5-Day Custom Greece Trips

plan and book your tailor-made trip with a local travel specialist

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Experience Greece's highlights and hidden gems! Our local travel specialists will help you put together an amazing custom trip that will show you an authentic slice of Greece's scenic beauty, culture, and history.

Want to explore the best that Greece has to offer? Get started by describing your ideal trip, and we'll connect you with a local specialist to plan out the details.

Greece Travel Insights

Colorful Greek home
Map of Athens and Nafplio - 5 Days
Athens and Nafplio - 5 Days

Live like a local in Greece's idyllic Argolic Gulf with this 5-day itinerary. You'll explore Athens for a few days, including a unique guided tour of some of the city's most important ancient sites before you head to seaside Nafplio, home to winding streets and a historic water fortress. Explore this beautiful area of mainland Greece, then get hands-on in an olive grove before you head home.

Walk any number of streets for a view of the Acropolis
Map of Best of Athens & Ancient Greece - 5 Days
Best of Athens & Ancient Greece - 5 Days

Long dominated by the omnipresent Parthenon, Athens mingles its classical past with a budding art scene and bustling markets. You'll spend five days exploring this city's many cultural treasures and cool neighborhoods—along with day trips to archaeological sites in nearby Mycenae. See why the epicenter of antiquity and philosophy is well worth a trip today.

The old port of Chania, built by Venetians in the 14th century
Map of Local Life on Crete - 5 Days
Local Life on Crete - 5 Days

The 5-day version of this compact itinerary focuses on the far west region of Chania. Arrive in Crete, the largest of the Greek isles, before heading to the traditional village of Vamos for a cooking class and two nights in a charming guesthouse. Take a guided village-to-village trek, visit the ancient Minoan palace of Knossos on a day trip, and stroll the waterfront in the city of Chania without feeling rushed.

Sunrise over the Parthenon
Map of Highlights of Athens - 5 Days
Highlights of Athens - 5 Days

A perfect fit for first-time visitors, this five-day city tour highlights both Athens' ancient history and modern culture. Visit the sleek Acropolis Museum, tour Athens' tasty food markets, and bask in the Riviera sun at the Temple of Poseidon.

The amphitheater at the Acropolis, Athens
Explore Mythical Athens - 5 Days

Ancient cultures and modern day life meet on this five-day exploration of Greece's capital city. Immerse yourself in the history of the Golden Age with a visit to the Acropolis and the Parthenon. Stroll the historic cobblestone streets of Athens' many neighborhoods, learn about the ancient rites of the Eleusinian Mysteries, and relax by the sea on the Athens Riviera.

Samaria Gorge pathway in Crete
Map of Athens and Crete Family Adventure - 5 Days
Athens and Crete Family Adventure - 5 Days

Visit Athens and Chania on this five-day itinerary that brings the whole family into the experience. After a mythology tour of the Acropolis and accompanying tour of some of the highlights of Athens, you'll head to the former Venetian port city of Chania to explore some of the nature and history of Crete.

Streets of the Naxos Kastro district
Map of Family Adventures in Athens and the Cyclades - 5 Days
Family Adventures in Athens and the Cyclades - 5 Days

See Athens and the Cycladic island of Naxos with this five-day itinerary. Start by taking your whole family up to the Acropolis to experience the myths of Classical Greece up close, then head down to the island of Naxos to explore its former Venetian castle district and lounge on the many beaches.

Paleokastritsa Bay on Corfu
Map of Enchanting Northern Greece & Corfu - 5 Days
Enchanting Northern Greece & Corfu - 5 Days

Northern Greece has been the home of mighty civilizations, including the Macedonians, Thracians, Romans, Byzantines, Slavs and Ottoman Turks. Get a five-day glimpse into their world with this itinerary.  From the bustling streets of Thessaloniki, you'll go on to see the monasteries of Meteora as they touch the sky, then follow the footsteps of Oydsseus to the Ionian Sea.

Taking in the Parthenon
Map of Family Holiday in Athens and Nafplio - 5 Days
Family Holiday in Athens and Nafplio - 5 Days

A short but sweet itinerary perfect for your short people. This five-day trip takes you to some of the child-friendly highlights of Athens and neighboring Nafplio, with storytelling at the Acropolis, a seaside bike tour,  a castle built to defend against pirates, and plenty more to see and entertain regardless of your age.

Pillars at the Library of Hadrian
Athens City Break - 5 Days

Get a taste of the Greek capital with this five-day tour. You'll start off with a stroll through the Athenian food scene and digest it with a mythology tour of the Acropolis, then put your lessons into practice as you take a cooking class under the Parthenon's watchful columns.

Hippocrates fountain in the Old Town square
Map of Discover Medieval Rhodes - 5 Days
Discover Medieval Rhodes - 5 Days

Get a glimpse of the evolution of a thriving medieval island turned modern getaway with this five-day itinerary. The island of Rhodes is home to an expansive old town along with a slew of forts, castles, and other features that will transport you back to antiquity.

Coast of Skopelos near Neo Klima
Map of Central Greece & Skopelos Exploration - 5 Days
Central Greece & Skopelos Exploration - 5 Days

If you're looking out for a place to go, dance your way through this five-day Greek itinerary featuring the island filming location of Mamma Mia. After landing in Athens, head down to the slopes of Mount Pelion and then out to Skopelos island where Meryl Streep and Amanda Seyfried worked on the 2008 film before you return to Athens.

Aristotelous Square in Thessaloniki
Map of Urban Adventures and History in  Athens & Thessaloniki - 5 Days
Urban Adventures and History in Athens & Thessaloniki - 5 Days

Make the most of your five days in Greece with this quick hit tour of its two largest cities. Start in Athens with a local wine tasting before touring the most famous site of them all — the Acropolis. After spending time learning about the ancient Greeks, head to some of the city's more modern neighborhoods, where you'll spot street art and wander through the markets, stopping to sample food along the way. Next, make your way to multicultural Thessaloniki, where you'll explore its Byzantine and Ottoman history on a walking tour of the city.

How it works
Chat with specialist icon Step 1
Tell us what kind of trip you want
Complete our quick travel quiz
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Chat with a local travel specialist
Work out the details together
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Securely book your trip
100% satisfaction guaranteed

Meet our Local Travel Specialists

Experienced travel agents with a passion for Greece
Travel specialist Chris Gravas
active 37 mins ago

Chris Gravas

I design entire journeys that mitigate issues before they arise. I ensure the best possible orchestration of all services included. I provide human accountability in real time. My name is...

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Travel specialist Eirini Tzoka
active 48 mins ago

Eirini Tzoka

My name is Eirini, I am a travel specialist and I was born and raised in Athens. My family originated from Northwestern Greece, and it was this area's raw beauty and long-standing heritage that got...

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Travel specialist Marianna Pianelli-Blatsouka
active 2 hours ago

Marianna Pianelli-Blatsouka

I’m Marianna, born between two cultures and now based in Athens. With Greek roots and an Italian sensibility, I design tailor-made journeys throughout Greece that blend refined comfort with...

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Travel specialist Penny Vasileiadi
active 2 hours ago

Penny Vasileiadi

I’m Penny, a Travel Specialist from Kalamata. I grew up among olive groves in the Peloponnese, and that close connection to local life still shapes the way I plan trips today. With a degree in...

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Trip Reviews for Greece

The latest reviews by travelers who booked their trip on kimkim

We were paired with Sydney as our Greece spec...
Greece | May 4 - May 14, 2026

B
Bill C.
Newark, NJ | Reviewed on May 21, 2026

We were paired with Sydney as our Greece specialist. It was the trip of a lifetime and I can’t stress how great Sydney was! EVERY place we stayed was in the perfect area. EVERY tour we went on was amazing! EVERY ride showed up right on time! We couldn’t have used a more knowledgeable and helpful planner. Perfect to a tee. Already thinking about what other country we will use KimKim for. Can’t wait!

Local specialist: Sydney Hubbard

Wonderful trip to Greece!
Greece | May 9 - May 18, 2026

J
Jeff S.
Atlanta, GA | Reviewed on May 20, 2026
All I can say about our trip to Greece is that it was wonderful . . . The Kim Kim Team was amazing and truly made a difference all the way through — from itinerary development, to planning and logistics, and responding to questions and issues along the way. Regardless of time — day or night — Kim Kim responded very quickly and was always helpful. All of the logistics from the US to Athens to Naxos to Santorini were flawless!! With all of the drivers and guides and passes/tickets... Read more

All I can say about our trip to Greece is that it was wonderful . . . The Kim Kim Team was amazing and truly made a difference all the way through — from itinerary development, to planning and logistics, and responding to questions and issues along the way. Regardless of time — day or night — Kim Kim responded very quickly and was always helpful. All of the logistics from the US to Athens to Naxos to Santorini were flawless!! With all of the drivers and guides and passes/tickets involved in the trip it was amazing that everything worked exactly as planned. The Kim Kim app with the itinerary, contact names and phone, tickets etc along with the chat feature was tremendously useful. The hotels were great, the drivers were prompt and courteous, the guides were knowledgeable and very easy/flexible to work with. I can’t say enough good things — probably the best trip that we’ve ever taken and Kim Kim was a key contributor. Will definitely use them in the future.

Local specialist: Siena Mueller

Athens/Paros/Santorini, Greece
Greece | May 9 - May 17, 2026

Kathleen
Kathleen C.
Ashburn, VA | Reviewed on May 20, 2026
From the very first interaction I had with KimKim, I was very pleased. The right questions were asked to create the perfect plan to explore Greece. Every detail discussed about the trip played out flawlessly each day. The travel team was also very responsive before and during the trip (we had to change one of our excursions) and it was cared for and our itinerary was updated in less than an hour! This was a trip of a lifetime and I am so grateful that KimKim made my dream a reality. Read more

From the very first interaction I had with KimKim, I was very pleased. The right questions were asked to create the perfect plan to explore Greece. Every detail discussed about the trip played out flawlessly each day. The travel team was also very responsive before and during the trip (we had to change one of our excursions) and it was cared for and our itinerary was updated in less than an hour! This was a trip of a lifetime and I am so grateful that KimKim made my dream a reality.

Activity Reviews
Morning Caldera Catamaran Cruise
Morning Caldera Catamaran Cruise
Santorini
Quality of Experience
Food
Guides, Drivers and Staff
Transport
Traditional Vineyards & Wine Tasting Experience
Traditional Vineyards & Wine Tasting Experience
Santorini
Quality of Experience
Guides, Drivers and Staff
Transport
 From Olive Groves to Vineyards: A Culinary Journey Through the Peloponnese
From Olive Groves to Vineyards: A Culinary Journey Through the Peloponnese
Athens
Quality of Experience
Guides, Drivers and Staff
Transport
Local specialist: Siena Mueller

Why travelers love kimkim

Custom trips for independent travelers who are too busy to plan
Customize your trip with the help of a local travel specialist

Kimkim has handpicked the world’s top local travel specialists so you will have peace of mind and an unforgettable trip that meets your exact requirements.

Authentic travel experiences

Kimkim’s local specialists ensure that you will have the best experience based on up-to-date local insights. On top of that, the vast majority of your money will go straight to support and grow local economies.

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Once you are happy with the trip, you can easily book via kimkim’s secure payment platform.

Local support during your trip

You can always reach your local specialist with a quick message or call in case you hit a snag during your trip, or simply want some great local recommendations.