Western Cyclades & Santorini Island-Hopping Week (Self-Launched)

Arrive on Paros (ferries from Athens/Piraeus take roughly 3–4.5 hrs; from Rafina or Naxos shorter). Check into a guesthouse in Parikia's old town, then walk the whitewashed lanes to the windmill at the port and the Panagia Ekatontapyliani church. Use the afternoon to finalise ferry tickets for the week at the local travel agencies or online — the Paros–Ios–Santorini legs are easy, but Folegandros–Kimolos–Milos is the tight bit, so confirm the days your boat actually runs. Sunset drinks on the Kastro walls, dinner of grilled octopus and Parian wine at a taverna behind the port.

🚌Blue Star Ferries or SeaJets from Piraeus to Paros, roughly £30–45 booked in advance

🛏Family-run guesthouse or hostel in Parikia old town (dorm £18–25, private double £40–60)

• →Walk Parikia old town and port windmill
• →Panagia Ekatontapyliani church
• →Book/confirm inter-island ferry tickets for the week
• →Sunset at Kastro

Morning ferry Paros to Ios (about 1–1.5 hrs). Drop bags at a guesthouse in Chora or near the port, then climb to the Panagia Gremiotissa church on the ridge and wander the maze of Chora's lanes. Afternoon at Mylopotas beach (local bus, ~£1.50) for a swim, or walk to quieter Kolitsani cove. Dinner in Chora — plenty of cheap souvlaki and gyros spots alongside the sunset bars on the hill towards the windmills.

🚌Blue Star Ferries or SeaJets Paros–Ios, approx £12–20

🛏Hostel or guesthouse in Ios Chora or near the port (£15–22 dorm, £35–55 private)

• →Panagia Gremiotissa church and Chora lanes
• →Mylopotas beach swim
• →Kolitsani cove walk
• →Sunset from the windmills above Chora

Morning ferry Ios to Santorini (Thira), ~45 mins. Store bags in Oia or at the port if you're moving on, then walk the caldera rim path from Fira to Oia if you want the classic hike (10 km, 3–4 hrs, no cost) or take the local bus. Have a late lunch at Ammoudi Bay, the little harbour under Oia's cliffs, then take the small local ferry across to Thirasia (about 15 mins) for dramatically cheaper rooms and a quieter view back at the caldera at sunset. If the meltemi is blowing or you're short on time, skip Thirasia and overnight in Fira or Karterados instead.

🚌SeaJets/Blue Star Ios–Santorini approx £10–18; local bus around the island ~£1.80 per ride; Ammoudi–Thirasia local ferry ~£5–8

🛏Guesthouse in Thirasia (£20–30) or budget rooms in Karterados/Fira (£30–45)

• →Fira–Oia caldera rim walk (free)
• →Lunch at Ammoudi Bay
• →Small local ferry to Thirasia
• →Caldera sunset from Thirasia

Ferry to Folegandros (timings vary — some days it's a direct 1–1.5 hr hop, other days you connect via Milos or Santorini, so check schedule days in advance). Check into a guesthouse in Chora, a beautifully preserved hill village with three connected squares full of tavernas. Walk the paved path up to the Panagia church for the classic Folegandros sunset over the cliffs, and if you have energy, follow the trail out to the Katergo beach viewpoint or take the small boat from Karavostasis to Katergo's pebble cove.

🚌Ferry Santorini/Thirasia–Folegandros approx £12–22 (may involve a connection)

🛏Guesthouse in Folegandros Chora or Karavostasis (£25–40)

• →Chora's three squares and cobbled lanes
• →Panagia church sunset walk
• →Katergo beach boat or trail
• →Taverna dinner in Chora

Morning ferry to Kimolos via Milos (the only realistic routing — roughly 2–3 hrs total with a change in Adamas). Kimolos is the tiny, unspoilt neighbour of Milos: Psathi port, then a 10-min walk or bus to Chora, a whitewashed village with a medieval castle core. In summer, local boat operators and the Municipality run day trips out to Polyaigos, the uninhabited island with turquoise coves and the famous blue-green waters — this is the self-booked equivalent of the sailing lunch stop. Back on Kimolos, try the local honey and cheese (kimolotyri) and swim at Prassa or Soufi beaches.

🚌Ferry Folegandros–Milos–Kimolos approx £15–25 total

🛏Guesthouse in Kimolos Chora or Psathi (£25–40)

• →Day boat trip to Polyaigos swim coves (approx £25–40)
• →Explore Kimolos Chora and castle
• →Prassa or Soufi beach
• →Local honey and cheese tasting

Short ferry or local boat Kimolos to Milos (Adamas), 20–40 mins. Base yourself in Adamas or Plaka. Rent a scooter or small car for the day (scooter ~£18–25, car ~£35–45 before fuel) because Milos's beaches are spread out and buses are limited — head to Sarakiniko's white moon-cliffs for the swim and cliff-jump photo spot, then Firiplaka, Tsigrado (a scramble down a rope ladder) and Paleochori. Evening in Plaka's lanes for the sunset over the gulf and a cheap taverna dinner near the bus stop for the next morning.

🚌Kimolos–Milos ferry/boat approx £6–10; scooter or car hire ~£20–45 for the day plus fuel

🛏Hostel or guesthouse in Adamas or Plaka (£20–35 dorm, £40–60 private)

• →Sarakiniko white cliffs swim
• →Firiplaka and Tsigrado beaches
• →Plaka sunset from the castle
• →Optional boat trip to Kleftiko (approx £30–50)

Morning ferry Milos to Sifnos (about 1–1.5 hrs). If you have a few hours, take the local bus up to Apollonia and the hill village of Artemonas for a wander and a plate of Sifnian chickpea stew, or head to Platys Gialos beach for the lunch stop the sailing tour made. Then take the afternoon ferry Sifnos to Paros (about 1 hr) and, if time allows, hop the 10-min ferry from Pounta to Antiparos for a swim and a final lunch before returning. Overnight in Parikia, ready for your onward ferry the next morning.

🚌Ferry Milos–Sifnos approx £12–18; Sifnos–Paros approx £15–22; Pounta–Antiparos ferry ~£2

🛏Guesthouse or hostel in Parikia, Paros (£18–30 dorm, £40–60 private)

• →Apollonia and Artemonas villages
• →Platys Gialos beach
• →Antiparos day hop and swim
• →Final dinner in Parikia