Best of Santorini: Ideal Greece Vacation

Best of Santorini - Ideal Greece Vacation - Classical view of Oia village with white and blue architecture

What to expect on this itinerary

Welcome to Santorini, the most iconic of all the Greek islands. Blue and white villages look like a fairytale, beaches of red and black sand abound, and the famous sunsets land over the brilliant turquoise waters. The steps, alleys, tavernas, and chatter fill every corner, and you will truly be able to relax. This best-of tour ensures that you will experience it all, but in keeping with the island, your vacation pace is relaxed, the vibe is laid-back, and there will always be a show-stopping view to enjoy.

Countries Visited

Greece

Places Visited

Santorini, Oia, Imerovigli, Firostefani, Fira, Kamari, Perissa, Pyrgos, Thirassia, Akrotiri, Nea Kameni, Agios Nikolaos, Mesa Vouno, Emporio

Suggested Duration

9 Days

Customizable Itinerary

Expand All
Day 1

Oia – Checking Out the Famous Sunset Views

Fly into Santorini and meet with your local guide, and travel straight to Oia. It will likely be mid-afternoon, and the sun will be bouncing down on the whitewashed walls with the Aegean Sea stretching out in all of the turquoise splendor. The colors are bright, and likely far more vibrant than the postcards have led you to believe. Check into your hotel and relax, and then venture out to take your first steps through the old town with a map in your hand. As the sun slowly fades, you can watch the show from your hotel terrace as the whitewashed houses reflect the color changes, and the sun dips slowly into the Aegean, creating one of the world’s most famous sunset scenes. You will have a private viewing, just like you do for the next week on this beautiful island.

What's Included:

Transfer
Accommodation
Day 2

Oia – Relaxed Day on Santorini

Day 3

Oia – Luxury Catamaran Day Cruise

Day 4

Oia – Villages and Ruins of Santorini Private Tour

Day 5

Oia – Santorini Winery Tour

Day 6

Oia – Walking the Volcano and Santorini By Helicopter

Day 7

Oia – Food Walking Tour in Fira

Day 8

Oia – Flexible Private Boat Tour

Day 9

Oia – Departure

Trip Highlights

  • Immerse yourself in the blue and white village of Oia with just over a week in Santorini’s quiet old town
  • Fly above Santorini on a helicopter tour, with the option of touching down in nearby Mykonos
  • Cruise around the Santorini coastline on a catamaran, stopping at beaches, hot springs and swimming spots
  • Discover the island’s tavernas and local food haunts on a private culinary tour
  • Spend a day tasting and touring your way through Santorini’s vineyards
  • Take a coastal walk from Oia to Fira and hike the volcanic caldera of Nea Kameni
  • Explore all the Santorini villages, including church-dominated Pyrgos and coastal Firostefani
  • Spend quiet time on the beaches, comparing the stretches of red and black sand
  • Set out on a private boat tour with your choice of destination
  • Travel back in history with an archaeological guide at the Akrotiri ruins

Detailed Description

Santorini is far more magical than it looks, as so much treasure is found as you engage with the culture of the island. You have probably seen the postcards of blue and white villages shimmering beneath the late-afternoon sun with the hot springs, the ruins, volcanoes, tiny villages, and luxurious swimming pools overlooking it all. Photos are just a snapshot and Santorini is never still as the water changes color through the day. Those mazy streets are animated by the sound of clinking glasses and quiet footsteps while local taverns are alive with laughter as fresh aromas greet you around every corner. Photos make Santorini seem fictional, but immerse yourself in the island, and its magic knows no bounds.

This handcrafted tour celebrates the very best of Santorini. Ultimately, this will be a relaxing vacation as you spend the week in the old town of Oia on the island’s western coast. Oia is quieter than Fira and is the largest of the old villages, so even on the last day of your vacation, you may turn up an alley you had not yet noticed. You will also be ideally situated to get out and explore the rest of the island, either on water or land. From Oia, there is a beautiful coastal walk to Firostefani and Fira, but a journey by road is also quick and easy, giving you the option to spend your evenings in either of these villages as well.

Oia is quiet most of the year and most of each day. There is a surge of visitors around dusk as it is the ideal place to watch the Santorini sunset. But even then, these people are easily avoided as you can relax in your private hotel terrace towards the top of the village. Gaze out on the world-famous sunset in privacy, or you can enjoy it from the swimming pool. Your boutique hotel is one of the finest in Greece and celebrates the unique character of Oia with signature décor and a very laid-back atmosphere.

Most days include a private tour or activity, so throughout your vacation, you will experience everything the island has to offer. Begin with a spa treatment to ease you into relaxation, and then take a luxurious catamaran cruise with a stop at beaches, islands, and hot springs. Discover the ancient village of Pyrgos and the ruins at Akrotiri, and spend a day at the best Santorini vineyards. Fly over the island by helicopter and walk on a volcanic caldera before finding the best local food in Fira’s taverns. You will take it all in with the best of Santorini over a very relaxing week.

Starting Price

$3,000 per person (excluding international flights)

Your Zicasso trip is fully customizable, and this sample itinerary is a starting place for your travel plans. Actual costs are dynamic, and your selection of accommodations and activities, your season of travel, and other such variables will bring this budget guideline up or down. Throughout your planning experience with your Zicasso specialist, your itinerary is designed around your budget. You can book your trip when you are satisfied with every detail. Planning your trip with a Zicasso travel specialist is a free service.

What's Included

  • Accommodations
  • In-country transportation
  • Some or all activities and tours
  • Expert trip planning
  • 24x7 support during your trip

Your final trip cost will vary based on your selected accommodations, activities, meals, and other trip elements that you opt to include.

4.9

Verified Traveler Reviews

Based on 742 reviews

Travel Review: Luxury Greece Vacation, Athens, Santorini, Mykonos, Delos, Delphi, Hydra, Akrotiri, Meteora, Local History & Culture

My daughters and I had an amazing 12 day trip to Greece!  In January, we made up a long list of all the places we wanted to see.  We wanted focus on the scenic beauty and archeological history of different Greek sites, and we were not disappointed!  We started in Santorini, then progressed to Mykonos, Delos, Hydra, Poros and Aegina, before turning our attention to the mainland, and covering sights in Athens, Sounion, ancient Corinth, Mycenae, Epidaurus, Nafplia, Olympia, Delphi, Kalambaka and Meteora.  Armed with that very long list, I contacted a few different travel agents.  I asked a local Hong Kong travel agent as well as sending off an inquiry to Zicasso.  Zicasso came back with two travel agency referrals, one of them was this travel company.

From the very beginning,our travel agent was very professional and helpful.  He worked around my travel schedule and our time difference to find a good time to Skype, and I sent him my list of places and sights that we wanted to include on this trip, along with our desired emphasis on the history and culture of Greece (rather than the wineries and shopping).  He assured me that he would work on the best itinerary, given our desire to visit various islands as well as archeological sights on the mainland, and that he would also recommend the good hotels for us.  My travel agent was willing to speak with me and also replied emails promptly, answering every small question in details in the itinerary as we went back and forth over a few weeks time.  He assured me that he would arrange for knowledgeable private guides and we would be able to soak in all the archeological and scenic sights that we wanted.  All of our tours with guides were private, and included all entrance fees and transfers.  The only group outing we had was a one day cruise to Hydra, Poros and Aegina.  Our guides were all knowledgeable and eager to share their passionate interests on the areas we were visiting.  They adapted to our pace and interests well.

We were greeted by our travel company's Santorini representative when we arrived in Santorini.  Our private transfer whisked us to our hotel and we were briefed on our prearranged tours for the time in Santorini.  Our hotel was a wonderful boutique hotel that our travel agent had assured us would have incredible views of the caldera.  We were floored by the breathtaking views and gorgeous sunsets!!  Our suite (a renovated sea captain's quarters built into the cliffside) included enough space all three of us, and we had delicious and wonderfully prepared breakfasts on a private patio each morning.  The hotel and its facilities were well maintained and we loved the three nights we stayed there.  We were within five to ten min walking distance of shopping in both Fira and Firastefani.  We had a five hour private tour the first day, driven by our young, friendly and exceptionally courteous driver.  Our guide gave us the tour around different areas of the island, including Profitis Ilias, Megalochori, Perissa and the black sand beaches, and then our expert historian guide, met up with us for the visit to Minoan Bronze Age archeological site of Akrotiri.  We then went back to meet up with the boat company, and took a three hour boat ride around the caldera, including visiting the Paila Kameni and Nea Kameni islands and the hot springs in between, and taking a short walk on the volcano crater (still active!). This boat ride was arranged at the last minute by our guide at our request to "see Santorini from the water" and he was very helpful in arranging this.  In addition our guide was able to help us make reservations for meals and extend our tour times to accommodate some last minute requests - and he would follow up by WhatsApp to ensure that everything was going smoothly.  On our second full day our driver took us to Oia, introduced us to some classic Santorini views, shops and unique finds (such as the book store and the nuts and pistachio store in Oia) and then to Imerovigli, where we hiked to Skaros Rock, to breathtaking views of Oia and the whole caldera.  We then went to pre-historic and Archeological museums, Emporio and all the way to Cape Akrotiri to see the Venetian light house.  Each day, our driver greeted us with a big warm smile and with offers for ice cold water whenever we returned to our car after each sightseeing stop.  By the time we left Santorini, we had fallen in love with the island!  We would highly recommend our driver and our guide to anyone looking for privately guided tours with a historical/cultural emphasis on Santorini.

We traveled by high speed ferry (all arranged by our travel agent) to Mykonos and were picked up by our travel company's representatives and brought to our hotel.  After the warm and courteous greeting and follow up in Santorini, we were a bit surprised by the quicker (more rushed) pace of Mykonos, which was reflected in our interactions with the agency representatives.  Our hotel in Mykonos was nice, but not as convenient as our Santorini hotel had been.  We felt a little worried walking the road (no pedestrian path) with busy traffic into Mykonos town, even though it was just 10 minutes away.  We only stayed one night in Mykonos, and our highlights were a boat ride and private guide to the UNESCO Delos Island and a walking tour with a private guide of Mykonos (including a museum visit).  Coincidentally, our guide to Delos is the daughter of our walking guide in Mykonos, so we had both mother and daughter guiding us during our short Mykonos stay. Our Delos guide, had had a long hot day with different tours by the time she met up with us for our 5pm tour, and it showed, as she gave us the information of Delos, but wasn't keen to stop or pause when we wanted to take photos or just soak in the atmosphere a bit longer.  Her mother, who gave us the walking tour the next morning, seemed more passionate about sharing the unique aspects of Mykonos' history and we enjoyed our walking tour with her.

After Mykonos we took a short flight to Athens, and our guide and driver were waiting for us.  Once settled into the spacious minivan (clean, Mercedes minivan) Our guide shared historical and anecdotal details of Cape Sounion, and the Temple of Poseidon, which we visited.  After the three hour tour, and she dropped us at the hotel in Athens.  Here, I must mention that our travel agent was willing to allow us to directly book with the hotels that I have loyalty status with so that I would receive my SPG points and travel benefits (some travel agents would not allow this).  This hotel has a great reputation and our interactions with the staff during this visit was great.  We only stayed 2 nights at this hotel, with our one full day in Athens being spent taking a one day cruise to Hydra, Poros and Aegina.  Of those three islands, Hydra was the most scenic.  We took advantage of a short walking tour on Hydra and also the panoramic tour offered by the cruise company on Aegina.  Apart from the initial boarding chaos (our transfer bus from our hotel to the port was one of the last to arrive and so we got onto an already crowded cruise ship without much information before leaving port on where to sit or what to expect), the one day cruise turned out to be a good one.  The following morning we checked out and started our four day private road trip with our driver and our guide.  We traveled in a Mercedes minivan with plenty of room for luggage as well as space inside the van for the long drives.  Each stop along the way was uniquely picturesque, historically significant, and a feast for our senses as well as our hunger to learn more about Ancient Greek civilisation and how it impacted Greece and western civilisation today.

Our travels took us to the following sights:

Day 1 - Corinth, Mycenae, Epidaurus and Nafplio.  We had to unfortunately skip Acro Corinth as the weather was very wet that day (the only rainy day in our otherwise sunkissed Greek holiday).  The chance to visit these UNESCO World Heritage sites was thrilling for all three of us. and our guide provided in-depth historical and cultural context as we visited each location.  Finishing up with our day with a one night stay in Nafplio at a hotel which is situated in the middle of an ancient Venetian fortress, was perfect.  We learnt that Nafplio was the second capital of Greece (after Aegina and before Athens became the capital) and enjoyed walking through its winding streets with the Venetian influences, which give Nafplio the nickname “the Naples of Greece”.

Day 2 - drive to Ancient Olympia - touring the UNESCO site which was the home for the Ancient Olympic Games and the Sanctuary of Zeus.  Again, our guide excelled in sharing his historical knowledge and his passion for sharing about the social and cultural impacts as he pointed out different archeological features and highlights was very apparent.  We even had a chance for the girls to do a short sprint in the Olympic stadium!

Day 3 - We stayed overnight after Olympia in Delphia, where we stayed at a boutique hotel. We had not realised that Delphi was situated high in the mountains, and were floored by the views from our hotel room balcony, and enjoyed warm Greek hospitality.  The next morning, we went to visit the UNESCO site, including the Ancient Sanctuary of Apollo and the Delphi Museum.  After the tour, we took the scenic route from Delphi to Kalambaka, where we stayed overnight in a quaint B&B.  The owners welcomed us warmly and had homebaked goods for our breakfast the next morning.

Day 4 - Kalambaka is a short drive from Meteora, another UNESCO World Heritage site.  An absolutely amazing feast for our eyes and cultural/historical curiosity, as we soaked in the views of monasteries perched on clifftops and mountain faces, and visited two of the largest ones, Great Meteora and Varlaarm Monasteries.  On the way back to Athens, we also stopped off quickly to learn about the historical significance of Thermopylae.  Our guide continued to be a wealth of historical information, interesting facts, and anecdotal stories to bring the historical and cultural contexts alive for us.

Our last two nights in Greece were spent in Athens, staying at the same hotel again.  We explored Athens on the penultimate day with our guide, taking a private Athens walking tour.  This included Monastiraki Square, the Acropolis, the Parthenon, the Erectheion, the Acropolis Museum, and seeing other sights such as Hadrian’s library, Hadrian’s gate, the Plaka, and the historic/tourist district of Athens.  We saved our last day to do some shopping before being picked up by our driver for our transfer back to Athens airport for our flights home.

In summary, this travel company and our agent, did a fabulous job making all the arrangements for us, from transfers, to hotels, and every little detail for our private tours.  Our agent was available before the trip by Skype and email, and during our time in Greece by phone and WhatsApp.  In addition, our agent ensured that our time on the islands was supported by able partner agencies.  In particular, the Santorini partner agency are to be commended for the memorable stay we had in Santorini.

See more

Greece Travel Review: Athens, Naxos, Santorini, Cooking Class, Sunset Catamaran Trip, Swimming, Snorkeling, 9 Nights
"Our trip was great! Zicasso’s trip planner was very responsive and made changes to allow for the ideal itinerary for us."

See more

Greece Honeymoon Review: Athens, Naxos, Santorini, Crete, Hiking, Sunset Cruise, Snorkeling, 10-Night Trip
We could not have had a better experience with Nikos and Anna.We arrived in Athens, picked up by an extremely friendly driver in a nice black car, had a private ride to the hotel where we spent the day exporing Plaka. Next, we flew to Naxos, a smaller, less touristy island that Nikos recommended for what we were looking for in our honeymoon. That ended up being our favorite island! We loved the island tour and sunset mythology walking tour. Our sunset cruise was cancelled due to high winds and big waves.We then took a ferry from Naxos to Santorini. There, we did the Imerovigli to Oia "hike" which was about 9 miles round trip. We also did an island tour that took us to many parts of Santorini. The sunset cruise we did there was unforgettable! The dinner served on board was fantastic and we had an incredible time swimming & snorkeling.From Santorini, we took another ferry to Crete. We did the Samaria Gorge hike there which was 10 miles and you finished in this small beach town that was stunning. Highly recommend bringing a swimsuit and change of clothes to make sure you're able to take a dip! We stayed in Chania which was a cool city on the harbor and a ton of shops.Nikos & his team were fantastic, helping us every step of the way with quick responses, great recommendations, and constant communication making sure we were enjoying our trip with zero stress. Highly recommend this traver company & Nikos!

See more

Review: Greece Vacation, Athens, Santorini, Crete, Rethymnon, Akrotiri, Heraklion, Samaria Gorge Hiking, Local Food & Wine

Our trip was amazing! Our agent built our itinerary well. Our guide in Athens was awesome! Loved our hotel in Athens, Rethymnon, and Santorini. Rethymnon old town was our favorite with so much history. Our hotel there was just perfect. Our hike up the Samaria Gorge was the highlight of our trip. We rented a car and drove to some beautiful beaches and had lunch at a fantastic little tavern recommended to us by staff at our hotel. Santorini is beautiful. I am so glad we requested a room with a hot tub on the balcony which we enjoyed every morning and night. Breakfast was delivered to our balcony every morning. I was so glad we were there in May at 72-73 degrees during the day in the sun was very hot, nights cool. We rented a car and traveled to a winery for wine tasting, I highly recommend. We also visited the Akrotiri ruins. We stayed in Imerovigli. We did the hike from Imerovigli to Oia in the morning before it got too hot. After visiting Oia and Fira we were glad we were staying in Imerovigli as it's not as busy. The food in all locations was so good. I was in salad, cheese, and wine heaven. All of the staff at the hotels provided us with exceptional service recommending things to do, restaurants, and activities.

The only negative we had is with the rental car companies which I let our agent know about (the reason for the 4 star). On Crete, our agent told us to bring the car to the port at Heraklion at 8 am park in the free parking and a agent would find us to pick up the car. After waiting till 8:40 am with no agent in sight and our departure on the ferry at 9 am, I found another car agent who contacted the rental car company and was given the OK to leave the key with them. This was very stressful for us. We live in the US and don't have cell service as the fee is too high outside of the US, so there was no way for us to contact our agent or the car rental agency. After contacting our agent, it appears they usually have the customers leave the car and they pick it up later, this however was not what we were told. On Santorini we had another issue. Our rental car was to be dropped off at 9:30 am. At 9 am I received a call from the rental car company asking if we needed a automatic (which is what our agent booked for us), I stated yes. He then said "I'll try to find one for you." I then received a call from staff at our hotel saying the rental car was going to be late they would be there at 10:15. At 11:15 is when the agent finally showed up with a brand new convertible Audi (this is way too much car and we were worried about damages to the car). The agent stated the car that was booked was not available. I was then told that we would need to pay $30 extra per day for full insurance. I was told by our agent that the insurance was included, the rental car agent said it was not. At that point I went back to the room and contacted our travel company (my agent not available) listed on our itinerary in Santorini and was told he did not know, but usually only basic insurance was included. We then told the car rental agency we would like to cancel the car, he then called the office and got the insurance included at no additional cost. We finally got the car by about 11:30 two hours past our original time. We also had them pick up the car at 6 PM instead of the next morning, however as far as I know, we did not get reimbursed for the delay in the car and the early pick up. 

See more

Travel Review: Trip to Greece, Athens, Crete, Santorini, Mykonos, Rethymno, Knossos Palace, Sunset Sailing, Hiking, Wine Tours

The good--My agent  was generally responsive to questions.  She provided me with all the relevant information, vouchers and tickets when we met up in Athens for the remainder of the trip.  We were provided with a mobile phone to use for the duration of the trip in case we needed to make local calls, which we got to keep in the end.  Transportation to and from Athens airport was seamless, the Athens hotel was nice and well located.  

However not all the tours and activites she set up were the best.  The Athens group tour was so atrocious we actually left and went off on our own.  

Activities set up in Crete were quite disorganized.  Our "guide" of Chania did not actually provide much information--he was just walking with us through the town.  It would have been less awkward and we would have enjoyed ourselves more doing that on our own.   We also would have preferred to have picked our own location for dinner.   he then drove us to Rethymno to our hotel, driving like a mad man.   He told us he would pick us up the next day for our tour.  In the morning however it was a completely different woman from a completely different company.   Also the description of the tour for that day (on our provided itinerary from our agent) was completely inaccurate, so we were not dressed appropriately (e.g. we were expecting a hike).  Luckily the tour with the Eco Tour company was quite nice, but it was strange that we had received so much conflicting information.    In general in Crete we spent a lot of time driving from city to city.  Seem like it would have made more sense to split up our stay between cities.  On our last day our driver inexclipably refused to meet us at our hotel, but rather at a coffee shop 10 minutes away, where he was apparently leisurely having his morning coffee.   Again, the driver was someone completely different from a different company than had been indicated.  Finally the hotel in Rethymno was not very good.  The room was very hot, had an odd odor, and we found a huge cockaroach in the middle of the floor 

Activities in Santorini were better and more consistent with what was indicated on the itinerary--sunset sail, winery tour.  hotel was nice but location was quite remote in Imerovigli.  Our atent had advised against staying in Fira, which was a good recommendation since it seemed quite touristy.   However I'm not sure why she didn't suggest staying in Oia, which seemed much nicer, with more restaurants in the area.  

Overall experience was good but I feel like I could have organized it on my own and probably done a better job.  Don't feel like I particularly got an "insider" tip from the travel agent.  

See more

Travel Review: Luxury Greece Vacation, 12-Day Trip
Our trip was amazing! Everything was organized perfectly. The hotels were fantastic and the services and tours were very well done. 

See more

Customizable Itinerary

This is a sample itinerary to inspire a personalized trip designed with your travel specialist.

28,000+ Verified Traveler Reviews