Hey Reader,
(⏱️ 1‑min 38‑sec read)
In September 2024, I spent 11 days exploring Greece with my wife, my best friend, and his wife and it was epic.
We visited Athens, Mykonos, Milos, and Santorini, and I wanted to simplify the planning process for you with this Ultimate Greek Islands Guide: when to go, what to do, where to stay, how to get around, and a few of our favorite ferry, food, and activity recs.
Let’s dive in 👇
When to Visit Greece
If you’ve been around here for a while, you know I’m a big shoulder season guy. September was perfect. Warm enough for beach days and cool enough at night to avoid sweating through dinner.
If you can, skip July and August—peak cruise crowds and high temps (especially in Santorini).
Best months:
- May–early June
- September
- Early October (if you're okay with cooler nights and fewer ferry routes)
Where We Went
Athens (1–2 nights)
Athens was our launch and landing spot. You’ll fly into ATH, and most major U.S. cities have solid options including new direct flights from Charlotte (CLT).
Where we stayed:
We booked two different Airbnbs, both walkable to restaurants and the Acropolis.
If you're using points, check out the Grand Hyatt Athens — great rooftop and bookable with Hyatt points.
Tips:
- Uber works well here.
- No need to over-plan meals—just wander and eat what smells good.
- You only need a night or two unless you're big on museums.
Mykonos
We ferried over using SeaJets (book early). Mykonos is the perfect party-meets-relaxation island.
Where we stayed:
An Airbnb near Paradise Beach — ideal if you want to hit beach clubs like Scorpios and Cavo Paradiso.
Top recs:
- Scorpios (Sunday sunset party)
- Cavo Paradiso (iconic open-air nightclub)
- 180 Degrees Sunset Bar – best view in town
- Dinner at Kastro’s (book exactly 14 days out)
- Cheap lunch: Saki’s Grill for gyros
Tip: Cabs are expensive (€35–40/ride). Sharing or using shuttle buses helps.
Milos (3 nights)
We wanted a more relaxed island, and Milos delivered. White rock beaches, scenic drives, and small-town charm.
Where we stayed:
A central Airbnb in Adamantas with a huge balcony—walkable to everything.
Must-dos:
- Rent an ATV and explore the island
- Sarakiniko Beach – looks like the moon
- Dinner at O! Hamos Tavern – beachfront & authentic
- Drinks at Utopia or Akrotiri for sunsets
Optional:
Santorini (3 nights)
We took a morning ferry from Mykonos (about 2 hours). Book private transport in advance the Santorini port is chaos.
Where we stayed:
An 2 bed 2 bath amazing view in Imerovigli—central, peaceful, and walkable. Beautiful caldera views without the Oia crowds.
Favorites:
Pro tip: Avoid Oia on cruise ship days (especially Tuesdays). You won’t need an ATV here taxis and walking are perfect.
Getting Around
- Ferries: We used SeaJets—book morning departures for smoother rides and fewer delays.
- Transport: Book taxis/shuttles in advance and ask for WhatsApp numbers.
Check Out These Greece Podcasts
World Travel Made Easy with Itinerary Boss is live!
I walk you through our exact itinerary across Athens, Mykonos, Santorini, and Milos how we got around, where we stayed, what we’d skip, and all the time and money saving strategies we used.
Whether you're flying on points, looking for hidden gems, or figuring out ferry routes this is the episode you don't want to miss.
The Ultimate Island Hopping Guide in Greece:
This is the perfect podcast for you to listen to if you're planning to island hop in Greece.
When and Where to Visit in Greece:
If you're short on time and trying to decide on an island or trying to pick when to go this is great for you.
Prefer Apple or YouTube?
→ Listen on Apple Podcasts
→ Watch on YouTube
If you enjoy the show: follow, share with a friend, and leave a 5-star review. It helps us keep creating helpful travel content!
Where We Stayed
- Athens: Place and near the Acropolis
- Mykonos: Beachfront Airbnb near Paradise Beach
- Santorini: Luxury cave house in Imerovigli
- Milos: Ocean View Villa in Adamantas — perfect for ATVs and dinner spots
➡️ If you're using points and wanting to stay at Hyatt, Hilton, Marriott, or IHG hotels I recommend Gondola AI to quickly search how many points or miles you’ll need for any hotel in Azores, Porto, Lisbon, or the Algarve.
It saves a ton of time, you'll book directly with the hotel and you'll get 5% cash back on all your bookings.
Our Favorite Experiences
Here are a few of the top recs we loved:
Packing Checklist
Planning Greece?
Grab our FREE Stress-Free Travel Starter Kit—includes a packing checklist, printable docs, gear links, and a budget tracker.
→ Download the starter kit here
If you're building your own Greece itinerary, I hope this helps save you time and stress.
If you’ve got questions about islands, ferries, or hotels, just hit reply, I’ve got your back.
Talk soon,
Ross
Founder, Itinerary Boss
Affiliate Disclosure: Some of the links above may earn us a small commission at no cost to you. We only recommend tools and tours we personally use and love.
