Greece: Walking the Greek Islands — Self-Launched

Start at Piraeus port (Metro Line 3 to Piraeus, then a 10-minute walk or €2 local bus to the ferry gates). Book a Blue Star Ferries or SeaJets ticket in advance online for the ~3.5–4.5 hour crossing to Tinos (fast ferry ~2h15). Arrive into Tinos Town (Chora), check into a family-run guesthouse near the port, and spend the afternoon wandering the marble-paved alleys, the Church of the Annunciation (Panagia Evangelistria) and the waterfront. Pick up a free walking map from the tourist office and get an early night before the hike.

🚌Athens Airport → Piraeus: Metro Line 3 ~€9 (or €1.20 suburban rail + metro). Piraeus → Tinos ferry: €25–40 one way depending on fast/conventional.

🛏Family-run guesthouse or budget hotel in Tinos Town (double/twin ~£45–60/night; dorm beds ~£20)

• →Piraeus–Tinos ferry crossing
• →Church of the Annunciation (Panagia Evangelistria)
• →Tinos Town old quarter walk

Follow the marked footpaths south from Chora around the rocky outcrop of Exomvourgo (the Venetian 'castle') — a scenic half-day walk of roughly 10–12 km linking hill villages such as Xinara, Loutra and Kardiani. Trails are waymarked but rocky; bring water, sun protection and grippy shoes. In the afternoon or early evening, join a small-group Tinos food walk through the old town — book direct with a local operator or via GetYourGuide (roughly £40–55), tasting local cheeses, cured meats, raki and honey. Alternatively, DIY a tasting circuit of the loukoumades and artisan bakeries around the market street for £10–15.

🚌Walking; optional local bus back from Kardiani/Pyrgos to Chora ~€2–3.

🛏Family-run guesthouse in Tinos Town

• →Exomvourgo castle loop hike (~10–12 km)
• →Tinos Old Town small-group food tour

Catch a morning ferry from Tinos to Naxos (~45 min–1h15; €15–25). Check in, then head inland: bus from Naxos Town to Halki (Chalki) in the Tragea valley (~30 min, €2–3), the island's old capital with its neoclassical houses and kitron liqueur distilleries. Visit a small family cheese-maker to see Arseniko being made and a vineyard for a wine tasting — these can be booked as a half-day small-group 'Naxos cheese and wine trail' tour via GetYourGuide or direct with local producers (around £45–65), or arranged independently at the Vallindras kitron distillery and village tavernas. Evening back in Naxos Town by the port.

🚌Tinos → Naxos ferry €15–25. Local KTEL bus Naxos Town–Halki €2–3 each way.

🛏Budget hotel or guesthouse in Naxos Town (Chora) ~£40–55/night

• →Tragea valley and Halki village
• →Arseniko cheese-making visit and tasting
• →Local vineyard wine tasting
• →Vallindras kitron distillery

A full day on foot through the Tragea valley and surrounding villages — the landscape that made Naxos wealthy in the Venetian and Byzantine eras through olive oil, wine and marble. A self-guided route of roughly 12–14 km links Halki, Moni, Panagia Drosiani (one of Greece's oldest Byzantine churches, 6th–7th century), and Apiranthos or Filoti, with taverna stops. If you'd like the historical context, a licensed local guide can be hired for a half-day (~£70–90 for the group, shared via a GetYourGuide small-group hike at ~£35–45 per person). End with an evening meal in Naxos Town.

🚌Local bus to Halki/Filoti €2–3; bus back from Apiranthos or Filoti €3.

🛏Budget hotel or guesthouse in Naxos Town

• →Tragea valley village-to-village hike
• →Panagia Drosiani Byzantine church
• →Apiranthos marble village

Join a shared day sail or catamaran cruise from Naxos Town — most operators run 6–7 hour trips down the west coast to Agios Prokopios, the islets of Paros or Koufonisia, with swim and snorkel stops, lunch and drinks included. Book via GetYourGuide, Klook, or directly with local operators at Naxos Marina the day before (shared trips typically £65–90 per person; private charters are far more). Bring reef-safe sunscreen and a rash vest; sea conditions can change quickly, so check the forecast and go with a licensed operator.

🚌Walk to Naxos Marina; most operators include hotel pickup or a short walk from town.

🛏Budget hotel or guesthouse in Naxos Town

• →Full-day shared catamaran/ sailing trip
• →Swimming and snorkelling stops
• →Lunch on board

Morning ferry Naxos → Santorini (Thira) (~1h15–2h; €25–40). Drop bags at your guesthouse in Fira, then walk the famous caldera rim path to Oia — roughly 10 km, 3–4 hours, with the best views in the Cyclades over the volcanic crater. It's exposed and hot in the middle of the day, so start early afternoon with plenty of water and proper shoes. Buses from Oia back to Fira run until late (€2). If you'd rather take it easy, swap the hike for a local bus to Oia and a wander, or a half-day island road tour (~£35–45).

🚌Naxos → Santorini ferry €25–40. Fira–Oia local bus €2.

🛏Guesthouse or budget hotel in Fira (book well ahead — ~£60–90/night shoulder season; dorms ~£25–35)

• →Fira–Oia caldera rim hike (~10 km)
• →Oia sunset viewpoints

Spend the morning exploring Fira on foot — the Archaeological Museum, the Catholic and Orthodox quarters, the cable car down to the old port (€6) or the 588 steps. In the late afternoon join a shared catamaran sunset cruise into the caldera, with a swim at the hot springs and dinner on board — book via GetYourGuide/Klook or direct in Fira the day before (~£80–110 for a shared semi-private trip with meal; basic group boats from ~£50). Most cruises finish around 20:30–21:00, with transfers back to Fira included.

🚌Walking in Fira; cable car €6 one way; cruise transfer included.

🛏Guesthouse or budget hotel in Fira

• →Fira old town orientation walk
• →Santorini cable car / old port steps
• →Shared caldera sunset cruise with dinner

Final morning for a swim at Kamari or Perissa black-sand beach (local bus €2.50 each way) or a slow breakfast with a caldera view. Santorini (JTR) airport is 15–20 minutes from Fira by local bus (€1.80–2.50) or taxi (€25–35 fixed-ish fare); if you're ferrying onward to Athens or another island, book the high-speed SeaJets or Blue Star crossing in advance. Depart at your leisure — no group transfer needed.

🚌Local bus Fira → Santorini Airport €2; taxi €25–35. Ferries onward from Athinios port (bus from Fira €2.50).

• →Free morning at a black-sand beach
• →Optional caldera-view breakfast