Skip to content
IslandHopper Escapes
Cycladic village and deep blue Aegean water in the Greek islands

14-day route · Greek Islands

14-Day Greek Island Explorer

Five islands in two weeks, ordered so no ferry leg wastes a day. Milos for coastline, Santorini for the caldera, Naxos for mountains, Paros for harbours and Mykonos to finish.

Route overview

  1. Athens
  2. Milos
  3. Santorini
  4. Naxos
  5. Paros
  6. Mykonos
  7. Athens
  • Kleftiko by rented boat on Milos
  • Sarakiniko's white rock at first light
  • Mount Zas hike on Naxos
  • Antiparos day trip from Paros
  • Delos ruins from Mykonos
CouplesBeachSailingCultureFoodBalanced pace

Day by day

The full 14-day schedule

Daily budgets are per person, cover accommodation share, food, activities and local transport, and are estimates only.

Day 1

Milos

FerryEst. €180 pp

Morning

Fly into Athens, transfer to Piraeus port.

Afternoon

High-speed ferry to Milos, check in at Adamas.

Evening

Waterfront dinner at Klima's fishermen's houses.

Activities

Food

Accommodation area

Adamas — central for ferries and car hire

Transportation

Piraeus → Milos, 3h high-speed, ~€70

Day 2

Milos

CarEst. €150 pp

Morning

Sarakiniko white rock formations at sunrise.

Afternoon

Papafragas and Firopotamos swims.

Evening

Plaka village sunset from the castle.

Activities

BeachHikingCulture

Accommodation area

Adamas

Transportation

Rental car, approx €45

Day 3

Milos

BoatEst. €215 pp

Morning

Full-day boat circuit to Kleftiko sea caves.

Afternoon

Snorkelling stops and lunch aboard.

Evening

Quiet dinner in Pollonia.

Activities

SailingSnorkellingIsland Tours

Accommodation area

Adamas

Transportation

Full-day catamaran, ~€110

Day 4

Santorini

FerryEst. €200 pp

Morning

Ferry Milos → Santorini.

Afternoon

Settle in Firostefani, caldera walk.

Evening

Sunset dinner on the rim.

Activities

CultureFood

Accommodation area

Firostefani

Transportation

Milos → Santorini, 2h, ~€65 (check limited sailings)

Day 5

Santorini

CarEst. €180 pp

Morning

Akrotiri excavation early.

Afternoon

Wine route inland, three estates.

Evening

Dinner in Megalochori.

Activities

CultureFood

Accommodation area

Firostefani

Transportation

Day rental, approx €45

Day 6

Santorini

TaxiEst. €160 pp

Morning

Fira to Oia caldera hike, 3h, start at 7am.

Afternoon

Ammoudi Bay swim and lunch.

Evening

Bus back; low-key evening in Fira.

Activities

HikingBeach

Accommodation area

Firostefani

Transportation

Bus/taxi back from Oia, ~€25

Day 7

Naxos

FerryEst. €160 pp

Morning

Morning ferry Santorini → Naxos.

Afternoon

Agios Prokopios beach afternoon.

Evening

Portara sunset and dinner in Chora.

Activities

BeachCulture

Accommodation area

Agios Prokopios

Transportation

Santorini → Naxos, 2h, ~€60

Day 8

Naxos

CarEst. €145 pp

Morning

Mount Zas hike from Filoti, 3h round trip.

Afternoon

Apiranthos village and late lunch.

Evening

Kitron tasting in Halki.

Activities

HikingCultureFood

Accommodation area

Agios Prokopios

Transportation

Rental car, approx €40

Day 9

Naxos

On footEst. €150 pp

Morning

Plaka Beach morning.

Afternoon

Kitesurf lesson at Mikri Vigla.

Evening

Seafood at Alyko.

Activities

BeachAdventure

Accommodation area

Agios Prokopios

Transportation

Beach day, no transfer

Day 10

Paros

FerryEst. €165 pp

Morning

Short ferry Naxos → Paros.

Afternoon

Naoussa check-in and Kolymbithres swim.

Evening

Harbour dinner.

Activities

BeachFood

Accommodation area

Naoussa

Transportation

Naxos → Paros, 35 min, ~€20

Day 11

Paros

BoatEst. €165 pp

Morning

Boat to Antiparos and the Blue Lagoon.

Afternoon

Antiparos cave and village lunch.

Evening

Sunset drinks in Parikia.

Activities

Island ToursSnorkelling

Accommodation area

Naoussa

Transportation

Day boat, 10–40 min crossings

Day 12

Mykonos

FerryEst. €255 pp

Morning

Ferry Paros → Mykonos.

Afternoon

Psarou or Agios Sostis beach.

Evening

Little Venice sunset and Chora dinner.

Activities

BeachNightlife

Accommodation area

Ornos or Chora

Transportation

Paros → Mykonos, 45 min, ~€45

Day 13

Mykonos

BoatEst. €240 pp

Morning

Delos by morning boat.

Afternoon

Fokos beach on the north coast.

Evening

Farewell dinner in Chora.

Activities

CultureBeachFood

Accommodation area

Ornos or Chora

Transportation

Delos boat, 30 min each way

Day 14

Athens

FlightEst. €150 pp

Morning

Last swim and breakfast.

Afternoon

Flight to Athens.

Evening

International connection home.

Activities

Food

Accommodation area

Athens airport hotel if needed

Transportation

Mykonos → Athens, 40 min

Budget

What this trip costs

All figures are estimates in the currency shown, based on shoulder-to-high season research. Verify prices at the time of booking.

Estimated budget breakdown for 14-Day Greek Island Explorer
CategoryEstimate (EUR (€))
Flights€260 international + €90 Mykonos–Athens
Accommodation€2,300 (13 nights, mid-range double, per couple)
Ferries & boats€290 per person
Food€720 per person
Activities€560 per person
Local transport€300 per person
Estimated total≈ €3,270 per person

Estimates only, per person sharing a double, shoulder-season rates. Currency EUR.

14-Day Greek Island Explorer: FAQs

Is five Greek islands in 14 days too many?
It is the sensible maximum. Each island gets two to three nights and every hop is under three hours, but you will spend five half-days in ports.
Why start with Milos?
Milos has fewer sailings than the rest of the Cyclades, so it is safest at the start when your schedule still has slack. It also connects directly to Athens.
Do I need to book ferries in advance?
In July and August, yes — four to six weeks ahead for named seats. In May, June, September and October a few days is usually enough.