike or scooter for the next day (~£15/day).

🚌Ferry Ios–Naxos £10–18

🛏Guesthouse in Naxos Chora or Agios Georgios (~£30/night)

• →Naxos old town and Kastro walk
• →Portara temple gate at sunset
• →Local market and bakery shopping

Do the skipper's Naxos day trip independently: take the local bus or hired scooter to the Temple of Dimitra near Sangri (£2 bus), then hike up Mt Zeus (1,004m, 2–3hrs return from Filoti) for panoramic Cyclades views. On the way back stop at a Naxian microbrewery for a tasting (£6–8) and eat at a village taverna in Filoti or Halki. Alternatively join a small-group Naxos highlights day tour via GetYourGuide (£35–45).

🚌Local buses £2–4 per trip, or scooter hire ~£15/day

🛏Guesthouse in Naxos (~£30/night)

• →Temple of Dimitra
• →Mt Zeus hike from Filoti
• →Microbrewery tasting
• →Village taverna lunch

Morning ferry to Mykonos (~40–50min, £12–20). Mykonos is pricey — book a hostel or guesthouse in Mykonos Town or Ano Mera well ahead. Afternoon: walk the windmills of Kato Mili and the Little Venice waterfront, and get lost in the maze of whitewashed lanes. Skip the £15 cocktails on the veranda if you're watching the budget — grab a supermarket beer and sit on the free seawall instead. Ferry out early tomorrow.

🚌Ferry Naxos–Mykonos £12–20; local buses £2

🛏Hostel or budget guesthouse, Mykonos Town (~£40/night)

• →Kato Mili windmills
• →Little Venice waterfront walk
• →Mykonos Town lanes

Short ferry to Syros (~40min, £10–15), the Cyclades' quieter capital. Syros is one of the best-value islands — guesthouses in Ermoupoli are noticeably cheaper than Mykonos or Santorini. Explore the neoclassical Vaporia district and the marble plateia, then climb to Ano Syros' Catholic hill town for sunset. Evening at a seafood taverna in Ermoupoli or the beach at Galissas by bus.

🚌Ferry Mykonos–Syros £10–15; local bus £2

🛏Guesthouse in Ermoupoli, Syros (~£28/night)

• →Ermoupoli neoclassical quarter
• →Ano Syros hill town walk
• →Galissas beach (bus £2)

Morning ferry to Paros (~45min, £10–16). Base yourself in Parikia or Naoussa. Visit the Panagia Ekatontapyliani church (free), then take the bus up to Lefkes, the old marble village, and walk a stretch of the Byzantine road trail back down to Prodromos (£2 bus, 1.5–2hr walk). Swim at Krios or Marcello beach in the late afternoon. Naoussa's harbour is great for a cheap grilled-fish dinner.

🚌Ferry Syros–Paros £10–16; local buses £2

🛏Guesthouse in Parikia or Naoussa (~£30/night)

• →Panagia Ekatontapyliani
• →Lefkes village and Byzantine road walk
• →Krios or Marcello beach swim

Ferry to Sifnos (~1–1.5hr, £15–22). Sifnos is Greece's foodie island — and surprisingly affordable off the main honeypot strips. Walk the cliffside Hora-to-Kastro path (about 3km, wonderful at golden hour), browse a working ceramic workshop in Kastro, and hike a section of the island's waymarked trail network. Dinner is the main event: chickpea stew, mastelo lamb and Sifnian wine at a taverna in Apollonia (~£18).

🚌Ferry Paros–Sifnos £15–22; local bus £2

🛏Guesthouse in Apollonia or Kastro, Sifnos (~£30/night)

• →Hora to Kastro cliff walk
• →Ceramic workshop visit (free)
• →Waymarked trail hike
• →Sifnian taverna dinner

Ferry via Milos or direct to Folegandros (~1.5–2.5hr, £18–28). The most raw and rewarding of the small Cyclades. Explore Hora's whitewashed lanes clinging to the cliff edge, walk up to the Panagia church for sunset over the caldera-like drop, and swim at Agali or Katergo beach (bus plus a short trail). This is the trip's slow-travel highlight — little to do but eat well, swim and watch the light change.

🚌Ferry Sifnos–Folegandros £18–28; local bus £2–3

🛏Guesthouse or rooms in Hora or Karavostasis (~£30/night)

• →Folegandros Hora cliffside walk
• →Panagia church sunset
• →Agali or Katergo beach

Morning ferry back to Santorini (~1hr, £18–28). Depending on your flight time, store bags at the port or Fira and do a last swim at Perissa or Kamari black-sand beach, or a volcano boat trip from Athinios (£20–25) if you have a full afternoon. Bus to the airport for departure. If you want to trim costs, ferries back via Milos can be cheaper in shoulder season — always compare on Ferryhopper.

🚌Ferry Folegandros–Santorini £18–28; bus to airport £2

🛏None (departure day)

• →Perissa or Kamari black-sand beach
• →Optional volcano boat trip
• →Airport transfer