My Big Fat Greek Cruise: The Secret to Successful Cruising

I have been fortunate to enjoy many blessings in my life, but at the very tip top of that list is that I was privileged to be born and raised in a small town, on a street named Shady Lane Circle, in Alabama, in the 1970s.  

When I think about what’s important to me and what really makes me, me (mostly good I hope)- I go back to this small town upbringing every single time.  

Of course I had no idea when it was all happening that being raised in my community would come to define me – in fact, I was that cliché twentysomething girl who just wanted out and 20 years later realized that all I wanted and needed in life was that warm, comforting feeling of friendship and love that only a small town can give you.  

The only downside of being raised in a small town as I was is that you spend forever trying to replicate it.

I haven’t quite done that yet (although I’m getting closer) but what I have done is join forces with my childhood friends who feel the same and travel the world with them!

Our chosen method of travel is: the cruise. And you may ask why — as there are lots of downsides to a cruise (crowds, buffets and less than desirable food, among others) but I feel strongly that if you choose the RIGHT cruise (Viking for example) AND take your friends with you, there’s no better way to travel.

Here are my reasons for being pro-cruise:

  • Option to have your own room
  • Multiple price points for all types of budgets
  • Meals together without much decisionmaking required and no one has to fuss over the bill (who drank Dom Perignon and who just had water, etc.)
  • You get to experience multiple destinations vs just one or two
  • Built in itineraries so there is something for everyone and all ages

Okay but here’s why I have come around to deciding that cruising with larger groups of friends is the way to go: one of the worst parts of a cruise can be the crowded, long, expensive and sometimes disappointing excursions that are offered as part of the itinerary.

With a large group – you can book your own private excursions with your friends and have control over what your day looks like. You can veer off from the masses and go to the same destinations that the cruise ship offers but in a more exclusive way with private vans, a private tour guide, a boat day as we did on the cruise this summer, a nice lunch that doesn’t cater to hundreds of people, etc. And in my experience, with a group similar to our size (15) – it is either the same price as the excursions or less expensive.

**Travel Hack**
Find the nicest hotel or resort in the port city — even if you have to take a taxi or an Uber to get there — and go and have drinks, lunch, dinner or a spa treatment to get that fancy hotel experience.

So to sum it up, the secret to successful cruising is: FRIENDS! Grab a group of yours and book a small ship (this is key for me – not a fan of the big ships) or river cruise. Always use a travel agent to help with the excursions and bookings and provide perks like upgrades and ship credits. And book a big table for dinner every night to re-hash the day – that’s the most fun.

In case you were wondering, we did not carry on…
My mom Sally – one of the OG Shady Lane Circle Moms – and me

Seven Day Greece & Dalmatian Delights Itinerary:
Arrive Athens – we accomplished a lot in Athens – more on that in a later post
Day One: Monemvasia, Greece – site to an ancient Greek fortress town and a beautiful lunch at Hotel Kinsterna, a five star boutique hotel
Day Two: Olympia, Greece – original site of the Olympic Games from 776 BC-393 AD
Day Three: Nydri, Greece – toured the Princess Islands via boat, summer home to Aristotle Onassis and Jackie O; great swimming here
Day Four: Brindisi, Italy/Puglia – we hired a private tour guide and van to tour the Trulli Houses of Puglia
Day Five: Dubrovnik, Croatia – this one also requires its own post – sensational day in this coastal town
Day Six: Zadar, Greece – we went on an incredible boat tour this day – ocean swims & a boozy lunch with fresh fish and vegetables
Day Seven: Venice, Italy – we extended our trip here for a day – more on this later as well

Boarding the ship in Athens. We arrived a day early and spent the night – we did so much in our short time there – more on that later. This ship is the Seabourn Encore, a “small ship” – which has about 268 cabins and between 450 and 600 passengers (compared to other cruise ships that can hold well over a thousand, some even holding almost 4000 people like the Disney cruise.)
STOP ONE: MONEMVASIA – our first stop after Athens was the fortress town of Monemvasia (built into the giant rock you see in the photo) – “The small island of Monemvasia is one of Greece’s best-kept secrets. Its medieval town was carved from a sea rock and is only accessible by causeway.”

There’s an entire little village inside that giant rock at the end of the causeway. It was so neat.

You can see our ship in the background. Notice there are no other cruise ships here — which is unusual in many ports; usually they are all lined up outside of large ports. Because Seabourn is a “small ship” we could dock in places that the larger ships cannot (read: less people).
Entrance to the fortress city
The original fortress door – not to nerd out but I thought this was very cool.
The views from the fortress city were incredible.
There are many adorable little cafés throughout the village.
There are no cars inside the village so this is how they cart the luggage up to the hotels and inns.

Per my earlier suggested travel hack, we found this lovely five star boutique hotel converted from a private mansion in Monemvasia called Kinsterna Hotel. We took a 15 minute Uber after our village tour and had the most incredible lunch and tour around the hotel. I also like to check the activities and experiences section on nicer hotels’ websites for inspiration on things to do in an area that a cruise may not offer but you could arrange to do privately.

Even the bathroom was chic – obsessed with that tile.
Meanwhile, back at the ship…
A little cocktail party for the Virtuoso guests.


My biggest surprise on this trip was how much I enjoyed visiting Olympia, UNESCO World Heritage site and home of the original Olympic games that were held every four years from the 8th century BC to the 4th Century AD. It was mind blowing to walk that site and see how much still exists. Archaeologists believe that massive flooding and mudslides caused by earthquakes ultimately destroyed the site but also contributed to the preservation of many of the relics. One tip: we visited the Archaeological Museum after we toured the grounds and I would recommend the opposite or at least stop in to see the model of the entire site before your tour so you can picture how it would have looked.

Greek coffee after lunch

STOP THREE – NIDIRI/PRINCESS ISLANDS – This was an excursion offered by the ship that we did end up taking – I absolutely loved this experience but realized that we could have scheduled a private tour for this as well with a group our size. We toured the islands and caves around Lefkada including the island of Skorpios that was once owned by Aristotle Onassis (recently sold to a Russian oligarch for $153M – we could see his security boats everywhere) and was home to Jackie Kennedy and her children for a time.

Jacqueline Kennedy Onassis, American Royalty
Mary Pat and Weezie, Shady Lane Circle Royalty, haha
Accompanied by Queen Cathy
I realize someone born in the 1970s shouldn’t be doing this but when in Rome…
Stopped for coffee and breakfast at a little Greek fishing village. Can you hear the Abba soundtrack playing?? Pictured here, Harriet, Sally, Liz and me.
And after another successful and fun day, back on the ship for dinner & a dance party. This night we went to the Thomas Keller restaurant – you have to make reservations and are only allowed to dine here once. It was excellent. And we would know since we ordered one of everything.
The Beautiful McGehee Girls.
This crowd loves to dance. And I love to jump apparently.
Known both of these beautiful women my entire life
We love a dance floor.
Katy pictured with our adopted Shady Lane Circle Sisters, Liz and Jane

STOP FOUR – TRULLI HOUSES IN THE REGION OF PUGLIA – Also a UNESCO World Heritage site, we visited the famous Trulli homes in Puglia. For this tour, we hired a private guide and driver and went to a beautiful restaurant and had another long, delicious lunch of pasta, fish and white wine…are you seeing a trend here?

From the UNESCO World Heritage site: “The trulli, typical limestone dwellings of Alberobello in the southern Italian region of Puglia, are remarkable examples of corbelled dry-stone construction, a prehistoric building technique still in use in this region. These structures, dating from as early as the mid-14th century, characteristically feature pyramidal, domed, or conical roofs built up of corbelled limestone slabs. Although rural trulli can be found all along the Itria Valley, their highest concentration and best preserved examples of this architectural form are in the town of Alberobello, where there are over 1500 structures in the quarters of Rione Monti and Aja Piccola.”
Inside one of the trullis with my trusty $18 Amazon Backpack.
One of the benefits of a private tour guide: they take you to an off the beaten path delicious restaurant without the crowds
The Encore also had a small sushi restaurant that we went to one of the nights. They don’t take reservations so get there early. Cheers Allison!
Cheesy? Yes. But also so much fun – a Stevie Wonder tribute performance by the ship’s singers.

STOP FIVE – ZADAR – This was probably my favorite day. None of us were overly interested in the excursions offered at this port so instead we rented two boats and a driver who took us all around these beautiful islands to different swimming caves and out to a memorable and delicious lunch of fresh fish, pasta and cold beer. It was such a fun day.

We had two boats – one for the moms and one for the daughters.
Daughter boat.
This lunch was so good.
The Before picture
And After…
The Shady Lane Circle Gals!
Until Next Time!! I can’t wait for the next adventure.

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