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Home » travel planning » Greece Trips: Island Hopping, Round Trips & Sailing Holidays

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Greece Trips: Island Hopping, Round Trips & Sailing Holidays

Tom & Ella
Last updated: 19. September 2025 12:56
By Tom & Ella
No Comments
11 Min Read

Miracles under the sun! Anyone who has ever been to the blue and white holiday paradise will come back again and again. Whether on an individual or package holiday, on a guided Greece Tour or on a road trip with your own car – the wonderful country in southern Europe wants to be discovered. A trip to Greece is an unforgettable experience!

Griechenland Reisen Inselhuepfen Rundreise Segeln
Welcome to Greece

In this article, we will introduce you to the country in more detail and show you different ways to Touring Greece. Especially newcomers to Hellas are overwhelmed by the abundance of islands and destinations in Greece. But don’t worry, you don’t have to plan everything on your own, Greece experts will take you by the hand.

Table of Contents
  • #1 Greece tours
  • #2 Active and hiking holidays in Greece
  • #3 Island hopping in Greece
  • #4 Sailing holidays and cruises in Greece
  • Things worth knowing about Greece

Griechenland Reise Karte Europa Mittelmeer Urlaubsziele

#1 Greece tours

Greece round trips are becoming more and more popular. In a short time you can see many highlights, whether with a rental car, your own car or a camper. The interesting mix of wild nature, picturesque beaches and historical sights makes a Greece Road Trip Something very special.

Griechenland Roadtrip Mietwagen Kykladen Inseln Rundreise
Greece round trip with your own car

An eventful individual Greece round trip on your own with a rental car or your own vehicle you can experience in these regions of the country:

  • Epirus tours: Arta (road trip around the Ambracian Gulf), Zagori (Road trip through the Zagoria villages), Parga (Road trip along the west coast of Greece)
  • Peloponnese tours: Peloponnese Tour (Road trip from Patras to the Mani to Corinth)
  • Macedonia tours: Western Macedonia (road trip from Prespa to Florina), Halkidiki Peninsula (road trip along the three fingers)
  • Central Greece – Thessaly tours: From Delphi to Meteora to the Mount Olympusand the Pelion

You can find out what you need to consider when renting a car and what traffic regulations you should know here: Car rental in Greece

Guided tours of Greece

Greece is new territory for you and you have never heard of Sirtaki and Bouzouki? Let yourself be at the Travel planning by Greece specialists with decades of experience. Especially for your first visit to Hellas, it is worthwhile to Greece Package Holidays or a guided round trip.

Orakel von Delphi Griechenland Rundreise Highlights
The Oracle of Delphi is considered a round trip highlight

We are advocates of healthy and sustainable tourism, so we do not want to recommend overcrowded bus tours or even all-inclusive holidays. In the meantime, very good German-Greek travel agencies in the field of experience, wine and ecotourism, which introduce Greece to interested holidaymakers off the beaten track.

Greece tours with Dimitrios Zachos

TheTravel Agency Greece Travel* Dimitrios Zachos offers island hopping and sailing tours as well as guided tours in Greece. Since 1988, the colleagues have been putting together round trips in Greece. Their program includes the country’s highlights, from the Meteora monasteries to Delphi and the picturesque Peloponnese.

➯ Here you can choose from suitable round trip combinations and get a discount on the tour price with the code “GM20” (please specify in the comments field): To the round trips of the travel agency

Joysters: Authentic Tours in Northern Greece

Macedonia in northern Greece is considered a real treasure trove. Lush vegetation, deep gorges and rushing waterfalls, as well as an impressive animal world with wolves and wild horses await explorers. The Greek Joysters Travel Agency by Nick and Kostas offers you tailor-made tours from Thessaloniki.

➯ Click here for the Greece Specialists for round trips to Northern Greece: Joysters Travel Agency

#2 Active and hiking holidays in Greece

Among insiders, Hellas has long been known as an outdoor and hiking paradise. Because Greece consists largely of massive mountain ranges and dense forests, even bears still live here. Rafting enthusiasts will get their money’s worth on the wild rivers of the country. The best conditions for an extended Hiking tour through Greece.

rafting griechenland venetikos fluss greek adventures
White water rafting in the Pindos Mountains

But the Greek islands are also hillier than you think. Crete even has the southernmost mountains in Europe (including the White Mountains and Ida Mountains). On islands like Thassos, Karpathos, Kefalonia or Samos you can experience a great hiking holiday. We tell you about our experiences on Samos in this article:Samos Active Holidays

Below is a small selection of attractive regions and places for an outdoor and Hiking holidays in Greece:

  • Prespa Lake National Park
  • Kerkini Lake National Park
  • Tzoumerka mountain massif
  • Pindos Mountains
  • Arcadia (including Lousios Gorge)
  • Island of Crete (e.g. Samaria Gorge)
  • IslandKalymnos (Climbing paradise)

Checklist what to pack for Greece

Mediteron: Hiking, sailing and experiencing in Greece

On a hiking holiday in unknown regions, you should rely on the experience of experts. The Greece specialists of the Travel agency Mediteronby Dimitrios Margonis allow you to enjoy a perfectly organized hiking tour in Greece. Adventure hiking according to the motto: “From the peaks to the sea”.

Griechenland Wanderurlaub Dodekanes Inseln Nisyros
Hiking in Greece: From the peaks to the sea

Combined trips are popular, where you hike one part of your Greece trip and sail the other part. This way you will experience the best of two “travel worlds”. Dimitri and his team will also be happy to put together an individual hiking tour for you. Simply select the region and period and you will receive a tailor-made adventure holiday.

➯ Save 5% on the total travel price with the discount code “greecemoments”. Click here for the Greece Specialists for hiking tours: Mediteron Travel Agency

#3 Island hopping in Greece

There is hardly a better way to Greek Islands than on an island hopping. Hellas has several island groups, including the popular Cyclades (including Mykonos and Santorini), the Dodecanese (including Kos and Rhodes) and the Ionian Islands (including Corfu and Zakynthos).

With a little organizational talent, you can create a Greece Island Hopping plan yourself. You book the flights to Greece as well as the respective hotels and ferry connections.

You can find more information and helpful tips in our separate article: Greece Island Hopping

Santorini Reise Inselhopping Reiseagentur Griechenland Spezialisten
Santorini: Coveted destination for islandhoppers

#4 Sailing holidays and cruises in Greece

Greece offers optimal conditions for sailors from all over the world. The Greek islands make up a whopping 80 percent of all Mediterranean islands, plus almost 14,000 km of coastline. Numerous beautiful sailing areas in Greece invite you to extensive sailing adventures.

Even inexperienced sailors and absolute beginners have fun on a Sailing holidays in Greece. Sailing trips are available either as a private trip or as a group trip with other holidaymakers. The most popular areas are the Ionian Islands, the Cyclades, the Sporades, the Saronic Islands and the Dodecanese.

Greek Islands Sailing Trip

We are happy to recommend the travel agency of sailwithus from Frankfurt. The colleagues offer tailor-made sailing holidays for beginners and advanced sailors in Greece and have received top reviews from holidaymakers so far.

➯ Here you can book your sailing trip in Greece: sailwithus

Segeln in Griechenland Kykladen Segelurlaub
Cyclades: A sailor’s paradise

Things worth knowing about Greece

Greece is located on the Mediterranean Sea in the southeast of Europe on the Balkan Peninsula. The country is about half the size of New Zealand and is home to just under 10 million inhabitants, of whom live in the capital alone Athens almost 5 million people. Except for the north, all other parts of the land are surrounded by the sea.

  • Capital: Athens
  • Second largest city: Thessaloniki
  • Largest island: Crete
  • Area: 132,000 km²
  • Language: Modern Greek
  • Currency: Euro/ € since 2002, before that drachma/ ₯
  • National flag: Blue and white stripes with white cross
  • Religion: Greek Orthodox Christianity
  • Highest mountain: Mount Olympus 2,917 m

Griechenland Karte Flagge Blau Weiss Reisen

You can find out even more helpful travel information and facts about Greece in the Greece Profile

Greece is considered to be 365-day travel destination. The Mediterranean climate ensures hot summers and mild winters. Sun worshippers are drawn to the country from June to September. Hikers and active holidaymakers use spring and autumn for their activities. The ski resorts on the Greek mainland delight winter sports enthusiasts from December to March.

  • Ø Temperature in July: 30.7 degrees
  • Ø Rainy days in July: 1 day
  • warmest place: Lindos on Rhodes
  • coldest place: Florina in Northern Greece

Detailed information about the weather and climate tables can be found in our article: Best time to visit Greece

TOP sights in Greece

Greece offers more than sun and sea. The country looks back on thousands of years of history, which has left its mark everywhere. Nature inspires with mountains and canyons, dense vegetation, waterfalls and even volcanoes. The dream beaches of the islands and coastal regions make everyone go into raptures.

Acropolis of Athens

The Acropolis of Athens is considered a landmark of the city. The castle-like complex is impressively situated above the metropolis. Greece fans would probably attribute the same importance to the ancient site as to Uluru (Ayers Rock) in Australia 😉

Griechenland Rundreise Athen Akropolis Sehenswuerdigkeiten
The Acropolis of Athens

Volcanic landscape of the island of Santorini

Santorini is considered the picture-perfect island of Greece. Some of the whitewashed villages are impressively located on the steep cliffs of a former volcano. The caldera (volcanic cauldron) was flooded by the sea. The unique backdrop makes the Santorini Holidays unforgettable.

💡 Help with the Greece Holiday Planning: You don’t know where to start and how to go about planning your trip to Greece? No problem, benefit from our years of experience with traveling to Greece and let us help you. We advise you on all your questions and concerns, even via video chat. You can book your consultation here: Travel Advice Greece

 

Palace of Knossos in Crete

The Knossos Palace was considered the centre of power of the Minoans (3,000 – 1,400 BC), the first advanced civilization in Europe and is therefore one of the most important archaeological sites in Greece. A visit to the restored site is one of the highlights of the Island of Crete.

Griechenland Sehenswuerdigkeiten Knossos Kreta Minoischer Palast
Impressive restoration: Knossos Palace in Crete

Navagio Bay on Zakynthos

Cliffs up to 200 m high frame a turquoise blue bay, in front of whose gleaming white sandy beach an old ship is stranded. The smuggler’s bay with the Zakynthos Shipwreck is one of the most popular stretches of coastline in all of Europe. A real highlight!

Meteora Monasteries in Thessaly

Built on bizarre rock formations at dizzying heights, the celestial Meteora Monasteries to float! It is not without reason that this spectacular landscape has already served as the backdrop for a James Bond film (“On a Deadly Mission”).

Meteora Klöster Griechenland Highlights
The Meteora monasteries are unique in Greece

Little Venice on Mykonos

In none Mykonos Holidays may a visit to Little Venice lack. The district is considered a typical catalogue picture for the Greek holiday. Directly by the sea lies the picturesque district with its wooden balconies, a romantic backdrop at sunset.

Medieval Old Town of Rhodes

The Old Town of Rhodes is one of the most interesting places in Europe. The crusaders of the Order of St. John shaped the cityscape for centuries. Today, the medieval alleys and former knights’ buildings are rightly part of the UNESCO World Heritage Site.

Rhodos Altstadt Mittelalter Gassen Unesco Reise
In the alleys of Rhodes Old Town

Ancient Sites of the Peloponnese Peninsula

Olympia, Epidaurus and Mycenae – hardly any other Greek region offers such a high density of ancient sites. The Peloponnese, which is only connected to the mainland at a narrow point (Corinth Canal), is ideal for a road trip.

Oracle of Delphi

The Oracle of Delphi, the former “navel of the world”, remains legendary and mysterious. The place of worship nestled in a sea of olive trees is hidden below the Parnassus Mountains. Not only history fans are attracted to Delphi. Delphi is very suitable as a detour on a round trip along the Gulf of Corinth.

Sarakiniko Beach in Milos

One of the most beautiful stretches of coastline in the country is located on the Cycladic island of Milos. The rock formations at Sarakiniko resemble a lunar landscape, the sea shimmers in the most beautiful shades of blue. This is exactly why Milos the epithet Island of Colors.

Milos Sarakiniko Tipps Urlaub
Moon landscape of Milos

You can find out what other highlights there are to marvel at on a trip to Greece here: Things to do in Greece

The most popular islands in Greece

One Journey to the Greek islands can quickly overwhelm, there are just too many islands. Of the thousand Greek islands, however, only a little more than a hundred are inhabited. Most holidaymakers steer one of the most important destinations for their trip to Greece most popular Greek islandsat. These destinations offer everything a holidaymaker’s heart desires.

  1. Crete ⭔ Crete Island ⤷ Our travel tips: Crete Highlights
  2. Rhodes ⭔ Dodecanese ⤷ Our travel tips: Rhodes Highlights
  3. Santorini ⭔ Cyclades ⤷ Our travel tips: Santorini Highlights
  4. Corfu⭔ Ionian Islands ⤷ Our travel tips: Corfu Highlights
  5. Zakynthos ⭔ Ionian Islands ⤷ Our travel tips: Zakynthos Highlights
  6. Kos ⭔ Dodecanese ⤷ Our travel tips: Kos Highlights
  7. Mykonos ⭔ Cyclades ⤷ Our travel tips: Mykonos Highlights
  8. Cephalonia ⭔ Ionian Islands ⤷ Our travel tips: Kefalonia Highlights
  9. Naxos ⭔ Cyclades ⤷ Our travel tips: Naxos Highlights
  10. Skiathos⭔ Sporades ⤷ Our travel tips: Skiathos Highlights

If you’re looking for an island for a special occasion (honeymoon, surfing, climbing), here’s some inspiration: Which Greek island is right for me?

Important entry information for your Greece round trip

Since Greece belongs to the EU, you don’t have to pay too much attention to during your trip to Greece. The country also has the common currency, the euro, so there is no need to exchange money on holiday. Important: Greece is in a different time zone (EET – Eastern European Time) and thus one hour before CET.

Documents for entry into Greece

To enter Greece by air, an identity card is sufficient. A passport is not mandatory, unless you are planning a trip to neighboring non-EU countries (e.g. Turkey). Children under 12 years of age require a children’s passport.

For those arriving by car, there is detailed information here: Getting to Greece

Segeln in Griechenland Reisen Segeltrip Kykladen
See you soon in Greece

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In this post, you will find affiliate links marked with an asterisk (*). If you book or buy something through one of these links, we receive a small commission. For you, the price remains the same. In this way, you help us continue to provide high-quality content for free. Did you like this post and you would like to say thank you? Then just buy us the next Greek coffee ☕️ To the coffee checkout


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Gia sou, it's great to have you here! We're Tom and Ella, the folks behind Greece Moments. We're travel journalists, parents, avid globetrotters, and we love a good Freddo Espresso. We've been running our Greece blog since 2019 and have personally visited more than 50 Greek islands during that time. Here at Greece Moments, we're passionate about sharing our love for this stunning country with you and providing you with the best travel tips for exploring Hellas on your own. Kalo Taxidi!
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We are Tom & Ella, and we have been in love with this blue and white paradise since 2009. On our Greece travel blog, we provide helpful travel tips and useful information for your vacation in Greece. Let yourself be enchanted by beautiful Hellas!

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