Planning a Trip to Greece

November 14, 2019

Thinking about planning a trip to Greece?

Do you know which islands you’d like to visit, the best season to book your stay, or how to make your way into the secluded beaches?

I recently went on a dream vacation to Greece I am breaking down everything from Athens, Mykonos, and Santorini to the best dates for travel and ‘must-do’ experiences! 

With 6,000 beautiful islands, of which 227 are inhabited, Greece is an amazing country to visit!! Greece was the place I chose to celebrate my big birthday, and the entire trip was beyond my wildest expectations! This trip has been on my radar for a while; did you know that I am half Greek?!

Planning a trip to Greece was a real vacation for me, although it was great, a travel advisor never goes on “vacations”! 

Every trip that I take I put in the time to do some work and to check out other hotels so that I am fully in the know for my clients.

What I will usually do is call up the hotels that I think my clients will adore, and schedule a site inspection with them for a time that coincides with my vacation.

During the site inspection, I look for things such as the hotel’s room types, how many restaurants are located on the property, how close the hotel is to the beach, and how close the hotel is to the town.

Santorini, Visting Greece, Plan a trip to Greece


We traveled to Greece at the end of September/early October and we visited Athens, Mykonos, and Santorini.  The weather in Athens was great but still super hot! Being the busy city that it is, there was no breeze at all.

In total, we only spent one full day in Athens because visiting a busy city is not high on my priority list. Although, I had to see it in order to experience it and also learn more about it!

We went on a walking tour and took in the sights of some very cool neighborhoods. We also visited the rocky hilltop town of Acropolis and while we were there, we stopped at the Acropolis museum. The Acropolis Museum is an archeological museum dedicated to showcasing the findings of the historic site of Acropolis.  Just outside the Acropolis, there is a cool neighborhood with plenty of markets and amazing restaurants. We stopped in that neighborhood to have a wonderfully delicious traditional Greek lunch!

We stayed at King George and at Hotel Grande Bretagne, great location and Great Bretagne has a rooftop restaurant with a wonderful view of the Acropolis!


Mykonos was by far our favorite island!

The island of Mykonos was not as busy as Santorini, and was full of many gorgeous wonderfully secluded beaches with the clearest of blue waters!!

If Mykonos is a stop during your trip to Greece, I highly recommend renting a car, scooter, buggy, or a 4 wheeler in order to travel to those secluded beaches.

My husband and I chose to rent a buggy (a vehicle with open sides) which allowed us to discover some amazingly beautiful beaches.

This was a little piece of heaven on earth for me because I love secluded beaches and for my husband because he loves driving around in those cool vehicles!

If you are interested in planning a trip to Greece, I will be sure to send you there.

Driving a Buggy in Greece, Touring Greece, Planning a Trip to Greece

If you are not the adventurous type, you can easily enjoy the many Beach Clubs that Mykonos has to offer. I have a long beach club list now to recommend to my clients! 

Staying at a beach club for the day can be pricey, but I recommend trying it at least once!

Beach clubs will typically rent you 2 lounge chairs and an umbrella with a starting fee of $150, which is a separate charge from any food or beverage that you may enjoy during your time there.

In the summer visitors spend the entire day at the beach club, well into the nighttime party, which Mykonos is famous for!

If you’re not really into the party scene, there are still many other activities to do & sights to take in.

Along with its many parties, Mykonos is also famous for its gorgeous sunsets.

Strolling around Old Mykonos Town was very interesting, it was like a maze!! At one point during my walk, I got lost and went in circles through the very narrow alley roads. That’s the point of a visit to Mykonos and Santorini, to get lost! Go for long walks/hikes and you won’t regret it! The views are just breathtaking! 

Old Mykonos Town was also full of charm, and many shops including high-end luxury shops.

I loved our hotel in Mykonos, Katikies, thank you for the great service!


Then it was time for us to head to Santorini, which I was so excited for! The island of Santorini was formed after a volcano erupted in the 16th century. The island is essentially on top of a crater! Santorini is just as beautiful as evidenced by all of the tourists who post about it on Instagram.

Church in Greece, Santorini Road, Planning a trip to Greece

We stayed in Oia, which is lovely because it has its own little town and we didn’t need to venture out anywhere else if we weren’t up to it. Santorini was definitely more of a relaxing time for me. While I was there I made sure to go on a few hotel inspections, but mainly I relaxed and enjoyed the gorgeous views and sunsets. There are also many restaurants in Oia to dine while enjoying the views of the sunset! I would recommend early reservations if you’d like to experience a sunset dining experience. The other towns located on the island were lovely as well, but Oia now holds a special place in my heart!

My favorite activity in Santorini was a sunset cruise, which is typically aboard a catamaran. You can go on the sunset cruise with a small group of people or you can rent one out privately for just you and your love. We chose a private sunset cruise in Santorini since it was my birthday celebration. Either option is great and aboard the cruise, they cook up and serve a wonderful Greek BBQ complemented by local wines! The cruise also lends you snorkeling gear in order to make a stop for swimming. If a sunset cruise throws off your schedule, you can also opt to take this trip in the morning. My husband and I enjoy wine, and we also went on a wine tour while in Santorini, it was really informative! Who knew Santorini was best known for its great wines. Our Santorini hotel was amazing! We’ve stayed at Canaves Oia Sunday Suites, it’s a boutique hotel, located in Oia, in the middle of town, but very quiet and exclusive!

Ready to plan your own trip to Greece? Here is what you need to know!

Know which season is best

If you are anything like me, I’m sure you’ve been mesmerized by the pictures of Santorini!

Whitewashed buildings and blue-domed churches cascade from the volcanic island’s cliffs towards the Aegean Sea, it’s gorgeous!

What those pictures don’t show you are tons of tourists who crowd the streets of these beautiful Greek Islands.

I would highly recommend traveling early in the season, around April or May. Conversely, you can travel late in the season, which is the end of September/early October.

I strongly recommend avoiding a trip to Greece in late October or beyond. Greece’s fall weather gets very windy which often cancels ferry services in order to avoid the high winds.

My husband and I traveled at the end of September/early October and we experienced a super windy day, it was not fun at all! I’m so thankful the rest of our days were amazing!


Sometimes “things” happen and you have to stop having fun

 While we were driving around Mykonos and having a great time, I got an email from the ferry company stating that our next day ferry to Santorini was canceled due to strike…What??!! We are not going to make it to Santorini???

 So I had to stop having fun to contact ferry companies and try to rebook our ferry. I thought I was going to miss Santorini. Luckily I found a ferry company that was registered under Cyprus and was not participating on the strike,  so after spending a couple of hours on the phone with bad connection/bad internet, I was able to transfer our tickets to them and left the same day just a little bit later and not on direct ferry as I had booked originally, but it’s ok, I just didn’t want to miss Santorini! 

And this is one example of the kind of service I provide as a Travel Advisor to my clients If this were to happen to you,  you would be able to contact me ( or my contact in Greece) and we would be dealing with the problem, not you! I’ll do the work and you have fun!


Touring Greece, Planning a trip to Greece, Fishing boats in Greece

Know where to go

Planning a trip to Greece during the summer but not interested in experiencing the crowds? Then we must talk, because Santorini & Mykonos may be out of the question! I can easily find you other islands to visit with easy access and less crowding to ensure that your experience is relaxing. In the summer season, cruise ships typically stop for the day in Santorini and Mykonos which leaves the islands inundated with heaps of visitors and that can sully your experience. Fun Fact: you’ll also see tons of bride & grooms everywhere! They travel in from China to Santorini with their bridal gown in tow and they spend the day on the island taking their wedding photos!

My recommendations for other beautiful islands to visit in Greece that do not experience crowding are Corfu, Paros, Antiparos, Naxos, Crete and more!

Coast of Santorini, Visiting Greece, Touring Santorini

Traveling from island to island

There are so many islands in Greece, some of which you can only fly to while others offer ferry services. The ferry experience was interesting and is not like anything you may have experienced traveling by ferry in the US. Everyone boards the ferry at the same time! While, overall, it was pretty organized, it did feel a bit like a large heard boarding the ferry at the same time!

Knowing where to stay

The gorgeous hotels of Santorini and Mykonos are rife with a multitude of steps and most of the hotels are located on cliffs!

If you experience any mobility issues, then walking up and down the stairs on these islands may not be for you.

Again, this is the reason that I like to visit different hotels during my vacation, so I can experience the full scope of what the hotel has to offer, before making a recommendation to my clients.

The hotel we stayed at in Mykonos also had many many stairs to climb, in order to access our room. I was exhausted, but I also learned that there were available rooms with easier access. For my clients, I would ask for those easy access rooms in a heartbeat!

If you are staying in Santorini, I also recommend staying at a hotel that is within walking distance to a town!

Santorini and Mykonos only have about 30 taxis with no Uber or rideshares. As you can imagine, 30 taxis are not enough for the number of visitors they experience on a daily basis! I highly recommend pre-booking a car service to pick you up at the airport or port.


Planning trips

This week I’ve been busy planning this awesome honeymoon to Greece for Shea and Scott!

A Family reunion in Corfu, Greece!

And a getaway to the east coast of Florida for a couple!

I’m also getting my Certification and Training on River cruises!



Are you still thinking about planning a trip to Greece? Are you dreaming about hopping from island to island and relaxing on the secluded beaches?

Your trip deserves to be full of once in a lifetime experiences!

I can help you navigate the ins and outs of planning the trip of a lifetime to Greece! Click the >> contact button << to get in touch!







© Scenic way travel 2023


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