Two Weeks in Greece

From Athens to the Islands

In late May and early June the weather in Greece is usually close to perfect: The sky is cloudless, the air is warm, and the Mediterranean has lost its winter chill. This is also a time when the new season’s tomatoes and peaches begin to appear. Few places in the world have fruit that is quite so super-saturated with flavor. Travel in Greece offers an irresistible combination of simple and immediate pleasures with a universal sense of a unique and ancient civilization. This itinerary introduces travelers to cultural highlights — in Athens, Epidaurus and Mycenae — as well as to the ravishing beauty of the Aegean Islands.

The best months for travel in Greece are May, June and September. Although July and August are the high season, they bring crowds, excessive heat and the meltemi winds that often blow incessantly through the Eastern Mediterranean.

Read our editor’s latest report from Greece, and learn what to pack for a trip to Greece.

Itinerary Highlights

Our itineraries are for your inspiration. Please contact a travel advisor to customize this itinerary to fit your needs.

  • Hike Mount Lycabettus and tour the Acropolis
  • Visit the Acropolis Museum
  • Sit with Athenians and watch the world go by in Kolonaki Square
  • Explore Porto Heli in the Peloponnese
  • Take a three-night cruise through the Cyclades
  • Enjoy the dramatic scenery of Santorini

Trip Overview

Day 1 : Athens
Arrive in Athens and check in to hotel
Day 2 : Athens
Hike Mount Lycabettus and tour the Acropolis
Day 3 : Porto Heli
Drive to Porto Heli in the Peloponnese
Day 4 : Porto Heli
Spend the day in Porto Heli
Day 5 : Porto Heli
Tour Spetse and Hydra
Day 6 - 8 : The Cyclades
Charter a yacht in the Cyclades
Day 9 : Paros
Arrive in Paros and check in to your hotel
Day 10 : Paros
Tour Lefkes and have dinner in Naoussa
Day 11 : Paros
Day trip to Naxos
Day 12 : Santorini
Sea journey to Santorini
Day 13 : Santorini
Touring Akrotiri and relaxing
Day 14 : Santorini
Wine tasting and sunset in Oia
Day 15 : Athens
Return to Athens
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Day 1 : Athens

On arrival, after the overnight flight from the United States, you will be transferred to our recommended property in Athens, Hotel Grande Bretagne, located at the heart of the city on Constitution Square. The hotel has been at the center of Athenian social and political life for more than a century. Having unpacked, relax beside the outdoor rooftop pool, with its view of Mount Lycabettus, the highest point in Athens. Later, you may wish to have a treatment or a massage in the GB Spa. Enjoy dinner in the hotel’s eighth-floor GB Roof Garden Restaurant, with its spectacular backdrop of the flood-lit Parthenon.

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Day 2 : Athens

If you are feeling energetic, get up early and take a taxi to Aristippou Street at the foot of Mount Lycabettus. From there, you can walk up to the 908-foot summit. The path is quite steep, and the ascent will probably last around an hour. (Alternatively, there is a funicular that takes just three minutes.) From the top, you will be treated to a stupendous panoramic view that encompasses the whole of the center of Athens (including the Acropolis and Parthenon) as well as the port of Piraeus and the nearest islands in the Saronic Gulf.

After breakfast, a private guide will take you to the Acropolis to see the Parthenon, built during the so-called Golden Age of Athens (460–430 B.C.), and the other classical structures, including the Propylaea, the Erechtheion and the Temple of Athena Nike. Afterward, you will visit the Acropolis Museum, a stunning three-story glass building with transparent floors.

Path to Mount Lycabettus
The Porch of Caryatids of the Erechtheion, an ancient temple on the north side of the Acropolis

Have a light lunch at a café in Kolonaki, the Greek capital’s most fashionable residential, restaurant and shopping district. (Kolonaki Square is where Athenians sit to drink coffee and watch the world go by.) You also may wish to visit some of the area’s boutiques; Voukourestiou Street is known for its jewelry. If you have energy for another museum, you could stroll to the Museum of Cycladic Art, housed within a neoclassical mansion, to view a collection assembled by Nicholas P. Goulandris, a member of the legendarily wealthy Greek shipping family.

For dinner, try Papadakis, an outstanding seafood restaurant located on the lower slopes of Mount Lycabettus, with a view of the Acropolis.

Day 3 : Porto Heli

This morning a private car will transfer you from Athens to the yachting center of Porto Heli in the Peloponnese (the peninsula that forms the southern part of the Greek mainland). The drive is approximately two-and-a-half hours, but along the way you will stop to visit the fourth-century B.C. Theatre of Epidaurus, the best preserved and arguably most beautiful classical theater, which is the scene of a famous annual summer arts festival.

Located 10 minutes by water taxi from Porto Heli, Amanzoe is a resort of 38 pavilion-style lodgings, set on a hilltop overlooking a bay backdropped by mountains. After lunch you may wish to relax by your private pool. Options for dinner at the hotel include the Restaurant, serving Greek and Mediterranean dishes, and Nama, for Japanese cuisine.

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Amanzoe

This hilltop complex overlooks olive groves and has a backdrop of mountains seen across a cobalt-blue bay, 10 minutes by water taxi from the pretty yachting village of Porto Heli.

Day 4 : Porto Heli

Today, you can spend time at the private full-service Beach Club, which offers four pools, a small spa, a pizza restaurant and a fleet of boats. Alternatively, you may wish to take a guided excursion to the site of ancient Mycenae, with its famous Lion Gate and Treasury of Atreus, dating from 1250 B.C. Enjoy a casual lunch in the lovely nearby town of Nafplio, overlooking the Gulf of Argos, with its spectacular Venetian fortifications and handsome central square.

For dinner, you can either return to Amanzoe or try one of the restaurants in Porto Heli.

The Lion Gate in Mycenae
Beach Club at Amanzoe

Day 5 : Porto Heli

Assuming that you do not want to spend your last day at Amanzoe relaxing either at the Beach Club or in the spa, you may wish to embark on a daylong tour of the exquisitely pretty neighboring islands of Spetse and Hydra aboard Amanzoe One, the resort’s Wally One powerboat. Private cars are prohibited on both islands, ensuring their continued tranquility, while Hydra’s horseshoe-shaped harbor is universally acknowledged to be one of the prettiest in the Mediterranean.

Port of Hydra
<i>Amanzoe One</i>

Day 6 - 8 : The Cyclades

This morning you will be driven to Piraeus, the port of Athens. After lunch at Varoulko Seaside, a Michelin one-star seafood restaurant in the Mikrolimano Marina, you will be transferred to your private motor yacht for a three-night cruise through the Cyclades. The vessel will have been arranged by our Fort Lauderdale-based partner, All Yachts Worldwide. Over the next three days, you will visit the islands of Kea, Kithnos, Serifos, Siros, Mykonos, Delos and Paros. A private yacht allows travelers to escape the crowds and to visit small harbors and deserted beaches that are otherwise inaccessible.

Mykonos at dusk
Deck on the Souraya

Day 9 : Paros

On arrival in Paros you will be transferred to the new 33-suite Parīlio Hotel, located a five-minute drive to the west of the glamorous and cosmopolitan village of Naoussa. With its huge cross-shaped pool and sensuously cool interior, the Parīlio creates a dramatic first impression. You may wish to pass the afternoon beside the private pool of your Sun Suite or spend time in the property’s attractive spa.

Enjoy dinner at the hotel’s exceptional restaurant, Mr. E, which is helmed by well-known chef Alexandros Tsiotinis. His market-driven “New Greek” menu uses the finest local produce and seafood.

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Parīlio Hotel

This magnificent hotel, situated a five minutes’ drive to the west of Naoussa, was created from an existing set of white sugar-cube buildings.

Day 10 : Paros

After a leisurely breakfast and the delivery of your hire car, drive inland for 20 minutes to Lefkes, the medieval capital of Paros. The town was once made prosperous by the nearby quarries, which produced the finest marble in the world. Parian marble was known to the ancient Greeks as “candlelight marble,” because light penetrates to a depth of almost an inch and a half, giving it the lustrous glow. Today, Lefkes itself is a quiet and pretty village with steep lanes shaded by mulberry trees. After a visit to the Yria ceramics atelier in nearby Kostos, have lunch at Aranto, a restaurant with a terrace that affords views to the channel between Paros and the neighboring island of Naxos.

This evening, drive to nearby Naoussa for dinner at Siparos, a casually elegant restaurant with beautiful views over Santa Maria Beach. As well as a wide variety of delicious small dishes, the menu features superlative grilled fish.

Traditional white Cycladic architecture in Naoussa
Village of Lefkes on Paros island

Day 11 : Paros

Today, make an escorted excursion to the adjacent island of Naxos. A 45-minute ferry ride from Paros, Naxos is the largest of the Cyclades — 20 miles from north to south — rising to an elevation of 3,291 feet at the summit of Mount Zeus. A private guide and driver will take you on a daylong customized itinerary, visiting archaeological sites, including temples of Demeter and Apollo, Byzantine churches and several charming villages, notably Apeiranthos and Halki.

Back in Paros, have dinner at Mediterraneo Taverna Ouzerie, a harborside seafood restaurant in Naoussa that serves impeccably fresh mezzes and outstanding grilled rock lobster.

Temple ruins on Naxos island
Octopus drying in the sun in Naxos harbour

Day 12 : Santorini

This morning, journey south to the dramatic volcanic island of Santorini. Currently, there are no flights, so you will travel either by a private motor yacht charter or aboard a high-speed catamaran ferry, which takes just under two hours to cover the 65 nautical miles.

Santorini is a 12-mile crescent of land, all that remains of a substantial island blown apart by a cataclysmic eruption 3,500 years ago. (The blast probably gave rise to the enduring legend of Atlantis.) Today stupendous cliffs rise from the sea-filled caldera to blinding whitewashed villages perched more than 1,000 feet above. The island itself is arid, with dark volcanic soil (that helps produce delicious dry white wines) and black sand beaches. Its principal attraction is the unforgettable view, both of the immense caldera and the surrounding islands of the Cyclades.

On arrival, you will be transferred to The Tsitouras Collection, our recommended hotel in the village of Firostefani. Historian-art collector Dimitris Tsitouras converted an 18th-century residence into five separate “houses.” Each accommodation features museum-quality antiques and paintings, along with a dining area. Amenities include a lovely freshwater pool with an adjacent café. In-room massage treatments are available.

Enjoy dinner on the hotel’s dramatic Maria Callas Terrace, where the menu emphasizes seafood dishes.

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The Tsitouras Collection

This unique mansion-hotel is set atop a breathtaking cliff, 1,000 feet above the sea. 

Day 13 : Santorini

Before the day becomes too hot, make a guided excursion to the archaeological excavation at Akrotiri, a Minoan Bronze Age settlement, located a 20-minute drive to the south. Lava engulfed the entire town around 1627 B.C., and it remained unknown to the world until 1867. Stroll through the ancient streets to see the implements and paraphernalia of daily life from more than 3,500 years ago.

Spend the remainder of the day relaxing beside the pool and reveling in the astonishing view. For dinner, try one of the excellent local restaurants in Firostefani.

The prehistoric city of Akrotiri
Red Beach in Akrotiri

Day 14 : Santorini

In the late morning, you will be driven to the Boutari Winery in the village of Megalochori for a private wine tour and tasting, followed by lunch. Boutari is acknowledged to make some of the finest Greek white wines, thanks to the rich black volcanic soil. The main grape grown is Assyrtiko, a variety indigenous to the island. The vines are cultivated close to the ground within a large encircling basket. This unique cultivation method is called kouloura, and it was developed to protect the grapes from intense sunlight and strong winds.

In the evening, take a taxi to the village of Oia, at the northwest tip of the island, the best place to watch the sun sink into the vast caldera. Afterward, enjoy a seafood dinner at Catch restaurant or feast on the outstanding meze at Melitini.

Sunset in Oia
View from a table at Catch restaurant in Oia

Day 15 : Athens

Those who wish to extend their trip may want to spend three or four days relaxing at Elounda Mare, our recommended resort on the island of Crete. (The hydrofoil from Santorini takes approximately two hours, and business class service is available.) This is an ideal place in which to lounge, read and enjoy the pleasures of the sun and sea.

Otherwise, you will take an early plane from Santorini back to Athens (45 minutes), connecting to an international flight to the United States.

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Elounda Mare Hotel

This sophisticated resort with 82 accommodations overlooks scenic Mirabello Bay near the busy resort town of Agios Nikolaos.

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