Dreaming of Greece: Island Hopping Itinerary for First-Timers

Part 2 of the Dreaming of Greece Series

So, you’re ready to live your Mamma Mia moment—or at least dip a toe into that iconic Aegean blue. After sharing why Geece is The Bucket List Destination That Will Have You Wanting For More in Part 1 of this series, I’m back with my go-to island hopping itinerary for first-time visitors. It’s a mix of ancient ruins, stunning sunsets, great food, and just the right dose of nightlife if you're traveling with young adults (or channeling your own inner 20-something).

And yes, I did include Mykonos. I know, I know—most Greeks think I’m nuts for suggesting it. But I’ll explain…

When to Visit Greece

Best Months: Late May–June or September–early October
Why? Fewer crowds, better weather, and more breathing room on ferries and beaches.
Peak Season Warning: July–August is hot—like frying-egg-on-a-rock hot—and packed with tourists. In recent years, that heat’s been even more intense. If you must go during that time, hydrate, find shade, and don’t say I didn’t warn you!

✈️ The Island Hopping Itinerary

Whether you’re working with two full weeks or just over ten days, here are two flexible options to help you make the most of your time in Greece. Both include a mix of culture, beach time, and those iconic sunsets you’ll dream about long after you’re home.

📝 Note: Flights from the U.S. to Greece are typically overnight, so you’ll land the next day. That’s why I’ve included one night here for your outbound flight—it counts toward your overall trip planning, even though you’ll be in the air.

🛫 Option 1: 12–14 Nights – The Classic Circuit

Great for first-timers who want a little bit of everything: city, islands, beach, and food.

🌙 U.S. Departure (1 night – overnight flight)

🏛️ Athens (2 nights) – History, rooftop views & recovery from jet lag

🌅 Paros (3 nights) – Chill beaches, charming towns & bakery heaven

 🌊 Mykonos (3 nights) – Glam beaches, great food & unexpected art finds

🏖️ Santorini (3 nights) – Cliffside views, wine tastings & iconic sunsets

🛬 Return via Athens – Fly home same day or stay 1 night before departure

⏳ Option 2: 10–11 Nights – The Slightly Shorter Escape

Perfect if you're limited on time but still want the best of Greece’s mainland + islands.

🌙 U.S. Departure (1 night – overnight flight)

🏛️ Athens (2 nights)

🌅 Paros (3 nights)

🏖️ Santorini (3 nights)

🛬 Athens (1 night) or add the night to one of the islands and fly out of Santorini, connecting via Athens or another European hub.

 Destination Highlights

ATHENS

Walk Where the Gods Once Played

Don’t skip Athens! It’s your time to adjust, soak up history, and enjoy the modern energy of Greece’s capital.

• Where to Stay

  • If you're only in Athens for a couple of days and want to hit the ancient sites, I recommend staying near the city center—close to the Acropolis or Syntagma Square. You’ll be walkable to just about everything, including rooftop bars with killer views.

  • But if you’re planning to stay a little longer—like I typically do—the Athens Riviera is the way to go. You’ll get the best of both worlds: culture and coastline. My personal favorite? Vouliagmeni. It’s elegant, beachy, and has just the right amount of that “I could live here forever” vibe.

• What to Do

  • Morning: Visit The Acropolis Museum—it’s modern, air-conditioned, and honestly one of the best museums I’ve ever visited.

  • Lunch: Find a shady taverna nearby, relax, and pace yourself.

  • Afternoon: Take a leisurely stroll through Syntagma Square, and don’t miss the ceremonial guards at the Tomb of the Unknown Soldier—it’s one of those quietly powerful moments worth pausing for. From there, head to the Acropolis in the late afternoon. By then, the cruise ship crowds will have thinned, the heat will have mellowed, and you’ll have a better chance of catching that magical sunset glow from the top.

  • ⚠️ Heads up: The Acropolis and other archaeological sites now require timed-entry tickets. I booked the last available slot at 4:30 PM, which gave me plenty of time to explore and stay until the sun began its golden descent.

  • 🎟️ Pro tip: Pre-purchase your tickets here to avoid lines and secure your preferred entry time.

Athens Guide coming soon with my favorite rooftop bars, hidden gems, and why I always pack Advil and a sun umbrella when I do the Acropolis climb.

PAROS

Pretty, Party-Ready, and Perfectly Greek

Paros is the island I always recommend for a first-time Greek island experience. It’s stunning, less crowded than Santorini or Mykonos, and easy to navigate.

• Where to Stay: Naoussa

  • Τhink cobblestone streets, lively tavernas, waterfront cocktails, and shops with just the right amount of temptation. It’s charming by day and buzzing by night, with a fun, walkable party scene perfect for younger travelers (and the young-at-heart).

• What to Do

• Right in town, you can grab a ride on a small ferry boats from Naoussa to beaches like Kolymbithres, Monastiri, and Lageri.

• Wander through Parikia or ferry over to Antiparos for a perfect day trip.

Paros Travel Guide coming soon(ish)—based on our 2019 trip. While some things may have changed, the island’s beauty and vibe are timeless. I’ll share a few highlights, but for the latest, double-check with local sites!

MYKONOS

More Than a Pretty Party!

Here’s the thing: every single person who finds out I’m Greek-American asks me about Mykonos. So even though most native Greeks roll their eyes and say, “That’s not real Greece,” I decided to take one for the team—and you know what? I’m glad I did.

No, we weren’t there for the all-night clubbing or wild beach parties (though you could easily find both if that’s your scene). We went for the views, the food, and unexpectedly... the art.

Let’s start with the food: For such a touristy island, we were pleasantly surprised—most of our meals were excellent, especially at the little harbor-side tavernas in Mykonos Town.

And the art? Unexpectedly incredible. We fell in love with the Galatis Art Gallery and even had the chance to meet the island’s emblematic artist, Giannis Galatis (pictured above with my husband and I). We ended up shipping home one of his original pieces, which now has a special place in our home. The gallery scene here feels modern and high-end without losing the island’s charm.

• Where to Stay: Nissaki Boutique Hotel in Platys Gialos. This is where we stayed, and I can’t recommend it enough. It has a gorgeous spa, dreamy views, walkable access to three beautiful beaches, and a restaurant that’s a gastronomic delight—from the unforgettable breakfast buffet to dinners that were next-level culinary experiences.

  As someone who's a little obsessed with what exceptional client experience looks like in my day job, I was seriously impressed. Nissaki sets the bar high—every detail, from service to ambiance, felt like they truly understood how to elevate a guest’s stay. And no, I’m not getting paid to say this—I just genuinely loved it that much. But if they ever need a brand ambassador…call me!

• What to Do (besides party)

• Wander through the winding alleys of Mykonos Town.

• Grab a cocktail in Little Venice at sunset.

• Explore the island’s galleries and boutiques.

• Eat. Then eat some more.

Mykonos Guide coming soon: My honest take on Mykonos—including how to enjoy it without becoming a club zombie, and why the food and art alone make it worth the stop.

SANTORINI

Views That Ruin You (In the Best Way)

Santorini is one of those rare places that actually does look like the postcards. From the iconic blue-domed churches to the jaw-dropping caldera views, it’s no wonder this island tops most Greece travel wish lists. And yes, it’s crowded. And yes, it’s still 100% worth it.

• Where to Stay

  • If your budget allows, stay on the Oia Caldera side. You'll have front-row seats to the most famous sunset in Greece—minus the jostling selfie-stick crowd. Many hotels offer private terraces where you can sip a glass of wine and watch the sky turn the most magnificent shades in peace.

• What to Do

  • Hike the cliffside path from Oia to Fira – The views are unreal, but wear real shoes (not flip-flops) and bring water.

  • Take a sunset sailing cruise – Bonus if it includes a swim in the caldera and dinner onboard.

  • Visit a winery – Santo Wines is often recommended, but I’ll be updating this soon with a more personal favorite that’s less touristy and just as scenic.

  • Wander the marble-paved paths of Oia and explore the boutiques, cliffside cafés, and art galleries.

⚠️ Safety Note: Watch for posted falling rock zones—they’re not just decorative.

Santorini recently experienced over 23,500 seismic tremors in just under a month, leading to temporary evacuations and heightened safety alerts. While activity has slowed, it’s a good reminder to stay alert. Don’t ignore warning signs, and avoid standing too close to cliff edges or unstable trail areas—the earth may look calm, but it’s still settling.

Pro Tip: If you time your visit right, you may catch a ceremonial flag-lowering event at the top of the island around sunset. It's a peaceful and powerful moment to wrap up your day—especially if paired with your favorite local wine and a good view.

Santorini Guide coming soon: what to book, what to skip, and how to soak in the magic without getting stuck in a crowd—or a crater.

Final Tips for First-Time Island Hoppers

🧳 Pack Light: Ferries + cobblestones = carry-on goals. Your back and your suitcase wheels will thank you.

⏰ Timing is Everything: Mid-morning museums, late lunches, and golden hour sunsets make all the difference.

👟 Footwear Matters: Sandals for strolling, sneakers for hiking, and maybe leave the heels at home (unless you're planning to reenact Mamma Mia).

☕ Order Like a Local: Freddo Espresso or Freddo Cappuccino (“freddo” = iced). You’ll thank me later.

🧭 P.S. This itinerary is a great starter for first-time visitors—but it’s definitely not the only way to experience Greece. I’ve also visited other incredible Cycladic islands like Tinos, Syros, and Naxos—each with its own personality, charm, and hidden treasures. And there are so many more still on my list to explore. Be on the lookout for upcoming posts where I’ll share some of those adventures—and maybe inspire your next island hop!

🎒 Coming Soon: Dreaming of Greece, Part 3 – My Big Fat Greek Family Adventure (Planning Edition)

We’re heading back to Greece—this time with my sister-in-law and our families to introduce our adult kids to their ancestral roots in Sparta and Crete. Grandpa is joining too…and if you’ve ever traveled with a man who wears three fanny packs at once, you already know there will be stories.

It’s part sentimental journey, part logistical juggling act, and 100% happening—with lots of goat cheese (aka Feta), local wine, and of course, my favorite Cretan spirit: Rakomelo.