Spectacular trip to Greece!
Greece
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Sep 21 - Oct 9, 2026
Sydney and her team planned a fabulous 19-day trip to Greece for my husband and I. We flew into Athens where we explored the ancient sections of the city and the Psyrri neighborhood. Highlights were the Acropolis and Museum, the Ancient Agora, the Central Market, and frolicking around the Plaka. Next up was Mykonos where we stayed above Old Town in the beautiful Vencia Hotel with stunning views overlooking the town. We explored the labyrinthine Old Town and enjoyed cocktails and mezze plate by the harbor while watching the sunset. One afternoon was spent "Off the Beaten Path" hiking with a guide in the rural countryside, visiting a farm, seeing wild goats on a hike to the beach, and swimming in the beautiful Aegean with Yummy Pedals and our excellent guide Demetra. It was amazing to get away from the tourists and see a bit about rural like in Mykonos. Our cruise to Delos and Rhenia was such fun with the opportunity to do some swimming/snorkeling in the Aegean and to tour the ancient ruins of Delos. Our third destination was Naxos where we stayed in the Melidron Hotel and Suites with ocean views in Agios Procopios south of Old Town. The little town was cute and the beach was phenomenal! The highlight for us in Naxos was our e-bike tour that took us up into the mountains to a goat/sheep/cheese farm, an olive mill, and lunch at family-run taverna. Santorini was our next stop in Greece where we stayed in aptly named Absolute Bliss hotel located in Imerovigli north of Fira. This hotel is located right along the Fira to Oia caldera trail and overlooked the caldera with mind-blowing views of sunsets. Early cold weather and crazier than usual winds kept us from going on a scheduled catamaran cruise, but we hiked and explored Oia, Fira and the caldera trail with the quintessential views of the caldera hillside and the towns. A second day took us on a privately guided tour of three wineries on Santorini with Santorini Experts. Our final destination was Crete where we spent a day in Heraklion visiting the Knossos Palace (site of the ancient Minoan civilization) and the Archeological Museum with a private guide. Very interesting and memorable! We also took time to explore the Heraklion Venetian Harbor and the Venetian fortress. In the evening, central Heraklion comes alive with restaurants, gelato stands, and street performers! Our next stop in Crete was in Chania where we stayed in the very historic Porto Del Colombo right in the heart of the old city. Chania is exceptionally charming, sort of Venice without the canals! We enjoyed exploring the old town especially with the help of our local guide, Goldy, who couldn't be more charming. The different cultural influences on the city was fascinating to learn about and to see first-hand. Viewing stunning sunsets across the harbor will be a forever memory. Foodies will not suffer here. So many options and with fresh fish everywhere! Our last day in Chania was spent on a semi-private guided tour with Chania Adventures up into the White Mountains where we stopped for a wine tasting and a delicious taverna lunch overlooking the Samaria Gorge. What a serene spot to listen to the wild goats on the hillside and take in the views of the mountains! Our last day in Greece was spent on the Athenian Coast at the lovely Azur Hotel. We had just enough time to walk along the waterfront, get one last gelato, and have a lovely sunset view from a seafood restaurant before we had to head back home.
Sydney and team did a fantastic job of setting up all hotels, transfers, and excursions which made getting around seamless and practically effortless!
Hotel Reviews
Ultra modern hotel in the Psyrri neighborhood, five minutes from Monastiraki Square and the Ancient Agora, but not in an area overrun by tourists. The neighborhood is "up-and coming", with some popular restaurants, and near the interesting Central Market. Some streets near the hotel were a little bit more grungy, but we never felt unsafe. The staff was extremely kind and the included breakfast delicious!
This hotel is located above Old Town but a short 5-10 minute walk gets you into the heart of Mykonos Town. The views from the hotel restaurant and pool are incredible as are the sunset views! The restaurant is pricey but delicious. Staff was so friendly and helpful.
Situated on the main road coming into the beach town of Agios Procopios, it is a charming hotel with rooms arranged like little villas, each with their own private balcony. Our room did have a view of the beach which was a 10 minute walk away. It was in easy walking distance into the little beach town with the numerous restaurants and tiny shops and the beachfront with abundant beach chairs. Since we were there during shoulder season, our beach chair rental was front row and paid for with one set of drinks from the adjacent bar. What a bargain! Incredible views of the sunset from the beach!
The views from our room's balcony was just jaw-droppingly beautiful. The room/suite had a circular bed with canopy, a large living room with indoor jacuzzi, an outdoor terrace with lounge chairs and an outdoor hot tub. You should expect to have to walk up/down a LOT of steps, so this would not be an ideal place for someone with mobility issues. The hotel is located right on the infamous Fira to Oia caldera trail but also near a number of charming in-town and caldera-view restaurants and a few shops in Imerovigli. Be aware that getting anywhere else (Oia, Fira, southern beaches, Akrotiri, or wineries) requires an expensive taxi ride unless you are willing to hike the caldera trail or walk down to the main road to catch a local bus. We loved the quieter location compared to the more touristy Oia or Fira locations.
Centrally located in Heraklion, sophisticated and modern vibe, with a lovely, abundant buffet breakfast.
What an interesting, historic, old hotel! It is so deep in the historic area that there is no street that runs near it. Our transport had to drop us off down at the harbor and we walked about 5-6 blocks through charming, cobblestone streets to find the hotel tucked into the heart of the historic Venetian section of Chania. It is a very old hotel with furnishings that match the architecture. Our hotel room was three flights up (no elevator) and the room itself was two stories! 10/10 for character for sure!
Situated within walking distance of the waterfront, this hotel is a converted apartment complex with a beautiful, modern aesthetic. Our room was a nice size with a beautiful balcony and comfortable bedding. Since we had to leave so early in the morning for our flight home, we did not have a chance to try their breakfast, but they provided us with a boxed breakfast which was delicious.
Activity Reviews
The Acropolis Museum was absolutely amazing! Highly recommend using the audio tour as you go through the museum. We went through the museum before visiting the Acropolis which was helped us understand better what we were seeing when we toured the Acropolis. Do not forget to tour the ruins underneath the museum!
A lifelong dream to see the Acropolis in person! Our tour guide was personable and knowledgable. The day started off rainy but ended up beautifully sunny, so be prepared by wearing comfortable footwear (no sandals) and raingear if rains is forecasted. Be prepared for A LOT of tourists, especially if the tour is in the late morning.
Privately guided 6 mile walk in rural Mykonos that took us to a farm with animals, past hillsides with wild goats, to a bay where we swam in the Aegean and took underwater photos, and then hiked backed along a donkey trail to the farm. Our guide, Demitra, of Yummy Pedals was so personable, fun and informative.
Lovely cruise out to Delos and Rhenia along with a delicious fresh lunch and a swim in the sea. I would have liked just a little bit more time on Delos (1hour).
While Mykonos Old Town is fascinating, it is filled with tourists. This activity was a nice opportunity to get out of the crowds and walk along quiet, rural goat paths and swim in an isolated bay in northern Mykonos. Our guide, Demetra, was personable, fun and funny telling us stories about the area and what life is like for the rural Greek family.
After days of racing around, we took a day to just sit on the gorgeous beach in Agios Procopios. Since it was shoulder season, it was not difficult to snag front row lounge chairs for the price of a couple of lemonades. The view was incredible and we stayed until the sunset.
Due to unseasonably cold and windy weather the day we were scheduled to do this activity, we cancelled and spent the day exploring Oia and Fira instead. October may not be the ideal time to do an 8-hour cruise until 9 pm unless you know that the weather is warm!
Exploring Chania is an amazing experience. Wandering through the cobblestone streets, stopping for a drink along the harborfront, and visiting some of the historical sites was a feast for the eyes, ears, and taste buds! Calling this activity Self-Guided Museums of Chania is a bit misleading since there was very little guidance about what to visit in Chania. A bit more information and/or a suggested walking tour with map would have made this a bit more instructive.
The owner of Chania Adventures picked us and another couple up for a trip up into the White Mountains where we visited an olive farm and did a wine tasting at a winery overlooking hillsides filled with olive trees. As we drove, our guide entertained us with multiple stories about himself and life in Crete. Along the way we learned about beekeeping and saw numerous hillside beehives, paused for goats crossing the road, and ended up high in the mountains near the trailhead for Samaria Gorge where we enjoyed a substantial, delicious lunch in the traditional Greek taverna style.
10/10 experience to tour this ancient ruin from the Minoan era. Our guide was incredibly knowledgable and led us on a pace that enabled us to fully appreciate the activity. I did not know that much about the Minoan civilization, but I was fascinated by the culture revealed.
This was a private tour with a very personable guide who picked us up and drove us to three very different wineries to learn more about how grapes are grown in Greece and how wine is made. The first winery, in Megalochuri, exhibited a smaller, family-run, intimate winery with a tasting of five wines. The second winery was a much larger and more modern operation where we tasted three wines along with a few other tourists. The last winery was tucked away in the hillside with a romantic, garden vibe where we gobbled up delicious dips, cheeses and more incredible wine!
We had a fascinating visit to the Central Market in Athens with its meat and fish market and the nearby spice, honey, olive, and deli shops. We also wandered through a lot of Athen's Plaka with its winding cobblestone streets, tourist shops, restaurants all with a view of the Acropolis above.
Our guide was superb taking us on a three hour walk through interesting neighborhoods to have us stop to taste some of the more unique food and drink of Athens. Cheeses, olives, wines, meats, honey, bougatsa, gyros, loukoumades, gelato, and a final stop to sip raki, ouzo, and mastiha. Oof! Our guide patiently gave us a lesson on the Greek alphabet which we promptly forgot after drinking the wine and ouzo!
We followed the Rick Steve's recommended walking tour for Old Town and learned so much about this unique town. Getting lost and wandering aimlessly was also a wonderful part of the experience! With the white buildings and blue accents, you truly explore this picture postcard town that is filled with sights, sounds, and smells never to forget!
Due to the timing of when our ferry arrived in Naxos, and the distance our hotel was from the Old Town Naxos, we never had a chance to truly explore Old Town.
Photographs do not do justice to the absolute beauty of Santorini. To truly take it in, we felt that we needed to walk the village streets, the caldera trail, and ride the buses. The clifftop towns and villages with their white buildings clinging to the hillside, the blue church domes, the views of the caldera were a photographer's dream.
The center of Heraklion is busy with tourists, vendors, street performers, and native Greek folk going about their lives. The history of Heraklion with its multiple historical/cultural influences is on display in the architecture and foods. Learning about the Minoan civilization was priceless and seeing the remnants of the presence of the Romans, Byzantines, Venetians, and the Ottomans was interesting. We spent a couple of hours exploring the Rocca a Mare Fortress or Koules which is a large harborfront fortress built by the Venetians in the 13th century.
Beautiful dinner on our last night in Greece overlooking the ocean as the sun set. A nice way to say our thanks and goodbyes to Greece for 19 wonderful days.
We met our guide, Goldy, a young Greek artist living in Chania for a three hour evening walk around the old part of Chania. Goldy brought the rich history of Chania alive as we walked and talked. She took us to an amazing spot to watch the sunset over Chania harbor and we ended up munching on delicious gyros at a family-run restaurant.