Luxury Greece Vacations, Trips and Tours

Breathtaking Backroads of Greece

Get off the beaten path in this Aegean paradise.

Having crafted countless Greece itineraries, Luxury Travel Advisor Patti Gallagher is a true expert. In this country known for its picturesque islands, Patti’s own journey starts in Athens, which is rich in history. Heading out to the coast, come along as Patti explores some of her favorite islands on the road less traveled.

The perfect beach awaits you on your luxury greece vacation

Why This Trip?

the Parthenon in Athens

Visiting Athens is truly a journey through time. Regarded as the birthplace of western civilization as well as the arts, sciences and philosophy, Athens is one of the world’s oldest cities. While taking in the sights, it is easy to imagine what life was like in ancient times.

Explore the Acropolis and its timeless temples of the Parthenon, Erectheion, and Athena Nike. Enter the historical Plaka area, close to the Thiseion Temple, dating back to the 5th century BC.

Sample Saganaki, a Greek fried cheese, at one of the many restaurants in the district. Meander past the ancient Agora and its remarkably restored Stoa of Attalus, Hadrian's Library, and the picturesque Tower of the Winds. And don’t miss Syntagma Square, where you can witness the changing of the Guards at the Tomb of the Unknown Soldier, right below the Parliament building.

From Athens, travelers can take a day trip to the Peloponnese Peninsula which hosts the most important archaeological sites of Greece, including Olympia, Epidaurus, and Mycenae. Visitors can run a lap at Olympia, site of the first Olympic Games. Enjoy the stunning landscapes of the wild Mani Peninsula and the charming old Venetian town of Nafplio. Catch the sunset after a long day of touring, on one of many amazing beaches on the peninsula.

Sunset Over the Cape 

A private vehicle will pick you up in the late afternoon to bring you to Cape Sounion, home of the Temple of Poseidon. After exploring the archaeological site and the stunning view of the Aegean Sea, it won’t take long for you to realize you are about to witness the most spectacular sunset you have ever seen.   

Once the sun sinks below the horizon, your driver will take you to a local restaurant where you will have an amazing view of the evening sky as the end of the sunset trails to dark blue. Watch as the lights come up on the ruins of the Temple of Poseidon while you enjoy a wonderful dinner. 

Exploring the Peninsula 

Your private driver will pick you up after breakfast to head out of Athens. The first stop is at the Corinth Canal, a manmade canal that connects the Gulf of Corinth in the Ionian Sea with the Saronic Gulf in the Aegean Sea. 

The canal is still active today; it is truly an amazing site due to the sheer size of it. From here, continue to Epidaurus, an important commercial center in the 4th century, where you will visit The Ancient Theatre of Epidaurus, which is still acoustically perfect – an incredible feat! 

Your guide will take you to a wonderful restaurant for lunch overlooking the sea. The family atmosphere and amazing cuisine almost makes it the highlight of the day. After lunch, visit Naplio, considered to be one of the most romantic cities in Greece before seeing the archaeological site at Mycenae. 

Santorini & Mykonos; Cyclades Islands
Santorini & Mykonos

A common first stop for travelers are the Cyclades Islands, Santorini and Mykonos. Santorini is scenic and serene, and truly one of the most romantic places on earth. It’s the perfect place to relax at your luxurious resort and watch the sun set while sipping wine. The island’s flooded caldera, long steep cliffs down to the sea, and white villages with bright azure domed roofs make it a perfect location for a spectacular vacation.

Contrasting Santorini is Mykonos, with its vibrant nightlife and bustling village. It’s a picturesque setting of a quaint fishing village with centuries old windmills towering over twisting roads. In true Grecian form, the island also offers the opportunity to explore the remains of temples, holy places, houses, and settlements dating back to the Neolithic and Roman eras. Mykonos is a wonderful combination of clear water beaches, history, and gastronomy.

Santorini Sunset Wine Tasting 

Sample the celebrated wines of Santorini and learn about some of the earliest establishments in the Mediterranean. Tour the vineyard and explore the cellars of each winery with their owners and operators for a glimpse at where the wine is bottled and matured. Taste the wines with expert commentary as the sun sets over the Aegean Sea. 

Sunset Catamaran Cruise   

There’s no better way to explore the crystal blue seas and islands around Santorini than on a private day cruise. In the warm sunshine, you will sail past some of the best-known Santorini landmarks and beaches. Your sailing trip begins at Amoudi and sails towards the breathtaking caldera, where you will be able to swim and have an incredible mud bath.  

Your second stop will be the famous Red Beach for more swimming, followed by a short jaunt at the White Beach, some picturesque sailing close to Indian Rock, the Minoan Bronze Age settlement of Akrotiri and an ancient lighthouse, before dropping anchor for a delicious barbeque with beverages onboard. Finally, drift down to the Oia village and admire the spectacular sunset before leisurely sailing back to the charming Amoudi port.

Learn to Cook Like a Local 

Discover the secrets of Mykonos’ cuisine by taking part in this interactive cooking class. Travel to a traditional farm estate and, under the watchful eye of a culinary instructor, learn how to conjure up delicious local recipes using fresh, seasonal ingredients. At the end of your lesson, savor your creations for lunch or dinner with your fellow cooks, accompanied by local wines. Afterwards, enjoy a walking tour of Ano Mera village. 

don't miss out on the islands of Hydra, Naxos & Sifnos
Additional Island Favorites: Hydra, Naxos & Sifnos

First time visitors to Greece always want to visit the two most popular islands, but there are over 6,000 islands, of which 227 are populated. Each island has its own characteristics and culture. While time constraints play into making this plan fit into an itinerary, it is always a good option to consider a few of Greece’s “lesser known” islands.

Explore Monasteries on Hydra 

Hydra is only two hours by ferry from the port of Piraeus. It is a cosmopolitan island that is known for its fine architecture, pebbly beaches, and charming overall character. One of the most noticeable things about the island is that there are no motor vehicles; transportation consists soley of mules and donkeys! With 300 churches and six monasteries throughout the island, plus so many gorgeous beaches, fabulous taverns and hiking trips, there are definitely plenty of places to see. 

Hiking from monastery to monastery on the old footpaths with your private guide, you can explore every detail of this beautiful island and its natural wonders. Traversing mountain paths, forest roads and cobblestone streets, explore natural paths with dense vegetation, visit forgotten hamlets and monasteries, tour museums, and glimpse views that will compensate the efforts of even the most demanding walker. A unique activity that leads to new destinations and guarantees images of enchanting beauty that each participant will carve into their memory (or save on your camera)! 

Naxos Boat Adventure 

Naxos is in close proximity to Mykonos and easy to fit into your itinerary. Its fertile landscape spans mountain villages, ancient ruins, and long stretches of beach. While on Naxos, you can visit the famous Portara, the ancient temple of Dimitra, and the medieval Venetian castle in the old city section of the capital. A day trip to Paros by catamaran is also a perfect way to spend the day.   

This boat adventure is perfect for those seeking to experience the ultimate in Greek island hopping. Spend the day discovering off-the-beaten-track beaches, coves, and the natural riches of the Cycladic islands. Explore all the parts of Naxos and Paros that are not accessible by foot or car as you sail, swim, and snorkel in the aquamarine waters. Enjoy a picnic lunch on a deserted beach. 

See Sifnos on Horseback 

Sifnos is known for its foodie reputation. Some may challenge that reputation and say the island is best-known for its pottery. Either way, all will agree the island is characterized by a peaceful and relaxing atmosphere that make it a popular destination among families. 

Sifnos has a wonderful balance of beautiful beaches, low-key nightlife, white Cycladic villages, and low-impact tourism. For people that are looking for the “real Greek Isles,” this is it! 

Explore the traditional hiking trails of Sifnos on horseback and get to know the beauty of the island from a different perspective. From a relaxing ride through the quaint village of Katavati to scenic trail riding adventures along the island's mountain trails, there are routes and options to suit all ages and levels of experience.

More Wanderlust

Join our travel community.
Thanks for subscribing to our newsletter.
There was an error subscribing. Please contact us at