My sister and I have just made our second trip to the southern Greek island of Kythira, and it’s really grown on us. In truth, Kythira deserves more than three days — but if three days are all you have, then here’s how you might spend them:
Day 1
Visit Melidoni Beach

Kythira has lots of beaches, and this well-serviced beach is a good introduction. The beach has some sand, the water is calm, and you can swim out to rocks to see tide pools. A small cafe serves drinks and has music that drove me a bit crazy. You have to pay for the umbrellas, but for your 10 Euros you get a towel clip, a trash bag, and a delicious paximadi (a sort of Greek biscotti). This is not our very favorite beach (more on those below), but we enjoyed our time there.
Stop by the Church of Aiyos Dimetrios

This cute, hobbit-like church is on the road to Melidoni, and while it’ll likely be closed, the exterior is worth a look.
Have lunch at Pierros in Livadi

The owner here is the consummate salesman, and he’ll give you a tour of the kitchen to help you choose your food. The stuffed eggplant is out of this world.
Visit Chora

Kythira’s capital is a lovely place for a stroll, and it’s worth making time both for the town itself …
… and for the ruins of the 12th-13th century Venetian castle at the top of the hill:

The views from the top are amazing …

… and if you’re hot, you can drop down to the coast after your visit and hop into the water at family-friendly Kapsali Beach.

Stay at Giannikas Apartments

We loved staying in these simple, clean, well-serviced, and high-value rooms just outside of Livadi. The views from the balconies out over the gardens and toward town can’t be beat.

Day 2
Hike and Swim in Milopotamos
The town of Milopotamos has a great set of shady hiking trails, the best of which runs along a river. You’ll walk past waterfalls, old mills, and mill houses as you meander gently downhill. If you’re lucky, you’ll find fresh fruit along the way (we took in a great haul of apricots after a good round of vigorous tree-shaking) …

… and you’ll have a chance to take a dip in one of the crystal-clear pools.

Make sure to follow the blazes carefully, though! After you’ve followed the trail through one of the old mills, it’s important not to veer off to the left (that trail will take you up into the mountains). Just stay along the river — and know that while the first set of pools you encounter is stunning, an even greater set of pools lies just a bit further on down the stream.
Have lunch at Platanos

Nothing beats sitting in the shade of the giant plane tree in the middle of the Milopotamos main square. The setting is delightful, and the Greek salad and imam baldi are delicious.
Shop at Karin Kythira

Clothing, jewelry, bags, sunglasses, home decor — we love this store! It’s beautifully laid out with high-quality wares.
Clamber down to Kalami Beach

Getting here isn’t for the faint of heart: you need to walk down a dirt road (don’t try to drive beyond the pavement!), hike down a trail, and then rappel down a brief section of rock (there are ropes to help you down, and it’s not as hard as it looks). But once you get there, you’ll be on one of the best beaches in Kythira — and you may have it all to yourself.
Day 3
Walk down 155 steps to Kaladi Beach

There are a lot of stairs here, but they’re well-maintained. Once you get down, you have your choice of three beaches, the last of which is absolutely tiny (and you have to go through a tunnel to get there). There’s not much shade here, but we lay in the tunnel and had a wonderful time.
Have lunch at Psomoladea

The food here is a little pricier than some, but wow, is it worth it.
Take a dip at Avlemonas

This isn’t a beach, per se — it’s a grouping of small man-made ledges — but the water is clear and the snorkeling is better than anything else we’ve found in Greece (though that bar remains very low). We really liked swimming here. And the town of Avlemonas, while looking very dry and hot, boasts a charming collection of white and blue houses that we haven’t seen anywhere else in southern Greece.

Have ouzo and a snack at Manolis Taverna

This is a great place to sit and have a bite while you wait for the ferry (we particularly like their green salad with dried figs).
Take a quick dip at at Diakofti

If you have time, it’s worth visiting this sandy beach just across from the ferry terminal (you can swim to both the right and the left of the pier above).
We were sorry to leave Kythira after these three days, but we’re hoping to go back!