5 Greek Islands Odyssey — Self-Launched Cyclades Island Hop

Land at Athens Airport and take the metro (Line 3, €9, ~40 min) or the X95 bus (€5.50) into the city, then metro to Piraeus port if time allows, or head straight from the airport. Book your Piraeus–Mykonos ferry in advance on Ferryhopper or Direct Ferries: the fast Seajets/SeaJets-style catamaran takes ~2h45 (approx £45–60) while the slower Blue Star conventional ferry takes ~5h (approx £32–40) — the slow boat is cheaper and far more comfortable in wind. On Mykonos, stay in Mykonos Town (Chora) rather than a hillside resort so you can walk everywhere. Evening: wander the backstreets, sunset at the windmills, dinner of gyros or a taverna meal in Chora.

🚌Metro Athens Airport → Piraeus (~€9) + ferry Piraeus → Mykonos (fast ~£50, slow ~£35)

🛏Family-run guesthouse or budget hotel in Mykonos Town (e.g. rooms in Chora or Fabrika area), ~£40–55/night double

• →Piraeus–Mykonos ferry crossing
• →Sunset at the Mykonos windmills
• →Evening wander of Mykonos Town backstreets

Catch the morning boat from the old Mykonos Town jetty to Delos (return ticket ~€20–25, plus €12 site entry; boats run roughly 9am–1pm return, no fixed schedule so check locally). Delos is a UNESCO-listed uninhabited island and one of the most important archaeological sites in Greece — allow 3–4 hours. Back in Chora, walk to Alefkandra (Little Venice) for the sunset and Matoyanni Street for shopping and a drink. Beach option in the late afternoon: bus to Ornos or Platis Gialos (€2).

🚌Local boat to Delos (~€20 return); island bus €2

🛏Same Mykonos Town guesthouse

• →Delos archaeological site (UNESCO)
• →Little Venice (Alefkandra)
• →Matoyanni Street
• →Beach time at Platis Gialos or Ornos

Mid-morning fast ferry from Mykonos to Paros takes roughly 45–60 minutes (~£25–35) — the shortest hop of the trip. Base yourself in Parikia (port town, good ferry links, cheaper rooms) or Naousa if you want nightlife and a prettier harbour. Settle in, then explore Parikia's Panagia Ekatontapyliani church (one of the oldest in Greece) and the Kastro quarter, and swim at Livadia beach a 10-minute walk from the port.

🚌Fast ferry Mykonos → Paros (~£30)

🛏Studio or guesthouse in Parikia or Naousa, ~£35–50/night double

• →Panagia Ekatontapyliani church, Parikia
• →Kastro old town walk
• →Swim at Livadia beach

Rent a scooter (approx €20–25/day) or use the KTEL island buses (€2 per ride) to hit the beaches: Chrissi Akti (Golden Beach) for windsurfing, Pounda for the kite-surf scene, Kolympithres for the weird granite rock formations, or Santa Maria on the east coast. Late afternoon head to Naousa, a postcard fishing village with a Venetian castle ruin on the waterfront, and eat grilled octopus at the harbour. Try local Parian wine and the island's famous 'gouna' (sun-dried mackerel).

🚌Scooter rental ~€20–25/day or island buses €2/ride

🛏Same Paros guesthouse

• →Chrissi Akti / Golden Beach
• →Kolympithres beach
• →Naousa village and Venetian Castle
• →Seafood and Parian wine in Naousa harbour

Ferry to Naxos is only 30–50 minutes (~£12–20) — some fast ferries do it in half an hour. Naxos is the greenest and most authentic of the Cyclades. Dump your bags in Naxos Town (Chora) and head for the Portara — the giant marble gate of an unfinished Temple of Apollo, right by the port, superb at sunset. Then explore the old town's Venetian kastro lanes and try Naxian cheese, kitron liqueur and potatoes.

🚌Ferry Paros → Naxos (~£15)

🛏Guesthouse or small boutique budget hotel in Naxos Town, ~£35–50/night double

• →Portara (Temple of Apollo gate)
• →Naxos Town Venetian kastro
• →Local kitron liqueur tasting

Hire a car or scooter (€25–35/day; buses are cheaper but infrequent to the villages) and drive inland to Apeiranthos (Aperathos) and Filoti — marble-paved mountain villages with tavernas and views across the Tragea olive plain. Stop at the Temple of Demeter en route. In the afternoon come down to Plaka or Agios Prokopios beach for a long swim. In the evening eat in a village taverna rather than the port — the food is better and half the price.

🚌Car/scooter rental €25–35/day (or buses €2–4 per leg)

🛏Same Naxos guesthouse

• →Apeiranthos village
• →Filoti village
• →Temple of Demeter
• →Plaka or Agios Prokopios beach

Fast ferry from Naxos to Santorini (Thira) takes roughly 1–1.5 hours (~£30–40); the slow Blue Star takes ~2h. Stay in Fira or Karterados/Imerovigli — caldera-view rooms are extortionate, so a budget hotel 10 minutes' walk inland saves you £100+ a night. Spend the late afternoon walking the caldera rim path from Fira towards Firostefani and Imerovigli for the classic sunset views without the cruise-ship crush of Oia.

🚌Fast ferry Naxos → Santorini (~£35)

🛏Budget hotel or guesthouse in Fira or Karterados (not caldera-view), ~£45–65/night double

• →Fira caldera rim walk to Imerovigli
• →Santorini sunset from Firostefani

Book the half-day volcano boat trip yourself — the classic old wooden boats leave from the Old Port below Fira (walk down the 600 steps or take the cable car, €6). Tickets are around €25–30 and cover Nea Kameni (active crater, ~1.5h walk to the rim) and swimming in the warm sulphurous springs off Palea Kameni. Book via GetYourGuide if you want a hotel pickup or English-escorted version (~£30–40), or just buy at the Old Port kiosks. Afternoon back in Fira for the Archaeological Museum or a black-sand beach at Kamari/Perissa (bus €2).

🚌Cable car down to Old Port (€6) or steps; island buses €2

🛏Same Santorini hotel

• →Nea Kameni volcano crater walk
• →Palea Kameni hot springs swim
• →Fira town
• →Kamari or Perissa black-sand beach

Santorini to Milos is the longest and most wind-exposed leg — around 2–4 hours depending on the vessel (~£35–50). Book on Ferryhopper well ahead in high season. Milos is the quiet, dramatic one: base in Adamas (the port) or Plaka for a more local feel. Spend the afternoon at the Mining Museum in Adamas or just walk the harbour and eat at a family taverna — try the local watermelon pie and 'pitarakia'.

🚌Ferry Santorini → Milos (~£40)

🛏Guesthouse or budget hotel in Adamas or Plaka, ~£40–55/night double

• →Adamas harbour
• →Milos Mining Museum (optional)
• →Local taverna dinner in Plaka

Rent a car or scooter (€25–35/day) — Milos' best sights are spread out and buses are limited. Hit Sarakiniko early before the crowds: the white volcanic moonscape is the most photographed spot on the island. Then drive to the fishing village of Klima with its colourful syrmata (boat-house doors) and, if you're up for it, the walk or swim to the Sykia cave near Kleftiko on the south coast. Boat trips around the island's west coast (~€60–90) are the alternative if you'd rather be on the water. Sunset at Plaka's kastro.

🚌Car/scooter rental €25–35/day

🛏Same Milos guesthouse

• →Sarakiniko Bay
• →Klima fishing village and syrmata
• →Sykia cave / Fyriplaka (or west coast boat trip)
• →Plaka kastro sunset

Ferry back to Piraeus: fast catamaran ~3h (~£50–60), slow Blue Star ~5–6h (~£38–45). If you have a late flight, drop bags at a Piraeus luggage locker and take the metro to Monastiraki for a last souvlaki and a view of the Acropolis before heading to the airport. If you want a final night in Athens, a hostel dorm or budget hotel near Monastiraki/Syntagma is £25–40.

🚌Ferry Milos → Piraeus (~£45) + metro to airport (~€9)

🛏None included (or optional Athens budget hotel ~£35–45 if flying next day)

• →Ferry back through the Cyclades
• →Optional Athens stop: Monastiraki and Acropolis views