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A Beginner’s Guide to Greek Island Hopping With a Group

Gorgeous sunsets, delicious food and wine, medieval villages, ancient monasteries, pink sand beaches, white sand beaches, stone beaches, volcanic rock beaches and more beaches are just a few of the things you’ll want to explore on a summer trip to Greece. We’ve been collecting a few favorites here and there – hotels, restaurants, sights and the like – and hope these recommendations will light a fire in you to book your travel.

Over two thousand islands make up Greece, about two hundred of which are inhabited. So, by no means is this an exhaustive list, but instead a beginner’s guide to jumpstart your group's plans.

Planning an event? Offer your guests exclusive room rates (without making a room block!) with this link →

Reporter: Alyssa Brown
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The Cyclades

Greece
The much-adored Cyclades are made up of 24 inhabited islands, most of which are easy to access via flight or ferry from Athens. There are 25 beaches on Mykonos alone, which is known best for its swimming spots and party scene. Honeymooners tend to flock to Santorini with its luxury hotels and satellite islands. The shoulder months of June and September are best for booking, as this group of islands gets packed in the peak of summer.
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Stay at Cavo Tagoo Mykonos

Mykonos, Greece
The whitewashed caves of Mykonos offer an inviting scene, and what you’ll find inside at Cavo Tagoo is a collection of equally inviting rooms, suites and villas – some with and some without pools or jacuzzis. This luxurious resort offers the best in views, spa treatments and sunsets.
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Eat at Fresh The Mykonos Project

Mykonos, Greece
Brunch is available all day, every day at Fresh The Mykonos Project. The best of this Greek patisserie is served up in a space that’s relaxing and warm with all the charms of a local café.
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Photo:Sophia Luxury Suites
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$290 avg. room rate
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Stay at Sophia Luxury Suites learn more

Bask in the sunshine or watch the sunset from your own private pool deck at Sophia Luxury Suites. This boutique getaway offers spacious, beautifully designed rooms that look right out to the perfectly framed turquoise sea.
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Go Wine Tasting at Domaine Sigalas

Santorini, Greece
Known not only for their internationally adored wines but also for their generous tasting menus, Domaine Sigalas is at the top of the list for local wineries to check out in Santorini.
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Go Cliff Jumping on Milos

Milos, Greece
Fluffy white volcanic rocks jaggedly drop straight into the sea at Sarakiniko Beach in Milos. If you dare to cliff jump, this may be the most lunar-like landscape to take the dive.
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Photo: Andrew Urwin
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Dine at Medusa Restaurant

Milos, Greece
Medusa sits right on the edge of the sea in the quiet, old fishing village of Mandrakia. A local tavern, this spot is one where you can easily waste away an afternoon or evening filling up on octopus, grilled sardines and local specialties like Milos’ pitarakia milou (cheese pies).
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Photo: Skinopi Lodge
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Stay at Skinopi Lodge

Milos, Greece
Glass doors open up to sunshine and salty air at this collection of eco-friendly villas overlooking the Aegean Sea. Skinopi Lodge – and Milos, for that matter – feels completely off the grid and unlike most of the bustling hotels in the Cyclades.
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Brunch & Coffee at Sousouro

Paros, Greece
For those finding clean eating to be a struggle in the culinary haven of Greece (one word: baklava), a trip to Sousouro in Paros should get you back on track. Avocado toast with farm eggs, bright grain salads and raw vegan treats are served alongside strong coffees and freshly squeezed juices.
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Photo: The Nest Shop
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Dine & Drink at Beach House Antiparos

Antiparos, Greece
Wander the island of Antiparos by day and head to Beach House for an evening pick-me-up or overnight stay. This seaside spot serves up authentic islander fare and classic cocktails. Anyone up for sunset and a spritz?
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The Saronic Gulf Islands

Greece
The Saronic Gulf Islands is the group closest to Athens, so super easy to get to via hydrofoil, passenger ferries and fishing boats. These islands are small and easy to explore the local history and culture via festivals and museums. The harbors tend to be the center of each island, with local taverns serving a lot of seafood and sailing reigning supreme as the local water activity.
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Explore Spetses by Vespa

Spetses, Greece
The island of Spetses doesn’t allow cars, but Vespas are a great way to explore if hoofing it simply won’t do. There are plenty of sights to see, but a tour of the best espresso and pastry spots would make a day well spent on wheels.
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Photo: Kate Holland
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Stay at Poseidonion Grand Hotel

Spetses, Greece
Add in a stay at the glamorous Poseidonion Grand Hotel if you want to get a taste of what life’s like for the jet setters of the Mediterranean. Spend your days lounging by the garden pool and getting pampered at the spa followed by nights spent gazing through the glass ceiling of the historic wing’s La Cupola Suite to the expansive starry skies above.
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Drink at Hydronetta

Hydra, Greece
The rocky shores at Hydronetta provide an awesome backdrop for boozy beachside hangs, both day and night. Sunset at this spot is worth waiting around all day for.
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Photo: Iro Harokopou
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Stay at Bratsera Hotel

Hydra, Greece
This car-free island offers a level of serenity many of us don’t get to experience in our modern-day hustle. Embrace the calm with a stay at Bratsera Hotel in Hydra’s town center, where the beautiful stone architecture gives a real sense of place amongst the gray stone captains’ homes. Hot tip: Bratsera is the town’s only hotel with a pool.
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Dine at Téchnē Restaurant & Social

Hydra, Greece
What was once a boathouse on the water’s edge is now Hydra’s favorite hangout, day and night. Téchnē is a comfortable indoor and outdoor dining scene that offers fresh, local food that’s easy to share with friends.
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The Dodecanese

Greece
A dozen islands make up The Dodecanese but Rhodes and Kos are the heavy-hitters for tourist purposes. The two islands have their own international airports, and getting from island to island within the Dodecanese is best done via ferry. Rhodes offers a historic mix of architecture blended with a more modern city and beaches dotted with pebbles and sand, while Kos is a mecca for cycling enthusiasts and tourists in search of historic ruins and interesting museums.
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Stay at Casa Cook Rhodes

Rhodes, Greece
Mediterranean design meets the bohemian set at Casa Cook Rhodes, and the result couldn’t be more on-point. The gorgeous rooms here open out to a veranda with hammocks, a swimming pool and a view of all the island’s glory. Read more about Casa Cook Rhodes here →
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Photo: Chris Hotel
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Dine & Drink at Chris Cafe at Chris Hotel in Skala

Patmos, Greece
The café at Chris Hotel in Skala peers over the edge of the water to both the harbor and the sea. The welcoming, sun-soaked space is a great place to recharge and grab a bite, a cocktail or both.
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Visit the Monastery of Saint John the Theologian

Patmos, Greece
A day trip to Patmos must include a visit to the still-working Monastery of Saint John the Theologian, where he was said to have received the gospel for the Book of Revelation. An architectural feast of domed archways, courtyards, roof terraces, chapels and more, the hilltop structure dates back to 1088 and has since been declared a World Heritage Site by UNESCO.
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Photo: Casa Cook Kos
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Stay at Casa Cook Kos

Kos, Greece
The boho influenced hotel group of the Greek islands, Casa Cook also offers a beautiful stay on Kos. This place feels like its own little safari village with lots of gardens, cozy lounging spaces and shared pools.
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Photo: Barbouni
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Dine at Barbouni

Kos, Greece
Barbouni serves local seafood by the seashore. This is exactly the kind of place you’ll want to be at sunset, just after exploring the island by bike for the day.
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The Ionian Islands

Greece
The seven verdant Ionian Islands sit alongside the west coast of Greece in the Ionian Sea. The culture is a mash-up of British, French, Venetian and their own, which is very much reflected in the architecture, cuisine and art. We’d recommend avoiding the Ionian Islands in August, when the European vacation crowds take over. At all other times, flying in is probably your best travel option, either via a connection in Athens or via some international airlines and charters. Overnight ferries are an option from Brindisi, Venice, Bari, Trieste and Ancona, or you can hire a charter boat if that’s your jam.
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Stay at Villa Aria learn more

Fair warning: we’re picking favorites here. And the favorite at The Peligoni Club is Villa Aria. With three bedrooms, a lovely private pool, generous outdoor spaces for dining and relaxing as a group, this spot is group getaway goals.
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Photo: Lauren Bullen
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Visit Shipwreck Beach (Navagio Beach)

Zakynthos, Greece
You’ll have to hop aboard a boat to get to this picturesque beach on Zakynthos. Shipwreck Beach is home to an abandoned smugglers’ ship and not much else – unless you count the surrounding limestone cliff faces, white sand beaches and pristine blue waters. You’re right. We’ll count them.
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Photo: rvk_loves
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Stay at The Rou Estate

Corfu, Greece
Perched on the cliffside above the bustle of Corfu, Rou Estate is a hamlet of historic village houses that have been restored and refreshed to appeal to a luxury crowd. It’s a fabulous place to rest between tours of the UNESCO-protected Old Town of Corfu and trips to the white-sand beaches and great waterfalls.
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Visit La Grotta Corfu

Corfu, Greece
Adventure to La Grotta Corfu for cliff diving in the bluest water. This hidden spot is seasonal and the snorkeling is top-notch.
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Dine & Drink at the Rooftop Restaurant at the Cavalieri Hotel

Corfu, Greece
Easily one of the world’s most gorgeous places for a rooftop cocktail, Cavalieri Hotel juts right over the edge of the sea. This epic spot overlooks some of the most notable Venetian old town sights.
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Photo: Nick Isden
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See the Village of Assos

Kefalonia, Greece
Perhaps the best way to see the tiny peninsula of Assos on Kefalonia is by hiking the hills above to get a view of the Venetian architecture and intricate layout of the 100-person town.
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Crete

Greece
The largest of the Greek islands, Crete has two airports that make travel from Athens easy. You can opt to take a ferry or high-speed hydrofoil, but travel time is typically fastest via flight. Spend your days on Crete exploring the pink sand beaches of Elafonissi, wandering ancient mountain villages, hiking the Samaria Gorge and bravely sipping the local moonshine.
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Photo: Salis
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Wine & Dine at Salis

Crete, Greece
Set overlooking Chania’s 14th-century harbor, Salis is the wind-down spot that makes throwing back a few bottles of wine seem like no big deal. These culinary pros do traditional Cretan cuisine with a bit of modern edge, growing vegetables in their own gardens and focusing heavily on local purveyors and winemakers.
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Photo: Tara Milk Tea
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Stay at Blue Palace, A Luxury Collection Resort And Spa

Crete, Greece
A stay at Blue Palace means you’ll be cozied up in a Mediterranean villa or suite with access to a private beach, poolside bars and maybe even your own private pool. Following your full-day hike of the Samaria Gorge, book some pampering at the spa and give the Thalassotherapy saltwater pools a go at soaking your sore muscle pain away.
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Stroll the Streets of Chania

Crete, Greece
Old world Greece meets new Greece at the historic Venetian port city of Chania. Take a stroll through the cobblestones streets and taste your way through the star restaurants of Cretan cuisine.
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Stay at Daios Cove Luxury Resort & Villas

Crete, Greece
Luxurious, sun-filled villas and suites overlook the turquoise cove of Vathi at Daios Cove. Treat yourself to spa services and a meal in at least one of the six dining spots on the grounds.
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Wine & Dine at Mama's Dinner Restaurant in Kissamos

Crete, Greece
On the other side of Crete, sits a fine dining restaurant on the sea that’s known for its authentic, local cuisine. Mama’s Dinner in Kissamos is a multi-generational family restaurant that celebrates authentic Cretan eats and shares a love for simply prepared seafood and delicious wines with its guests.
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The Sporades

Greece
The Sporades Islands are an archipelago along the east coast of Greece, with four of the 24 islands actually inhabited. The scene is comprised mostly of small villages with tons of lush greenery, sparkling blue water and golden sandy beaches. Fly into Skiathos or Skyros via Athens, or hop in a ferry or hydrofoil for most other destinations. We’d encourage you to eat. Eat often and eat well, as this region is known for its incredible access to produce and seafood.
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Kayaking Skopelos

Skopelos, Greece
Skopelos is a haven for the water sports inclined, especially with its National Marine Park. Grab a kayak for the day and explore the many islands of Alonissos at your own pace.
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Photo: Atrium Hotel
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Stay at Atrium Hotel

Skiathos, Greece
Nestled into the landscape of Skiathos, Atrium Hotel is gorgeous little jewel of a boutique hotel. Rooms here are bright and luxurious, with views of the sandy beaches and giant pool patio below.
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Drinks at The Borzoi Club

Skiathos, Greece
Great music, great cocktails and great ambience make The Borzoi Club exactly the place you’ll want to be post sundown. Keep an ear out for happenings here, as this spot is known to put on fabulous parties.
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Photo: Marmita
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Wine & Dine at Marmita

Skiathos, Greece
Classics like oven-baked feta, steamed mussels baked in white wine, and grilled meatballs with pita bread make up the menu at this traditional eatery in Skiathos. Marmita isn’t your grandmother’s place, but it easily could be, especially if your grandmother had excellent taste in furnishings.
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Stay at Bourtzi Boutique Hotel

Skiathos, Greece
A contemporary 38-room hotel located in central Skiathos, Bourtzi tows the line between being totally flash in the shared spaces and all about serenity inside the suites. Book a stay here if you’re looking for something a little outside the norm.
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The Northeast Aegean Islands

Greece
These thirteen islands are the closest to Turkey and were historically heavily influenced by Asia Minor and Byzantine Empire culture, as seen in its varied food and wine, medieval fortress villages, local dialect and traditions. Samos, Limnos and Lesvos have international airports while Chios and Ikaria airports are domestic. Island hopping within the archipelago is best done via ferries.
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Stay at Armonia Bay Hotel

Samos, Greece
Hidden in the cove of Armonia Bay, this luxe paradise is exactly what you’d expect in a boutique Mediterranean hotel: whitewashed walls, rooms that open out to the turquoise seas and gardens, and air so salty you can practically smell it through the photos.
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Photo: The Pastards
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Dine at The Pastards

Chios, Greece
This casual pizza and pasta joint is the perfect place to fuel up between fortress village hopping and learning about the old castles and monastery of Chios.
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Watersports & Glamping with Surf Club Keros

Limnos, Greece
Surf Club Keros offers surfing, wind surfing and kite surfing classes for all learning stages, including people with disabilities. Also, the beachside glamping is a great option if you’re looking to soak up every second of sand-in-toes possible.
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Stay at Kaliopi Luxury Studios With Surf Club Keros

Limnos, Greece
Keros Beach in Limnos is known most for its dependable kite surfing, wind surfing and surf camp. Surf Club Keros offers apartment-style stays that are great if you’re looking for something a little more polished than their beachside glamping setup.
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