The Ultimate Two-Week Peloponnese Itinerary

  • Travel and Leisure
  • Fodors
  • USA Today
  • New York Times
  • National Geographic
  • Washington Post
  • Vogue
Price
from $5,400
Duration
15 days
Destinations
Athens, Nafplio, Monemvasia, Kalamata, Ancient Olympia, Athens

Get a price estimate for this trip

Month of travel
Month of travel
No. of travelers
No. of travelers
Accommodation level
Accommodation level
Route for Athens, Nafplio, Monemvasia, Kalamata, Ancient Olympia, Athens tour

If you're looking to experience the real Greece, look no further. This two-week itinerary across the charms of the Peloponnese, this rugged region in Southern Greece that screams authenticity and diversity, is your ticket to a Greek adventure to remember. After a mandatory stop in Athens to explore its historic treasures and take in its vibrant ambiance, your trip across the Peloponnese starts in quaint Nafplio, a seaside town steeped in history. From there, more history awaits in Ancient Olympia, the birthplace of the Olympic Games. Your next stop is Costa Navarino, an exclusive resort set in a location of rare natural beauty, before you continue to Mani, one of the most untouched sub-regions in Greece, a land steeped in legends and myths. Speaking of myths, no word can better describe your next destination than mythical. Monemvasia, this windswept fortress town built on a rock in the middle of the sea, is a dreamy place to visit. Your final stop before you head back to the Greek capital is Sparta, known for its ancient past and the medieval wonder that is Mystras.

One of our team members in Greece will be available to you leading up to and during your trip to answer any questions and arrange local services. You will receive access to your Guest Page, with its information on the best these destinations have to offer, including things to see and do, and other inside tips from restaurant recommendations to tipping advice. Upon arrival, we will provide you with a local SIM card or eSIM with data that you can use to reach your local JayWay contact throughout your trip. In all of our destinations, we offer a variety of memorable 3-5 star accommodation options, including boutique hotels and charming B&Bs. With our firsthand experience, we can ensure they are all clean, comfortable, and centrally located, with local ambiance.

Itinerary

  1. Day 1 Arrival in Athens

    Although it's hard to not keep craning your head to take in the spectacle of the Acropolis at the center of town (especially when it's lit up at night), there's more to Athens than its dense concentration of ancient ruins. Athens is a center for contemporary art, with modern galleries sitting beside museums stuffed with art dating back millennia. This combination of the old and new is especially clear at the Odeon of Herodes Atticus, a spectacular open-air theater that has hosted concerts and plays for nearly 2,000 years. The city's culture is also reflected in its diverse food and drink, which combines traditional Greek favorites with influences from across the Mediterranean, and the world, as fitting Athens' deep history as a humming harbor hub. While Athens' variety is enough to keep you busy, from the hidden back alleys of the center, to the city's showy coast, the city works well as a base for day trips, whether down the coast, or to the Peloponnese. Head to oracular Delphi, or hunt for where Lord Byron's carved his name into the monumental Temple of Poseidon at the tip of Cape Sounion.
    Upon your arrival in Athens, a driver will meet you and drive you to your centrally located accommodation. The drive takes about 45 minutes, depending on traffic.
    Our representative will then meet with you to answer any questions you have and to get you settled for the rest of your trip.
    Love at First Sight

    Love at First Sight

    Athens has plenty of rooftop venues to take advantage of the opportunity to see the Acropolis shining at night. They have become popular hubs for nightlife among locals. One of our favorite rooftop bars is POINT A (Acropolis Point), which is the only bar that provides views of both the Acropolis and the modern elegant lines of the Acropolis Museum, lit beautifully at night. POINT A has a relaxed vibe and Greek cuisine with a twist. It’s perfect for couples and even families or groups of friends. If you happen to stay around the Monastiraki district, you should definitely visit A for Athens cocktail bar and restaurant, a popular venue among locals. Hytra and GB Roof Garden are full-on luxury restaurants and bars that can provide perfect romantic evenings. We guarantee that if you spend your first night dining at one of those places, you will quickly fall in love with the mind-blowing views and lively city.

    Suggestion to explore on your own

  2. Day 2 Your First Full Day in Athens

    Athens Highlights Mythology Group Tour

    Athens Highlights Mythology Group Tour

    Discover the myths behind the greatest landmarks in Athens. Learn about Greek gods and heroes, and discover what really hides behind ancient myths. At the same time visit the best landmarks and sites in Athens, such as the Acropolis (Parthenon, theater of Dionysus, temple of Athena Nike, temple of Erechtheion, and the sanctuary of Asclepius), Olympian Zeus’ temple, the Ancient Agora, and the temple of Hephaestus.
    • Activity Level : Moderate
    • Duration : 4 hours

    Included in your vacation package price

  3. Day 3 Traveling to Nafplio by Private Transfer / Arrival in Nafplio

    Nafplio by Private Transfer with a Quick Stop for Photos at the Corinth Canal
    Today, a private driver will take you to the beautiful Nafplio. You'll depart in the morning based on your preferred departure time, and the driver will pick you up at your accommodation in Athens. Along the way, you'll make a short stop to see the Corinth Canal and have the opportunity to take some photos. Please note that this is a non-guided transfer. The duration of the journey is about two hours, not including the time spent at your short stop.
    Steeped in history and almost unbearably romantic, Nafplio is one of the most picturesque seaside towns in Greece. Nafplio's dramatic fortresses, neoclassical mansions, and nearby ancient ruins narrate the town's diverse history, a pivotal moment of which was when Nafplio became the first capital of modern Greece. While in Nafplio, you can take long seaside walks, savor authentic cuisine at quaint traditional restaurants, and visit UNESCO-listed archaeological sites, only a short drive away.
    Upon arrival to Nafplio, your driver will take you to your centrally located accommodation.
  4. Day 4 Your First Full Day in Nafplio

    Nafplio Town Private Walking Tour

    Nafplio Town Private Walking Tour

    This charming walking tour, with a licensed guide, is around Nafplio, Greece's first modern capital. Wander the old town's enchanting alleyways and immerse yourself in captivating tales and rich heritage. Discover architectural wonders like the First Parliament and the Archaeological Museum. Delve into Nafplio's fascinating history and timeless allure.
    • Activity Level : Light
    • Duration : 1 hour

    Included in your vacation package price

  5. Day 5 Your Second Full Day in Nafplio

    Mycenae & Epidaurus Private Tour

    Mycenae & Epidaurus Private Tour

    On this private guided tour, you will first visit ancient Mycenae, where myths of King Agamemnon come to life amidst UNESCO-listed ruins like the Cyclopean Walls and the Lion's Gate. Then, you will explore the Archaeological Museum of Mycenae to delve deeper into the civilization's sophistication and wealth. Then, journey to Epidaurus, home to a renowned ancient theater celebrated for its remarkable acoustic design. Discover its significance as a healing sanctuary dedicated to the god of medicine, Asclepius, and visit its museum, too.
    • Activity Level : Light
    • Duration : 5 hours

    Included in your vacation package price

  6. Day 6 Traveling to Monemvasia by Private Transfer / Arrival in Monemvasia

    Monemvasia by Private Transfer
    Today, you will leave Nafplio and travel to Monemvasia. A driver will pick you up at your accommodation based on your preferred departure time and take you on a three-hour journey. Please note this is a non-guided transfer.
    A stranded rock in the Aegean Sea, a medieval castle town, and endless tales of conquerors and merchants render Monemvasia a true fairytale destination in Southern Greece. Often nicknamed The Gibraltar of The East, Monemvasia Castle is one of the finest examples of defensive architecture, offering travelers the once-in-a-lifetime opportunity to spend the night within the walls of a sleepy yet exciting fortress where time seems to have stood still. From walking along dramatic ramparts to sipping local sweet wine on a terrace overlooking the deep blue sea to waking up to the most majestic sunrise, Monemvasia will make you feel as if you're stepping inside a dream.
    Upon arrival to Monemvasia, your driver will take you to your centrally located accommodation.
  7. Day 7 Your First Full Day in Monemvasia

    Monemvasia Lower and Upper Town Private Tour

    Monemvasia Lower and Upper Town Private Tour

    On this private tour of Monemvasia's Lower Town, 14 centuries of history await you in the 'Gibraltar of the East'. Explore living archaeological sites and delve into the city's rich maritime heritage, once a bustling port renowned for its exquisite wines. Ascend to the Upper Town's archaeological site, discovering remnants of aristocratic residences and marveling at the Haghia Sophia church with panoramic views of the Aegean Sea. Wander through hauntingly beautiful ruins and capture breathtaking panoramas, immersing yourself in Monemvasia's timeless allure.
    • Activity Level : Moderate
    • Duration : 2 hours

    Included in your vacation package price

  8. Day 8 Your Second Full Day in Monemvasia

    Private Cooking Class Experience

    Private Cooking Class Experience

    Join a local chef on a journey into selective Greek gastronomy, uncovering ancient culinary secrets amidst lush surroundings. Step into the enchanting oasis of Liotrivi Historical Mansion's garden, where nature and culinary delights converge in your outdoor kitchen. Here, you will engage in hands-on cooking sessions using fresh local ingredients, refining your skills under expert guidance. Culminate your experience with a sensory feast of what you have prepared, elevating Greek gastronomy to new heights in a celebration of culture and culinary artistry.
    • Activity Level : Easy
    • Duration : 2 hours 30 minutes

    Included in your vacation package price

  9. Day 9 Traveling to Kalamata by Private Transfer / Arrival in Kalamata

    Kalamata by Private Transfer
    Today, you will leave Monemvasia and travel to Kalamata. A driver will pick you up at your accommodation based on your preferred departure time and take you on a two-and-a-half-hour journey. Please note this is a non-guided transfer.
    Under the shadow of the majestic Taygetus Mountain and touched by the glistening waters of the Messinian Gulf, Kalamata is a city that vibrates with life and boasts centuries of history. Known throughout the world for the top-quality - and delicious - Kalamata olives, the city is the perfect base from where to embark on a fascinating road trip across the region of Messinia and beyond. A short drive from Ancient Messini and a handful of medieval castles, Kalamata is also surrounded by captivating natural landscapes. Whether you're a foodie, a history enthusiast, or an adventurer at heart, Kalamata won't disappoint.
    Upon arrival to Kalamata, your driver will take you to your centrally located accommodation.
  10. Day 10 Your First Full Day in Kalamata

    Kalamata Olive Routes E-Bike Group Tour

    Kalamata Olive Routes E-Bike Group Tour

    Explore Kalamata’s ancient olive groves on this guided E-Bike Tour, gliding effortlessly along traffic-free trails through lush hillsides. Pause for a delicious picnic amid centuries-old trees and continue your ride through stunning silver-green landscapes. Adventure, serenity, and nature’s beauty combine for an unforgettable experience.
    • Activity Level : Moderate
    • Duration : 4 hours

    Included in your vacation package price

  11. Day 11 Your Second Full Day in Kalamata

    Scenic Private Tour of Coastal Mani

    Scenic Private Tour of Coastal Mani

    Explore the Coastal Charms of Mani, soak in breathtaking views from the Balcony of Kardamyli, wander historic village streets, and discover the picture-perfect Natural Port of Agios Nikolaos. Experience dramatic coastlines, hidden coves, and unforgettable Mediterranean vistas.
    • Activity Level : Easy
    • Duration : 4 hours

    Included in your vacation package price

  12. Day 12 Traveling to Ancient Olympia by Private Transfer / Arrival in Ancient Olympia

    Ancient Olympia by Private Transfer
    Today, you will leave Kalamata and travel to Ancient Olympia. A driver will pick you up at your accommodation based on your preferred departure time and take you on a one hour and forty-five minute journey. Please note this is a non-guided transfer.
    The birthplace of the Olympic Games, Olympia is one of the most fascinating places to visit in Greece. The UNESCO-listed archaeological site of Ancient Olympia was where people from all over Greece met every four years to take part in the famous games that helped shape the identity of the Greek nation. History aside, Olympia boasts a unique location in the heart of Western Peloponnese, an authentic region where you can sample the divine products the Greek land yields, such as honey, olive oil, and wine, in a setting of unparalleled natural beauty.
    Upon arrival to Ancient Olympia, your driver will take you to your centrally located accommodation.
    Olympia Wine Flavours Private Experience

    Olympia Wine Flavours Private Experience

    Discover the vineyards of Ancient Olympia at Greece’s first green winery. Meet the family behind the revival of the ancient Tinaktorogos vine, explore their historic cellar, and savor a tasting of four local wines paired with traditional snacks, a true taste of history and flavour.
    • Activity Level : Easy
    • Duration : 1 hour 30 minutes

    Please ask your travel advisor for the cost to add this to your package

  13. Day 13 Your First Full Day in Ancient Olympia

    Ancient Olympia Site Private Tour and Marble Workshop

    Ancient Olympia Site Private Tour and Marble Workshop

    Discover ancient Olympia with a certified guide and archaeologist, exploring its iconic site and museum while unveiling the myths behind this UNESCO landmark. After immersing yourself in its rich history, take part in a creative workshop to sculpt a personalized souvenir, your own meaningful memento from this extraordinary place.
    • Activity Level : Light
    • Duration : 4 hours

    Included in your vacation package price

  14. Day 14 Traveling to Athens by Private Transfer / Arrival in Athens

    Athens by Private Transfer
    Today, you will leave Ancient Olympia and travel to Athens. Your driver will pick you up at your accommodation based on your preferred departure time and take you on a three-hour and forty-five-minute journey. Please note this is a non-guided transfer.
    Although it's hard to not keep craning your head to take in the spectacle of the Acropolis at the center of town (especially when it's lit up at night), there's more to Athens than its dense concentration of ancient ruins. Athens is a center for contemporary art, with modern galleries sitting beside museums stuffed with art dating back millennia. This combination of the old and new is especially clear at the Odeon of Herodes Atticus, a spectacular open-air theater that has hosted concerts and plays for nearly 2,000 years. The city's culture is also reflected in its diverse food and drink, which combines traditional Greek favorites with influences from across the Mediterranean, and the world, as fitting Athens' deep history as a humming harbor hub. While Athens' variety is enough to keep you busy, from the hidden back alleys of the center, to the city's showy coast, the city works well as a base for day trips, whether down the coast, or to the Peloponnese. Head to oracular Delphi, or hunt for where Lord Byron's carved his name into the monumental Temple of Poseidon at the tip of Cape Sounion.
    Upon arrival to Athens, your driver will take you to your centrally located accommodation.
    Athens by Night Food and Wine Tasting Private Tour

    Athens by Night Food and Wine Tasting Private Tour

    Seeking an extraordinary Greek culinary experience to tease your senses? Follow an expert food guide on a quest to discover Athens by night, and experience exquisite Athenian delicacies. Enjoy the best views of Athens after dusk and explore sophisticated eateries to devour the finest of authentic Greek cuisine, including the best souvlaki in town! And to top it all off? A wine tasting focused on indigenous local varieties (plus ouzo!)

    • Activity Level : Easy
    • Duration : 4 hours

    Please ask your travel advisor for the cost to add this to your package

  15. Day 15 Departure Day

    Today a driver will pick you up from your accommodations and take you straight to Athens' airport, which is generally a 45-minute drive, depending on traffic.

Ideas to customize your trip further

  • Acropolis & Parthenon E-Bike Group Tour

    Activity level : Moderate
    Duration : 4 hours 30 minutes

  • Acropolis for Families Private Tour

    Activity level : Moderate
    Duration : 2 hours

  • Ancient Corinth Tour & Nemea Wine-Tasting Private Tour

    Activity level : Moderate
    Duration : 9 hours

  • Athens E-Bike Group Tour

    Activity level : Moderate
    Duration : 2 hours 30 minutes

  • Athens E-Bike Private Tour

    Activity level : Moderate
    Duration : 2 hours 30 minutes

  • Athens Highlights Mythology Private Tour

    Activity level : Moderate
    Duration : 4 hours

  • Athens Markets and Chronicles Group Tour

    Activity level : Light
    Duration : 4 hours

  • Athens Myths & Tales Group Walking Tour

    Activity level : Light
    Duration : 4 hours

  • Athens Riviera Sunset Group Cruise

    Activity level : Easy
    Duration : 3 hours

  • Athens Sea Kayaking Small Group Tour

    Activity level : Moderate
    Duration : 8 hours

  • Athens by Night Food and Wine Tasting Private Tour

    Activity level : Easy
    Duration : 4 hours

  • Athens by Night Food and Wine Tasting Small Group Tour

    Activity level : Easy
    Duration : 4 hours

  • Athens by Tuk-Tuk Afternoon or Evening 2-Hour Private Tour

    Activity level : Easy
    Duration : 2 hours

  • Athens by Tuk-Tuk Morning or Afternoon 3-Hour Private Tour

    Activity level : Easy
    Duration : 3 hours

  • Beat the Heat Acropolis Group Tour

    Activity level : Moderate
    Duration : 2 hours

  • Best of Ancient and Modern Athens Private Tour

    Activity level : Moderate
    Duration : 6 hours

  • Best of Athens in a Day Private Walking and Driving Tour

    Activity level : Moderate
    Duration : 7 hours

  • Delicious Athens Food Group Tour

    Activity level : Light
    Duration : 3 hours 30 minutes

  • Delphi Full-Day Group Tour

    Activity level : Strenuous
    Duration : 9 hours

  • Delphi Private Day Trip

    Activity level : Moderate
    Duration : 11 hours

  • Fast Track Arrival Services at Athens Airport

  • Greek Dance Private Lesson

    Activity level : Moderate
    Duration : 2 hours

  • Half-Day Morning Athens Group Cruise

    Activity level : Light
    Duration : 5 hours

  • Hiking Sounio National Forest Private Tour

    Activity level : Moderate
    Duration : 3 hours

  • Hydra Island Private Day Trip with Horse Ride

    Activity level : Moderate
    Duration : 11 hours

  • Inspiring Sounio - Temple of Poseidon Sunset Private Trip

    Activity level : Moderate
    Duration : 5 - 6 hours

  • Meteora Group Day Trip from Athens

    Activity level : Light
    Duration : 13 hours

  • Museum of Acropolis Private Tour

    Activity level : Easy
    Duration : 2 hours

  • Mycenae and Nafplio Private Day Trip

    Activity level : Moderate
    Duration : 11 hours

  • Sculpt a Mythical Creature from Greek Myths Small Group Tour

    Activity level : Easy
    Duration : 2 hours

  • Sounio Half-Day Private Tour

    Activity level : Easy
    Duration : 5 hours

  • The Bohemian Side of Athens Group Tour

    Activity level : Light
    Duration : 4 hours

  • The Great Eats and Streets Private Tour

    Activity level : Light
    Duration : 5 hours

  • The Three Island Group Cruise

    Activity level : Light
    Duration : 11-12 hours

  • Trace the Footsteps of Saint Paul - A Private Biblical Tour of Athens and Corinth

    Activity level : Moderate
    Duration : 9 hours

  • Wine Tasting with Acropolis Views Group Experience

    Activity level : Easy
    Duration : 2 hours

Athens, Nafplio, Monemvasia, Kalamata and Ancient Olympia

What's Included in your trip

Here are all the services provided as part of your complete vacation package. See what every JayWay trip includes. Please let us know if you'd like to upgrade any transfers or add any additional tours or excursions to your itinerary.

Included

  • 2 nights accommodation in Athens
    3 nights accommodation in Nafplio
    3 nights accommodation in Monemvasia
    3 nights accommodation in Kalamata
    2 nights accommodation in Ancient Olympia
    1 night accommodation in Athens
  • Breakfast (hotels only)
  • Athens Airport Transfer
    Athens - Nafplio Private Transfer with a Stop at the Corinth Canal
    Nafplio - Monemvasia Private Transfer
    Monemvasia - Kalamata Private Transfer
    Kalamata - Ancient Olympia Private Transfer
    Ancient Olympia - Athens Private Transfer
    Athens Airport Transfer
  • Athens Highlights Mythology Group Tour
    Nafplio Town Private Walking Tour
    Mycenae & Epidaurus Private Tour
    Monemvasia Lower and Upper Town Private Tour
    Private Cooking Class Experience
    Kalamata Olive Routes E-Bike Group Tour
    Scenic Private Tour of Coastal Mani
    Ancient Olympia Site Private Tour and Marble Workshop

What's excluded in your package

  • Flights to and from Europe.
  • Tips for Tour Guides, Drivers and Local Reps.
  • Meals (other than breakfast if included in room rate and meals listed as included in food tours and excursions, unless explicitly stated otherwise).
  • Parking fees for your Rental Car (if you are booking one with us) unless otherwise indicated. Some hotels provide free parking facilities.
  • Travel Insurance. See the insurance link on our website

Benefits of traveling with JayWay

A JayWay vacation is more than the sum of its parts. Our team work tirelessly to ensure your experience is memorable for all the right reasons. Your trip is personalized to maximize your enjoyment. You're taken care of every step of the way.

  • A travel advisor who speaks your language

    We will make sure that all your requirements and interests are taken into account in preparing your itinerary.

  • Detailed pre-trip preparation to make the most of every day

    Your Europe-based Tour Manager will be in touch by email and phone a month before you arrive to finalize timings.

  • A totally tailored itinerary for your vacation

    Your trip is customized for you by an experienced trip planner and an expert on the region.

  • A choice of hand-picked hotels and excursions

    We've personally inspected and tested all the hotels and local tour providers we work with to ensure quality.

  • Personalized Guest Page to make sure you're not missing out

    Packed with detailed information and recommendations curated by locals on the best things to do, see and eat.

  • On-trip concierge service to smooth out any bumps in the road

    Your tour manager is at your service throughout your journey. We'll provide a local SIM so you can stay connected.

Glowing Reviews From Our Guests

4.94 reviews

Review by Melissa, Kim, Leah, Brylea, Lyle & Judy
JayWay was great to work with, extremely professional and responsive. Our trip was complicated with a lot of moving parts and it was SEAMLESS. All our transfers were on time or ahead of schedule. The local team that accommodated us was amazing, kind, and helpful.

- Melissa, Kim, Leah, Brylea, Lyle & Judy - Montana

Review by Alicia & Brandon
JayWay was absolutely amazing. From planning, to meeting the on-site agent that helped us a lot, to all of the tour guides and transfers we couldn’t have done any of that on our own. We absolutely loved our experience!

- Alicia & Brandon - South Carolina

Review by Ernie, Christina, Nevin, Nathan & Noah
Definitely worth it. Will use again when we come to Europe again. Thanks for helping make the trip so memorable.

- Ernie, Christina, Nevin, Nathan & Noah - Colorado

Get your personalized itinerary based on this trip.

Chat with us

Unlock Your Custom Trip Plan

Where would you like to go? Choose one or more. Hold Ctrl (Cmd on a Mac) to select several.

We will contact you within 1 working day to discuss your requirements and prepare a truly customized trip plan for you.

©2026 JayWay Travel Inc.