Self-Launched Cyclades Island Hopping: Santorini, Ios, Small Cyclades, Naxos, Mykonos, Syros & Paros
10 days · Cyclades, Greece
G Adventures charges £2,000
No-markup version: ~£508 per person
Estimate only, not a guaranteed price. Always verify costs independently before booking.
A solo-friendly, self-launched version of G Adventures' 10-day Santorini-to-Santorini sailing trip — swapping a skippered 57ft yacht for Greece's excellent inter-island ferry network. You'll still hit the same Cycladic highlights (Santorini's caldera, the Small Cyclades, party island Ios, Venetian Naxos, Mykonos' windmills, Syros' neoclassical capital and Paros' whitewashed villages), but you'll stay in hostels and family guesthouses, book your own snorkelling/hiking/sailing day trips via GetYourGuide or directly with local operators, and travel on Blue Star Ferries and SeaJets fast catamarans for a fraction of the group-tour price. Pace is flexible and weather-led, just like the original — but you keep the savings, the freedom and the choice. Costs are approximate backpacker/budget estimates in GBP and exclude international flights.
Day-by-day
Arrive Santorini — Fira & caldera sunset
Santorini (Fira)
Fly or ferry into Santorini (JTR airport bus to Fira is about €2; ferries dock at Athinios and connect by KTEL bus for €2-3). Check into a Fira or Karterados hostel. Spend the afternoon walking the caldera rim path from Fira to Oia (about 3 hours, free, bring water) and catch sunset from a viewpoint rather than paying for a caldera cruise. Book your onward ferry to Ios tonight for tomorrow.
🚌Airport bus or KTEL bus from Athinios port (~£2-3)
🛏Hostel in Fira/Karterados, dorm bed (~£22)
- →Caldera rim hike Fira to Oia (free)
- →Fira old town and Museum of Prehistoric Thera (€6)
- →Sunset at Oia or Imerovigli Skaros Rock
Ferry to Ios — Chora & Mylopotas Beach
Ios
Take the morning fast ferry or conventional ferry Santorini to Ios (about 1 hour, £12-20 depending on vessel). Ios is the party island of the Cyclades but has a lovely whitewashed Chora and a huge sandy beach at Mylopotas. Walk up to Panagia Gremiotissa church and the windmills above Chora for the sunset, then eat at a taverna in the lanes off the main square rather than on the front. Hostels here are plentiful and cheap.
🚌Fast ferry Santorini–Ios (~£12-20); local bus to Mylopotas (~£2)
🛏Ios hostel or guesthouse, dorm/private (~£20)
- →Ferry Santorini–Ios
- →Chora old town and Panagia Gremiotissa
- →Mylopotas Beach swim
- →Sunset at Chora windmills
Ios — Homer's Tomb hike & beach day
Ios
Hike the marked trail from Chora up to Homer's Tomb (claimed burial site of the poet) on the northern tip — roughly 2 hours each way through scrub and wildflowers, free and a proper leg-stretch. Afternoon at Psathi or Manganari beach by local bus or shared water taxi. Evening is when Ios comes alive: bar-hop Chora's lanes, but eat first — gyros and souvlaki are £3-5.
🚌Local buses (~£2-4)
🛏Ios hostel or guesthouse (~£20)
- →Hike to Homer's Tomb (free)
- →Psathi or Manganari beach
- →Chora nightlife
Ios to the Small Cyclades — Koufonisia
Koufonisia (Small Cyclades)
Take a ferry from Ios toward the Small Cyclades (there are direct services to Koufonisia in high season; otherwise connect via Naxos). Ano Koufonisia is tiny, car-free-feeling and ringed with turquoise coves you can walk between: Pori, Finikas and Fanos beaches are all within 30-40 minutes on foot from the port. Stay in a small family guesthouse and eat at one of the handful of tavernas on the harbour.
🚌Ferry Ios–Koufonisia (~£10-18)
🛏Koufonisia family guesthouse/studio (~£28)
- →Ferry Ios–Koufonisia (via Naxos if needed)
- →Coastal walk to Pori and Finikas beaches
- →Harbour taverna dinner
Koufonisia — boat trip to Kato Koufonisi
Koufonisia
Book a small local boat excursion to Kato Koufonisi (the uninhabited twin island opposite) — these run from the main harbour in summer and cost around £20-25 for a half-day with swimming stops; a good self-bookable stand-in for the yacht's snorkelling and swim stops. Bring your own mask (or hire on the island) and a picnic. The original tour includes a Naxos wildlife/conservation awareness session — you can replicate the spirit of it on Naxos tomorrow by joining a local nature walk.
🚌On foot; boat excursion
🛏Koufonisia family guesthouse/studio (~£28)
- →Local boat trip to Kato Koufonisi with swim stops (~£22)
- →Snorkelling from the boat
- →Sunset on the harbour
Ferry to Naxos — Chora, Portara & Venetian town
Naxos
Ferry to Naxos (about 1-1.5 hours). Naxos is green, mountainous and the least over-touristed of the big Cyclades. Walk up to the Portara, the giant marble gate of the unfinished Temple of Apollo, for sunset over the water. The old town is a Venetian-Genoese maze of alleys below the Castro — wander it freely. For the conservation angle the original tour includes, ask at the port tourist office about local walks and wildlife; Naxos has excellent marked trails and the Aria Spring walk.
🚌Ferry to Naxos (~£8-15); local bus (~£2)
🛏Naxos town hostel or guesthouse (~£24)
- →Ferry Koufonisia–Naxos
- →Portara and Temple of Apollo (free)
- →Old town and Castro
- →Book a GetYourGuide Naxos food or hiking tour (~£30-45, optional)
Naxos — Mount Zas hike or inland villages
Naxos
Hike Mount Zas (1,004m, the highest point in the Cyclades) from Filoti village — a proper 3-4 hour round trip with a cave shrine of Zeus near the top, free and spectacular. Alternatively hire a car or scooter for the day (from about £30) to explore Apiranthos, Halki and the Tragea olive groves. Buses from Naxos town to Filoti are cheap and frequent.
🚌Local bus to Filoti (~£3) or car hire (~£30)
🛏Naxos town hostel or guesthouse (~£24)
- →Mount Zas hike from Filoti (free)
- →Cave of Zeus
- →Inland villages: Apiranthos and Halki
- →Local kitron liqueur tasting
Ferry to Mykonos — windmills & Little Venice
Mykonos
Morning ferry Naxos to Mykonos (1-2 hours). Mykonos is expensive to sleep in, so book a hostel in the backstreets of Chora or Mykonos Town early. Do the free highlights: the Kato Mili windmills, Little Venice's balconies over the water and the pelican mascots. Sunset cocktails on a Little Venice veranda are pricey (£12-18 a drink) but you can buy a beer from a mini-market and sit on the rocks west of the windmills for free.
🚌Ferry Naxos–Mykonos (~£15-25)
🛏Mykonos Town hostel, dorm (~£35)
- →Ferry Naxos–Mykonos
- →Kato Mili windmills (free)
- →Little Venice
- →Paraportiani church
Mykonos to Syros — Ermoupoli
Syros (Ermoupoli)
Ferry to Syros (about 45 minutes to 1 hour). Ermoupoli is the Cyclades' capital and looks nothing like the rest — grand neoclassical squares, a marble-paved main square and a working shipyard. Climb the 400-odd steps to Ano Syros, the old Catholic hilltop town, for the best view in the islands. Syros is cheaper than Mykonos and the food is excellent — try local loukoumi sweets and a fish dinner at the harbour.
🚌Ferry Mykonos–Syros (~£10-18)
🛏Syros guesthouse or hostel (~£26)
- →Ferry Mykonos–Syros
- →Ermoupoli Miaouli Square
- →Climb to Ano Syros (free)
- →Vaporia quarter and harbour tavernas
Paros or Athens departure — the choice is yours
Paros or Athens
Two good endings. Option A: catch the morning ferry to Paros (about 45 min-1 hr), walk Parikia's whitewashed lanes and the Panagia Ekatontapyliani church, hike or bus to Lefkes and Naoussa, and fly or ferry out from Paros (PAS) — good if you want to keep going. Option B: take the ferry or fast catamaran straight back to Santorini (about 2-3 hours) or to Athens/Piraeus (about 4-5 hours) for your flight home. Build in a buffer day if you're flying out — Greek ferry schedules and meltemi winds can shuffle plans.
🚌Ferry Syros–Paros (~£10-15) or Syros–Santorini/Athens (~£25-45)
🛏None (onward travel) — add a hostel night if needed (~£25)
- →Optional ferry to Paros and Parikia old town
- →Panagia Ekatontapyliani (free)
- →Ferry onward to Santorini or Athens
Self-launched vs. G Adventures
| This itinerary (self-launched) | G Adventures | |
|---|---|---|
| Price per person | ~£508 | £2,000 |
| Duration | 10 days | 10 days |
| Who books it | You and your group, direct | Tour operator, guided group |
| Savings | £1,492 per person (75%) | |
Estimate only, not a guaranteed price. Always verify costs independently before booking.
Want to see more G Adventures-style trips? Check them out here.~£508
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: Santorini, Ios, Small Cyclades, Naxos, Mykonos, Syros & Paros cost?+
Doing it yourself with this self-launched itinerary costs an estimated £508 per person for 10 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 G Adventures?+
Yes — G Adventures charges around £2,000 per person for a similar tour. Doing the same route independently, using the same standard of accommodation and activities, costs an estimated £508 — a saving of roughly £1,492 (75%) per person.
How long is the Cyclades, Greece trip?+
This itinerary runs 10 days, covering 10 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 beaches, adventure, backpacker 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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