Greek Island Hopping, Fiftieth Birthday and the Boss Bar Santorini


On arrival first impressions were disappointing. It was noisy and busy and I couldn’t find our transport.

The place was full of pushy, impatient taxi drivers who all wanted to take us to the town.  It was clear to me already that we are now on an island with an airport and the ambiance was quite different.  One driver even nearly convinced me that he was our lift but he wanted 10 euros so I knew that it wasn’t right.  Sally and Charlotte climbed aboard a taxi van full of beefy Australians and were disappointed when I eventually found our arranged transport and they had to pick up their packs and get off again. I think the beefy Australians were disappointed too!  Now that we had our lift things were looking up.


We were driven to our accommodation, which turned out to be exceptionally good even though it seemed a bit remote.  I was a bit disorientated because it wasn’t where I expected it to be and for the first time this holiday I was a bit disappointed.

Never mind ‘Boss Bar’ tonight!

Actually the accommodation was really excellent, nice and spacious and on two floors with an upstairs bedroom and a double bed for me.  The best bed so far.  There was an Internet, which didn’t work but it was the thought that counts, and a lovely balcony overlooking a swimming pool and terrace.  It was very quiet and it didn’t seem as I though anyone else was staying there.  We tried the pool immediately and afterwards I walked into the village to get some essential alcohol supplies.

That cheered me up even more and ‘Boss Bar’ time was getting much closer.


We were all eagerly anticipating our evening out and we showered and changed and walked into the village.  The apartments were very new and there was no proper road into the village so we had to walk across a field and past a snarling guard dog kept chained up in a little shelter on the edge of the field.  I can’t imagine what it was doing there, there was nothing to guard.  Its jaws were salivating and it eyed me up and down as though it was choosing a main course off of the pedigree chum menu at a top canine restaurant and I quickened my pace just enough to pass by quickly enough without giving away the fact that I was actually bricking myself.

We were all in a very good mood now and we walked all along the busy seafront trying to pick out what we recognised and what had changed in the two years since we came last.  There were a couple of new tavernas and some different shops here and there but essentially it was much the same, but nothing could have prepared us for what was to come.

OMG’ the ‘Boss Bar’ had gone.

In its place was a cheap cocktail bar with plastic furniture and tacky lights and no Greek bouzouki player either.  I was devastated, for a moment I hoped beyond hope that I was mistaken and was in the wrong place.  I walked on for a while in absolute bewilderment hoping that I had misjudged our position and the bar would be just around the corner.  But after a few metres I realised that there was no mistake, it had gone and in a day of disappointments we had to endure another, and the biggest and bitterest of them all.

The ‘Boss Bar’ really had been an excellent place, the staff there were friendly, the food was good, the beer was cold and the prices were reasonable.  There was always complimentary ouzo to finish the evening (except when there was complimentary melon which quite frankly wasn’t so good) but the place had my fullest recommendation.  On my 50th birthday a very substantial meal for nine cost only €85, I left a hundred, the owner refused such a generous tip, I insisted, and he completed our meal with at least €25 worth of complimentary sweets and drinks.

Santorini Boss Bar 2004

With chins dragging along the floor we walked back along the front and had to settle for an alternative taverna. We were in such a state of shock that we didn’t really know where we were or what to do next but we came across a bustling, busy little place and found a table to sit and try and recover.  It wasn’t so bad but it wasn’t the ‘Boss Bar’.  The food was nice, they served Mythos and there was a bouzouki player and his pal on the accordion and they were very good.  It was cheap too, so no complaints there.  Unfortunately there was no complimentary ouzo!

At the end of the end of the day I was a bit despondent so resolved to hire a car tomorrow. We were sure that things would get better.

Santorini Sunset

11 responses to “Greek Island Hopping, Fiftieth Birthday and the Boss Bar Santorini

  1. Would you recommend Santorini? We are looking to return to the Greek Islands next year and I have always wanted to travel to this particular Island.

  2. That’s what I love… an honest blog! The first photo was a dream, you look at it with the first words popping into your mind of, sunshine, peace & sheer beauty & then I started to read 🙂
    At least we are not fooled into thinking that it’s always perfect. Photos don’t have sound and are panoramic limited.
    Thanks for guiding us to better choices…

    • Santorini is a must see island – it is so photogenic – but for me it is very overrated, busy and expensive and it has lost the charm of the Greek islands. There are others that I would recommend over and above, Naxos, Paros and Ios spring to mind, no airport and no harbour for the monster cruise ships and so much more traditional. As for the sunsets – well, they are the same wherever you choose to be. Thanks for reading and commenting.

  3. Pingback: Corfu, My Family and Other Disasters – Arrival | Have Bag, Will Travel

  4. Pingback: Looking Back on 2014 | Have Bag, Will Travel

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