Bestseller

Cyclades island hopping: Paros, Naxos and Santorini

Eight days from island to island: fishing harbours, wine and a sunset at Oia

5.0(1) Code ITH-GR-02

  • Duration8 days · 7 nights
  • DestinationsGreece
  • Group with a Greek-speaking tour leader10–20 people
  • LevelEasy
  • Tour leaderGreek · English
  • FlightsNot included
  • Minimum ageFrom age 6

Overview

Three islands, three different faces of the Cyclades: Paros with its fishing villages and marble-paved lanes, Naxos with its old town, olive groves and long sandy beaches, and Santorini with its caldera. Ferry tickets are included and your Greek coordinator is beside you at every boarding.

The days have a holiday rhythm: morning walks, a swim in the sea, free time for coffee and wandering the lanes. You dine on grilled fish by the water on Naxos, taste Assyrtiko at a Santorini winery and watch the sun sink behind Oia.

Highlights

  • Ferries between Paros, Naxos and Santorini, tickets included
  • Lefkes and Naoussa: marble-paved lanes and a fishing harbour on Paros
  • Naxos town and the Portara gate at sunset
  • The Tragea valley and the marble village of Apeiranthos
  • A dinner of grilled fish by the sea on Naxos
  • The Santorini caldera: Fira and the villages above the volcano
  • Assyrtiko wine tasting at a winery on volcanic soil
  • Sunset at Oia

Accommodation

7 nights in 4★ hotels: 2 on Paros, 2 on Naxos, 3 on Santorini

  • Paros: 4★ hotel in Parikia (2 nights)
  • Naxos: 4★ hotel in Naxos town (2 nights)
  • Santorini: 4★ hotel in Fira or in a village on the caldera (3 nights)

Meals

7 breakfasts and 3 dinners; lunches are free

Transport

Scheduled ferries and local minibus transfers

Itinerary

8 days, stop by stop. Open a day to see what is planned: the map shows where you will be.

  1. Day1 From Piraeus to ParosPiraeus – Paros (Parikia)

    Meet your coordinator at the port of Piraeus and board the ferry to Paros. On deck the air smells of salt and the islands appear one by one on the horizon. On arrival in Parikia you transfer to the hotel, stroll through the white lanes past the Church of a Hundred Doors (Ekatontapyliani) and sit down to a welcome dinner.

    • Ferry
    • Dinner
  2. Day2 Lefkes, Naoussa and the seaParos: Lefkes – Naoussa

    A minibus takes you up to Lefkes, a mountain village of marble-paved lanes and white houses. Then comes Naoussa, with wooden fishing boats moored in the little harbour beneath the Venetian fortress, and a coffee by the water. The afternoon is free for a swim from a sandy beach.

    • Coach
    • Breakfast
  3. Day3 To Naxos: the town and the PortaraParos – Naxos (Naxos town)

    Ferry to Naxos, a short crossing over the Aegean. In Naxos town you wander cobbled lanes from the Bourgos quarter up to the Kastro, among bougainvillea and bright blue doors. In the late afternoon you walk along the causeway to the Portara, the marble gateway of an unfinished temple of Apollo, as the sun goes down.

    • Ferry
    • Breakfast
  4. Day4 Tragea, Apeiranthos and a dinner by the seaNaxos: Tragea – Apeiranthos

    By minibus you cross the Tragea valley, with its olive groves and small Byzantine churches, and stop at Halki, where you can try kitron, the local citron liqueur. At Apeiranthos you walk its marble lanes. The afternoon brings a free swim from a sandy beach, then a dinner of grilled fish beside the sea.

    • Coach
    • Breakfast · Dinner
  5. Day5 To Santorini: the calderaNaxos – Santorini (Fira)

    The ferry sails into the Santorini caldera, with white villages along the top of cliffs of red and black lava. You transfer to the hotel and spend the late afternoon in Fira: lanes with blue domes, cafés with a view and the sun sinking over the volcano.

    • Ferry
    • Breakfast
  6. Day6 Volcanic wines and sunset at OiaSantorini: winery – Oia

    In the morning you visit a winery among vines trained into low baskets on volcanic soil and taste Assyrtiko and other local varieties with small bites. The afternoon belongs to Oia: white houses, blue domes and a sunset over the caldera that draws the whole village out to watch it.

    • Coach
    • Breakfast
  7. Day7 A free day on SantoriniSantorini (Fira – Imerovigli)

    A free day: swim from black volcanic sand beaches such as Perissa or Kamari, or walk part of the caldera path between Fira and Imerovigli. You can book an optional boat trip to the volcano. In the evening, a farewell dinner with a view over the caldera.

    • Breakfast · Dinner
  8. Day8 Return to PiraeusSantorini – Piraeus

    A last breakfast on Santorini and a transfer to the port. The ferry leaves the caldera behind and crosses the Aegean to Piraeus, where you arrive in the afternoon or evening depending on the sailing. Our services end there.

    • Ferry
    • Breakfast

Dates and prices

Prices are per person in a double room. Choose your departure and book online in just a few minutes.

9May2027

9 – 16 May 2027

  • 8 days
  • Tour leader: Alexandros Theodorou
from€1,230
20 seats available
Book
23May2027

23 – 30 May 2027

  • 8 days
  • Tour leader: Alexandros Theodorou
from€1,290
18 seats available
Book
6Jun2027

6 – 13 Jun 2027

  • 8 days
  • Tour leader: Panos Rafailidis

−12% off

€1,620€1,420
20 seats available
Book
20Jun2027

20 – 27 Jun 2027

  • 8 days
  • Tour leader: Stelios Papageorgiou

−13% off

€1,710€1,480
20 seats available
Book
4Jul2027

4 – 11 Jul 2027

  • 8 days
  • Tour leader: Ioanna Dimitriou

−12% off

€1,770€1,550
20 seats available
Book
18Jul2027

18 – 25 Jul 2027

  • 8 days
  • Tour leader: Thanos Konstantinou
from€1,610
20 seats available
Book
1Aug2027

1 – 8 Aug 2027

  • 8 days
  • Tour leader: Ioanna Dimitriou

−11% off

€1,810€1,610
20 seats available
Book
22Aug2027

22 – 29 Aug 2027

  • 8 days
  • Tour leader: Dimitris Karagiannis
from€1,550
17 seats available
Book
5Sept2027

5 – 12 Sept 2027

  • 8 days
  • Tour leader: Giorgos Stavropoulos
from€1,420
20 seats available
Book
19Sept2027

19 – 26 Sept 2027

  • 8 days
  • Tour leader: Ioanna Dimitriou
from€1,350
20 seats available
Book
3Oct2027

3 – 10 Oct 2027

  • 8 days
  • Tour leader: Alexandros Theodorou
from€1,230
20 seats available
Book

  • Single room: supplement of €290
  • Children aged 2 to 11: 85% of the adult price
  • Infants under 2: €150

What is included

Included in the price

  • Scheduled ferries in economy class: Piraeus–Paros, Paros–Naxos, Naxos–Santorini, Santorini–Piraeus
  • 7 nights in 4★ hotels, twin rooms with private bathroom: 2 on Paros, 2 on Naxos, 3 on Santorini
  • 7 breakfasts and 3 dinners (welcome on Paros, fish on Naxos, farewell on Santorini)
  • Transfers between ports and hotels, and island excursions by minibus
  • Greek coordinator throughout, from Piraeus to Piraeus
  • Guided visits: Lefkes, Naoussa, Naxos town, Apeiranthos, Fira and Oia
  • Wine tasting at a Santorini winery
  • Support from the agency before and during the trip
  • Protection against organiser insolvency under EU Directive 2015/2302

Not included

  • Flights or other tickets to Athens, and transfers to and from Piraeus
  • Lunches, dinners not listed and drinks
  • Entrance fees to sites and museums, where charged
  • Optional excursions, such as the boat trip to the volcano
  • Tips, personal expenses and local accommodation taxes, if applicable
  • Travel insurance (optional, but recommended)

Optional extras

  • Basic travel insuranceCover for medical expenses, assistance and baggage during the trip, calculated as a percentage of the total…
  • Travel insurance with cancellation coverIncludes the basic cover plus a refund of cancellation costs, with broader cancellation reasons, within the…
  • Private transfer to and from Athens airportA private car with driver from your address in Athens to the airport and back, so that your trip starts and…
  • Extra night before or after the tripOne or more nights in a 4★ hotel with breakfast, in Athens before departure or at the last destination after…
  • Departure from ThessalonikiFor travellers in northern Greece: a connecting flight from and to Thessaloniki, so you can join the group…
  • Optional excursions packageAn amount per person for the optional excursions your coordinator suggests during the trip, such as a scenic…
  • Extra checked bagOne additional suitcase in the hold, up to the weight the airline allows (usually 20–23 kg), outward and…
  • Farewell gala dinnerA multi-course dinner with local wines and a toast, in a special venue in the final city chosen by your…

Useful information

Documents and visas

EU and Schengen citizens need only a valid identity card or passport; keep it with you, as it may be asked for on the ferries. For everyone else, entry requirements depend on nationality and may change. We will send you up-to-date guidance after booking.

Best time to go

Departures run from May to October. In May and June the sea is still cool and the days gentle; July and August bring heat, crowds and often the meltemi wind; September has the warmest sea and October offers quiet and cooler evenings.

Physical fitness

Easy level, but with a fair amount of walking on paved lanes and steps, especially on Santorini. Because you change island three times and some hotels are reached by steps, travel with light luggage. The ferry crossings last from about an hour to several hours.

What to pack

Swimwear, a towel, sandals and grippy shoes for polished marble, a hat, sunglasses and sun cream. A light jacket for the deck and cooler evenings. If you are prone to seasickness, ask your doctor or pharmacist for advice before travelling.

Traveller reviews

5.0/ 5

1 review

  • 51
  • 40
  • 30
  • 20
  • 10

Santorini, Naxos, Paros: the islands seen with new eyes

I am from Athens and thought I knew the Cyclades. And yet the sunset over the Santorini caldera, the lanes of Naxos with their bougainvillea and the fishing boats in the little harbour of Naoussa on Paros made me see them differently. I did not have to think about luggage or ferry timetables. The fish dinner by the sea on Naxos was one of the loveliest meals of the summer.
Katerina M.Greece · June 2026

All traveller reviews

FAQ

What happens if ferries are cancelled because of the meltemi wind?

In summer, especially in July and August, the meltemi can delay or cancel sailings. Your coordinator then arranges alternatives from the ferries available and keeps you informed throughout; for safety, the order or timing of transfers may change. Please do not book a flight home on the same day the tour ends.

What luggage should I bring, with so many steps and three islands?

Choose a soft bag or a small trolley case plus a daypack. You change island three times and in some villages the hotel is reached by steps and narrow lanes. Your coordinator will help with boardings and transfers, but luggage remains your own responsibility.

Where do we meet, and how do I get to Piraeus?

We meet at the port of Piraeus on the morning of the first day; you will receive the exact time and spot after booking. Flights to Athens are not included. Because the return ferry arrives in the afternoon or evening, we advise booking your flight home for the following day.

Is the tour suitable if I get seasick?

The ferry crossings last from about an hour to several hours, and with the meltemi the sea can be rough. If you are prone to seasickness, ask your doctor or pharmacist for advice before travelling and choose a seat towards the middle of the ship, low down.

All frequently asked questions

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