What could be more essentially Greek than sailing from one idyllic island to another? Even the experience of getting from island to island, with your feet propped against the deck railing as the blue Aegean slips by, can seem like a dream come true. Okay, a reality check: You might soon learn that the term “you can’t get there from here” originated in the Greek islands, and even the best-laid plans often fall victim to weather, mechanical breakdowns, or last-minute schedule changes. Here, though, is a plan that, provided all goes well, might fulfill any island-hopper’s dreams. If you don’t have a full 2 weeks to spend, you can lift out any portion of this tour.

Day 1: Athens & the Acropolis

Arrive in Athens and get settled in a hotel. You can’t come to Greece without getting at least a glimpse of some of the ancient marvels of Western Civilization. Relax a bit first, though: Summer hours keep most monuments and museum open late, plus sights in the sprawling capital are fairly concentrated. The Acropolis is probably within walking distance of your hotel, maybe even within sight. The ascent through the Beule Gate and up a well-worn path is stirring, and what lies beyond is even more so: The ruins of the perfectly proportioned Parthenon and surrounding temples, summoning up the glory of classical Greece. Continue with a walk through the Acropolis Museum, where the sculptures and statuary that once adorned the Acropolis temples are on display, including a section of the magnificent Parthenon Frieze. Then stroll along the Grand Promenade, a cobblestone-and-marble, pedestrian-only boulevard that skirts the Acropolis Hill. You’ll get a glimpse of the Theater of Dionysus, where the newest dramas of Aeschylus, Sophocles, and Euripides once delighted audiences. Plunge back into the present day, by following Adrianou (Hadrian) Street through the colorful Plaka neighborhood. End your day by strolling around the evocative ruins of the Ancient Agora, once the business and political hub of ancient Athens. Then it’s time for dinner, maybe beneath a shady plane tree at a long-time favorite, the Platanos Taverna.

Day 2: Athens to Alonissos

You’ll spend the day on the move, first traveling from Athens by morning bus to—depending on boat schedules—either Ayios Konstantinos or Volos, two mainland ports each 3 to 4 hours north of Athens. Boats depart from both for Alonissos, 2 hours off the mainland by hydrofoil, 4 1/2 hours by ferry. Any good travel agency in Athens can help you make arrangements for the combined bus and boat trip. You’ll probably settle onto the island in time for a sunset cocktail on the terrace of your hotel—a good choice is the Paradise, nestled above Parikia, the port, amid pines with outlooks over a serene bay that’s one of the best spots on the island for a refreshing swim. Enjoy a seafood dinner at Archipelagos, on the Parikia waterfront.

Day 3: Hora & Kokkinokastro

You’ll quickly learn that the life on Alonissos is pretty slow-paced, and you might be tempted to spend the day in a lounger and soak up some sun, as many northern European visitors do. If you feel like being a bit more active, however, hike from Parikia up to Hora, the old hilltop capital, in less than an hour along an old, stepped mule track—do this in the morning, though, before the heat of the day. In summer, a bus makes the trip, and also goes out to the beach at Kokkinokastro, about 3km (2 miles) north of Patitiri, where the walls of the ancient city of Ikos are visible beneath the waves. Snorkelers and divers might want to stop in at Alonissos Triton Dive Center, in Patitiri and arrange an excursion to one of the outlying shipwrecks.

Day 4: National Marine Park

Alonissos is surrounded by the waters of the 2,200 sq. km (849 sq. miles) National Marine Park of Alonissos Northern Sporades, the largest marine protected area in the Mediterranean, encompassing eight islands (of which only Alonissos is inhabited), 22 rocky outcroppings, and the waters that surround them. The park is home to the highly endangered Mediterranean monk seal, as well as falcons, dolphins, and wild goats. Excursion boats from the dock in Patitiri make day-long outings through the scattered island refuges, stopping for lunch, swimming, snorkeling, and a walk to the island’s one outpost of civilization, the all-but-abandoned Megistis Lavras monastery.

Day 5: Alonissos to Skyros

It’s time to move on to another Sporades, adrift by itself in the Aegean. You’ll appreciate just how remote Skyros is when you try to get there. Check boat schedules with one of the agencies on the Parikia waterfront. In the summer, a few boats a week travel directly from Alonnisos to Skyros; otherwise you’ll need to sail from Alonissos to Kymi, on the island of Evvia, where you can get a ferry to Skyros. With a day of travel you’ll probably arrive before sundown, in time to see the spectacle of mirage-like Skyros Town, with its white, flat-roofed houses clinging to a high rocky bluff. That’s where you’ll want to settle in for 2 nights, either in the heights of Skyros Town at the Nefeli or another hotel within walking distance of Skyros Town.

Day 6: Skyros Town

You can divide the day between sightseeing in Skyros Town and spending some time on the beach without traveling very far. Do your exploring of Skyros Town in the morning, to spare yourself the uphill climbs in the heat of the day. A mandatory stop is the Manos Faltaits Historical and Folklore Museum, where you’ll see examples of the local plates, embroidery, weaving, carved furniture, and clothing that are still a part of everyday life on the island. A sandy beach stretches just beneath Skyros Town at Magazia, at the bottom of a stairway from Plateia Rupert Brooke. That’s Rupert Brooke as in the famous British World War I poet, who died on Skyros in 1915. A huge statue in the square commemorates him.

Day 7: North & South

Skyros is an island divided, between the fertile, forested north and the arid, rugged south. You can see easily see both is a day of exploring by rental car. First set your sights on Palamari, at the northern tip of the island, where behind the sandy beach are remnants of walls built by ancient settlers. The island’s best beach is here in the north, on the west coast at Agios Fokas, where little bays are edged with white pebbles. A single road leads south through a desolate, rocky landscape and ends at Tris Boukes Bay, where Rupert Brooke is buried in a simple grave.

Day 8: Skyros to Sifnos

This is another day full of travel, with an early start on the 7 or 8am ferry from Skyros to Kymi; the crossing takes a little less than 2 hours. Once in Kymi, you’ll board a bus for the 2 1/2-hour trip down to Athens, and from there take the metro to Piraeus. If all goes well, you’ll be in Piraeus with plenty of time to spare for 3 or 4pm (depending on the day) sailings to Sifnos. That will put you in Sifnos around 9pm, in time for a late dinner—actually, an early dinner by Greek standards. If you stay at the delightful hilltop Petali, dine on the terrace there, looking out over the Apollonia villages.

Day 9: The Apollonia Villages & Kastro

Spend the morning rambling through the island’s capital, Apollonia, really a cluster of six villages (or five or seven, depending on whom you ask) that tumble across the inland hills in haphazard fashion. Flagstone footpaths wind down to the town’s main square, Plateia Iroon (Hero’s Square), where the Popular and Folk Art Museum is a showplace for island embroidery, weaving, and traditional Sifnian earthenware pots and jars. Relax over a light meal on the terrace of the Gerontopoulos Café, just off the square in the Hotel Anthousa, then catch a bus or follow the well-marked footpath down to Kastro, a somberly medieval fortress town where tall Venetian-era houses line a maze of little lanes. In one of them, an archaeological museum shows off bits of pottery and friezes from the Greek and Roman city that occupied these heights 3,000 years ago. The prettiest sight in town is the Church of the Eftamartyres (Seven Martyrs), atop a sea-girt promontory far beneath a clifftop promenade that skirts the town’s outer flanks. Get on the bus for the trip out to another incredibly picturesque spot, Chrysopigi, a beloved monastery on a rocky islet. You’ll want to step into the tranquil courtyard and simple church if they’re open, but the real reason to come here is to swim at sandy Apokofto beach, nestled alongside an adjacent cove.

Day 10: Profitis Elias o Pilos & Vathy

Put on some sturdy walking shoes and set out early in the cool of the morning for the hour-long hike up to the island’s most famous monastery, Profitis Elias o Pilos. The path is fairly easy, but steep; O Pilos means “high one,” and the monastery sits atop a 850m (2,789 ft.) summit. At the top, one of the few monks in residence will probably offer you a glass of cool water. The descent is easier, naturally, and you can spend the rest of the day beneath a pine tree along the beach at Vathy. Buses serve this serene village, where Monastery of the Taxiarchis Evangelistrias (Archangel of the Annunciation) seems to rise right out of the surf.

Day 11: Sifnos to Patmos

The beautiful monasteries on Sifnos should have whetted your appetite for your next destination: Patmos, one of Greece’s holiest islands, where St. John the Apostle supposedly received his divine revelations. First, though, you’ll have to get there, and the logistics will make you wish for some divine intervention, or a private yacht. The easiest way is to take a morning boat from Sifnos to Piraeus, where you can immediately hop on the afternoon boat to Patmos, arriving in the late evening. To enjoy the island in style—and you deserve some spoiling after all that travel—settle into the Petra Hotel and Apartments or Porto Scoutari.

Day 12: Patmos & the Holy Sights

First stops on Patmos (well, after a morning swim) are the island’s two famous religious sights: the Cave of the Apocalypse, perched on a hillside above Skala, the port; and atop the hill, the fortress-like Monastery of St. John, with its treasure-filled frescoed chapels, surrounded by medieval Hora. Buses from Skala serve both. Begin by exploring Hora, a labyrinth of whitewashed stone homes, shops, and churches. After a visit to the monastery, walk down the well-marked path to the famous cave where St. John the Divine (aka the Apostle) allegedly received the word of God. From there, it’s an easy descent back down to Skala.

Day 13: Psili Ammos

Time out for a beach day. Set your sights on Psili Ammos, an isolated fine-sand cove bordered by cliffs. It’s possible to walk to Psili Ammos from the little settlement of Diakofti, about a 30-minute trek on goat paths (wear real shoes) but most sunseekers arrive by one of the caiques leaving Skala harbor in the morning and returning around 4 to 5pm. Groves of pine trees provide plenty of shade, and a simple taverna sells snacks. End the visit on a romantic note, with an excellent dinner on the seaside terrace at Benetos, just outside Skala in Grikos.

Day 14: Symi

Take a morning ferry from Patmos to Symi, where you’ll pull into beautiful, mansion-lined Yialos harbor. You’ll want to climb the 375 or so wide stone steps, known as the Kali Strata (the Good Steps), to picturesque Horio, the old island capital. There the Archaeological and Folklore Museum shows off a replica of an old island house. You’ll still have time for an excursion out to Taxixarchis Mihailis Panormitis, an unexpectedly grand white-washed monastery dedicated to the patron saint of seafaring Greeks, tucked away on Symi’s hilly, green southwestern corner. A charming museum is filled with wooden ship models, and a heavily frescoed church and chapels open off a courtyard. The best way to reach the monastery is by boat, although there is also twice-a-day bus from Yialos and Horio. While there, count on a refreshing swim in Panormitis Bay.

Day 15: Back to Athens

Now it’s time to head back to Athens. Depending on timing, you can catch the once-a-week boat from Symi to Piraeus or sail to Rhodes and take one of the overnight ferries than run a bit more frequently from there. Then, of course, there’s plan B—a quick flight from Rhodes to Athens where you can get ready for your flight home.

Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.