Friday 2 December 2022
  • :
  • :

Bucket List Trip – Day 4 – Departing Sikinos For Santorini

We agreed to be ready for breakfast at 8 and to sail by 9 so that we could maximize our time in Santorini. We were all very excited that Eric was able to re-route us to Santorini especially when he and George had first reported that it was impossible andwe were all prepared to get the most out of our time there. The seas were as calm as they had been all week and we had a very smooth sail into Santorini by about noon. We soon find out that there were not many accommodations for sailboats or any boats for that matter in Santorini and as it turned out, Eric spent the rest of the day negotiating the weather and the locals for an acceptable location to tie up for the day and night.

While Eric fought the good fight, we climbed the (by US standards) ancient, steep and dangerous path from the water up the cliff to the village of Oia to begin what turned out to be a fabulous day in Santorini. I can not over-exaggerate how treacherous the climb was and with two kids, who wanted to run and look over the edge of every steep cliff, it was by far the most nerve-racking time of our trip. It took us about 25 minutes and all 4 adults were sopping with sweat by the time we reached the beautiful shopping village of Oia at the top of the summit. We were so spent that we were totally focused on finding the first tavern that would allow us to get lots of water, cool off, eat lunch and grab a quick internet connection. In the Blue Sky Cafe we were able to achieve all of the above and the food so good that this is the first restaurant that I mention by name.

We spent a couple hours shopping the jewelry stores, art galleries, local trinket shops, and ice cream shops (multiple times for the boys as a reward for great behavior and stamina in climbing the cliff) in Oia before heading to the bus stop/taxi stand to find our way to my favorite village in Greece, Fira. We were fortunate to walk up on a very nice (much newer and higher quality than when I have been in Santorini before 12 years ago and more) AIR-CONDITIONED bus. The shopping in Fira was great as well and in addition to other Greek keepsakes, I was excited to purchase “authentic” Greek soccer jerseys for the boys and me. We ended our time in Fira with happy hour at what I believe is the most beautiful place on earth (it’s even better at sunset, but we had to get a move on to head back in the direction that we were going to meet Eric), the top of the cliffs of Fira were you can see the beautiful Mediterranean in all directions. The picture above reveals the beauty, but you have to be there in person to really totally consume and appreciate how beautiful it is. Contact me if you need a tour guide for your visit!!! 🙂

After happy hour we caught the bus back to Oia for a quick dinner by Greek standards, about 90 minutes, and then had perfect timing for our walk down to the port of Amoudi, where Eric would meet us in the dingy for a 30 minute ride across the bay. Our timing was perfect in relation to the sunset. This path down the cliff was far less treacherous and about a third of the journey was on a real walking path with fabulous shops on each side. Note to self: always take the ascent from Amoudi up/down from the water. For the 20 minute descent, as we turned each corner, we got another tremendous view of the sunset until we reached the docks. Perfect timing and the perfect end to a great day in Santorini. Three cheers to Eric for finding a way to get us to Santorini and to fight the fight to get us a mooring for the night!!!


NOTE: Follow Joe on Instagram (j0elavelle) if you’d like to see more pictures of these beautiful islands.

To follow Joe’s journey and receive the latest episode from intrepid Living DIRECT to your INBOX, you can subscribe here. Or, you can subscribe DIRECT to iTunes here!

Today’s episode is brought to you by Combatant Gentlemen, the premier online destination for high-quality and affordable menswear. Combatant Gentlemen cuts out all of the middlemen and markups in their production process — they own their factories, they plant their own cotton, and they even own their own sheep! As a result, they’re able to offer 100% Italian wool suits for $160, dress shirts for $25, and silk ties for $16. Whether you need clothes for work or play, Combatant Gentlemen has your back.

Joe Lavelle
Follow me
Latest posts by Joe Lavelle (see all)

JOE LAVELLE is a Healthcare Management and Technology Consultant with a record of successfully meeting the business and technology challenges of diverse organizations including health plans, health delivery networks, and health care companies for 25 years. Joe worked his way up through Cap Gemini and Andersen Consulting to the partner/VP level of at First Consulting Group, Technology Solutions Group and Santa Rosa Consulting. After running his own company, Results First Consulting, for 12 years Joe Co-Founded intrepidNow with Todd Schnick to create incredible content to dramatically improve the sales and marketing efforts of their clients.