Island-Hopping the Cyclades: Athens to Santorini (Self-Launched)
15 days · Greek Islands (Cyclades)
G Adventures charges £1,900
No-markup version: ~£1,290 per person
Estimate only, not a guaranteed price. Always verify costs independently before booking.
A self-launched take on G Adventures' 15-day sailing trip from Athens to Santorini. Instead of a 57ft yacht with a skipper, you'll use Greece's excellent ferry network (Blue Star Ferries, SeaJets, Golden Star) to hop the same Cycladic islands — Athens/Piraeus, Kea or Kythnos, Syros, Mykonos, Naxos, Paros/Antiparos, Ios and finally Santorini — staying in hostels and family guesthouses and booking day sails, snorkelling and wine tastings yourself. You get the same whitewashed villages, turquoise swimming coves, tavernas, windmills and viewpoints, plus a bit of actual sailing on a day trip, for a fraction of the group-tour price. Costs are rough budget-traveller estimates in GBP and exclude international flights.
Day-by-day
Arrive Athens — Piraeus and the Acropolis at golden hour
Athens / Piraeus
Fly into Athens and take bus X96 from the airport straight to Piraeus (~£4.70, 60-75 mins) — the same route the tour group uses to reach Zea Marina. Check into a hostel in Piraeus or Monastiraki, then head up to the Acropolis area in the late afternoon (Filopappou Hill is free and gives you the postcard view) and eat at a taverna in Psyrri. Pick up your first ferry tickets for tomorrow and buy a Greek SIM/eSIM if you need one.
🚌Airport bus X96 to Piraeus (£4.70); metro/walk around town (~£1.20)
🛏Hostel dorm in Piraeus or Monastiraki (~£22)
- →Filopappou Hill sunset viewpoint (free)
- →Psyrri taverna dinner wander
- →Buy ferry tickets at Piraeus port agencies
Ferry to Kea (Tzia) — the quiet Cycladic gateway
Kea
Take the morning ferry from Lavrio (bus from Athens, ~£4) or a fast boat from Piraeus to Kea — about 1 hour, ~£12-16. Kea is where Athenian weekenders go: no mass tourism, good hiking trails, and the lovely hill town of Ioulida. Walk the ancient kart track path to Karthea or just swim at Koundouros. Guesthouse night in Ioulida or Korissia.
🚌Bus Athens-Lavrio (~£4) + ferry to Kea (~£14)
🛏Family guesthouse in Korissia or Ioulida (~£30)
- →Hike the Ioulida-Karthea ancient path
- →Swim at Koundouros or Otzias beach
Kea to Syros — the Cyclades' capital
Syros (Ermoupoli)
Morning ferry back toward the main Cycladic line and on to Syros (~£12-18, 1.5-3 hrs depending on route). Ermoupoli is the elegant, almost Italianate capital of the Cyclades — marble squares, an opera house, and Ano Syros stacked up the hill. Climb to Ano Syros for sunset, then eat at a seafood taverna on the waterfront.
🚌Ferry Kea-Syros (~£15)
🛏Guesthouse or hostel in Ermoupoli (~£32)
- →Ano Syros hilltown walk and sunset
- →Ermoupoli waterfront tavernas
Syros beaches and shipbuilding heritage
Syros
Spend the day on Syros's underrated beaches — Galissas, Kini and Delfini are all reachable by local bus (~£3). Kini has a fishing-village feel and a good sunset. In the afternoon visit the Neorion shipyards area and the industrial heritage of Hermoupolis. Book your onward ferry to Mykonos tonight.
🚌Local buses to Galissas/Kini (~£3)
🛏Guesthouse in Ermoupoli (~£32)
- →Kini and Galissas beach day
- →Hermoupolis old town heritage walk (free)
Syros to Mykonos — windmills and Little Venice
Mykonos
Short fast ferry to Mykonos (~£15-22, 40 mins-1 hr). Check into a hostel (Mykonos is pricey — book early, and consider staying in Mykonos Town's edge or Paraga). Do the classic loop: the five Kato Myloi windmills, Little Venice at sunset, and a cocktail on a veranda over the water — exactly what the tour group does on arrival day.
🚌Ferry Syros-Mykonos (£18)
🛏Hostel dorm near Mykonos Town or Paraga (~£38)
- →Kato Myloi windmills (free)
- →Little Venice sunset
- →Mykonos Town backstreets walk
Mykonos free day — beach hopping and Delos option
Mykonos
Choose your own Mykonos day. Option A: catamaran or small-boat day sail with snorkelling and lunch out of Ornos/Agios Ioannis (~£75-95, bookable on GetYourGuide) — the closest thing to the tour's yacht day. Option B: take the 30-min ferry to Delos archaeological site (~£20 return plus £10 entry) and combine with a swim at Paraga or Elia beach on return. Book the ferry to Naxos for tomorrow.
🚌Local buses to beaches (~£2); or Delos ferry (~£20)
🛏Hostel dorm near Mykonos Town (~£38)
- →Catamaran day sail with snorkelling (~£85)
- →Delos ruins visit (~£30 incl. tickets)
Mykonos to Naxos — the greenest Cycladic island
Naxos
Fast ferry to Naxos (~£18-25, 40-50 mins). Naxos is far more affordable than Mykonos and has the best mix of mountains, beaches and history. Afternoon: visit the Portara gate at sunset, the castle quarter and the old market lanes. This mirrors the tour's G for Good wildlife/conservation stop on Naxos — you can visit the Naxos wildlife awareness centre or the Axiothea cultural venues yourself.
🚌Ferry Mykonos-Naxos (£20); bus to town (~£2)
🛏Guesthouse in Naxos Town or Agios Georgios (~£30)
- →Portara at sunset (free)
- →Naxos castle quarter and old market walk
Naxos — Mount Zeus hike or Plaka beach
Naxos
Two great options: hike Mount Zas (Zeus), the Cyclades' highest peak at 1,004m — 3-4 hours return with huge views, reachable via bus to Filoti (~£3). Or take the bus to Plaka and Mikri Vigla for a long sandy beach day with a lagoon swim. Evening in Naxos Town with local kitron liqueur.
🚌Local buses (~£5)
🛏Guesthouse in Naxos Town (~£30)
- →Mount Zas hike (free, self-guided)
- →Plaka beach day
Naxos to Paros — Antiparos and the Cycladic countryside
Paros
Short ferry to Paros (~£10-15, 30-45 mins). Base in Parikia or Naoussa. Afternoon: take the little ferry to Antiparos (~£3) and explore the cave and quiet beaches, or cycle the Paros coastal lanes. Catch sunset at Naoussa's Venetian harbour fortress.
🚌Ferry Naxos-Paros (£12); Antiparos shuttle boat (£3)
🛏Guesthouse in Parikia or Naoussa (~£32)
- →Antiparos cave and beach (~£8)
- →Naoussa harbour sunset (free)
Paros — windsurfing, kite or Lefkes village
Paros
Paros is a wind and water sport hub: try a 2-hour beginner windsurf or kite lesson at Pounda or Golden Beach (~£45-60). Alternatively visit the inland village of Lefkes, hike part of the Byzantine road toward Prodromos, and taste local cheeses and wine at a family producer. Book Ios ferry for tomorrow.
🚌Local buses (~£4)
🛏Guesthouse in Parikia or Naoussa (~£32)
- →Windsurfing lesson (~£50)
- →Lefkes and Byzantine road walk (free)
Paros to Ios — chora lanes and Mylopotas
Ios
Ferry to Ios (~£15-20, 1-1.5 hrs). Ios is the younger, cheaper, livelier island — whitewashed Chora up the hill with a maze of lanes and bars, and Mylopotas beach with a long sand crescent. Afternoon swim and sunset at the Panagia Gremiotissa church viewpoint, then dinner in Chora.
🚌Ferry Paros-Ios (£18); port-to-Chora bus (~£2)
🛏Hostel dorm in Chora or Mylopotas (~£24)
- →Chora lanes and Gremiotissa sunset (free)
- →Mylopotas beach swim
Ios — boat trip to secluded coves
Ios
Join a small-group boat trip around Ios's south coast — Manganari, Tripiti and the quieter coves with swimming and snorkel stops (~£35-50, book locally at the port or via GetYourGuide). Back in the evening, eat grilled octopus by the harbour at Ormos.
🚌Local buses (~£3)
🛏Hostel dorm in Chora or Mylopotas (~£24)
- →Ios coastal boat trip with snorkelling (~£45)
Ios to Santorini — caldera walk at sunset
Santorini (Fira)
Morning ferry to Santorini (~£20-30, 1 hr). Santorini is expensive — stay in Karterados or Fira's outskirts in a guesthouse rather than an Oia caldera cave. Afternoon: walk the Fira-to-Oia caldera rim path (3-4 hours if you do the lot, or the Fira-to-Firostefani section for a taster). Sunset in Oia is busy — the quieter Imerovigli or Skaros Rock viewpoint is a better bet.
🚌Ferry Ios-Santorini (£25); local bus to Oia (~£2)
🛏Guesthouse in Karterados or Fira outskirts (~£40)
- →Fira-Oia caldera rim walk (free)
- →Imerovigli and Skaros Rock sunset (free)
Santorini — volcano sail, wine and black beaches
Santorini
Book a half-day catamaran or sailing trip around the caldera with hot springs swim and a stop at the volcano (~£80-110 for a shared trip, including lunch and wine — a great last-day taste of sailing). Alternatively, spend the day on the black sand at Perissa or Kamari and do a sunset wine tasting at Santo Wines or Venetsanos (~£25). Book your onward transport for tomorrow morning.
🚌Local buses (~£4)
🛏Guesthouse in Karterados or Fira (~£40)
- →Caldera catamaran trip (~£90)
- →Santo Wines sunset tasting (~£25)
Depart Santorini
Santorini
Take the local bus from Fira to Santorini Airport (~£2, 20 mins) or to Athinios port if continuing by ferry. If you're flying out, aim for a mid-afternoon flight to allow for ferry or bus delays. Alternatively, extend with a fast ferry to Crete or a slower route back via Naxos and Athens.
🚌Local bus to airport (~£2)
🛏—
- →Transfer to airport or port
Self-launched vs. G Adventures
| This itinerary (self-launched) | G Adventures | |
|---|---|---|
| Price per person | ~£1,290 | £1,900 |
| Duration | 15 days | 15 days |
| Who books it | You and your group, direct | Tour operator, guided group |
| Savings | £610 per person (32%) | |
Estimate only, not a guaranteed price. Always verify costs independently before booking.
Want to see more G Adventures-style trips? Check them out here.~£1,290
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 Island-Hopping the Cyclades: Athens to Santorini (Self-Launched) cost?+
Doing it yourself with this self-launched itinerary costs an estimated £1,290 per person for 15 days in Greek Islands (Cyclades). 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 £1,900 per person for a similar tour. Doing the same route independently, using the same standard of accommodation and activities, costs an estimated £1,290 — a saving of roughly £610 (32%) per person.
How long is the Greek Islands (Cyclades) trip?+
This itinerary runs 15 days, covering 15 day-by-day stops through Greek Islands (Cyclades).
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, slow-travel trip through Greek Islands (Cyclades), 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?
Drop your comment below — if you've done a similar route, tell us what worked, what you'd add, or what you'd skip.
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