Building the Itinerary
It’s our 25th anniversary this year. We couldn’t do a special trip — because every trip is the trip of a lifetime — so we’re revisiting some of our greatest hits:
- England, the first real trip we did outside the USA (that is, that wasn’t to an all-inclusive)
- Australia and New Zealand, the longest trip we’d ever done (until we went back)
- And Greece, still my favorite place to vacation
We planned this to be a pretty relaxed trip, organized around spending time at the beach and doing some walking. Since we’re going to the beach we planned this for fall, when it should still be warm there but not hot. We knew we wanted to end the trip on Santorini and wanted to revisit Chania on Crete. Beyond that, I thought about visiting Meteora on the mainland, and Skopelos to check out a different island group, but that felt like too much work, so we’ll save those for a future visit. I looked at other islands in the Cyclades but in the end decided two islands was enough hopping and we’d focus on western Crete and Santorini.
This trip was planned around availability at one of our favorite hotels anywhere: Stelios Place on Santorini, which we found on our first trip to Greece. We love it and Perissa. It’s our favorite beach town and is a great place to relax. So we booked that for the end of our trip, then worked backwards from there.
We’ve been to both islands before and have already done our must-dos on each — Knossos and the Samarian Gorge on Crete, the walk to Oia on Santorini — plus some others, like museums in Chania and a sunset cruise on Santorini. So we have some possible sights and activities in mind, but nothing we really must fit in.
Usually our second (or later, this is our third trip to Greece, and my sixth) visit to a place is more relaxed than the first. Probably because we’ve checked off some of the must-dos and don’t feel so compelled to fit things in. On a first visit we pack more things in.
With the two islands figured out I looked at other places on Crete to check out.
- We like the atmosphere in old Greek towns and neighborhoods so that led us to Rethymno. I was there on a day trip in the 90s and it looked cool. It also looks like a good base for exploring some of the interior of Crete and maybe the opposite coast.
- Palaiochora sounds like another low-key beach town we might like, and a good base for exploring parts of the southwest coast of Crete that aren’t reachable by road.
- We’re spending a couple of nights at Elafonisi because I really want to go to that beach and we heard it gets really busy with daytrippers and we’d like to be there while the daytrippers are gone. (That’s our one must-do for this trip.)
We easily have time for another stop or two but this trip we really leaned into spending more time in each place rather than our usual 3-4 nights per stop. We’re flying in and out of Chania so we could have visited it either when we arrive on Crete or when we leave. We chose to put it at the end since that will put us close to the airport for our flight out. Plus we’ve been there before so there will be no pressure to run around and see things.
Overnight stops in Athens are necessary for getting into and out of the country. We’ve already been to the Acropolis and other downtown sights so we’ll stay within easy reach of the airport.
So we end up with the following:
- Athens (1 night)
- Rethymno (6 nights)
- Palaiochora (6 nights)
- Elafonisi Beach (2 nights)
- Chania (8 nights)
- Santorini (10 nights)
- Back to Athens to fly out (1 night)
Overall this was a pretty easy itinerary to put together. It was fun learning about other islands and areas as I decided on where exactly to go and I know we’ll be back in Greece again so what I learned won’t go to waste. One of these trips I will tear myself away from the islands and see something of the mainland. But not this trip. This trip, we relax.
Accommodations
Greece has loads of options for places to stay, including lots of the smaller, locally-owned places we like.
- I booked Stelios Place on Santorini first since it was key. It’s a couple of minutes walk from the beach and restaurants, has a pool, and is well under $100 per night.
- In Chania I chose a place in the old town yet near the town beach. We stayed in the old town on our first visit and liked it. This time we went for a place still in the old town but closer to the beach since we plan to spend more time there.
- In Rethymno I found a place in the old town with unique architecture.
- In Palaiochora we picked a place convenient to the beach and to restaurants and such. Even though we’ll have a car we still don’t want to drive to dinner if we can avoid it.
- There’s only one place to stay in Elafonisi so that was an easy choice.
- In Athens we’re only flying in and out. On arrival we’ll be at the Holiday Inn, since we arrive late and leave the next day. When we leave we’ll have an afternoon to kill so we’re staying at the Hotel Avra on the coast. We’ve stayed there before; they have a convenient shuttle and a decent restaurant, and there’s a nearby beach and some other places we can walk to if we feel like it. I booked both airport stays with Delta Stays to get the annual credit.
I booked all the accommodations about 10-11 months out. About half my choices are under my $150 threshold. Every place has a terrace, since we’ll want to be outdoors as much as possible. All but Stelios Place has a kitchen.
Transportation
I wanted to take a ferry from Crete to Santorini but there just aren’t any good options. The best was by way of Milos, which would be nice if we wanted to go back there, but we don’t. So we’re flying from place to place within Greece. Less scenic, but quicker.
Unusually for us, we’ll be renting a car on Crete until we get to Chania. While we only plan to use it much for a couple of day trips while we’re in Rethymno and to get from place to place, it made sense to keep it in between. If we do any day trips from Chania or Perissa we’ll take the bus.
Sights & Activities
The one must-do is Elafonisi Beach, where we’ll spend a couple of nights.
Other than that we plan day trips from Rethymno to the Arkadi monastery, Margarites village for pottery, Spili for the village and some walking, and Preveli for the beach and falls. I’ve just learned that Preveli was hit with a wildfire recently, so we may not go there after all. Don’t need to clog a disaster zone.
From Palaiochora we’ll take the ferry to Chora Sfakia and Loutro. We may drive to Sougia and to nearby hikes.
In Chania and on Santorini we’ll wing it. Near Chania are monasteries on the Akrotiri peninsula, ruins at Aptera, Vamos and other villages, and botanical gardens. On Santorini we may take the bus over to the villages on the caldera side and poke around. We haven’t really spent any time over there. We may try the hike to ancient Thera again; we’ll see how the vertigo is doing.
Food & Drink
We love Greek food, so my only difficulty will be deciding among my favorites. I look forward to lots of souvlaki, gyros, salads, and slow-cooked casseroles and stews. And taramasalata! And local snacks like pistachio nuts. Crete has some local specialties to sample. Maybe we’ll bring back some olive oil, saffron, or wine.
We’ll have a kitchen at all but one of the places we’re staying. Not that we plan on doing any cooking! Maybe some meals of local mezes (small plates) or leftovers. Greek meals can be very filling.