
Moussaka
Moussaka is a hearty baked casserole dish made with layers of eggplant, minced meat, and tomato sauce, topped...
Kalamata, nestled in southern Greece’s Messinia region, is famed for its lively waterfront, rich history, and gourmet olive oil. In early October, the weather is pleasantly warm, perfect for exploring the city’s Byzantine castles, open-air markets, and chic seaside restaurants with friends.
The city pulses with vibrant culture, from traditional dance performances to stylish rooftop bars overlooking the Gulf of Messinia. Indulge in luxury at high-end resorts, sail along the coast, or take a private wine tour—Kalamata’s blend of heritage and modern comfort makes it an excellent getaway for a group seeking a sophisticated and memorable escape.
Customized for these preferences:
Travel StyleTravelling with friends
Dates08-12 October 2025
BudgetHigh budget
AccommodationHotel, apartment or house, villa
Interests and Activities:
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Location
Peloponnese
Currency
Euro (EUR)
Religion
Greek Orthodox Christianity
Population
69,919
Language
Greek, English spoken
Electricity
230V, 50Hz, Type C/F
Time zone
UTCEET (UTC+2)
Country code
+30
Internet access
Widespread 4G/5G, fast broadband, moderate cost
Climate
Mediterranean, mild winters, hot dry summers
Language:
Greek
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goodbye
yes
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To reach Kalamata, the quickest way is by flying directly into Kalamata International Airport, which receives seasonal flights from many European cities, especially during warmer months. For a high-budget trip with friends, consider chartering a private jet or booking business-class tickets for extra comfort.
Alternatively, you can fly into Athens and take a luxury private transfer or hire a car for a scenic 2.5-3 hour drive to Kalamata. While trains are limited, intercity buses offer service from Athens, but a private transfer is more flexible for groups. October can bring occasional rain, but travel is rarely disrupted—just pack a light rain jacket.
Kalamata enjoys a Mediterranean climate, with hot, dry summers and mild, wet winters. Sunshine is plentiful from May through October, making it popular for outdoor sightseeing and beach visits. Gastronomy thrives year-round, with local olive oil and fresh seafood always in season.
From October 8 to 12, you can expect pleasant fall weather—daytime highs near 24°C (75°F) and cooler evenings. Occasional rain showers become more likely, but extreme weather is rare. Festivals and cultural events often celebrate the olive harvest, so it’s a great time to experience local arts, culture, and tours.
Kalamata is famous for its olives, high-quality olive oil, fresh seafood, and local specialties like kalamari gemisto (stuffed squid), lahanodolmades (cabbage rolls), and the sweet diples. Must-try drinks include local wines and ouzo. For high-end dining, visit Kastraki Meteoro, Oinopantopoleion 29, or Mia Zoi restaurant; for elegant coffee or cocktails, try Luna Lounge or Luna Lounge Bar.
Luxury seekers will love fish and seafood at DIONYSOS, or contemporary Greek tasting menus at Kardamo. Tipping in Greece is customary but not obligatory—rounding up the bill or leaving 5–10% is appreciated. Many restaurants cater to vegetarians and offer seasonal, fresh ingredients; always reserve ahead in summer due to high demand.
Moussaka
Moussaka is a hearty baked casserole dish made with layers of eggplant, minced meat, and tomato sauce, topped...
Souvlaki
Souvlaki is a popular Greek street food consisting of small pieces of grilled meat (often pork or chicken)...
Spanakopita
Spanakopita is a savory Greek pastry made with crispy phyllo dough and filled with a flavorful mixture of...
Dolmades
Dolmades are grape leaves stuffed with a seasoned mixture of rice, pine nuts, and herbs. They are often...
Baklava
Baklava is a sweet and indulgent pastry made with layers of finely shredded phyllo dough, honey, and chopped...
For a luxurious stay with friends, focus on high-end hotels along Navarinou Street near the beach, such as the Pharae Palace or Horizon Blu, both offering sea views and excellent amenities. Boutique hotels in the historic center, like Rex Hotel, offer charm and easy access to Kalamata’s nightlife and restaurants.
Splendid villas and upscale apartments are plentiful through Airbnb, Booking.com, and local agencies—ideal for groups seeking privacy and comfort. Look for villas with private pools or sea views in the Verga or Mikri Mantinia neighborhoods, just a short drive from the city center.
In October, accommodation prices are lower than summer, but book early to secure the best homes or suites for your group, especially during the Kalamata International Dance Festival or other local events.
Begin your journey by settling into Kalamata and experiencing its vibrant energy with a deep dive into local culinary delights and welcoming cultural experiences.
Kick off your trip with a premium guided tasting tour inside Kalamata’s bustling Central Market. Sample local olives, cheeses, honey, and artisanal sweets while learning about the region’s rich food traditions and meeting local producers.
Dive into Kalamata’s history at the Benakeion Archaeological Museum, home to fascinating artifacts from ancient Messenia. Enjoy a private guided tour to gain insightful context about the city’s past and its cultural evolution.
Savor Kalamata’s culinary excellence with a high-end dining experience at one of the city’s best seafront tavernas. Indulge in creative takes on traditional dishes, fresh local seafood, and regional wines with views of the Messinian Gulf.
Best Seller: Semi-Private Athens Morning Food Tour (15+ tastings)
Discover the Greek culinary culture on a 4-hour walking tour around Athens' food scene. Let your local guide lead you through the best food spots the historical city has to offer and indulge in 15 different tastings of local flavors. Browse through the vibrant Athens Central Market, visit local shops, bakeries, traditional taverns, and restaurants and taste your way through Athens like a local!
Organic Olive Grove tour & Olive oil tasting & lunch in Kalamata!
An experience designed for olive oil and nature lovers who have a passion for olive oil, nature, tradition and traditional Greek gastronomy! Along with our professional and certified expert, you’ll discover the key aromas, flavours & tastes and will learn which olive-oil variety to pair with your favourite food. Everything that you need to know about this gift from the nature, you will learn it along with people who have a great passion and love about olive trees and olive oil! Light or Full lunch (optional, upon request and at an extra charge) If you wish to conclude your olive oil experience with a delicious light or full lunch, full of Messinian flavours, in one of the most welcoming family restaurants in the heart of Kalamata’s historic centre, just let us know and we can arrange it for you! A memorable, private and personalized experience exclusively for you and your beloved ones, because, once booked for the day no other guests are added in the experience!
From $143 USD
Athens Greek Food Tour Small-Group Experience
Join us on a delicious journey around Athens through the city’s most foodie neighbourhoods and experience Greek gastronomy at its best. Our small-group (10-12 ppl) ensures ultimate personalisation, flexibility and safety. - Start off at a deli to learn all about the renowned Mediterranean diet, sampling iconic flavors like Kalamata olives, traditional local cheeses, and rich tapenades. - Indulge in the famous Greek street food scene, tasting fresh and flavorful bites that locals love. This is your chance to experience the casual, lively side of Greek cuisine. - Enjoy a small plates meal and savour authentic, comfort Greek cuisine served with a local drinks at a family-run restaurant. Learn about Greeks' way to get together and have fun! - Satisfy your cravings with finger-licking local desserts and a special-flavoured local product found exclusively in Greece! Vegetarians rejoice! There are options for you in every spot. Contact us for PRIVATE tour requests (at an extra cost).
From $96 USD
Olive oil Mill Visit-Kalamata Olives and Olive oil Tasting
Enjoy an authentic experience, in a small greek village and discover the olive culture of Greece!Visit a modern Olive Mill and an olive oil Press-Museum and be amazed by the story and the taste of the famous kalamata olives and the extra virgin olive oil! Local goods are "paired" with olive oil so as to experience the full taste of the region.Open up to the olive world, taste the extra virgin olive oil of Kalamata and explore the culture, the tradition, and the gastronomy of Messinia.
From $54 USD
Private Athens Morning Food Tour (15+ tastings) - Best Seller
Our amazing private and personalized walking food tour promises to cast light on the city’s tastes and culinary customs. Watch locals shop at the Central Market, chat to vendors, and visit traditional food spots for 15 tastings of treats such as pies, loukoumades, home-cooked main dishes and desserts, all accompanied by food stories and tips you’d otherwise miss. Entirely customizable and definitely fun, this food tour will leave you full of food and fond memories!
From $167 USD
4 Days Classical Private Tour/ Corinth,Mycenae,Nafplio,Sparta,Olympia,Delphi
We visit Greece, Corinth, Sparta, Ancient Olympia, Nafplio, Mycenae, Delphi, Thebes... as travelers, not as tourists. Schedule is flexible, but most importantly our drivers are seasoned travelers and are dedicated to helping you live the tour of your life, that is suited to your needs and lifestyle, allowing all passengers to enjoy the scenic drive, stopping wherever you desire, take photos, have a break, swim. Like all vacations in Greece local food is high in our list of things to do, we will taste local gastronomy and wines We can arrange accommodation for you in selected Boutique Hotels A'class or 3/4* Hotels with breakfast at an additional cost from 140€ per double room / weekend-holidays 160€ per double room - if more than 2 rooms 10% less. (Driver's room complimentary).
From $1372 USD
Greece cultural tour 12 days from Athens; Greece mainland UNESCO places.
This off-season balanced tour is aimed for people who interesting in the history of Greece, to walk that ancient historical places where are roots of culture of our civilization. During this tour we will visit 6 places that are on the list of UNESCO. Many other we going to visit places now expecting to be on UNESCO list; such places are prepared, available for public for fraction of cost, and are on so called UNESCO tentative list.
From $4244 USD
8 Days Peloponnese: Sightseeing, Historical & Tasting Private Tour from Athens
Take a unique sightseeing & photography small group size tour, which will guide you not only in Greek History (Bronze Age to modern times), but guide you also into landscape and scenery photography. We visit majestic Peloponnese and photograph the most interesting ancient & medieval sites, castles, monasteries, villages, landscapes. Tour is also about sunset and sunrise photography so be prepared to venture into the most beautiful sceneries for our photography historical trip. Like all vacations in Greece local food is high in our list of things to do, we will taste local gastronomy and wines Nikolaos your driver is a professional artist and worked as photographer & portrait painter for websites & newspapers. His passion not only for History, but for architectural, landscape and people photography led him to pursue photography tours. Kalavryta, Olympia, Pylos, Methoni, Mani/ Cape Tenaron, Monemvasia, Sparta, Nafplion... are his best choices in Peloponnese. See his photos & portraits
From $2743 USD
Athens Full Day Private Tour
Explore Athens in a private, full-day experience that brings together heritage, comfort, and local knowledge. Visit the Acropolis, Panathenaic Stadium, and other significant landmarks — guided by a professional driver who offers thoughtful insights. Enjoy a relaxed pace, a personalized route, and the freedom to discover the city without the limits of fixed itineraries or group constraints. This tour is designed for travelers who value authenticity, seamless organization, and unforgettable moments. Full-day private Athens tour with knowledgeable local driver Custom itinerary with flexible timing Private air-conditioned vehicle with pickup and drop-off Authentic experience suited to all group types
From $203 USD
Footsteps of Apostle Paul from Athens to Corinth, Private Day Tour
This tour gives us the opportunity to visit and explore the places where St. Paul preached to the ancient Greeks in Athens and Corinth, in a day. The tour starts by visiting the “Areos Pagos” (literally, Mars Hill) at the foot of the Acropolis. Continuing our tour to our next stop, the “Agora”, we’ll have the opportunity of a sightseeing in the centre of Athens. (Temple of Zeus-1896 Olympic stadium-Presidential Palace-Greek Parliament-Changing of the Guards). With our visit to the “Agora” we conclude the Athens part of our tour and we continue to visit Corinth and the Corinth Canal. The Canal (approx. 6 km long connecting the Aegean with the Ionian Sea)where we have a brief stop for photos. Then we visit Ancient Corinth where we visit the museum and the archaeological site where the “Bema” is. We conclude our tour in Corinth with lunch in a traditional Greek taverna and we start our return trip to Athens via Kechries, the port of Corinth from where St. Paul sailed to Ephessus.
From $283 USD
Private Day Trip To Delphi
Our 25 years experience and the combination of stunning natural scenery and the legacy of a fascinating and diverse cultural heritage of Delphi makes this day trip from Athens an irresistible option. You will discover the fascinating historical, cultural and geographic landscape of the regions
From $302 USD
Athens Sightseeing Private Tour
Athens, the oldest city in Europe. This 4 hours tour gives you the opportunity to observe the striking contrasts that make Athens such a fascinating city. Ancient Athens is one of Europe's oldest cities, one with a continuous history whose beginnings can be traced some 5.000 years ago. The Greek capital is known as the cradle of democracy and western civilization, a vibrant cosmopolitan hub with a rich culture, a long history and a mild climate. Where Socrates, Plato and Aristotle once became active, today are housed breathtaking archaeological sites and Museums such as the Acropolis including Parthenon and picturesque alleys in Plaka.
From $185 USD
Accessible Tour In Athens, 3 Hours Athens Panorama Shore Excursion
This Accessible tour in Athens is designed for people with limited mobility or in a wheelchair. The Athens Panorama private tour - shore excursion lasts approximately 3 hours, it is a relaxed tour, that allows you to make the most out of your visit to the city. It combines the modern and ancient parts of the city and is truly worth taking. Highlights Of The 3 Hours Athens Panorama Accessible Tour In Athens - It is a harmonious mixture of ancient and modern Athens - It includes all the major sites of Athens, such as Plaka, Syntagma Square, Panathenaic Stadium, Kolonaki-the high end neighbourhood of Athens, Lycabettus – the highest hill of Athens - Admire the Acropolis and the Parthenon without the strenuous climb to the top of the hill - Pickup and drop off at your cruise terminal or your hotel in Athens by an English-speaking tour driver - Travelers can customize the tour within the itinerary!
From $286 USD
5-Day Peloponnese Greece Adventure
This is a 5-day tour like no other in the Peloponnese because it combines all the must-see archaeological and historical sites with the most beautiful, off the usual touristic track, scenery of the region. From Ancient Corinth, Olympia, Messini, Mycenae and Epidaurus to medieval towns of Nafplion, Monemvasia, Methoni, Pylos and Mystras, to spectacular caves of Diros and the Natural habitats of famous Voidokilia and Peroulia beaches, this is one of its kind experience. Marvel at the local traditional cuisine on seafront fish selected restaurants with spectacular view and rest in 4 star exceptional hotels. Travel with our new private luxury MERCEDES BENZ limos - minivans - minibuses in safety,comfort and style and let your local professional English speaking tour driver to make you feel like a local.
From $2201 USD
Private Sailing Parties and Events Cruise 4 or 7 Hours
A private boat chartering to serve all your parties and events to give you a uniquely one of a kind experience. Plan engagements, birthdays, vow renewals, or just a special day away from the ordinary.
From $960 USD
4 Days Christmas in Greece Private Tour
Live the experience of Christmas in Greece! You may not believe it but in Greece winter means cold, snowmen and elves! Travel back in your childhood and feel like a local...
From $1431 USD
An exciting exploration of Peloponnese at ancient Corinth, Mycenae and Nafplio
Highlights of this tour to Corinth, Mycenae, Nafplion • The impressive Corinth Canal • The archaeological site of Ancient Corinth with its agora and museum • The Arched Tombs of the Kings and the Lion’s Gate in the archaeological site of Mycenae • The picturesque town of Nafplio • The inviting landscape of the Peloponnese Peninsula • Travelers can customize the tour within the itinerary!
From $501 USD
Private Day Trip to Sparta from Kalamata (Price per Group)
Enjoy a full-day adventure to the city of Sparta. A city which offers you a ‘laconic’ journey back in time throughout Greek history. Begin the 2-hour drive from Kalamata with a convenient pickup at your hotel, then ride in a comfortable, climate-controlled vehicle over the scenic Taygetos mountains. See significant sites in both modern and historic Sparta, including the Acropolis of Ancient Sparta, the Olive Oil Museum, and more on this guided, small-group tour. Take a full-day private tour to historic Sparta in an air-conditioned vehicle. View the stunning landscape of the Peloponnese peninsula. Learn the history of Ancient Sparta from an informative leader. Enjoy the convenience of hotel or cruise port pickup and drop off.
From $596 USD
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From US $139 for 7 days cover
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