Planning a trip to Greece can feel like a dream come true and a logistical nightmare at the same time, especially when you're trying to make the most of its breathtaking islands, ancient history, and vibrant culture. This 12-day itinerary is designed to help you explore the best of Greece, balancing iconic landmarks with serene beaches and charming villages. From the historic wonders of Athens to the rugged beauty of Crete, the romantic sunsets of Santorini, and the unique landscapes of Milos, this guide offers a perfect blend of adventure, relaxation, and unforgettable experiences. Whether you're a first-time visitor or returning to Greece for another round of exploration, this itinerary has everything you need for a trip of a lifetime, but will leave you wanting to return to explore even more islands.

*Greece by plane & ferry*

The appeal of Greece for many tourists is the ability to hop from island to island via ferry. While seemingly easy on paper, it’s actually quite arduous during the hot, busy months. If traveling from the U.S. with say 9-10 days, you could potentially spend 3+ afternoons in transit between the islands. In many cases, it’s more efficient to fly from island to island, especially when you land in Athens and you’re already at the airport. A flight from Athens to Crete is necessary, but between the Cycladic Islands, a ferry will do if the weather allows!

IMPORTANT GREECE TRAVEL TIPS

Plan Around the Seasons
- Best Time to Visit: Late spring (May-June) and early fall (September-October) offer pleasant weather, fewer crowds, and more affordable prices. Peak summer months (July-August) can be very crowded, especially on popular islands like Santorini and Mykonos.
- Packing: Bring light, breathable clothing for summer and layers for cooler evenings in spring or fall. Don’t forget comfortable shoes for exploring cobblestone streets and ancient ruins.
Understand the Island Ferries
- Booking: Book ferries in advance during peak season. High-speed ferries save time but may cost more, while traditional ferries are slower and more scenic. You can also fly between many of the main islands, which at times is more efficient and reliable especially during windy months like August when ferries cancel frequently.
- Timing: Allow buffer time in your itinerary if connecting ferries, as delays can occur due to weather. If flying between islands, book early for the best deals.
Embrace Greek Dining Etiquette
- Meals: Lunch is typically between 1-3 PM, and dinner often starts after 8 PM. Don’t rush your meal—Greeks love to take their time over food.
- Tipping: It’s customary to leave a small tip (5-10%) or round up the bill, especially in tavernas.
Cash is King
- Many places take Visa or Mastercard (no Amex), however cash is still the most widely used especially on the smaller islands. I recommend taking cash out a local bank ATM during your first stop.
Pack Medicines
- Dramamine: If you’re prone to motion sickness, then prepare well in advance. The ferries can be tough on windy days or long rides, but for the most part the boats are large enough where symptoms should be minimal. What got me worse than the ferries are the roads. Every single island road is small, winding and bumpy and taking a car is unavoidable.

Athens

There’s a high likelihood your trip to Greece will begin and end in Athens, as it’s the country’s most well-connected airport. The challenge often lies in deciding where to fit 1–2 days in the city before heading off to the islands. If you’ve already visited Athens, you might choose to skip it altogether. However, for first-time visitors, I recommend saving Athens for the final days of your trip—especially if you plan to explore distant islands like Crete that require a domestic flight.

To streamline your travel, consider flying directly to Crete upon arrival in Greece. From there, you can work your way back to Athens using a combination of ferries and flights. This approach minimizes multiple trips to the airport and allows you to end your journey with Athens’ rich history and iconic landmarks.

Hotels

Contact me to book your hotels and receive exclusive perks like complimentary room upgrades, hotel credits, etc.

Activities/Sightseeing

Acropolis, Parthenon and Acropolis Museum
Parthenon
Bar hopping (several of the “Top 50 Bars in the World” are in Athens!)
Walking food tour

Santorini

When you picture Greece as a first-time visitor, the iconic blue domes of Santorini likely come to mind. This stunning island is famous for its whitewashed buildings, breathtaking caldera views, and world-renowned sunsets. However, it’s important to approach your visit with realistic expectations. Santorini is a popular stop for cruise ships, meaning thousands of additional tourists flood the island daily, making an already busy destination feel even more crowded. Summers can be scorching, and the steep, rocky pathways—particularly in Oia, where most visitors flock—can be challenging to navigate. Choosing the right hotel location is crucial for easy access to restaurants and to avoid the throngs of tourists lining up outside your door for photos.

Additionally, Santorini is one of Greece’s most expensive destinations, which can come as a surprise if you’ve visited smaller, more affordable islands like Milos or Paros. Transfers to and from the docks or airport can easily exceed $100 each way. While these realities aren’t meant to deter you, understanding what to expect—especially during peak summer months—can help you plan and enjoy your trip to Santorini more fully.

Hotels

Contact me to book your hotels and receive exclusive perks like complimentary room upgrades, hotel credits, etc.

Activities/Sightseeing

Fira to Oia
Sunset catamaran around the caldera
Lunch at Armeni’s Fish Tavern
Wine tasting
Horseback riding

Milos

Milos is nothing short of magical—like something straight out of a Mamma Mia dream. While it’s easy to combine with neighboring islands like Santorini, Naxos, and Paros, Milos stands out for its natural beauty rather than bustling nightlife or high-end shopping. This island is all about the outdoors, offering stunning landscapes and unique experiences. Compact in size, Milos is easy to explore, but be cautious when navigating the narrow village streets. Parking is limited, and parking tickets are strictly enforced—if you do receive one, you can settle it directly with your rental car company upon returning the vehicle.

What truly sets Milos apart is its unforgettable landscape. The island’s most famous attraction is Sarakiniko, a moonscape beach with dramatic white rock formations that make it one of the most striking beaches in Greece. It’s a popular spot for both tourists and locals, who often gather to jump off the rocks into the crystal-clear waters. For a more comprehensive experience, a day-long catamaran tour around the island is highly recommended, allowing you to explore hidden coves, impressive rock formations, and dazzling turquoise waters.

Hotels

Contact me to book your hotels and receive exclusive perks like complimentary room upgrades, hotel credits, etc.

Domes White Coast Milos (Newer, adults-only with a rental car company onsite)
Milos Cove (Where Eugene Levy stayed on his show, The Reluctant Traveler)

Activities/Sightseeing

Full day catamaran around the island
Walk around Plaka
Beach hopping
Dinner at Medusa
Dinner at Oh Hamos

Crete

Crete is a destination I could return to year after year and never grow tired of its charm. As Greece's largest island, Crete feels like a world of its own, with a distinct culture, unique cuisine, and even its own accents—much like how Texas stands out within the U.S.! Impressively, Crete produces over half of the food for the other Greek islands, meaning you’ll enjoy the freshest, locally sourced ingredients during your visit.

You could easily spend a full week exploring Crete, and if your schedule allows, it’s well worth dividing your time between Elounda and Chania, two of the island’s more popular destinations with plenty of luxury hotels. Renting a car is the best way to explore, as it allows you to discover off-the-beaten-path beaches and hidden gems. However, be prepared for narrow, winding roads, which can be particularly tricky to navigate at night. The effort is rewarded with breathtaking landscapes and charming villages at every turn.

If you’re arriving by ferry from Santorini, you’ll dock in Heraklion. For those flying in, you can choose between Chania or Heraklion, depending on where you plan to start your adventure. Crete’s unique character, stunning scenery, and rich history make it a must-visit destination in my eyes.