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The Ultimate Two-Week Peloponnese Itinerary

15 Days / 14 Nights

Athens, Nafplio, Monemvasia, Kalamata, Ancient Olympia, Athens

from$5,400 per person

as seen in
Travel and LeisureFodorsUSA TodayNew York TimesNational GeographicWashington PostVogue

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.

Route for Athens, Nafplio, Monemvasia, Kalamata, Ancient Olympia, Athens tour

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What's Included

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.

Athens

2 Nights Accommodation
Breakfast (hotels only)
Athens Airport Transfer
Athens Highlights Mythology Group Tour
Athens - Nafplio Private Transfer with a Stop at the Corinth Canal

Nafplio

3 Nights Accommodation
Breakfast (hotels only)
Nafplio Town Private Walking Tour
Mycenae & Epidaurus Private Tour
Nafplio - Monemvasia Private Transfer

Monemvasia

3 Nights Accommodation
Breakfast (hotels only)
Monemvasia Lower and Upper Town Private Tour
Private Cooking Class Experience
Monemvasia - Kalamata Private Transfer

Kalamata

3 Nights Accommodation
Breakfast (hotels only)
Kalamata Olive Routes E-Bike Group Tour
Scenic Private Tour of Coastal Mani
Kalamata - Ancient Olympia Private Transfer

Ancient Olympia

2 Nights Accommodation
Breakfast (hotels only)
Ancient Olympia Site Private Tour and Marble Workshop
Ancient Olympia - Athens Private Transfer

Athens

1 Night Accommodation
Breakfast (hotels only)
Athens Airport Transfer

package excludes:


  • Flights from and to your home country.
  • 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.

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.

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

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

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.

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.

2 Nights in Athens

2 Nights in Athens

3 days in Athens

2 Nights 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.

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.

Day 1

Day 1 - Arrival in Athens

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

Suggestion to explore on your own

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.

Love at First Sight

Day 2

Day 2 - Your First Full Day in Athens

Athens Highlights Mythology Group Tour

Athens Highlights Mythology Group Tour

Included in your vacation package price.

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

Day 3

Day 3 - Traveling to Nafplio by Private Transfer

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.

Nafplio by Private Transfer with a Quick Stop for Photos at the Corinth Canal
We also offer the following excursions in Athens

Acropolis & Parthenon E-Bike Group Tour
Moderate4 hours 30 minutes
Acropolis Museum Private Tour
Easy2 hours
Acropolis for Families Private Tour
Moderate2 hours
Ancient Corinth Tour & Nemea Wine-Tasting Private Tour
Moderate9 hours
Athens E-Bike Group Tour
Moderate2 hours 30 minutes
Athens E-Bike Private Tour
Moderate2 hours 30 minutes

3 Nights in Nafplio

3 Nights in Nafplio

4 days in Nafplio

3 Nights in Nafplio

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.

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.

Day 3

Day 3 - Arrival in Nafplio

Upon arrival to Nafplio, your driver will take you to your centrally located accommodation.

Day 4

Day 4 - Your First Full Day in Nafplio

Nafplio Town Private Walking Tour

Nafplio Town Private Walking Tour

Included in your vacation package price.

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

Day 5

Day 5 - Your Second Full Day in Nafplio

Mycenae & Epidaurus Private Tour

Mycenae & Epidaurus Private Tour

Included in your vacation package price.

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

Day 6

Day 6 - Traveling to 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.

Monemvasia by Private Transfer
We also offer the following excursions in Nafplio

7 Villages Cycling Private Tour
Strenuous4 hours
Artichoke Adventure Group Tour
Easy3 hours
Chef's Table Group Experience
Easy2 hours
Epidaurus Private Tour
Light2 hours 30 minutes
Half-Day Morning or Sunset Group Cruise
Easy4 hours 30 minutes
Half-Day Morning or Sunset Private Cruise
Easy4 hours 30 minutes

3 Nights in Monemvasia

3 Nights in Monemvasia

4 days in Monemvasia

3 Nights in Monemvasia

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.

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.

Day 6

Day 6 - Arrival in Monemvasia

Upon arrival to Monemvasia, your driver will take you to your centrally located accommodation.

Day 7

Day 7 - Your First Full Day in Monemvasia

Monemvasia Lower and Upper Town Private Tour

Monemvasia Lower and Upper Town Private Tour

Included in your vacation package price.

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

Day 8

Day 8 - Your Second Full Day in Monemvasia

Private Cooking Class Experience

Private Cooking Class Experience

Included in your vacation package price.

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

Day 9

Day 9 - Traveling to 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.

Kalamata by Private Transfer
We also offer the following excursions in Monemvasia

Liotrivi Mansion Private Tour with Meal
Easy2 hours 30 minutes
Monemvasia Lower Town Private Tour
Light1 hour
Olives and Olive Oil Private Tasting Experience
Easy1 hour

3 Nights in Kalamata

3 Nights in Kalamata

4 days in Kalamata

3 Nights in Kalamata

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.

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.

Day 9

Day 9 - Arrival in Kalamata

Upon arrival to Kalamata, your driver will take you to your centrally located accommodation.

Day 10

Day 10 - Your First Full Day in Kalamata

Kalamata Olive Routes E-Bike Group Tour

Kalamata Olive Routes E-Bike Group Tour

Included in your vacation package price.

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

Day 11

Day 11 - Your Second Full Day in Kalamata

Scenic Private Tour of Coastal Mani

Scenic Private Tour of Coastal Mani

Included in your vacation package price.

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

Day 12

Day 12 - Traveling to 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.

Ancient Olympia by Private Transfer
We also offer the following excursions in Kalamata

Ancient Messene Private Tour
Moderate4 hours
Bike Group Tour in Kalamata
Light3 hours
Castles of Messenia Private Tour
Moderate3 hours
Kalamata Private Walking Tour
Moderate1 hour 30 minutes
Natural Beauties of Messenia Private Tour
Moderate5 hours
Sea Kayak Kalamata Half-Day Group Tour
Moderate4 hours

2 Nights in Ancient Olympia

2 Nights in Ancient Olympia

3 days in Ancient Olympia

2 Nights in Ancient Olympia

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.

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.

Day 12

Day 12 - Arrival in Ancient Olympia

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

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

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

Day 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

Included in your vacation package price.

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

Day 14

Day 14 - Traveling to 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.

Athens by Private Transfer
We also offer the following excursions in Ancient Olympia

Ancient Olympia Site Private Tour
Easy2 hours 30 minutes

1 Night in Athens

1 Night in Athens

2 days in Athens

1 Night 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.

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.

Day 14

Day 14 - Arrival in Athens

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

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

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

Day 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.

We also offer the following excursions in Athens

Acropolis & Parthenon E-Bike Group Tour
Moderate4 hours 30 minutes
Acropolis Museum Private Tour
Easy2 hours
Acropolis for Families Private Tour
Moderate2 hours
Ancient Corinth Tour & Nemea Wine-Tasting Private Tour
Moderate9 hours
Athens E-Bike Group Tour
Moderate2 hours 30 minutes
Athens E-Bike Private Tour
Moderate2 hours 30 minutes