The olive road · CHEESE
Good cheese tastings take small groups and the best-known ones fill weeks ahead. Below: the 12 to book early, what each includes and how they differ.
Spend seven hours in rural Crete with a local English-speaking guide, often Linda or Electra. Visit the ancient Olive Tree of Vouves, a bakery, cheese maker, honey and olive-oil producer, and family winery. Tastings include Cretan breads, cheeses, honey, olive oil, local delicacies, and up to 20 wines.
“Our guide was amazing. She truly loves her job. Very enthusiastic and knowledgeable”
Join a small tasting beneath the Acropolis for five Greek wines, five regional cheeses, olives, and bread rusks. Your English-speaking wine expert, such as Tonia, Theo, Anastasia, or Evalina, explains Greek grapes, wine regions, tasting technique, and the stories of Dionysus through a virtual vineyard tour.
“We learned a lot about Greek wine and history of Greek wine, Anastasia was a great teacher and very friendly. Highly recommended if you are into wine”
Start at 5pm in Piazza Torquato Tasso for a 2.5-hour walk through Sorrento’s lanes, history, lemon growing, artisans, and food traditions. Guides such as Nino, Georgia, Sandra, Giovanni, and Alexandra lead tastings of cheese, salami, olives, bruschetta, olive oil, wine, and limoncello. The group is limited to 15 people.
“This was such a great way to see Sorrento. The first part was a short walking tour and then we stopped and had some of the most delicious cheeses, meats, bruschetta along with wine etc. The lemon tour and vineyard was also a major highlight with limoncello! Do this when you first arrive!”
Spend a full day in Stellenbosch tasting South African wine, chocolate, cheese and olives at several estates. Guides such as DD, Dee, Elma and Elmer are praised for clear explanations, flexible pacing and strong food-and-wine pairing advice. Pickup and drop-off are included, with groups capped at 13.
“We didn't expect a private tour so it was a nice surprise Visited 3 places all lovely in their own right. Our guide not sure about spelling - Elmer was very knowledgeable Took the tour at a good pace and didn't force us into going anywhere too heavy for lunch as we only really wanted a sandwich. Picked us up on time at our hotel with no problem”
Meet Elisabeth at Il Fiorello Olive Oil Company in Fairfield for a two-hour tasting on her family’s olive farm. Walk through the grove, learn how to judge extra virgin olive oil, pair oils with snacks, then taste Northern California wines and two local cheeses. The small-group format keeps the experience personal and easy to follow.
Visit Podere la Marronaia, an organic family farm about 800 meters from San Gimignano, for four wines, six olive oils, local cheeses, bruschette, and a truffle-based meal. The outdoor setting looks toward the town towers and nearby vineyards. This private, English-language tasting lasts about 45 minutes and does not include transport.
“This was a nice little surprise to find a charming vineyard in San Gimignano that was small and family owned and there for generations. The wine, olive oil and balsamic vinegars was delicious!”
Spend about three hours with a Cretan family at their olive groves and greenhouses. Learn about olive harvesting and sustainable farming, taste extra virgin olive oil, watch Mama Stela make cheese, and share homemade Cretan food, juices, and raki beneath a wooden roof. Groups are limited to 12.
“The tour was really nice! Especially because it's a private tour so it was just the two of us. They prepared real Cretan food which we had not tried before on the island. It was really delicious! The stories about the farm were really interesting and it was great to learn more about olives. We were so pleased we went on this tour and we highly recommend it”
Marianna Papagrigoriou and her family welcome you to Cretan Vibes Farm for a 2.5-hour look at rural Crete. Walk through olive groves and greenhouses, learn how extra virgin olive oil is made, watch Mama Stela prepare mizithra cheese, then share homemade food, refreshments, and Raki beneath a wooden roof.
“Hôtes très agréable, ambiance sympathique. Je recommande !!”
Spend one hour with sommelier Anton tasting six organic, biodynamic, natural, and orange wines from Greece. Pair them with cheese, small nibbles, herbs, spices, grape must, and extra virgin olive oils while learning how ancient grape varieties and modern winemaking shape each glass. The tasting is in English and suits adults interested in wine, food, and Greek traditions.
“Thank you for an amazing wine tasting! We really enjoyed everything - the history and stories about the Greek wine, and of course the taste of it! The owner of the wine shop is enthusiastic and warm, and we felt very lucky to have found this place. We recommend this wine tasting for everyone interested in learning about wine and Greece in general.”
Spend about eight hours touring three wine estates on the Franschhoek, Stellenbosch, or Paarl Wine Routes. Your driver-guide handles hotel pickup, transport, and commentary while you taste wine with chocolate and cheese, plus olive oil at selected estates. Groups are capped at 12, and guide Elmo is praised for his wine expertise.
“Everything was perfect. Our guide Elmo was extremely knowledgeable on wine tasting and we learned a lot. Had an amazing time”
Travel by car from Florence’s main train station to Fattoria Palaia in the Chianti countryside. Sommelier Leonardo leads tastings of 10 organic Tuscan wines and 10 Italian cheeses, followed by a traditional lunch with pasta, olive oil, and balsamic vinegar. The small group is limited to eight people and returns to Florence after about five hours.
“Wineing and dining in Tuscan province is always something great but Leonardo - the wine master and the owners of the Factoria Palaia make it exceptional. The setting is picturesque, located at the hill, overlooking vineyards and olive gardens. You can dine outside and experience the sunset over the valley.”
Meet at Balu' Cookinpuglia in Lecce’s old town for a one-hour tasting led in English or Italian. You’ll compare three Puglia extra virgin olive oils, pair them with regional cheeses, and enjoy one glass of wine. Michale has been praised for explaining the oils and choosing local cheeses and wines.
“We very much enjoyed our olive oil cheese and wine - it was super interesting to hear about the olive growing in Italy and have a professional take us through the tasting of the different oils”
By what you do, not by what is nearest.
