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Greek Island Hopping Holiday: Santorini, Paros, Naxos & Mykonos

Sample Itinerary | Places to Visit | Hotels to Stay | Dates

Greek Island Hopping Holiday: Discover the Best of the Cyclades - Tailor-Made Itinerary Including Santorini, Paros, Naxos & Mykonos

from £2,298 per person

Sample Itinerary Hotels to Stay Places to Visit Optional Extras

Greek Islands Hopping Itinerary: Santorini, Paros, Naxos & Mykonos

Experience the beauty of the Cyclades Greek Islands with our flexible, tailor-made island hopping holidays. This 12-night itinerary is a sample only – you can choose to stay longer or shorter on any island, or even select different islands altogether, as long as convenient ferry connections are available.

Enjoy one of the best selections of 4* to 5* boutique hotels in Greek islands, either in the heart of charming island towns or directly on the beach – the choice is yours. Whether you're seeking romance, local culture, golden beaches, or breathtaking scenery, we’ll create a personalised itinerary just for you.

Day 1: Santorini Arrival

Fly directly to Santorini from your regional airport any day of the week (subject to flight availability). Our representative will greet you at the airport and provide a private transfer to your hotel. Enjoy your first evening soaking in the views of the Aegean Sea and the famous caldera.

Day 2–3: Explore and Relax in Santorini

Santorini, the most iconic of the Greek Islands, offers dramatic volcanic cliffs, whitewashed villages like Fira and Oia, and incredible sunset views. Wander the cobbled streets, visit the black sand beaches, or simply relax at your luxury hotel. After three nights, we’ll arrange a private transfer to the ferry port for your journey to Paros.

Day 4–6: At Leisure in Paros

With its rolling hills and traditional Cycladic architecture, Paros is a hidden gem in the Aegean. Explore Parikia, visit the stylish fishing village of Naoussa, or unwind on golden beaches with crystal-clear waters. After three nights in Paros, you'll continue your journey to the nearby island of Naxos.

Day 7–9: Discover and Enjoy Naxos

Naxos is the largest and most fertile island in the Cyclades, offering lush landscapes, ancient ruins, and long sandy beaches. Explore Venetian castles, charming villages, and sample delicious local produce. After three nights of authentic island life, we’ll transfer you to the ferry bound for Mykonos.

Day 10–12: Glamour and Tradition in Mykonos

Famous for its cosmopolitan lifestyle, Mykonos blends glamour with traditional charm. Stroll through the whitewashed alleys of Mykonos Town, relax on beautiful beaches like Ornos and Psarou, or enjoy fine dining and boutique shopping. After your three-night stay, your journey comes to a close.

Day 13: Return Flight from Mykonos

We’ll collect you from your hotel and provide a private transfer to Mykonos Airport for your return flight home.

The above itinerary can also be reversed, depending on flight availability from your preferred airport. This Greek Island Hopping itinerary is just a starting point. Whether you’re looking for a longer escape, a shorter getaway, or want to explore different island combinations, we’ll tailor every detail to match your travel style. From flexible durations to handpicked boutique hotels and seamless transfers, your ideal Greek island holiday is completely customisable.

Your reversed itinerary will be as follows:

Day 1: Mykonos Arrival

Fly directly to Mykonos from your regional airport any day of the week (subject to flight availability). Our driver/representative will greet you at the airport and provide a private transfer to your Mykonos hotel. Enjoy an overnight stay in Mykonos.

Day 2-3: Explore and Relax in Mykonos

Take time to explore one of Greece's most famous islands. Mykonos, known for its charming white-washed architecture and vibrant atmosphere, offers a blend of glamour and tradition. From its picturesque beaches to the lively streets, there's something for everyone to enjoy. After three memorable nights, we'll transfer you to the ferry port for your journey to Paros.

Day 4-6: At Leisure in Paros

Paros boasts unparalleled natural beauty, with rolling hills and crystal-clear beaches. The capital, Parikia, is a stunning Cycladic village with whitewashed houses and a Venetian castle overlooking it. Spend three nights relaxing and exploring this captivating island before heading to Naxos.

Day 7-9: Explore and Relax in Naxos

Naxos, the largest and greenest of the Cyclades islands, awaits you with its golden beaches and stunning landscapes. Enjoy leisurely days by the clear waters, surrounded by lush greenery and historical treasures like Venetian castles and monasteries. After three unforgettable nights, embark on a ferry to Santorini.

Day 10-12: Explore and Relax in Santorini

Santorini, the most photographed Greek island, offers breathtaking views of the Aegean Sea. Its unique volcanic landscape and picturesque towns, such as Fira, make it a must-visit destination. Climb the iconic steps to Fira and soak in the beauty of this remarkable place. After exploring Santorini, you can either return home or extend your stay in other charming islands.

Day 13: Return Flight

As your journey comes to an end, we'll pick you up from your Santorini hotel and provide a private transfer to Santorini airport for your return journey.

Experience the magic of the Cyclades Greek Islands with our carefully curated itinerary. Immerse yourself in the beauty, culture, and history of Mykonos, Paros, Naxos, and Santorini.

Santorini Palace 4* BB - Santorini

The Santorini Palace, with its beautiful Cycladic architecture, offers breath-taking views of the volcano. It is in the ideal location to benefit from the many attractions of Fira,

Harmony Boutique Hotel 4* BB - Mykonos

This charming hotel is ideal for those who want to soak up the atmosphere of the old town and port of Mykonos. The Harmony Boutique Hotel lives up to its name by succeeding in combining the simplicity of the local architecture of whitewashed cube-like houses, with effortless style and comfort.

Iria Beach Art Hotel 4* BB - Naxos

A beach-front setting ensures that this recently renovated hotels is extremely popular with Naxos holidaymakers. The Iria Beach Art Hotel is built in the traditional Cycladic architectural style and is set right next to Agia Anna Beach, one of the most beautiful beaches in Naxos, with its golden sand and clear waters.

Paros Agnanti Hotel 5 BB - Paros*

AAn incomparable location at the entrance of the gulf of Parikia, offers its guests panoramic views of the sea and of the picturesque island town.

The hotel consists of four cubic buildings built in the Cycladic architectural style, with arches, whitewashed walls, blue paintwork, and bare stone. Each is built on a hill providing an unobstructed view out to the sea and overlooking Parikia.

Cyclades Greek Islands

Greece has over 6000 islands and islets dotted throughout the Aegean and Ionian seas, of which only 227 are inhabited.

They offer adverse landscape of beaches, bays, coves and coastal caves, which combined with their laid-back ambience and temperate climate make them popular summer holiday destinations.

Greek Islands private tours

Private Half Day Tour by catamaran 15:30 - after sunset

Sail on a catamaran in Caldera to celebrate the famous Santorini sunset. Cruise the waters between Caldera and the small volcanic island, Thirasia, to the Red and White beaches, the hot springs, past the volcano and, finally, enjoy the sunset from the boat as your BBQ lunch or dinner is freshly prepared.

Foody Walking Tour - Mykonos

Private Half Day Tour (4h)

In about 3 hours not only you will be shown the famous monuments but also you will be given the opportunity to discover some of the “hidden gems” of the Chora of Mykonos.

Santorini & Paros & Naxos & Mykonos : 12 nights - prices from	Apr, May, Oct	Jun, Sep	Jul, Aug
Santorini 3 nights 4* BB, Paros 3 nights 4BB, Naxos 3 nights 4 BB, Mykonos 3 nights 4* BB	£2,298	£2,500	£2,750

Price Includes

Flights to Santorini and return from Mykonos – or vice versa, depending on your preferred route and flight availability
Private transfers on all islands – from airports or ferry ports to hotels and return
Accommodation in carefully selected 4*and 5* boutique hotels, based on bed & breakfast (BB)
Ferry tickets between the islands, arranged to suit your travel schedule

Flight Information

Flights are included in the package price, but the final cost may vary depending on your departure airport and flight times. We can book flights from any UK airport upon request. Once your flights are confirmed, we will issue your ATOL certificate, ensuring your package is financially protected in case of any airline failure.

Early booking discounts & loyalty discounts

Call 0330 390 0999 Request Quotation

General Travel Information Booking Conditions COVID-19 Information

Speak to a Specialist

Akin has been to all these places and experienced all these holidays.

Give him a ring to discuss your holiday in detail on 0330 390 0999 or send an email.

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"We just returned from a week in Cappadocia Turkey. Diamond star Experience were really helpful and friendly throughout our experience with all aspects of the holiday. Our flight was delayed and I received contact from Oguzhan and Rica telling me that they had arrange later pick up from the airport when arriving in Turkey. Mustafa our driver was warm and friendly throughout our stay .The transfer and 3 day tours were fantastic , Our guide was really knowledgeable and looked after us while we toured this remarkable place The highlight was the Balloon ride in the morning a truly magical experience . I can not fault any part of the holiday and the service of Diamond Travel Experience . Easy to contact through what’s app anytime which was a great touch . I would strongly recommend Diamond star Experience for booking a holiday , We will def book again with them when returning to Turkey. Thanks and well done ! A truly wonderful Break" Mrs Wilson - 21 Aug 2025

"A week's trip on Perla del Mar captained by Mustafa, with chef Dohan, and crew Cem, Emre and Meric turned out to be the best family holiday we had ever booked. Akin's recommendation of the boat was spot on. Dohan's menu and cooking was absolutely excellent. The crew went out of their way to assist us at every opportunity and their care and attention to the children on the trip was exemplary. There wasn't a single fault that on the whole trip, the transfers worked perfectly, the crew were there to greet us at Marmaris and led us through the alleys to the waterside where the amazing boat in front of us was to be ours for a week. We were all taken aback and realised that Mum's mad dream was coming to fruition. A holiday found by google, sold to us by Akin who took the trouble to explain everything turned out to be beyond the dreams of all of us. Canoeing in quiet coves, swimming and snorkelling to our hearts content then served with drinks and snacks before amazing meals and enjoying the trips between coves became the order of each day. I can firmly recommend this holiday to anyone. It was simply amazing." Christine - 25 May 2025

" We went to Diamond Star experience because they offer multi-centre holidays and had good ratings. We were in no way disappointed with what was organised. We said that we wanted a few days in Athens and then a week on a relatively quiet island. Akin made a proposal (Athens then Naxos) and then, when we agreed, organised everything. The Athens hotel was central and accessible to the main sites and to restaurants, and was of very good quality. The choice of Naxos for the island was equally good and we stayed in an excellent three star hotel on the edge of the town within easy reach of the beach and restaurants. All transfers were efficiently organised and even when there was a transport hiccup (our fault!) there was a phone call from the Athens back-up team within the hour to find out what had happened.
Thank you very much, Akin and staff, for a really enjoyable holiday and for service which can be easily be recommended. " Mr Alan Fraser - 19 May 2025