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.

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Meet our Local Travel Specialists

Experienced travel agents with a passion for Greece
Travel specialist Marianna Loupou
active 12 hours ago

Marianna Loupou

I’m a travel specialist with a genuine love for creating one-of-a-kind experiences that feel just right for each traveler. My journey in the travel world has taken me through many exciting paths, ...

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Travel specialist Chris Gravas
active 12 hours 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 Marianna Pianelli-Blatsouka
active 4 mins 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 Effie Parasyrakis
active 9 hours ago

Effie Parasyrakis

My name is Effrosyni, I typically originate from the island of Crete but I was born and raised in Athens, Greece. I have lived for 8 months in France and 3 years in Santorini, Greece. I have a...

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Trip Reviews for Greece

The latest reviews by travelers who booked their trip on kimkim

Best Trip of Our Lives!
Greece | Sep 4 - Sep 15, 2025

D
Dylan R.
Ashburn, VA | Reviewed on Mar 27, 2026
We had an amazing time on our trip to Greece and still think about it often to this day. Everything was planned perfectly and we had little to worry or think about besides enjoying our time. All transportation was seamless and the hotels were excellent. Sienna did an absolute amazing job based on my initial guidance and we made very small changes to her first itinerary. 6/5 stars! Only comments we have just to assist future travelers:
1. The travel from the ferry to the hotel in Sifnos is...
Read more

We had an amazing time on our trip to Greece and still think about it often to this day. Everything was planned perfectly and we had little to worry or think about besides enjoying our time. All transportation was seamless and the hotels were excellent. Sienna did an absolute amazing job based on my initial guidance and we made very small changes to her first itinerary. 6/5 stars!

Only comments we have just to assist future travelers:
1. The travel from the ferry to the hotel in Sifnos is very short and probably does not require a car.
2. It is recommended to tip 10% on all tours, but with everything being booked through KimKim we had no idea what 10% was. Maybe just include a note for recommended amount on each tour/excursion?

Hotel Reviews
SanSal Boutique Hotel
Chania

Great location and friendly staff

Authenticity & Character
Location
I
Staff
Cleanliness & Comfort
NLH Monastiraki
Athens
Authenticity & Character
Location
Staff
Cleanliness & Comfort
Manili Boutique Suites & Villas
Archanes

Very Nice

Authenticity & Character
Location
Staff
We were only here for one night, but it was special nonetheless
Cleanliness & Comfort
Liana Beach Hotel & Spa
Naxos

Could have stayed here for the rest of my life and been happy!

Authenticity & Character
Location
Perfect spot on the island. Our room was a short walk to the private part of the beach. We could just relax and be served right in the chairs.
Staff
Very helpful. Coordinated a rental car to be dropped off for us right at the hotel.
Cleanliness & Comfort
Sifnos House
Sifnos

Amazing location with great staff!

Authenticity & Character
Location
Short walk from the ferry and a really great spot on the island.
Staff
Awesome! Very helpful!
Cleanliness & Comfort
Activity Reviews
Private Sailing Trip to Balos Beach & Gramvousa Island
Private Sailing Trip to Balos Beach & Gramvousa Island
Chania

Another great boat day and a perfect way to end the trip. We once again had the boat to ourselves and a great crew to make us feel special.

Quality of Experience
Guides, Drivers and Staff
Transport
Samaria Gorge Hiking Day Trip
Samaria Gorge Hiking Day Trip
Chania

A lot of work, but some of the most amazing views Ive ever seen! Drive back down was very windy, so if you get carsick just be prepared.

Quality of Experience
Guides, Drivers and Staff
Transport
Traditional Cretan Cooking Experience
Traditional Cretan Cooking Experience
Chania

Made to felt like part of the family and had some truly amazing food made by us!

Quality of Experience
Food
Guides, Drivers and Staff
Transport
Private Culture Walk with Food Tastings & Tavern Meal
Private Culture Walk with Food Tastings & Tavern Meal
Naxos

Best food of the trip! The culture we saw was amazing as well. Each island truly has its own history.

Quality of Experience
Food
Guides, Drivers and Staff
Transport
Half Day Private Boat Outing to South Naxos
Half Day Private Boat Outing to South Naxos
Naxos

So great! We had the boat to ourselves and the captain truly made us feel special. Much better than the crowded catamarans we saw around. We were able to go place to place much faster.

Quality of Experience
Guides, Drivers and Staff
Transport
Private Hike in South Sifnos
Private Hike in South Sifnos
Sifnos

Very nice. Would like to have had a little more time to hangout, but amazing nontheless.

Quality of Experience
Guides, Drivers and Staff
Transport
Taste of Sifnos: Food, Culture & Village Life
Taste of Sifnos: Food, Culture & Village Life
Sifnos

Delicious! Felt like a local!

Quality of Experience
Guides, Drivers and Staff
Transport
Self-Guided Lycabettus Hill Visit
Self-Guided Lycabettus Hill Visit
Athens
Ancient Athens Acropolis & Mythology Walk
Ancient Athens Acropolis & Mythology Walk
Athens

Very fun and interesting.

Quality of Experience
Guides, Drivers and Staff
Transport
Local specialist: Siena Mueller
Siena
Siena Mueller
Local specialist in Kimkim HQ | Replied on Mar 30, 2026

Thank you so much for taking the time to share this amazing feedback! Making sure your honeymoon was a 6-star experience was my ultimate goal. It sounds like your hotels & experiences were incredible. I hope you'll travel with kimkim again in the future (maybe a 1-year anniversary trip?)! ❤️✨

The guides were all very knowledgeable and fr...
Greece | Mar 2 - Mar 9, 2026

Lee
Lee G.
Chicago, IL | Reviewed on Mar 11, 2026
The guides were all very knowledgeable and friendly. Yiannis was excellent and was a fine companion. He made everything so easy for me. There was so much to see in a short time and the schedule made it possible to see all of the sights I wished for. The accommodations were excellent. I hope to come back some day and see more of your beautiful country! Read more

The guides were all very knowledgeable and friendly. Yiannis was excellent and was a fine companion. He made everything so easy for me. There was so much to see in a short time and the schedule made it possible to see all of the sights I wished for. The accommodations were excellent. I hope to come back some day and see more of your beautiful country!

Hotel Reviews
Monastiri Guesthouse
Kalampaka - Meteora
DAYS City Suites
Patras
Leto Nuevo Hotel
Nafplio
Mosaikon
Athina
Activity Reviews
Ancient Corinth Guided Tour
Ancient Corinth Guided Tour
Greece
Acropolis Guided Tour
Acropolis Guided Tour
Athens
Local specialist: Marianna Loupou

We had such an incredible time on our trip to...
Greece | Oct 6 - Oct 14, 2025

J
Joanna W.
Chicago, IL | Reviewed on Feb 17, 2026
We had such an incredible time on our trip to Greece! Angela (Aggeliki) was incredible to work with. We were nervous having never used KimKim before, but it turned out to be a great decision for us. Angela helped us create a great itinerary, was always available and responsive if we had questions or changes during the trip, and ensured everything was easy and streamlined. All our transportation drop-offs and pickups were on time and easy to navigate. She sent us all our ferry tickets in... Read more

We had such an incredible time on our trip to Greece! Angela (Aggeliki) was incredible to work with. We were nervous having never used KimKim before, but it turned out to be a great decision for us. Angela helped us create a great itinerary, was always available and responsive if we had questions or changes during the trip, and ensured everything was easy and streamlined. All our transportation drop-offs and pickups were on time and easy to navigate. She sent us all our ferry tickets in advance. All the tours were incredible - especially the individual tour in Tinos and the small group tour in Santorini. We loved the hotels she picked for their unique features and charms. Overall we had a blast!!

Hotel Reviews
14 Reasons Why
Athens

Excellent breakfast, centrally located, perfect home-base for a few days in Athens!

Authenticity & Character
Location
Staff
Cleanliness & Comfort
Infinity View Hotel Tinos
Tinos

LOVED this hotel. Views were incredible. Make sure to use the bug deterrent thing on the wall, though, if you're going to keep your windows open!

Authenticity & Character
Location
Staff
Cleanliness & Comfort
Activity Reviews
Athens Highlights Mythology Tour
Athens Highlights Mythology Tour
Greece

Great tour, considering how crowded this area of Athens is! Very informative, great guide, good equipment so we could hear.

Naxos Town Food Tour - afternoon with dinner
Naxos Town Food Tour - afternoon with dinner
Naxos

I thought this was a good tour. However, such a large group was a bit trickier to navigate. And Naxos is so small that we ended up visiting several places that I had already visited in my first day of sightseeing the area.

Quality of Experience
Guides, Drivers and Staff
Athens Wine Tasting Tour & Nightlife
Athens Wine Tasting Tour & Nightlife
Athens

Fotis was a lovely guide, we learned a lot about local food and liquors - such a fun start to our Athens visit!

Quality of Experience
Guides, Drivers and Staff
Panoramic Tour 2025
Panoramic Tour 2025
Santorini

Great tour - Maria was a lovely guide! I was a little bummed that our itinerary had initially included Oja but then the tour didn't go there - but regardless, we still had a fantastic time on this tour! Highly recommend.

Quality of Experience
Guides, Drivers and Staff
Transport
Tinos Full Day Tour
Tinos Full Day Tour
Tinos

Tour guide was wonderful - love how the tour was so individualized and took us to lots of unique locations all across Tinos. One of my favorite parts of our Greece trip.

Quality of Experience
Guides, Drivers and Staff
Transport
Local specialist: Angela (Aggeliki) Giannioti
Angela (Aggeliki)
Angela (Aggeliki) Giannioti
Local specialist in Greece | Replied on Feb 17, 2026

Yeia sou Joanna,

Thank you so much for sharing your feedback on your experience.
I am delighted to know that you had a wonderful time here in Greece with us.
Tinos is one of my favorite, too! Has this charm and such a relaxing vibe, right?
We would love to see you coming back one day. There are so many more I would be thrilled to show you in my amazing country. 🙂

Until our paths meet again take care and safe travels!
Angela and the GA Trips team

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.