16-Day Greek Island Hopping Self-Launched Adventure: Milos, Santorini, Koufonisia, Naxos, Paros & Mykonos

Land at Athens Eleftherios Venizelos (ATH) and make your own way into the city. The cheapest option is Metro Line 3 (blue) direct to Syntagma, ~€9 (£8), or the X95 express bus to Syntagma for ~€5.50 (£4.70) — the operator's private airport transfer is easily replaced. Check into a Plaka or Monastiraki hostel or budget guesthouse, get a Greek SIM/eSIM (Cosmote or Vodafone tourist plan, ~€10-15), then wander Monastiraki Square for a first gyros dinner (~€4). Book your onward ferry to Milos tonight via Ferryscanner or Direct Ferries.

🚌Metro Line 3 ATH to Syntagma ~€9 / bus X95 ~€5.50

🛏Budget hostel or guesthouse in Plaka/Monastiraki (dorm from ~£22, private double ~£45)

• →Airport metro/bus transfer to central Athens
• →Evening stroll in Monastiraki and Plaka
• →Pick up Greek SIM/eSIM
• →Book Milos ferry online

Beat the crowds and heat with an 8am timed-entry ticket to the Acropolis (book direct on the official etickets.tap.gr site, €20 summer/€10 winter — or the €30 multi-site pass covering Ancient Agora, Kerameikos and more). Skip-the-line private guiding is optional; a GetYourGuide small-group Acropolis tour with a licensed guide costs ~£35-45. In the afternoon do your own Monastiraki food crawl: souvlaki with tzatziki, olives, loukoumades and pastries from the stalls around Mitropoleos Street, ~£12 total. Finish at Areopagus Hill for a free sunset view over the Parthenon.

🚌Walking / Athens metro day ticket €4.10

🛏Budget hostel or guesthouse in Plaka/Monastiraki (dorm from ~£22, private double ~£45)

• →Self-booked Acropolis, Parthenon, Erechtheion & Temple of Athena Nike entry
• →Optional GetYourGuide Acropolis small-group guided tour
• →DIY Monastiraki street-food tasting walk
• →Sunset from Areopagus Hill

Head to Piraeus port by metro (Line 1 to Piraeus, €1.20) in time for a morning high-speed ferry to Milos (Seajets/Hellenic Seaways, roughly 3-5 hrs, £40-55 one way). Book through Ferryscanner or Direct Ferries a few weeks ahead. On arrival in Adamas, walk or take the local bus to your guesthouse. Settle in, swim at Papikinou Beach and visit the Aphrodite of Milos statue in the Archaeological Museum (€3) — or just enjoy Adamas harbour for dinner, fresh seafood ~£12.

🚌Athens metro €1.20 + Piraeus-Milos fast ferry £40-55

🛏Adamas guesthouse or hostel (dorm ~£25, private double ~£50)

• →Metro to Piraeus port
• →High-speed ferry Piraeus to Milos
• →Papikinou Beach swim
• →Archaeological Museum (Aphrodite of Milos)

The island's signature day out: a full-day boat cruise along the wild south coast to Kleftiko sea caves, plus Arkoudes and Kalogries beaches. Book independently via GetYourGuide or directly with a local operator (e.g. from Adamas or Pollonia), roughly £50-70 including a buffet lunch — far less than the marked-up optional excursion on the original tour. Bring reef-safe sunscreen and a snorkel. Alternative budget option: take the local bus to Firiplaka and Tsigrado beaches instead (~£2 each way plus free cliff scramble).

🚌Walk / local bus to boat departure port

🛏Adamas guesthouse or hostel (dorm ~£25, private double ~£50)

• →GetYourGuide/local-operator Kleftiko & Arkoudes boat cruise with lunch
• →Swimming and snorkelling in sea caves
• →Optional bus trip to Firiplaka and Tsigrado beaches

Hop the ferry from Milos to Santorini (typically via a connection at Ios or a direct Seajets run; total 2.5-5 hrs, £40-60). Book early — this is a busy route. On arrival at Athinios port, take the public bus up to Fira (€2.50) rather than a taxi, then a local bus to your base. Oia is the classic spot but pricey; Fira, Karterados or Perissa offer better-value hostels. First sunset from Fira's caldera edge is free and almost as good as Oia's.

🚌Ferry £40-60 + local bus €2.50

🛏Fira or Karterados hostel/guesthouse (dorm ~£28, private double ~£60)

• →Ferry Milos to Santorini
• →Public bus Athinios port to Fira
• →Caldera-edge sunset walk in Fira

Book a semi-private or small-group caldera catamaran cruise yourself on GetYourGuide or Klook (~£60-90) covering the Hot Springs, Nea Kameni volcano, Aspronisi, the Ancient Lighthouse, Akrotiri, Indian Rock, Red Beach and White Beach with swimming and snorkelling. Most include a BBQ lunch — Greek salad, shrimp saganaki, grilled skewers, roasted veg, pasta, dolmades — matching the operator's onboard menu. Cheaper alternative: pay the €5 volcano entrance and hike Nea Kameni from Fira port on the local boat (~€20). End the day with the Oia sunset via public bus (€2) — arrive 90 minutes early to claim a spot.

🚌Local buses €2-4

🛏Fira or Karterados hostel/guesthouse (dorm ~£28, private double ~£60)

• →GetYourGuide/Klook caldera catamaran cruise with BBQ lunch
• →Hot Springs swim, Red & White Beach snorkelling
• →Nea Kameni volcano hike (budget alternative)
• →Oia sunset via public bus

Take the morning ferry from Santorini to Koufonisia (often changing at Naxos; 3-6 hrs, £35-50). This tiny island is the tour's quietest stop — expect xe ones, sandy beaches and a laid-back chora. On arrival walk from the port to your rooms (the village is minutes away) and spend the afternoon at Finikas or Pori beach — Pori has the famous natural sea pool. Grab a fresh-fish taverna dinner in the chora, ~£12-15.

🚌Ferry £35-50

🛏Koufonisia guesthouse or studio (dorm ~£22, private double ~£45)

• →Ferry Santorini to Koufonisia
• →Afternoon at Finikas / Pori beach
• →Chora taverna dinner

A full free day on one of the smallest Cyclades. Rent a bike or walk the coastal path between the beaches — Fanos, Platia Pounta (kitesurf spot), Italida and Pori — all reachable without a car. Optional: take the small excursion boat to Kato Koufonisia for a quieter beach and taverna lunch (~£15-20). Because the original tour calls this a car-free idyll, note that the port area does get busy with vehicles and ferry traffic in high season — the car-free feel is on the walking paths, not the harbour.

🚌Bike rental ~£8 / local boat ~£15-20

🛏Koufonisia guesthouse or studio (dorm ~£22, private double ~£45)

• →Coastal walking path between beaches
• →Bike rental
• →Optional boat trip to Kato Koufonisia
• →Snorkelling at Pori

Short morning ferry across to Naxos (roughly 1-2 hrs, £15-25) — the cheapest and easiest hop of the trip. Check in near Naxos Town (Chora), then walk the causeway to the Portara, the giant unfinished Apollo temple gate, for sunset. Wander the old Venetian Castle quarter (Kastro) and the Bourgos alleyways. Dinner of Naxian cheeses, potatoes and grilled fish ~£12.

🚌Ferry £15-25

🛏Naxos Town hostel/guesthouse (dorm ~£22, private double ~£45)

• →Ferry Koufonisia to Naxos
• →Portara (Temple of Apollo) sunset walk
• →Venetian Castle / Kastro quarter stroll

Rent a car or scooter for the day (~£30-40 + fuel) to reach the mountain villages independently, or use the KTEL local bus from Naxos Town (Halki ~€2, Apeiranthos ~€3.50). In Halki, tour the historic Vallindras Kitron distillery with tasting (~£5) and visit a family olive press for an olive-oil production tour and tasting (~£8-12). Continue to Apeiranthos, the marble village, for a self-led walk of its lanes and small museums. Back in Chora, hit the beach at Agios Georgios before dinner.

🚌KTEL bus from €2 each way or rental car ~£30-40 + fuel

🛏Naxos Town hostel/guesthouse (dorm ~£22, private double ~£45)

• →Vallindras Kitron distillery tour & tasting in Halki
• →Family olive press tour and olive oil tasting
• →Apeiranthos village self-guided walk
• →Optional car/scooter rental

A very short crossing from Naxos to Paros (35-50 min, £10-18). Base yourself in Parikia or Naousa — Parikia is cheaper and better connected. Afternoon exploring Parikia's Panagia Ekatontapyliani church (free) and the Kastro and Frankish castle remains. Evening on the waterfront with a loukoumades or ice cream, then watch the ferries come in from the port front.

🚌Ferry £10-18

🛏Parikia hostel/guesthouse (dorm ~£24, private double ~£50)

• →Ferry Naxos to Paros
• →Panagia Ekatontapyliani church visit
• →Parikia Kastro and old town walk

Use the KTEL local bus network (day pass options available) to explore Paros's villages independently: Lefkes (mountain village and Byzantine road start), Piso Livadi and Logaras beaches, and Naousa's pretty fishing harbour. In Lefkes or Marpissa, sit in a traditional kafeneio for Greek coffee and homemade orange pie (~£4) and try your hand at tavli (backgammon) with locals. Visit the Byzantine Agia Triada chapel near Lefkes on foot. If you'd rather have a guide, a GetYourGuide Paros villages day tour runs ~£50-70.

🚌KTEL local buses from €2 per hop

🛏Parikia hostel/guesthouse (dorm ~£24, private double ~£50)

• →Bus-hopping between Lefkes, Piso Livadi, Logaras and Naousa
• →Greek coffee and orange pie in a kafeneio
• →Tavli (backgammon) with locals
• →Byzantine Agia Triada church walk
• →Optional GetYourGuide villages day tour

Morning ferry Paros to Mykonos (40-60 min, £15-25). Drop bags at a Mykonos Town (Chora) hostel or a cheaper base in Platis Gialos/Paradise Beach, then visit a local farm for a wine, olive-oil and food tasting with a vineyard and olive grove walk — independent Mykonos farm tasting experiences book on GetYourGuide/Klook for ~£35-55, and the menu mirrors the operator's (extra virgin olive oil, Kalamon olives, louza, kopanisti, pastries). Evening in Little Venice and the Matogiania lanes, with live Cycladic music in a Chora bar.

🚌Ferry £15-25 + local buses €2

🛏Mykonos Town or Platis Gialos hostel/guesthouse (dorm ~£30, private double ~£70)

• →Ferry Paros to Mykonos
• →GetYourGuide Mykonos farm wine, olive oil & food tasting
• →Vineyard and olive grove walk
• →Little Venice and Matogiania evening stroll
• →Live Cycladic music in Chora

Book a semi-private cruise to Delos and Rhenia directly with a local Mykonos operator or via GetYourGuide (~£55-80) — it covers the Delos archaeological site (UNESCO, extra €12 site entry) and swimming and snorkelling at Rhenia Island with a BBQ lunch on board. Do NOT book optional excursions through the original operator via a marketplace — reviewers on this very trip reported being charged $369 for a boat trip that cost $125 direct. Book direct, or take the public Delos boat from Mykonos Old Port (~€20 return) and add the site ticket yourself for a DIY version. Wind down at a Chora cocktail bar.

🚌Local bus to Old Port + boat (included in cruise or ~€20 DIY)

🛏Mykonos Town or Platis Gialos hostel/guesthouse (dorm ~£30, private double ~£70)

• →Direct-booked Delos & Rhenia semi-private cruise with BBQ lunch
• →Delos archaeological site (UNESCO)
• →Swimming and snorkelling at Rhenia
• →Alternative DIY: public Delos boat + independent site ticket

The long sail back — Mykonos to Piraeus on the conventional ferry takes 5-6 hours (£35-50) and the high-speed about 3.5-4 (£50-65); book early for the best fares. On arrival, metro or bus from Piraeus back to your Athens hostel. Final evening in Athens: rooftop view over the Acropolis from a Monastiraki bar, last souvlaki supper ~£10, and packing.

🚌Ferry £35-65 + metro €1.20

🛏Budget hostel or guesthouse in Plaka/Monastiraki (dorm ~£22, private double ~£45)

• →Ferry Mykonos to Piraeus
• →Metro Piraeus to central Athens
• →Final Monastiraki evening and Acropolis view

Self-transfer to Athens International Airport by metro Line 3 from Syntagma (~€9, 40 min) or the X95 bus from Syntagma (~€5.50). Allow at least 3 hours before an international flight. If your flight is late, squeeze in one last Acropolis-museum-free walk through the National Garden. Trip complete — six islands, one ferry network, and no group markup.

🚌Metro Line 3 ~€9 or X95 bus ~€5.50

🛏N/A — departure day

• →Metro or X95 bus to Athens International Airport
• →Optional final walk in the National Garden