Greece Road Trips & Itineraries

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Greece Travel Insights

Monastery of Panayia Pantanassa at Mystras
Map of Mainland Greece Road Trip - 7 Days
Mainland Greece Road Trip - 7 Days

Take a week to drive through the mythological territory of mainland Greece with this itinerary. Your seven days will start and end in Athens, covering the historical sites and sprawling castles of the Peloponnese along the way.

Pass through the Lion Gate at Mycenae, said to have been the home of Agamemnon
Map of Mainland Greece Road Trip - 10 Days
Mainland Greece Road Trip - 10 Days

Get ready for gorgeous views and a healthy dose of history on this 10-day self-drive tour of Athens and the Peloponnese. You'll learn about ancient Greek mythology at the Acropolis, visit the home of Helen of Troy, and see where the Olympics were born. Along the way, you'll sample wines at the vineyards of Nemea, explore the Byzantine castle of Mystras, and consult the oracle at Delphi.

A traditional village at Mani, Greece
Map of Mainland Greece Road Trip - 14 Days
Mainland Greece Road Trip - 14 Days

Take in the sights and flavors of the countryside on this two-week road trip around mainland Greece. Starting in Athens, you'll explore the Acropolis and sample local delicacies before making your way to the Peloponnese. Here you'll encounter traditional villages, ancient castles, beautiful Byzantine architecture, and fascinating archaeological sites. Go wine tasting in Nemea, consult the oracle at Delphi, and see the birthplace of the Olympics along the way.

The view from Navarino Castle overlooking Pylos Bay
Map of Mainland Greece Road Trip - 12 Days
Mainland Greece Road Trip - 12 Days

Immerse yourself in history and culture on this 12-day trip encompassing Athens and the Greek countryside. Learn about Greek mythology straight from the source at the Acropolis before heading west to the Peloponnese. Go wine tasting at the vineyards of Nemea, visit Byzantine castles, and stroll the streets of traditional villages. See where Helen of Troy lived and where the Olympics were born, and consult the oracle at Delphi before ending your road trip back in the capital.

View from the archaeological ruins at Mycenae
Map of Mainland Greece Road Trip - 8 Days
Mainland Greece Road Trip - 8 Days

In just over a week, this itinerary will take you from the Acropolis in Athens to the Byzantine ruins of Mystras to the hills of Delphi. Along the way, you'll visit important archaeological sites, stroll the pretty streets of towns brimming with history and culture, and enjoy unforgettable views.

Drive along Greece's pristine coast on this 16-day road trip
Map of Mainland Greece Road Trip - 16 Days
Mainland Greece Road Trip - 16 Days

On this 16-day road trip across Greece, you'll see historical sites, sample local flavors, and discover beautiful castles and monasteries. Spend a few days in the capital, learning about the Acropolis and enjoying the culinary delights of the modern era. Then, drive along the Peloponnese and Mani peninsulas to sample wine in Nemea, explore several archaeological sites, relax on pristine beaches, and discover picturesque villages before ending your journey back in Athens.

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Meet our Local Travel Specialists

Experienced travel agents with a passion for Greece
Travel specialist Eirini Tzoka
active 4 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 Chris Gravas
active 15 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 2 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 Marianna Loupou
active 55 mins 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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Trip Reviews for Greece

The latest reviews by travelers who booked their trip on kimkim

Fabulous 50 in Greece
Greece | Apr 1 - Apr 15, 2026

Adria
Adria Y.
Florida, USA | Reviewed on Apr 27, 2026
Working with Penny from KimKim was a pleasure from start to finish. She was so easy to work with and I could tell she loves her job. She created a dream trip with everything we asked for to make my husband’s 50th birthday feel special. Every hotel and excursion was spot on, and the private transfers made everything seamless and worry free.
We decided to travel in the shoulder season over Easter and Greek Orthodox Easter and Penny made sure the places we visited were open and ready for...
Read more

Working with Penny from KimKim was a pleasure from start to finish. She was so easy to work with and I could tell she loves her job. She created a dream trip with everything we asked for to make my husband’s 50th birthday feel special. Every hotel and excursion was spot on, and the private transfers made everything seamless and worry free.
We decided to travel in the shoulder season over Easter and Greek Orthodox Easter and Penny made sure the places we visited were open and ready for visitors. We normally plan our own trips but since we wanted to visit various islands and we were traveling in the shoulder season, I wanted to make sure we didn’t encounter any issues. Plus, who wants to stress over a two week celebratory trip? I can tell you we never stressed on this trip!
We stayed in Athens, Chania and Heraklion in Crete, Imerovigli in Santorini, and Chora, the port in Naxos. Crete and Santorini were our favorite islands. All of the islands had their own beauty and the Greek people were always so friendly and welcoming. Greece is very clean and crime free, at least where we were! Our hotels were amazing, our favorites being the SanSal next to the old town in Chania and Cresanto Luxury Suites. Both were very close and walkable to restaurants and shopping. The guest relations/ concierge were wonderfully helpful and fun to talk to. The rooms were spacious. SanSal had the best sea view and Cresanto had the best shower with instant hot water the whole trip. There was a bit of construction happening at Cresanto while we were there but the room was soundproof and it didn’t bother us. They are expanding. we had our own plunge pool but the weather was still chilly so we didn’t take advantage. I will say it is not very private as the walkway is right in front of the pool so even though it is private from the suites on either side, anyone walking past can see right in.
Our favorite experiences on the trip were a Cretan cooking class in the White Mountains booked by Penny, and experiencing Santorini over Greek Orthodox Easter, specifically the Pyrgos Fire Celebration on Good Friday. I’m only calling out a couple things but we did have an excursion almost daily, most coordinated through Penny at KimKim and they were all great. The cooking class stood out because it took place in a sweet couple’s home who were so hospitable, we had a wonderful small group, a cozy fire (chilly, rainy day) and got to feed the neighbor’s sheep. Mr. George, the husband even shared his personal barrel of wine with us which was wonderful and he had put it in the barrel when he was 15. Great stories and family history. Fun and informative tour guide who interpreted for us as Mr. George didn’t speak English and his wife (very sweet and head chef) only spoke a small amount but was hilarious. We ate what we made and everyone had a wonderful time.
The Pyrgos village lights up on Good Friday with giant candles over every possible surface. It made the most beautiful and memorable sight, celebrating the resurrection of Jesus. It’s an entire procession through the hilltop village along with burning crosses. Wall to wall people as Greeks come from all over to celebrate. This was a once in a lifetime experience and something only done on Santorini. If you find yourself in Santorini over this timeframe I encourage you to attend this must see event.
Penny, thank you for putting so much thought into our trip and for always being available to answer questions. Oh also, we did very much enjoy the couples massage you arranged for us in Athens! Thank you for everything!
I highly recommend KimKim for planning your next trip! I’ve already recommended them to everyone I’ve talked to about our fabulous trip and I hope we take another trip where we are able to use them soon!

Hotel Reviews
Cresanto Luxury Suites
Santorini

Very close and walkable to restaurants and shopping in nearby Imerovigli. Angela was wonderfully helpful and fun to talk to. The suite was spacious and unique with the sky light. Cresanto had the best shower with instant hot water the whole trip. There was a bit of construction happening at Cresanto while we were there but the room was soundproof and it didn’t bother us. They are expanding. we had our own plunge pool but the weather was still chilly so we didn’t take advantage. I will say the personal pool is not very private as the walkway is right in front of it so even though it is private from the suites on either side, anyone walking past can see right in.

Authenticity & Character
Location
Staff
Angela
Cleanliness & Comfort
SanSal Boutique Hotel
Chania

My husband and I loved this hotel. It was walkable to everything and had great sea views. We also loved the spacious room. Very clean and the concierge/ guest relations team were wonderful.

Authenticity & Character
Location
Close to old town
Staff
Everyone we encountered at the front desk was terrific as was the restaurant/ bar staff.
Cleanliness & Comfort
Activity Reviews
Private Villages of Naxos Tour
Private Villages of Naxos Tour
Naxos

Our favorite stop was the pottery shop! Marble village was also cool. Oh and the olive oil press where we were able to do a tasting of olives and olive oil.

Quality of Experience
Guides, Drivers and Staff
Transport
Private Santorini Cultural Highlights Guided Tour with Wine Tasting
Private Santorini Cultural Highlights Guided Tour with Wine Tasting
Santorini

This was a private tour and we loved our tour guide. She was very knowledgeable and easy going. It was a lovely day to wander around Santorini.

Quality of Experience
Guides, Drivers and Staff
Transport
The 7 Villages Of Apokoronas Small-group Tour
The 7 Villages Of Apokoronas Small-group Tour
Greece

We enjoyed wandering up the mountainside and visiting different village. From tea, to cheese, to lunch, it was a relaxing day. We also loved wandering around the orange orchard and grabbed a great view of the white capped mountains from an unexpected spot.

Quality of Experience
Food
Guides, Drivers and Staff
Transport
The Real Cretan Cooking Small-Group Experience
The Real Cretan Cooking Small-Group Experience
Chania

Our favorite of the trip! Don’t miss out. The cooking class stood out because it took place in a sweet couple’s home who were so hospitable, we had a wonderful small group, a cozy fire (chilly, rainy day) and got to feed the neighbor’s sheep. Mr. George, the husband even shared his personal barrel of wine with us which was wonderful and he had put it in the barrel when he was 15. Great stories and family history. Fun and informative tour guide who interpreted for us as Mr. George didn’t speak English and his wife (very sweet and head chef) only spoke a small amount but was hilarious. We ate what we made and everyone had a wonderful time.

Quality of Experience
Wonderful and informative tour guide, and the sweetest family.
Food
Guides, Drivers and Staff
Transport
The Acropolis & Acropolis Museum Private Guided Tour
The Acropolis & Acropolis Museum Private Guided Tour
Athens

The guide was extremely knowledgeable! Poor weather but it made for fewer crowds which was a bonus especially while exploring the grounds.

Quality of Experience
Guides, Drivers and Staff
Transport
Local specialist: Penny Vasileiadi

KimKim did a great job planning our trip to G...
Greece | Apr 15 - Apr 25, 2026

Miriam
Miriam S.
Ashburn, VA | Reviewed on Apr 26, 2026
KimKim did a great job planning our trip to Greece. We stayed in Athens, Naxos and Santorini. The locations that we stay at were centrally located and nice. Our guides were great including Elena at the Acropolis, Elizabeth in Athens, Photos for the Athens nightlife, Alex in Naxos and Panos is Santorini. We had an awesome lunch at a culinary atelier in Vourvoulos that was fantastic! Angeliki was our travel agent and was always available to answer questions even over the weekend. It was a... Read more

KimKim did a great job planning our trip to Greece. We stayed in Athens, Naxos and Santorini. The locations that we stay at were centrally located and nice. Our guides were great including Elena at the Acropolis, Elizabeth in Athens, Photos for the Athens nightlife, Alex in Naxos and Panos is Santorini. We had an awesome lunch at a culinary atelier in Vourvoulos that was fantastic! Angeliki was our travel agent and was always available to answer questions even over the weekend. It was a fabulous and memorable trip. The only fail was our accommodations in Oia which was a shared suite for 4 people which was very uncomfortable. Other than that, I would rate it a 10. Thanks for a memorable trip! Yamas!!

Hotel Reviews
Ode Villa Santorini
Santorini

Nice location but not as expected. The “junior suite” was more for kids and not 4 adults. The loft was a joke for 2 adults. You could not even stand without hitting your head!!

Authenticity & Character
Second suite not made for 4 adults. Needs more bathrooms and bedrooms.
Location
Located close to the waterfront and you could see the sunset from out deck
Staff
The man that made of breakfast was nice.
Cleanliness & Comfort
Second suite not made for adults. Place seemed old and not in good shape.
Castle Mansions
Naxos

Great accommodations

Authenticity & Character
Near the castle and you could see the ocean from our balcony
Location
Centrally located but tucked away so not too loud. Could see the ocean in the distance and near the castle.
Staff
Very nice
Cleanliness & Comfort
Clean and nice
Athens Woo Suites
Athens

This place was awesome and centrally located to everything in Athens. It was in the square with Athens church. The ladies at the front desk were friendly and helpful and the free breakfast was a great touch!!

Authenticity & Character
Small boutique hotel
Location
Centrally located and a great view of the cathedral and square.
Staff
Very friendly and helpful with recommendations
Cleanliness & Comfort
Clean and newly renovated
Activity Reviews
Cheese, Wine & Deli Tour in Naxos!
Cheese, Wine & Deli Tour in Naxos!
Naxos

Alex and Victor were great!!

Quality of Experience
Guides, Drivers and Staff
George was awesome!!
Transport
Naxos Highlights Tour
Naxos Highlights Tour
Naxos

Alex was great and informative!!

Quality of Experience
Food
Authentic food especially the goat was great!!
Guides, Drivers and Staff
George was awesome!!
Transport
All time classic Santorini 2026
All time classic Santorini 2026
Greece

Panos was great!! Very knowledgeable!! And the tour and the old city was fantastic. The lunch at the culinary school was the icing on the cake. Food was authentic and great!! We also visited a monetary on top of a mountain with a great view and then went to a restaurant/bar with a fantastic view. The whole tour and day was fantastic overall. Thanks Panos!! :)

Quality of Experience
Fantastic experience all around!!
Food
Guides, Drivers and Staff
The driver was amazing. We went up to a monastery on a tight rode and it was amazing that we came back alive!! They truly are professionals!!
Transport
Full Day Private Cruise to Panteronisia, Feira, Antiparos Town & Paros
Full Day Private Cruise to Panteronisia, Feira, Antiparos Town & Paros
Naxos

Beautiful ride. We went to a cave and blue lagoon. Also got off in Antiparos to look around. Very fun!!

Quality of Experience
Beautiful views!!
Guides, Drivers and Staff
Guide was good.
Transport
Private Sunset Cruise with Catamaran Lagoon 380/400
Private Sunset Cruise with Catamaran Lagoon 380/400
Santorini

This was the best experience of our trip. We did not expect a beautiful sunset as it had been cloudy all day and were surprised by the most beautiful sunset ever! The crew was so nice and friendly and fun!! Maria our hostess was great!!!

Quality of Experience
Great crew and we had a fabulous time. The sunset was FANTASTIC as well!! Great finale to our trip!!!!
Food
Food was BBQ on the boat. Great experience!!
Guides, Drivers and Staff
Maria our hostess was awesome. The captain was great. She even took our picture. One of the crew was even dancing to our music selection. They were great and we had a fabulous time!!! Best part of the trip!!!!!!!
Transport
Our ride was short but memorable because we backed all the way down the hill at about 30 mph!! LOL
Athens Nightlife Tour: Music & Dance Experience
Athens Nightlife Tour: Music & Dance Experience
Athens

Photos was awesome! You truly got the flavor of Greek nightlife and their zest for life. He was fun to be around and his enthusiasm was contagious.

Quality of Experience
Guides, Drivers and Staff
Photos was great!! So much fun and full of life. His enthusiasm was contagious and dancing was really fun!!
Transport
The Delicious Athens Food Tour afternoon
The Delicious Athens Food Tour afternoon
Greece

Elizabeth was awesome. Very knowledgeable and fun!

Quality of Experience
Guides, Drivers and Staff
Transport
Acropolis, Museum & Mythology Tour
Acropolis, Museum & Mythology Tour
Greece

Our tour guide Elena was great. Very knowledgeable and provided good information.

Quality of Experience
I don’t think you could fully appreciate this experience without knowing the background info provided by the guide.
Guides, Drivers and Staff
Very knowledgeable and added enough info without being boring.
Transport
It’s amazing how good the van and bus drivers are in this country!!
Local specialist: Angela (Angeliki) Giannioti
Angela (Angeliki)
Angela (Angeliki) Giannioti
Local specialist in Greece | Replied on Apr 27, 2026
Thank you so much for your kind words — it truly means a lot. I’m so happy to hear that you enjoyed your time across Athens, Naxos, and Santorini, and that the guides and experiences stood out — especially that lunch in Vourvoulos, one of my personal favorites as well! It was an absolute pleasure assisting you throughout your trip, and I’m glad I could be there whenever needed. I also truly appreciate your feedback regarding the accommodation in Oia. I’m very sorry to hear that it didn’t... Read more

Thank you so much for your kind words — it truly means a lot.

I’m so happy to hear that you enjoyed your time across Athens, Naxos, and Santorini, and that the guides and experiences stood out — especially that lunch in Vourvoulos, one of my personal favorites as well!

It was an absolute pleasure assisting you throughout your trip, and I’m glad I could be there whenever needed.

I also truly appreciate your feedback regarding the accommodation in Oia. I’m very sorry to hear that it didn’t meet your expectations in terms of comfort — this is valuable feedback, and I’ll absolutely take it into account moving forward to ensure an even better experience for future travelers.

Thank you again for trusting me with your journey to Greece — and I hope to welcome you back for another adventure in the future.

Yamas!
Angela

Wonderful planning and vacationing experience
Greece | Apr 11 - Apr 18, 2026

C
Caitlin C.
Ashburn, VA | Reviewed on Apr 22, 2026
Chris did a wonderful job planning our Greece vacation, as well as ensuring our trip was going as planned while we were enjoying it! We were in good hands and would recommend Chris for future trips! Read more

Chris did a wonderful job planning our Greece vacation, as well as ensuring our trip was going as planned while we were enjoying it! We were in good hands and would recommend Chris for future trips!

Hotel Reviews
Blue Dolphins Hotels & Villas
Firostefani, Santorini

The views the views the views!! The room was great with the master bed facing out to the beautiful views! The staff was very friendly and the breakfast brought to your room was phenomenal!

Authenticity & Character
The hotel was exactly the feel I was looking for!
Location
Walkable to town and food, right on the cliff with amazing views
Staff
Very helpful and friendly!
Cleanliness & Comfort
Princess of Naxos
Naxos

The staff were very friendly and accommodating - they wanted to make sure we had a good trip and offered great suggestions and help if needed.

Authenticity & Character
Location
15-20 min walk to town, but right on the beach
Staff
Very helpful and engaging! Offered great suggestions for what to do including renting cars, driver service and booking tours.
Cleanliness & Comfort
Achilleas Hotel
Athens

It was within walking distance to all of the Athens adventures, shopping and food that we wanted.

Authenticity & Character
Location
Walkable to all the things we wanted to do - food, tours and shopping
Staff
Cleanliness & Comfort
Activity Reviews
All Time Classic Santorini
All Time Classic Santorini
Santorini

I felt like we got to see so much on this tour!

Quality of Experience
Such a variety - different beaches, great views, amazing food adventure!
Food
Exceptional!!
Guides, Drivers and Staff
Both our driver and guide were just as wonderful on day 2!
Transport
Perfect
We Guide You In The Past
We Guide You In The Past
Santorini

This was so cool and I knew nothing about this prior to coming! Our guide knew lots of great details

Quality of Experience
Guides, Drivers and Staff
Both the driver and guide were great!!
Transport
Perfect for our family
Naxos Old Town, Castle & Portara Sunset Tour
Naxos Old Town, Castle & Portara Sunset Tour
Naxos

I loved this tour because there was so much more to the city than I would have realized on my own! It was great to learn the history of the town and see the different architecture and history.

Quality of Experience
Tour guide was great and very knowledgeable
Guides, Drivers and Staff
The guide was very friendly and knowledgeable
Transport
This was a walking tour and felt very doable even for my two kids - ages 6 &7
Naxos Villages Food Tour
Naxos Villages Food Tour
Naxos

I loved that this tour went inland to the small villages, we got to see so much more than the “tourist” perspective, as well as meet great people and try delicious food!

Quality of Experience
Felt very authentic from the locations we went to, the information we were provided, the people we met and the food we ate.
Food
So great to try so many delicious things! A great variety!
Guides, Drivers and Staff
Our driver and guide were both great!
Transport
The transport van was perfect
Mythology for Families
Mythology for Families
Athens

Our tour guide was wonderful - she was so engaging with the kids and brought different activities for them to do too!

Quality of Experience
The tour guide! She was knowledgeable and very kid / cat friendly!
Guides, Drivers and Staff
Best part was our guide
Local specialist: Chris Gravas
Chris
Chris Gravas
Local specialist in Athens, Greece | Replied on Apr 22, 2026

Dear Caitlin,

Thank you very much for your kind words, recommendation and wonderful review! I really appreciate you taking the time to share your impressions and experiences from your trip. I will share your feedback with all related drivers, partners and guides, they will surely appreciate it.

Should you wish to plan a future trip to Greece and/or Italy, you know where to find me.

Until that time, all the best and safe travels!

Warm greetings,
Chris

Why travelers love kimkim

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