
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 $142 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 $95 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 $53 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 $1363 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 $166 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 $4217 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 $2726 USD
Half Day Athens Sightseeing Tour with Acropolis Museum
This tour gives you an opportunity to observe the striking contrasts that make Athens such a fascinating city. Our expert guides will take you to see the Panathenaic Stadium where the first Olympic Games of modern times were held in 1896 (short stop). Continue and pass by the Prime Minister's residence (ex Royal Palace) guarded by the Euzones in their colorful uniform, the Temple of Olympian Zeus, the Hadrian's Arch, the Parliament and the memorial to the Unknown Soldier, the Academy, the University, the National Library, the Constitution Square (Syntagma). On the Acropolis visit the Architectural Masterpieces of the Golden Age of Athens: The Propylaea, the Temple of Athena Nike, the Erechtheion and finally "the harmony between material and spirit", the monument that "puts order in the mind", the Parthenon. Continue and visit the place where at last the statues found their home and admire the wonders of the classical era: The new Acropolis museum.
From $151 USD
Santorini Private Sightseeing Tour
Explore magical Santorini on this Private Sightseeing Tour. After a convenient hotel, airport, or port pickup, craft your dream itinerary with a knowledgeable local guide and visit sites like the picturesque village of Oia, the beautiful Blue Dome Church, the Black and Red beaches. Enjoy a delicious glass of wine at a local winery and capture panoramic photos from Prophet Elias Monastery.
From $196 USD
Corfu Full-Day Private Sightseeing Tour
Enjoy a sightseeing tour at the best place in Corfu. From Kanoni admire the view of Pontikonisi island the small isle symbol of Corfu. Paleokastritsa is one of the most famous tourist place in Corfu island. This place has in fact very clear sea water and many lonely rocky coves which are fantastic for all those who love snorkeling. You have the opportunity to visit several lovely bays. . Angelokastro - “Castle of Angels” or "Angelos's castle" is located at the top of the highest peak of the island's shoreline in the northwest coast near Palaiokastritsa and is one of the most important Byzantine castles of Greece
From $260 USD
Shared Helicopter Tour Santorini 20 minutes - 2 passengers
As Austrian Company with a branch office in Greece we operate helicopters since 2008 all over Greece. We are an operator - not a Broker. Sightseeing in Santorini can be quite exhausting, especially during the summer months, as it gets crowded and really hot! But there is an alternative: you can fly over the island and go sightseeing on a helicopter. During the helicopter tour in Santorini, you will enjoy the great views to Oia, Caldera, and the volcano while flying over the island. The helicopter for this tour is our Robinson R44 - up to 3 passengers.
From $699 USD
Indulge to the beauty of Greece with the 4 days Classical Greece private tour
The four days private tour to Epidaurus, Nafplion, Mycenae, Olympia, Delphi and Meteora is a great value for money tour which is considered one of the most popular tours in Greece. If you wish to escape everyday life and see the best of Greece, you should not miss the chance for our Classical Greece Tour, which is a 4 days private tour in Greece. The essential sites of this private sightseeing tour in Greece include, among others, Epidaurus, Nafplion, Mycenae, Olympia, Delphi and Meteora. Highlights of the 4 days tour in Greece • You will be driving along picturesque and beautiful countryside in Greece • You will get to visit the important sites of Epidaurus, Mycenae and Delphi, as well as Olympia, the original birthplace of the Olympic Games • You will see the largest bridge in Europe, in Rio – Antirio • Travelers can customize the tour within the itinerary!
From $3224 USD
E-Bike Ancient Messini Way
The site of ancient Messene or Messini lies in a fertile valley approximately 30 km away from Kalamata. Picturesquely situated on a hillside the remains of this vast ancient city are one of Greece’s best-preserved archaeological sites and one of the most beautifully situated. Our guided e-bike tour here is a journey at the surrounding hidden gems of the ancient site inside a unique lush landscape. Your e-bike takes all the effort out of the ride, so you can absorb the awe-inspiring atmosphere of this Greek paradise. Additionally, once here one can enrich the overall experience with a self-guided tour inside the ancient city to get the full picture and the maximum experience of this amazing place.
From $101 USD
Private Santorini Full-Day Guided Sightseeing Tour
Enjoy personalized attention from your native Santorini guide and get an eye-opening look into historic places, listen to in-the-know commentary and capture marvelous island views. Travel in style as you hit the top attractions on Santorini. The more you discover, the more you'll want to see. The tour that includes Oia, Imerovigli, Firostefani, excavations of Akrotiri (by yourself), Red Beach, Black Sand Beach, Profitis Ilias, Pyrgos village or Megalochori traditional village, and Venetsanos winery or Agyros estate optional. The perfect way to get to know Santorini in one day.
From $302 USD
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