Duration: 12 Days / 11 Nights

Availability: April to October

from $2700 CAD

INDULGE IN LUXURY UPGRADES

Accommodation:

  • Exclusive stays in luxury resorts, boutique hotels, or historic castles
  • Private villas with personal butlers and chefs
  • Rooms or suites with panoramic views
  • Amenities such as Private Pools / Jacuzzis

Transportation:

  • Luxury VIP vehicles
  • Private chauffeur-driven cars or limousines
  • First-class or private jet travel
  • Helicopter transfers between destinations
  • Luxury yacht charters for coastal or island hopping
  • First Class VIP Ferry tickets

Activities:

  • Private personalized guided tours with expert guides or escorts
  • Private access to museums, art galleries, and historical sites
  • Customized adventure activities like hiking, Sea Kayaking, Biking, Rock climbing or scuba diving
  • Spa and wellness packages with exclusive treatments and facilities

Dining:

  • Gourmet dining experiences at Michelin-starred restaurants
  • Private chef-prepared meals in unique settings (e.g., beach, vineyard, rooftop)
  • Wine and champagne tastings with sommelier-guided tours

Personal Services:

  • 24/7 personal concierge services
  • Customized itineraries tailored to individual preferences
  • Special arrangements for celebrations, such as weddings, birthdays or anniversaries
  • Private shopping experiences with personal shoppers

Entertainment:

  • VIP access to concerts, theater shows, or sporting events
  • Private screenings at iconic movie theaters
  • Behind-the-scenes tours of film studios or fashion houses
  • Nightlife concierge services for exclusive club access

Wellness and Relaxation:

  • Exclusive access to world-class spas and wellness retreats
  • Yoga and meditation sessions in serene natural settings
  • Private beach or poolside cabanas with dedicated staff

OVERVIEW

Embark on a captivating self‑drive adventure from historic Athens to sun‑soaked Kalamata and medieval Monemvasia. Discover scenic coastlines, ancient sites, charming villages, and authentic Peloponnese culture at your own pace on this unforgettable Greek journey.

  • Athens: The capital and largest city of Greece, famous for its ancient history, culture, and monuments. Explore the Acropolis, the Parthenon, the National Archaeological Museum, and more.
  • Kalamata: A vibrant coastal city in Messenia, known for its long sandy beach, historic Old Town, scenic castle views, rich olive‑oil heritage, and lively food culture. Visitors enjoy museums, waterfront strolls, and easy access to nearby natural and archaeological sites.
  • Monemvasia: A breathtaking medieval fortress town carved into a rock island, offering cobbled alleys, Byzantine churches, sea views, and timeless charm—an unforgettable blend of history, romance, and serenity.

This is a tailor-made itinerary flexible and independent.

We can alter this itinerary from accommodations to excursions based on individual preferences and recommendations from your travel advisor.

PACKAGE INCLUDES

  •  3 Night Accommodations in Athens w/breakfast
  • 4 Night Accommodations in Kalamata w/breakfast
  • 4 Night Accommodations in Monemvasia w/breakfast
  • Rental Car Manual or Automatic Compact with Unlimited mileage
  • Half-day shared guided tour of Acropolis & Acropolis Museum
  • Entrance fees
  • All transfers on a private basis
  • Hotel taxes & VAT

 

ACCOMMODATIONS

Your itinerary and its accommodations are based on your requirements, budget, and recommendations from your travel clients/advisor’s trip assessment.

  • Your choices are from 3-star, 4-star, 5-star hotelsboutique hotels, bed and breakfasts or villas.
  • The appropriate accommodations that fit your requests will be included in your itinerary/quote
  • Because we value quality, we do not work with hotels that are less than 3-stars
  • Our direct collaborations help us receive the best pricing possible and the most competitive pricing

Day 1: Athens

Arrive at Athens International Airport and transfer to your hotel for check in. The remainder of the day at leisure to enjoy your first taste of Athens and rest after your flight. Discover Plaka, the oldest district of Athens, located under the Acropolis, the only district where you may see the Greek capital as it was 100 years ago or enjoy a spot of shopping at Ermou, Kolonaki and Voukourestiou streets.

Day 2: Athens

Athens City Tour & Acropolis Museum (S.I.C.) – 5.0H: From the Acropolis to Omonia Square, with the half-day sightseeing and Acropolis museum tour you’ll see all the famous sites of ancient and modern Athens on this comprehensive morning tour. Hear insightful commentary from your guide and pass top Athens attractions including the Tomb of the Unknown Soldier, Greek Parliament building and Presidential Palace. Offering a perfect overview of the modern city, this guided half-day tour will help you get your bearings if this is your first visit to Athens. Begin your carbon-neutral Athens half-day tour with a photo stop at Panathinaiko Stadium where the first Olympic Games took place in 1896. It is the only stadium built out of white marble. Proceed, passing by Zappeion and Temple of Olympian Zeus. You will then pass the Athens Trilogy which includes the University of Athens, the Academy of Athens, and the National Library. Continue passing by National Garden, Hadrian’s Arc, St. Paul’s Church, Parliament, Tomb of the Unknown soldier, Schliemann’s House (Numismatic Museum), Catholic Cathedral, Old Parliament, Constitution Square ,Russian Orthodox Church, and finally ACROPOLIS (visit Propylae the gateway, Temple of Athena Nike, Parthenon, Erechtheion with its Porch of Maidens). Stroll up to the UNESCO-listed site that served as the ancient citadel, and tour the buildings as you hear how they reflected Athens’ prosperity in the 5th century BC. Continue the expert guided Athens sightseeing and museum tour with a pleasant short walk passing by Herodion and Dionysos Theater, in order to visit the ACROPOLIS museum. Avoid and skip the lines of the new museum. Main attractions such as votives, artifacts of every day life, statues from archaic period, Caryatids, and of course the Parthenon hall with the metopes, the pediments and the frieze will impress you.

INCLUDES: EXCLUDES:
  • Transport by luxury A/C bus
  • Acropolis & Acropolis museum entrance fees
  • Hotel Pick up and drop off service
  • Services of a Professional and licensed guide
  • Whispers
  • All taxes
  • Gratuities (optional)
  • Personal expenses

DAY 3: ATHENS - KALAMATA

Athens to Kalamata via Nafplio (approx. 295 km / 4.5 hrs): Collect your rental car and cross the Corinth Canal, a dramatic engineering cut linking the Aegean and Ionian seas—perfect for a short photo stop. Continue to the romantic town of Nafplio, Greece’s first modern capital, and wander its marble lanes and bougainvillea‑draped squares before ascending (or driving up) to Palamidi Fortress for sweeping gulf views. In the late afternoon, drive onward through Argolida and Arcadia to seaside Kalamata. Check in and enjoy a relaxed evening on the promenade. Overnight in Kalamata.

DAY 4: KALAMATA

 

Kalamata Old Town & Beach Time: Discover Kalamata’s characterful Old Town, visiting the Church of Ypapanti and the Historical & Folklore Museum to learn how the city blossomed through trade and olives. Continue to the waterfront for a leisurely lunch of Messinian cuisine, then unwind on Kalamata Beach, where organized sections offer loungers, cafés, and sunset views across the Messenian Gulf. Optional: a guided olive oil tasting introduction. Overnight in Kalamata.

DAY 5: KALAMATA

Ancient Messene & Coastal Relaxation: Set out for Ancient Messene, one of Greece’s best‑preserved archaeological sites, where the theater, stadium, and fortifications convey the scale of this Hellenistic city in a serene rural setting. After your visit, return via the coast for a lazy afternoon at Santova or Mikri Mantinia Beach, alternating swims with seaside taverna tastes—fresh fish, village salads, and local wines. Overnight in Kalamata.

 

DAY 6: KALAMATA

Mani Peninsula & Diros Caves: Drive south into the storied Mani, a land of stone towers and dramatic capes. Pause in elegant Kardamyli, immortalized by Patrick Leigh Fermor, then continue to Areopoli with its stone‑paved streets and tower houses. Highlight the day with a boat ride inside the Diros Caves, gliding through subterranean chambers of stalactites and mirrored waters. Return to Kalamata by sunset along coastal roads framed by olive groves and sea. Overnight in Kalamata.

DAY 7: KALAMATA - MONEMVASIA

Kalamata to Monemvasia (approx. 195 km / 3 hrs): Follow a scenic route across Laconia’s landscapes toward Monemvasia, a medieval stronghold dramatically fused to a rock island by a slender causeway. Check into your boutique hotel—ideally within the castle walls—to soak up the unique ambiance of cobbled alleys, Byzantine chapels, and stone manors. Enjoy a candlelit dinner in the Lower Town with sea breezes and starry skies. Overnight in Monemvasia.

DAY 8: MONEMVASIA

The Fortress City of Monemvasia: Dedicate the day to exploring Monemvasia at a gentle pace. Wander the Lower Town’s labyrinth before ascending to the atmospheric Upper Town for panoramic views that sweep across the Myrtoan Sea. Visit the cliff‑perched Church of Agia Sofia, one of the fortress’s most photogenic landmarks, and break for coffee in a vaulted café. In the afternoon, browse local cellars for Laconian wines and artisanal products, then linger for sunset gilding the stone walls. Overnight in Monemvasia.

DAY 9: MONEMVASIA

Day Trip to Elafonisos (drive + ferry ~1.5 hrs each way): Set off early for the small ferry from Pounta to Elafonisos Island, famed for Simos Beach—twin crescents of fine sand and luminous turquoise waters that rank among Greece’s most stunning. Spend an unrushed day swimming, relaxing on the dunes, and sampling island specialties at beachside tavernas before returning to Monemvasia in the golden hour. Overnight in Monemvasia.

 

DAY 10: MONEMVASIA

Villages & Flavors of Laconia: 

Explore the surrounding Laconian countryside with unhurried visits to stone villages such as Nomia, Talanta, and Velies. Stop at an olive estate to learn about cultivation and taste premium extra virgin olive oils, perhaps pairing with local cheeses and rusks. Back in Monemvasia, enjoy a final evening inside the castle, taking in the quiet magic of lantern‑lit lanes and the rhythmic sound of waves at the ramparts. Overnight in Monemvasia.

DAY 11: MONEMVASIA - ATHENS

Monemvasia to Athens (approx. 320 km / 4.5 hrs): Depart after breakfast for the drive north to Athens, passing through the Peloponnese’s rugged hills and plains. Upon arrival, return rental car and choose between a cultural afternoon—Benaki or Cycladic Art Museums—or coastal downtime along the Athens Riviera via tram. Celebrate your last night with a fine‑dining experience or a casual meze feast in buzzing Psyrri. Overnight in Athens.

DAY 12: ATHENS DEPARTURE

On your final day, enjoy a relaxed morning before your scheduled departure. A private transfer will take you from your hotel to Athens International Airport, ensuring a smooth and comfortable end to your journey. With unforgettable memories of ancient sites, scenic drives, and coastal charm, your self-drive adventure through the Peloponnese comes to a close.

TOUR INCLUDES:

  • 3 Night Accommodations in Athens w/breakfast
  • 4 Night Accommodations in Kalamata w/breakfast
  • 4 Night Accommodations in Monemvasia w/breakfast
  • Rental Car Manual or Automatic Compact with Unlimited mileage
  • Half-day shared guided tour of Acropolis & Acropolis Museum
  • Entrance fees
  • All transfers on a private basis
  • Hotel taxes & VAT

TOUR EXCLUDES:

  • International flight tickets
  • Personal expenses
  • Customary tips to drivers, guides and escorts
  • VISA expenses, if necessary
  • Accommodation tax: per room per night, pay directly to the hotel