How to Choose the Perfect Greek Island: A Guide for First-Timers

You've decided on Greece. Now comes the impossible question: which island?

With over 200 inhabited islands scattered across the Aegean and Ionian Seas, choosing just one (or a few) can feel overwhelming. Each has its own character, beaches, and personality. Some are world-famous; others remain delightful secrets.

After welcoming over 500 guests to Skiathos since 2019, we've heard every variation of this question. Here's our honest guide to help you find your perfect Greek island match.

Understanding What Matters Most

Before diving into specific islands, ask yourself these questions:

Your Travel Style

• Do you want to see iconic landmarks, or discover hidden gems?
• Are you drawn to lively scenes or peaceful escapes?
• How important is nightlife versus early morning beach walks?

Practical Considerations

• How long is your trip? (Some islands need more time to appreciate)
• Are you island-hopping or settling in one place?
• What's your budget? (Costs vary dramatically between islands)
• Are you traveling with children? (Beach safety and facilities matter)

The Beach Factor

• Do you prefer sandy or pebble beaches?
• Organized with sunbeds, or wild and undeveloped?
• Calm waters or waves for water sports?

Keep your answers in mind as we explore the options.

The Famous Names: What to Expect

Santorini: The Iconic Postcard

Best for: Couples, honeymooners, sunset chasers, Instagram enthusiasts

Santorini needs no introduction. The dramatic caldera, whitewashed buildings with blue domes, and legendary sunsets make it arguably the most photographed island in the world.

The Reality:

• Breathtakingly beautiful, but also extremely crowded (especially cruise ship days)
• One of the most expensive Greek islands
• Beaches are volcanic—black or red sand, interesting but not the soft golden beaches you might imagine
• Best experienced in shoulder season (May, late September, October)

Our Take: Visit once for the experience, but don't expect a relaxing beach vacation. It's about the views, the wine, and the romance.

Mykonos: The Glamorous Party Island

Best for: Party-goers, luxury seekers, those who want to see and be seen

Mykonos has transformed from a charming fishing village to a global hotspot for celebrities, DJs, and high-end travelers. World-famous beach clubs, designer boutiques, and nightlife that runs until sunrise.

The Reality:

• The most expensive island in Greece
• Beautiful beaches, but many are dominated by pricey beach clubs
• Incredible energy during peak season
• Windmills and Little Venice remain genuinely charming
• Works well for families with teenagers who want independence

Our Take: If you want Greece's most glamorous party scene, Mykonos delivers. But it's a completely different experience from traditional Greek island life.

Crete: The Mini Continent

Best for: Road-trippers, history buffs, foodies, families wanting variety

Greece's largest island is so diverse it's practically a country. Ancient Minoan palaces, dramatic gorges, mountain villages frozen in time, and beaches ranging from pink sand to palm-lined lagoons.

The Reality:

• Needs at least a week to appreciate (ideally two)
• Requires a car to explore properly
• Tourism is concentrated in certain areas; venture beyond for authenticity
• Incredible local cuisine and wine scene
• Weather is slightly different from other islands (can be warmer)

Our Take: Perfect for travelers who want everything—history, nature, beaches, food—in one destination. Not ideal for a short trip.

Rhodes: The Medieval Gem

Best for: History lovers, families, those who want more than beaches

Rhodes combines stunning beaches with one of the best-preserved medieval towns in Europe. The Old Town is a UNESCO World Heritage Site, with cobblestone streets, ancient walls, and centuries of layered history.

The Reality:

• Larger island with diverse regions
• Old Town can get crowded with cruise visitors
• Eastern coast has calmer, warmer waters (better for families)
• More affordable than Cyclades islands
• Good infrastructure and easy to navigate

Our Take: An excellent choice if you want to balance beach time with cultural exploration. The Old Town alone is worth the trip.

Corfu: The Venetian Beauty

Best for: Families, culture seekers, those wanting easier access

Corfu's Venetian, French, and British influences give it a unique character among Greek islands. Lush and green with elegant architecture, it's often called the most cosmopolitan of the Ionian islands.

The Reality:

• Excellent for families—calm Ionian Sea, good facilities
• Beautiful but different aesthetic from Cycladic islands
• Corfu Town's UNESCO-listed old town is magnificent
• Northeast coast has dramatic scenery; south has sandy beaches
• Well-connected with direct European flights

Our Take: Ideal for families and those wanting a greener, more European-feeling Greek island. The Ionian Sea is calmer than the Aegean—great for young children.

The Hidden Gem: Skiathos

Now let us tell you about the island we call home.

Why Skiathos Stands Out

Skiathos is part of the Sporades—Greece's greenest island group, covered in pine forests that sweep down to meet golden sand beaches. While it draws visitors (especially from the UK), it retains an authenticity that more famous islands have lost.

What Makes Skiathos Special:

Over 60 Beaches: No, that's not a typo. On an island just 12 by 6 kilometers, you'll find more than 60 beaches—from organized stretches with beach bars to hidden coves accessible only by boat or hiking trail. Koukounaries Beach was once rated among the best beaches in the world.

Pine Forest Setting: Unlike the arid Cyclades, Skiathos is verdant. Hiking trails wind through fragrant pine forests. The scent of herbs fills the air. The landscape provides natural shade and a completely different atmosphere.

Easy to Reach: Direct flights from Athens take just 30 minutes. During summer, direct flights operate from multiple European cities. Ferries connect to the mainland (Volos, 2.5 hours) and neighboring islands.

Authentic Greek Character: Skiathos Town has the whitewashed beauty and winding lanes you'd expect, but without the overwhelming crowds or inflated prices of Mykonos or Santorini. Real tavernas serve real Greek food to a mix of locals and visitors.

Perfect for Families: The beaches are generally gentle with shallow waters. The bus system covers the southern coast. Restaurants welcome children. And the atmosphere is relaxed rather than party-focused.

The Sporades Archipelago: From Skiathos, easy day trips reach Skopelos (the "Mamma Mia" island) and Alonissos (Greece's first marine park, with pristine waters). Island hopping is simple and affordable.

A Typical Day in Skiathos

Morning starts with a swim at a beach near your accommodation. Maybe Troulos or Agia Paraskevi on the southern coast, with crystal-clear water and a beachside coffee.

Mid-day, escape the heat with lunch at a traditional taverna—perhaps grilled fish, Greek salad, and local wine. Retreat to your villa for an afternoon siesta or swim in your private pool.

Late afternoon, explore Skiathos Town. Wander through the old port, discover artisan shops, watch the boats come and go. Perhaps a sunset drink at one of the waterfront bars.

Evening brings dinner—maybe at a hidden gem taverna in Kechria where locals actually eat, serving family recipes passed down through generations. The meal stretches for hours, as Greek dinners do.

After dinner, a stroll along the harbor, or for the energetic, some of the island's bars come alive (though nothing like Mykonos intensity).

Return to your villa under a sky full of stars, with the sound of cicadas and the scent of pine.

Who Should Choose Skiathos?

Ideal for:

• Families with children of any age
• Couples seeking romance without crowds
• Groups of friends who want beaches by day and optional nightlife
• Nature lovers and hikers
• Those wanting authentic Greece at reasonable prices
• First-time visitors to Greek islands
• Travelers combining islands (easy connections to Skopelos and Alonissos)

Maybe not ideal for:

• Those seeking iconic Cycladic white-and-blue aesthetic
• Visitors wanting intense nightclub scene
• History buffs seeking ancient ruins (limited archaeological sites)

Island Comparison at a Glance

Making Your Decision

Choose Santorini if...

You want the iconic Greece experience at least once, you're traveling as a couple, and you understand it's about the views rather than beach relaxation.

Choose Mykonos if...

You want world-class nightlife, designer shopping, and celebrity-watching, and budget isn't a primary concern.

Choose Crete if...

You have at least a week, want incredible diversity (beaches, mountains, history, food), and plan to rent a car and explore.

Choose Rhodes if...

You want to combine beach time with serious history exploration, especially the magnificent Medieval Old Town.

Choose Corfu if...

You're traveling with young children, want calm waters, or prefer a greener, more European-feeling island.

Choose Skiathos if...

You want exceptional beaches without excessive crowds, authentic Greek atmosphere, easy accessibility, and excellent value. Especially if you're traveling with family or seeking a relaxed pace with optional evening buzz.

Your Next Step: Where to Stay

So you've chosen Skiathos (excellent choice, we think). Now the question becomes: hotel, apartment, or villa?

After years of welcoming guests, we've seen how dramatically accommodation choice affects the overall experience. A private villa in the peaceful Kechria hills versus a hotel room in busy Skiathos Town creates two entirely different vacations.

Read next: Skiathos Villa vs Hotel: Why Private Villas Win Every Time

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The team at Damari Luxury Retreat has been hosting guests in Skiathos since 2019. Our two luxury villas in the Kechria area offer private pools, sea views, and the authentic Greek island experience we've described. Learn more about our villas or get in touch with your questions.