What I’ve Learned from Planning 30+ Dream Trips to Greece

Written By Krista Nannery

The Acropolis in Athens

If you’ve ever dreamed of hopping around the Greek islands — Santorini sunsets, Mykonos beach clubs, Paros charm, Crete’s wild beauty — you’re not alone. Greece is one of my top-selling destinations for a reason. But after planning countless trips there for families, couples, and friend groups, I’ve learned that there’s a big difference between a good Greek vacation and a seamless, luxurious one. (But remember luxury means different things to different people.)

Here are 14 things most travelers don’t know about visiting the Greek islands — and a few ways I can help make your trip smoother, chicer, and even more unforgettable. Need more tips? Book a complimentary travel consultation here.

1. You don’t have to take the ferry.
Yes, ferries are a classic part of island-hopping — but sometimes, a quick 1 hour flight is far more efficient (and gentler if you’re prone to seasickness). Many islands have small regional airports with daily flights from Athens.

2. Not all ferries are created equal.
Some ferries take hours, stop at every rock in the sea, and board like a cattle call. Others are high-speed catamarans with assigned seating and business class lounges. I’ll help you choose the right one for your route (and your nerves).

3. If you do take the ferry — pack light.
Getting on and off the ferries in peak season can be hectic. You’ll often have to haul your own bags up steep ramps, through crowds, and across hot concrete. You’ll also be asked to check larger suitcases in the luggage area at boarding — and yes, you’ll be reunited with your bags later, but it’s often a sea of identical bags in a tight space. If you can, stick to carry-on or pack smart with standout luggage tags and brightly colored luggage.

Milos, Greece

4. You can do a lot without going to Mykonos or Santorini.
Mykonos and Santorini are popular for a reason, but they’re not the only show in town. Islands like Milos, Naxos, and Folegandros offer jaw-dropping views, authentic charm, and far fewer crowds. Plus, the pricing can be more attractive than Mykonos and Santorini as well. Greece is a large place! There are a lot of beautiful islands.

Pretty Paros, seriously one of my favorite places.

5. Paros might be the island you’re actually looking for.
It’s chic, well-connected, and has a little bit of everything: beautiful beaches, great restaurants, stylish boutique hotels, and charming towns like Naoussa. Many of my clients end up loving Paros the most. Interested? Check out Parillo, a Virtuoso property where you’ll receive complimentary breakfast for two, a $100 hotel credit, and priority for upgrade by booking through me.

Naxos

6. Naxos is a dream for families.
It has shallow beaches, friendly locals, fantastic food, and a relaxed pace that’s ideal for kids. Plus, it’s just a quick ferry from Paros or Mykonos.

7. There are some great cruises that visit the lesser-known islands.

Here are some of my favorite cruises that visit Naxos, for example…

As a reminder, I am a preferred partner with all of these cruise lines and can add onboard credits that you can’t get by booking direct. Ready to talk Greek crusing? Book a complimentary travel consultation here.

8. You can visit Hydra on a day trip from Athens — and it’s magical.
Hydra has no cars, just donkeys and water taxis. It's elegant, historic, and feels like a step back in time. Perfect for a peaceful overnight or a romantic escape from the city. Check out this day tour to Hydra from Athens.

Crete

9. Don’t underestimate Crete — it’s practically a country.
Crete is massive, with everything from gorgeous beaches and mountain villages to Michelin-worthy cuisine and ancient ruins. Plan on at least 4–5 nights, and don’t try to see it all in one go. Here are some of my favorite hotels on Crete where I can upgrade your stay with complimentary breakfast for two, a hotel credit, and more.

10. Book your transfers ahead of time.
Island ports and airports can be chaotic, especially in high season. Work with me and I’ll arrange private transfers in advance so you’re not dragging suitcases down a dock in 90-degree heat looking for a taxi that doesn’t exist. Book a complimentary travel consultation here to talk more.

11. Greece is not a last-minute destination.
The best hotels and ferry seats get snapped up early — especially in June, July, and August. You’ll get better rooms, better logistics, and better pricing when you book early. For July of next year, it’s not crazy to start planning in August or September of this year! (Most hotels start taking bookings 330 days in advance.)

12. The beaches are not always sandy.
Expect pebbles or even volcanic rock on many islands. Some are dramatic and beautiful but not exactly barefoot-friendly. But that’s okay! One of my most amazing moments was having dinner in Naxos overlooking the water…where white marble was washing up on the beach. I pointed it out to me server and he said, “We’re in Greece. What did you expect?”

13. Greek cuisine is even better outside of the big-name islands.
The food is delicious everywhere, but the culinary scene on less-touristy islands like Tinos, Syros, and Sifnos is off-the-charts — think local chefs, grandma-run tavernas, and farm-to-table heaven.

14. Some islands are only a short hop from Athens.
You don’t have to travel hours to feel far away. Spetses, Aegina, and Kea are reachable in under two hours and are perfect for a quick getaway or a first-timer’s intro to island life.

15. Greece in the summer is better with a plan.
There’s a carefree spirit to the islands — but behind every flawless Greek vacation I plan, there’s a lot of strategy: coordinating ferry times with hotel check-ins, navigating island combinations that actually work, and avoiding overhyped spots that won’t deliver on your expectations.

Ready to plan your Greek vacation? Book a complimentary travel consultation here to talk more.

About Krista

I’m a Virtuoso luxury travel advisor based in West Palm Beach, Florida. Prior to moving to Florida to take care of my elderly mom with Parkinson’s Disease, I spent over 11 years living and working in London, England. My career and personal travel have taken me all over the world. To date, I’ve been to 78 countries. Now I bring the joy of travel to others as a Virtuoso travel advisor. I offer a 30 minute complimentary vacation consultation for anyone looking to plan their next trip.

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Krista Nannery
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