Self-Launched Cyclades Island Hopping: Athens, Kythnos, Serifos, Kimolos, Milos, Sifnos
8 days · Cyclades, Greece
Trails Beyond charges £2,090
No-markup version: ~£573 per person
Estimate only, not a guaranteed price. Always verify costs independently before booking.
A self-launched version of Trails Beyond's 8-day catamaran sailing tour, rebuilt as an independent ferry-hopping loop through the Western Cyclades. You'll cover the same islands — Kythnos, Serifos, Kimolos, Milos and Sifnos — plus the Temple of Poseidon at Cape Sounio, using Greek island ferries instead of a chartered catamaran. Expect long ferry decks, swim stops at Kolona and Sarakiniko, cliff-top Choras, Kleftiko's sea caves (by day boat trip from Milos) and plenty of taverna dinners. This trades the crewed yacht's comfort for genuine budget travel: shared rooms in family-run guesthouses, self-booked day trips and supermarket breakfasts. Costs are rough estimates based on 2025/26 shoulder-season backpacker rates and exclude flights to Athens.
Day-by-day
Arrive Athens & Cape Sounio sunset
Athens / Alimos
Land in Athens and take Metro Line 3 plus a local bus or the X96 airport express to the coast around Alimos/Glyfada (about £4-5). Check into a budget guesthouse or hostel near Alimos Marina — the same departure point as the original sailing tour. In the afternoon take local bus 122 or the KTEL coastal bus down to Cape Sounio to see the Temple of Poseidon at golden hour (site entry around £8, free on some national holidays). Swim at a nearby cove if the weather's kind, then eat grilled fish at a Glyfada taverna. Buy ferry tickets online tonight for tomorrow's crossing.
🚌Airport express bus or Metro + local bus, ~£5
🛏Family-run guesthouse or hostel dorm near Alimos Marina/Glyfada, £22-30
- →Temple of Poseidon at Cape Sounio
- →Sunset coastal walk
- →Glyfada seaside dinner
Ferry to Kythnos & Loutra hot springs
Kythnos
Catch a morning ferry from Piraeus or Lavrio to Kythnos (Merichas port) — roughly 1.5-2 hours, £10-15. Kythnos has no airport and is only reachable by sea, exactly as on the sailing route. Drop bags at a guesthouse in Merichas or Loutra, then take the local bus to Loutra for the natural hot springs (free, open-air) and a swim. In the evening explore Chora's whitewashed lanes and eat at a family taverna in Dryopida. Book your onward Serifos ticket at the port agent or online the same day.
🚌Ferry Piraeus/Lavrio to Kythnos, £10-15; local bus £2-3
🛏Guesthouse in Merichas or Loutra, £25-30
- →Loutra hot springs
- →Chora and Dryopida village walk
- →Kolona viewpoint
Kythnos to Serifos: Chora & Venetian fortress
Serifos
Morning ferry to Serifos (about 45-60 minutes, £7-10). Serifos' Chora is one of the Cyclades' most photogenic hill towns — hike or take the local bus up from Livadi port, then walk the stepped path to the Venetian fortress viewpoint above the town. Afternoon swim at Livadakia or Psili Ammos beach (bus or a 20-minute walk). Dinner of local cheeses, revithada and fresh fish in Chora. Lodgings are mostly small studios and rooms above tavernas.
🚌Ferry £7-10; local bus £2
🛏Studio or rooms in Livadi or Chora, £28-35
- →Chora hill town walk
- →Venetian fortress viewpoint
- →Livadakia beach swim
Serifos to Kimolos & Prasa beach
Kimolos
Ferry Serifos to Kimolos via Milos (roughly 1.5-2 hours, £10-14; some crossings land at Milos where you switch to the short Kimolos link). Kimolos is tiny and quiet — check into rooms in Horio or Psathi port. Walk to Chora (Horio), a maze of white alleys and the castle quarter, then bus or walk to Prasa, a green-sand beach with a beach bar. Sunset from the old windmills. Supermarket picnic dinner keeps costs low, or a simple taverna at Psathi.
🚌Ferry £10-14; local bus £2
🛏Guesthouse/rooms in Horio or Psathi, £25-32
- →Horio village and castle walk
- →Prasa beach
- →Sunset at the windmills
Kimolos to Milos: Sarakiniko & Klima
Milos
Short ferry hop to Milos (15-30 minutes, £5-8) — the island the original tour anchors at for cave swimming. Base yourself in Adamas or Pollonia. Take the local bus to Sarakiniko's moonscape white rock formations, then continue to the ancient theatre, the catacombs and Klima's syrmata boat-house village. Rent a scooter or small car for a day (scooter £20-25, car from £35-45 plus fuel) if you want to reach Plaka and Firopotamos too. Ferry companies run seasonal boats out to Kleftiko — book a half-day Kleftiko and sea-cave trip from Adamas for tomorrow (about £35-45).
🚌Ferry £5-8; local bus £2; optional scooter/car hire £20-45
🛏Guesthouse or budget hotel in Adamas, £30-38
- →Sarakiniko beach
- →Catacombs and ancient theatre
- →Klima fishing village
- →Plaka village
Kleftiko & Polyegos boat trip
Milos
Half-day boat trip from Adamas to Kleftiko's sea caves and Polyegos island for swimming, snorkelling and cliff scenery (around £35-45 including a basic lunch or bring your own). These are the same anchorages the catamaran uses, just on a shared tourist boat — book direct with a local operator or via GetYourGuide a day or two ahead. Back in Milos by mid-afternoon: shower, then take the evening ferry to Sifnos (about 1-1.5 hours, £10-14) or stay one more night if the schedule is awkward.
🚌Boat trip £35-45; ferry Milos-Sifnos £10-14
🛏Guesthouse in Kamares or Apollonia, Sifnos, £28-35
- →Kleftiko sea caves
- →Polyegos swim and snorkel stop
- →Kamares beach
Sifnos: Kastro, Apollonia & Kolona-style beaches
Sifnos
Sifnos is the food island of the Cyclades — revithada, mastelo and honey. Walk or bus from Kamares to Apollonia and on to Kastro, a clifftop medieval village with a tiny archaeological museum. Afternoon at Platis Gialos or Vathi beach (bus £2-3), or a marked hiking trail between villages if you want the steps in. Evening in Apollonia's lanes with a long taverna dinner. Note: the original route finishes back at Kythnos and Athens — if you're on a tight schedule you can ferry Sifnos back to Athens via Milos instead (check schedules).
🚌Local buses £3-5
🛏Guesthouse in Kamares or Apollonia, £28-35
- →Kastro village and fortress
- →Apollonia lanes
- →Platis Gialos or Vathi beach
- →Village hiking trail
Sifnos to Piraeus / Athens departure
Athens
High-speed or conventional ferry from Kamares back to Piraeus (about 2.5-4 hours, £15-25). From Piraeus take Metro Line 1 or the airport express bus to the airport. If you have time, squeeze in an hour at the Acropolis Museum or Plaka. Buses and metro are cheap (£1.20-2 per ride) but leave a healthy buffer — Cyclades ferries do cancel or delay in strong winds, so don't book a tight same-day flight home.
🚌Ferry Sifnos-Piraeus £15-25; metro to airport £2 or express bus £5
🛏None (departure day) or one night near Piraeus, £25-35
- →Piraeus waterfront
- →Optional Acropolis Museum or Plaka stroll
Self-launched vs. Trails Beyond
| This itinerary (self-launched) | Trails Beyond | |
|---|---|---|
| Price per person | ~£573 | £2,090 |
| Duration | 8 days | 8 days |
| Who books it | You and your group, direct | Tour operator, guided group |
| Savings | £1,517 per person (73%) | |
Estimate only, not a guaranteed price. Always verify costs independently before booking.
Want to see more Trails Beyond-style trips? Check them out here.~£573
estimated per person
You never pay Travel Crew for this — you pay hostels, transport, and activity providers directly, the same as if you'd booked it all yourself.
This publishes your dates so other travellers can find and join you — no tour operator needed.
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Frequently asked questions
How much does Self-Launched Cyclades Island Hopping: Athens, Kythnos, Serifos, Kimolos, Milos, Sifnos cost?+
Doing it yourself with this self-launched itinerary costs an estimated £573 per person for 8 days in Cyclades, Greece. This is an AI-generated estimate based on typical budget-traveller prices — actual costs will vary by season and how you book.
Is this cheaper than booking with Trails Beyond?+
Yes — Trails Beyond charges around £2,090 per person for a similar tour. Doing the same route independently, using the same standard of accommodation and activities, costs an estimated £573 — a saving of roughly £1,517 (73%) per person.
How long is the Cyclades, Greece trip?+
This itinerary runs 8 days, covering 8 day-by-day stops through Cyclades, Greece.
How do I join this trip?+
You can join an existing open departure using this itinerary if one is scheduled, or launch your own departure with your own dates and invite other travellers to join you — no tour operator required.
Isn't it easier to just use a tour operator?+
Well, yes, a tour operator will book all the individual parts of your travel for you and provide a guide. That's obvious, but doing this has the potential to save the group thousands, which can in turn improve your itinerary substantially or save you huge amounts of money. Also, when you launch a departure, Travel Crew has tools in place to help you book the individual sections of the trip or make it easier for you to do this as a group. Really, you do not need a middle man. If you are more comfortable paying more and using a middle man, then you should certainly do this.
Is it safer to book through a tour operator?+
Arguably, there isn't much difference. A self-launched trip runs on the same principle as a group travel crew: collective responsibility, everyone looking out for each other, the same way it would if a group of friends organised the trip themselves — because that's exactly what's happening. You should always take out travel insurance before you go, self-launched or not; that doesn't change either way. Every open departure is published publicly with real dates and a real trip organiser, so it's never an anonymous arrangement, and our support team is reachable any time you need help, including in an emergency while you're away. Longer-term, we're building direct relationships with ground DMCs in popular destinations, offered as an optional paid add-on for extra on-the-ground support. Ultimately, though, the group is responsible for its own conduct and safety on a self-launched trip, same as on any trip you plan yourself.
What kind of trip is this?+
This is a adventure, beaches, culture trip through Cyclades, Greece, self-launched rather than run by a tour operator — you organise it with a group you find or bring yourself.
Would you like to name the operator, name the trip, or have any suggestions about how to improve this itinerary?
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