Building the Itinerary
Full disclosure: I’m writing this 12 years after the trip, so it’s more of a retrospective. And I really think this is a good itinerary for a first trip to Greece for a couple of weeks.
This trip actually came together quickly, after discovering that I could get away for a couple of weeks in early fall. It was also one of our milestone example of going 1 street over: It was our first visit to a country where neither of us spoke the language. Though I had been there three times.
Greece was — and still is — my favorite place to travel, and I wanted to share it with Steve while also exploring new territory together. We could only get two weeks off, so we scheduled around Labor Day to give us an extra day or so.
- Athens was a must for logistics and because of the Acropolis and other ancient sites.
- Crete was a must because I missed the Samaria Gorge on my previous visit and wanted to revisit Knossos with Steve.
- Santorini was a must because it’s Santorini. (And yes it is magical and unique, and we’re heading there for the third time soon.)
- I also wanted to include another more typical Cyclades island. It came down to Naxos and Paros and I chose Naxos because its old town sounded great.
We started in Athens and worked our way south to Crete. That worked well traveling by ferry. Here’s the final outline:
- Athens (2 nights)
- Naxos (4 nights)
- Santorini (3 nights)
- Heraklion (1 night)
- Chania (4 nights)
- Athens (1 night)
You could easily swap or drop some of the islands on this itinerary, as long as you pay attention to ferry routes. Traveling between islands within the same island group is often easy. It gets more complex — and takes longer — if you start hopping between groups. If you only have a week I would suggest focusing on Athens and Rhodes, which offers both beaches and historic sites.
Accommodations
Our budget was tighter in 2014 so that drove our choices. The prices shown here are 2026 prices.
- In Athens I chose the Athens Cypria Hotel (€171) for its central location. It worked well.
- On Naxos I chose the Chateau Zevgoli (€85) for its location in the old town. I figured we would like the atmosphere better and could take the bus to the beach. We did.
- On Santorini I chose Stelios Place (€57) because it sounded perfect and it was. Close to the beach and restaurants and with a pool. Friendly, comfortable, and not fancy; just excellent value. We’ll be heading there for our third visit soon.
- On Crete I chose the Lato Boutique Hotel (€109) for our one night in Heraklion for its proximity to the port and the bus station and because it had a restaurant on site. Since we were only there for the night I didn’t want to fuss with finding a restaurant, etc. It was a bit of a splurge for us back then but well worth it, with one of the best (included!) breakfast buffets I’ve seen anywhere at any price.
- In Chania I chose Vranas Ambiance Hotel (€148) for its old town location and price. The price has increased substantially (but is still within our budget) and it looks like they’ve substantially renovated. I would have stayed there on our upcoming trip but wanted someplace closer to the beach.
I would stay at any of these again, and recommend them to others. Athens was our most expensive stay, Santorini was our least expensive.
Transportation
For me, part of the classic Greek island experience is taking a ferry. Not a modern high-speed ferry, but a good ol’ fashioned ferry with an open deck. They’re harder to find now but still out there, and I baked that into this trip.
A great tool for exploring Greek ferries is Greek Ferry schedules. You can fill in a starting or ending port and it will tell you where you can get ferries to or from there. For example, I entered Chania as the end point and it tells me I can get a ferry there from Milos or Piraeus (Athens). Once I selected a starting point, I can search actual ferries. It will list any schedules including days of the week, times, company, and ship type, and when the schedule is good for. (Which is important, because ferries are seasonal. Ask me how I know. [link to Amorgos trip]) It’s great for exploring options since you don’t have to enter exact dates or even both ends of the route.
Once you’ve found a ferry, FerryHopper is a great place to book your tickets.
Some islands have airports, so flying may also be an option. If going island to island you might have to change planes in Athens, but the flights are all pretty short.
Once on an island we walked and used buses to get around, which worked well.
We took Blue Star ferries from Piraeus (Athens) to Naxos and then onto Santorini. Don’t miss the arrival in Santorini. It’s a great view of the famous caldera. We took a modern high-speed ferry from Santorini to Heraklion. Boring but efficient. We could have taken an overnight ferry from Crete back to Piraeus but it was cheaper to fly and spend the night in a hotel, so we did.
The bus between Heraklion and Chania had a luggage compartment below so was manageable with baggage. Stelios Place offered free pick up and drop off to port or airport, which was handy. (And Stelios himself did the driving.) They no longer do that, but they will arrange transport for you.
In Athens we took the express bus to and from the airport.
The biggest chunk of the transportation budget was about $300 for ferries. The various buses added another $120 and our flight from Chania to Athens was $110. (In 2026 a flight from Athens to Chania was $360 for two.)
Sights & Activities
Our itinerary was built around the following high priority sights and activities:
- The Acropolis and its museum and other ancient sites in Athens.
- The old town on Naxos.
- The island of Delos, a UNESCO World Heritage site, via a day trip from Naxos. (The trip also included Mykonos, which was not a priority but at least we got to see it without expending a lot of effort.)
- The Minoan site of Knossos.
- Hiking the Samarian Gorge.
We were easily able to fit those in plus have some time to just wander and get a feel for the location, though I would have liked more time in Athens. Costs included entry fees to historic sites and museums, three tours, and beach chair/umbrella rental.
Food & Drink
We love Greek food so that’s what we ate except for one night when we had pizza. We were able to try local specialties on Naxos and Crete. Breakfast was included on Naxos and in Heraklion. We ate most of our meals out.
See our destination posts for details on what and where we ate.
Resources
- We used Lonely Planet Greece (Kindle format) as our main resource
- Matt Barrett’s Greece Guides has been around forever and is an encyclopedic resource to travel in Greece.