Greece Sailing and Adventure
Mon 14 September 2026
Greece Adventures
Two small group trips to Greece. Sailing the Cyclades with G-Adventures and Mainland Highlights with Intrepid.
This is our first trip with Intrepid, so it will be interesting to compare the two largest small-group travel specialists.
Travel Dates: September 17, 2026 - October 6, 2026
G-Adventures: Sailing Greece - Santorini to Santorini (Sun. Sep 20, 2026 to Tue. Sep 29, 2026)
Trip Plan:
Due to prevailing winds and weather, the Trip Reality:
We arrived in Santorini a few days early, partly to recover from jet lag before sailing and partly to explore and enjoy the island. The island features in many movies and TV shows. Grace chose a nice hotel up the hill from the airport, very convenient. Two top-rated restaurants were just a short climb up the hill. We visited the Wine Museum; it was listed as a top, award-winning museum in Europe. They had interesting dioramas, though a bit dated. We tasted several excellent Santorini Classic white wines.
We enjoyed some great meals. We also hiked up to the castle and 5-bells village at the very top of the hill.
Sept 17-19: Pre-Tours
Transfer to Oia to begin the trip:
Itinerary
Day 1 Santorini
Arrival day. Join the group at 11 am for a welcome meeting, then take a short water taxi to Thirassia to start your journey through the Cyclades.
We took a water taxi to meet the sailing ship in Thirassia's harbor (the next island across from Santorini).
Our skipper is Jean Luc; it turns out this is the boat that my skipper from the Sailing Canary Islands trip last December normally operates. She was taking a break, and Jean Luc is G.'s backup captain.
Fellow travelers are Tay, Kim, Andrew, Ryan, Russ, and Laura.
I took anchor duty on the boat (this means I get up front on the bow and control the winch to drop or lift the anchor, feather the chain on pickup, tie off a snug when anchoring, etc.). Other duties could have been fendering or line-tossing.
We sailed to Ios and docked in the harbor.
Days 2-4 Cyclades - Ios/Small Cyclades/Naxos
Ios
We made a trip up to the highlands to visit a cheese-making farm. This farm has made cheese for multiple generations. After the visit, we had free time, then hiked to the island's highest point for a sunset view.
Folegandros
Folegandros has a nice, quiet beach. The island is uninhabited, but there was evidence of an enterprise with beach chairs and umbrellas. They were all locked up, as we are just past the shoulder season for the beach crowds. Grace enjoyed walking the beach; about half the group hiked over the ridge to see another sunset. Grace and I opted out and joined the rest for a sundowner glass of wine on the beach while we waited for them to return.
Antiparos and Naxos
Today's sail took us to Antiparos, then on to Naxos for the evening. The sea is starting to get a little rougher. In Naxos is the Door of Apollo. These are the ruins of the temple of Apollo, famous because National Geographic adopted its likeness for its logo.
We enjoyed sunset and dinner. We also got the full experience: music, plate smashing (OPA!), and Greek line dancing.
Day 5 Naxos
We stayed in Naxos. Today we had an organized tour of the island. We met with a local guide, Laura, and visited ruins, churches, a quarry, local villages, and an olive tasting. Overall, a fun-filled day.
Naxos Wildlife and Conservation Awareness Experience
Prepare for an immersive educational experience led by experts at the Naxos Wildlife Protection Association, an established wildlife rescue and first-aid station, and a G Adventures-supported initiative, offering valuable insights into sea turtle conservation. During this community tourism visit, travelers will gain a deeper understanding of sea turtle biology, the threats they face, and the essential rescue protocols for assisting injured or sick turtles. Enjoy an informative discussion about the program and leave with a heightened awareness of the responsible actions needed to safeguard these beautiful marine creatures and their natural habitats.
Days 6-9 Small Cyclades
Sept 25th.
Sept 26th. Swim the Caves and the 'grounding' incident. TBD Sept 27th. The waterspouts. TBD: add the video
Day 10 Santorini
High waves today on the sail back to Santorini. Not quite as high as the Atlantic swell on my Canary Islands trip, but significant. We did manage to get back to harbor in Thirassia. We visited a winery, then had dinner at an overlook restaurant on top of the hill. It was very windy and cool. Everyone wrapped up in a blanket to eat on the patio.
Departure Day Santorini
Depart after breakfast. Depending on weather conditions and access, the drop-off location may vary. A shuttle transfer will take you from Thirassia to Santorini Island, where you can explore or relax before your onward journey.
We booked a hotel near the airport and on the beach for a recovery (and laundry) night before flying up to Athens to meet the Intrepid group.
Our flight is in the afternoon (Sept 30th), and we'll meet the Intrepid group at our hotel at 6 pm for dinner.
Intrepid Travel:Mainland Greece Discovery
Tour Description:
Discover ancient ruins in Athens, including the Acropolis, a UNESCO World Heritage site and ancient citadel featuring the iconic Parthenon temple dedicated to the goddess Athena.
Visit the Sanctuary of Apollo, home of the Oracle of Delphi. Take a guided tour through the archaeological sites, see numerous monuments and temples, visit the reconstructed Athenian Treasury, and learn about the region's myths and stories.
Climb the stairs to the top of Meteora and discover the UNESCO World Heritage-listed 14th-century monasteries that are perched on a series of ancient rock pinnacles.
Indulge in the many flavors of Greek cuisine, like moussaka (layered eggplant or potato, meat, and a creamy sauce) or grilled lamb and tzatziki, over dinner at a traditional taverna as Rembetika music floats around you.
See some of Greece's best sites with curated activities and plenty of free time. Maybe visit the Panathinaiko Stadium, which hosted the first Olympic Games in Athens, or walk along the waterfront to the White Tower in Thessaloniki.
Day 1 - September 30th
The flight was delayed, and a taxi from the airport to central Athens took nearly an hour. We got to the hotel around 5:45 and met the group on the rooftop at 6 pm. Great view of the Acropolis.
Day 2 - October 1st
Today we took a walking tour of the Acropolis ruins. It was a 15-minute walk from the hotel, and we passed several other archaeological ruins (Hadrian's Library and the Roman Agora)
Day 3
This morning we visited Intrepid's charity partner, Naomi. This NGO was founded to support migrant and disadvantaged women and girls by teaching sewing (and cooking) skills. They recycle/upcycle textiles. We also toured some markets in Athens to see fish/meat, vegetables, and spices. We had a free afternoon; Grace and I walked to the White Tower and toured the museum within. We also saw the harbor statue of Alexander the Great. We planned to visit Paul's spring, where Paul reportedly drank, and a small church nearby. However, we scrapped that plan for late-afternoon rest and recovery.
Day 4/5 Meteora
We'll spend the next two days here. Meteora is a famous rock formation, the largest of its type in the world. It's even more picturesque because, in the 11th century, monks moved in and built monasteries on the high rocks. This protected them from the invading armies. 6 of the 24 monasteries are still active. We'll visit three of them and take lots of viewpoint and sunset pictures of the rock formations.
Day 6 - Thermopoli and Delphi
Today we drove to Delphi, stopping at Thermopoli (famous for the 300). The site was unimpressive; the water/landscape has changed in 3000 years, so it's hard to imagine how it was a choke point. The only indication is a monument. The drive was pretty; we crossed a few mountain ranges and drove through agricultural valleys. We saw the sea of olives near Delphi. It is a plain covered in over 1 million olive trees.
We visited Delphi and its museum. The museum is impressive, with a few almost unique exhibits, like a very rare (only 7 known in the world) brass statue of a chariot driver in victory.
Day 7 - Return to Athens
Today we take a public bus back to Athens. I forgot my Kindle in the seat pocket, so I'll have to buy a new one when I get home.
We had a farewell dinner. Grace and I have an early morning flight back to Denver.
-
Labor Day Launch 2026
-
Arkansas Cycling
