Greek Islands Wanderer – Hike, Feast, Explore | Under 35

Trip Length 7 Days
Group Size 4-16
Activity level
Starting from
$2,299 for REI Members
$2,499 for non-members
Departures May 2021-Sep 2022

Be a beach adventurer in the Greek Islands on a guided 7-day trip with hiking, wild swimming, ruins, free time and epic food.

Spoiler: these islands are legendary for a reason. Come explore Paros, Amorgos and Santorini, three sun-honeyed Mediterranean Edens full of surprises. Think Venetian castles and seaside ruins. Plus scenery so gorgeous that calling it “Instagram-worthy” is kind of an insult. This journey is designed especially for travelers aged 18–35. (But anyone over 18 can join.) You’ll wander off the tourist route with Anastasia and Archelaos, friendly local guides who know all the secret spots—and make killer Greek coffee.

Every day is an odyssey—see what we did there?—of history, hiking and playing in the impossibly blue Aegean Sea. Also eating. So much eating. You’ll swim in the magical waters of Panteronissia, the Blue Lagoon. Feast on simple yet exquisite fare at our guides’ fave village tavernas. Visit ruins, sea caves and secluded beaches with deep blue waters. Savor a spectacular sunset hike overlooking Santorini’s volcanic caldera. Spend a day sailing amongst islets to swim, cliff-dive and have a floating picnic. Use bountiful free time to follow your own bliss. Sound good? Join us for an adventurous taste of the real Greece.

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Trip Highlights

  • Wild-swim the warm, crystalline waters of Panteronissia, the Blue Lagoon
  • Experience local life, eating in village tavernas and traveling with Greek guides who love sharing their culture
  • Use free time to kayak, hike, take Greek cooking lessons, and more
  • Spend a day sailing and adventuring along the sunny coast of Antiparos, with caves, ancient ruins, and cliff jumping (optional, of course)
  • Hike the 2,000-year-old Byzantine Road and the famous caldera rim path on Santorini


This trip is rated Easy Active [2]. Hikes range from 4.7 to 6.6 miles over uneven terrain. Participants should be comfortable in water and able to swim.

  • Hiking
  • Cruising

What's Included

Lodging and meals as noted in the daily itinerary; one glass wine with included dinners; ferry transfers between islands; professional guide services.


Hotels, 6 nights

Your Adventure Itinerary

Day 1

Voyage to Paros

We rendezvous in Athens (sounds like the beginning of a spy thriller, haha). Meet our guide for orientation and head to lunch at a bustling Athenian taverna. From there we transfer to the port where we board a ferry for the start of our island-hopping adventure. Arrive on Paros and check into our hotel in Naoussa, the island’s most picturesque town. Naoussa is built amphitheatrically around a tiny port packed with colorful traditional fishing boats and ringed with seaside cafes. Lunch included.

Ferry: 4 hours

Pinch-me moment: When you first lay eyes on our first destination: the sun-kissed Greek island village of Naoussa.

Day 2

Hike the Byzantine Road

You know the Venus de Milo, the famous ancient sculpture thought to depict the Greek goddess of love and beauty? It’s carved of marble from this island. And how appropriate. Paros is drop-dead gorgeous. We begin the day with baklava and good, strong Greek coffee. A leisurely start gives you time to check out Lefkes, a traditional village garlanded with meandering stone walls and spritzed with lemon trees and bright pink bougainvillea. Then we set out on the ancient Byzantine Trail, walking a marble stone road laid in Christian Roman times. Soak up the blue vistas and the scent of thyme and wild sage. Wind through the white village of Prodromos. End at the sea in Piso Livadi. Choose from many tavernas and beach cafes for a light bite or more traditional Greek lunch. Enjoy beach time and cool off with a swim, stand-up paddle boarding or snorkeling. Late afternoon, we return to Naoussa to enjoy an evening together amidst twinkling village lights and the creaking of fishing boats rocking in the harbor. Breakfast and dinner included.

Hiking: 4.7 miles; Elevation gain/loss: 243’/-919’

Note: Cost of optional beach activities not included.

Pinch-me moment: Walking a thousand-year-old stone road through timeless countryside.

Day 3

Cliff Jumping, Beach Ruins & the Blue Lagoon

How many shades of blue are there, really? Prepare to find out. Setting out from the village of Aliki, we board a traditional fishing boat and cast off for an island-hopping adventure. Imposing cave-riddled cliffs rise around us, guarding remote islets and storied Antiparos, an island crowned with a Venetian castle. Leap from the boat to wild swim in the crystal-blue waters of Panteronissia, sometimes called the Blue Lagoon. Cliff-jump at Mastichari Cave if you dare. Enjoy a floating picnic lunch on the boat. Walk the white sands of Despotiko Beach, where the remains of an ancient Greek sanctuary continue to yield archaeological insights. Take one last dip in the warm waters in a breathtaking hidden bay. Back in Naoussa, choose from lots of tasty options for dinner. Our guides are happy to recommend their favorites, of course. Breakfast and lunch included.

Swimming, beach time, and boat time: 7 hours

Pinch-me moment: Strolling near the ruins of an ancient Apollonian temple and hestiaron (ritual banquet hall) to the sound of lapping surf.

Day 4

Explore a Cinematic Island

Pack your camera, open your eyes and experience the Greek Isles from a local perspective. Today, you wander Amorgos, an island brimming with visual treasures, with plentiful free time to follow your own bliss. The classic French film The Big Blue was filmed on this jewel of the Cyclades. Little-known compared to its larger neighbors, Amorgos is as authentic as it gets, with whitewashed villages and shepherds tending their flocks, plus a layered history that includes periods of occupation by pirates, rule by the Venetians and conquest by the Ottoman admiral Barbarossa. We settle into our hotel overlooking Aegiali Bay and then you’re free to roam. Our guides can help you choose from the abundant options. Relax in the hills with walking paths and amazing views of the Aegean. Venture to the Hellenistic-period Tower of Agia Triada. Take a lesson in pottery, traditional dance or Greek cooking. Hike with our guide. Go stand up paddle boarding. Wander the village and valley, camera in hand, on a DIY photo safari. Climb the steps of Ano Potamos for a jaw-dropping sunset. Breakfast included.

Ferry: 2 to 4 hours; Activity: optional activities; cost not included and paid on site.

Pinch-me moment: Discovering the hiking trails here are called blue paths because it is possible to see the sea at every turn.

Day 5

Ancient Seaside Wonders & Epic Greek Feast

Our destination this morning is the Monastery of Hozoviotissa. From Amorgos’ interior and the settlement of Asfontilitis, we hike a meandering trail into an almost surreal scene: a gleaming white 11th-century monastery built into a sheer cliff hanging high above the sea. The monastery is home to a revered icon of the Virgin Mary, brought over from Palestine long ago. Next, we continue our hike to Chora, a village set high above the Aegean. Its landmarks bear witness to its deep history: windmills, Byzantine churches, a 13th-century castle built by Venetian brothers. Back at the hotel, we take the afternoon to chill on the beach, explore, enjoy quiet time away from the group (we’ve got your back, introverts), or partake in the many activities mentioned on Day 4. In the evening, we meet up with our guide and fellow adventurers for a multicourse Greek dinner. Breakfast and dinner included.

Hiking: 5.5 miles; Elevation gain/loss: 939’/830’; Activity: optional activities; cost not included and paid on site.

Pinch-me moment: Toss-up between the dreamlike monastery by the sea and the epic multicourse Greek feast.

Day 6

Oia Village Ramble & Volcano Hike

Ever met a supermodel? Santorini is the Greek Isles equivalent. A quick ferry ride delivers us there today. Marvel at the sight of multicolored cliffs rising up from a craggy volcanic caldera. Beneath the island’s beauty lies a tumultuous natural history; here, around 1600 BC, a volcanic eruption wiped out an entire civilization. We check into our hotel just steps away from the famous black-sand Kamari Beach before heading to the caldera side of the island. Our destination: the photogenic village of Oia. (You’ll recognize it. Guaranteed.) We take some leisurely time exploring its narrow cobblestone streets and discovering why it’s one of the most visually popular destinations in Greece. Then we hike the volcano. Specifically, on paths of black lava rock along the edge of the caldera, high above the sea. The blue endlessness of the views inspire and exhilarate us. We end in Fira to savor our last sunset together over a traditional Greek meal in a restaurant overlooking the caldera. Tonight, we can hang out at a beach bar and toast to new friends, happy memories, and the immortal beauty of the Greek Isles. Breakfast and dinner included.

Hiking: 6.6 miles; elevation gain 1800’/loss 1100’; ferry: 1 hour

Pinch-me moment: Taking in the iconic vision of Santorini’s bell towers outlined against the shockingly blue Aegean.

Day 7

Sunrise on Santorini

Sleep in if you choose, or rise early to catch the legendary Santorini sunrise. Our odyssey concludes after breakfast. You'll then depart Greece (transferring on your own to the Santorini airport or ferry terminal) or stay a bit longer to explore on your own. For those with late afternoon flights or ferries, or who are extending their stay independently, our guide can hook you up with the best guided sea kayaking excursion on the spectacular south coast. Breakfast included.

Optional guided sea kayaking excursion: 3 hours; not included in trip and subject to availability.

Pinch-me moment: Not to state the obvious but the sunrise on Santorini. (Or sleeping in and waking up to Greek Isles sunshine.)

Gear List

This gear list has been created to help you choose the best equipment for the trip. Try to bring only what is necessary, as this will help you and the field staff. The weather and other conditions at the time of your arrival will dictate what clothing and equipment you will be required to use each day and what (if anything) can be left behind. It may be a necessary precaution that you bring certain items on the list, even if it is uncertain whether or not they will be needed.

What to pack

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Travel documents

  • Airline Tickets (Confirmation and Itinerary)
  • Final Bulletin (Emailed Prior to Departure Date)
  • Valid Passport

Contact Us

Feel free to give us a call at 800-622-2236 should you have any questions regarding the gear list. The staff at our stores and Direct Sales (800-426-4840) will also be happy to help you with gear questions. Or check out REI Expert Advice , which has great information to help you prepare for your trip.