Planning a trip to Greece in May? These are the destinations locals are choosing right now, from Nafplio and Monemvasia to Thessaloniki and beyond.

There is a brief window in Greece, just before the season shifts, when the weather has settled and the crowds haven’t yet arrived.

May sits right in that space, and this is the time when Greeks begin travelling again. Around the May Day long weekend especially, short domestic trips pick up, with people choosing places they can reach easily and enjoy without much planning.

These are not necessarily the headline islands. They are towns and smaller cities that offer good food, a strong local atmosphere, and a sense of familiarity that makes a few days away feel longer. 

This year, that pattern is clear. Search demand has risen for a handful of mainland destinations, pointing to where Greeks are choosing to go right now, just before the pace of summer takes over.

Nafplio

Just under two hours from Athens, this has long been one of the country’s most reliable weekend escapes. It was the first capital of modern Greece, and that history still shapes the town, from the Venetian fortresses to the neoclassical houses that line its streets.

In May, it feels like the ideal escape. The 999 steps up to Palamidi Fortress are still manageable before the heat sets in, and the old town has space to move through without feeling crowded. Athenians tend to arrive late on a Friday, settle into long lunches by the harbour, and stay out until way after midnight. It is not a place that requires a strict itinerary. You walk, you stop, and take in the moment. 

Monemvasia

Further south in the Peloponnese, the pace shifts. This beautiful medieval town sits behind fortress walls, connected to the mainland by a narrow causeway, and once inside, the spectacular setting takes over.

May is one of the best times to be here. The stone streets hold onto the cool of the morning, the light is softer, and walking up to the upper town is still comfortable. It is a place that suits a slower pace. Early walks, late dinners, and time spent looking out over the sea tend to shape the day, and if you feel like venturing out, Monemvasia Winery is worth visiting for its connection to Malvasia wine.

Nafpaktos

On the northern side of the Gulf of Corinth, this is a place Greeks return to often, even if it rarely appears on international itineraries. The small Venetian harbour, framed by defensive towers and lined with cafés, is the focal point of the town.

Everything is within easy reach. You can walk from the harbour up to the castle in under an hour, stop for coffee without thinking ahead, and find somewhere to eat without a reservation. That simplicity is part of the appeal. For a long weekend, it offers exactly what people are looking for, a change of pace without the need to organise too much around it.

Volos

A working port city, Volos has built its identity around tsipouro. This tradition dates back to the early 20th century, when dockworkers and fishermen would gather after work for a drink with whatever was available to eat. Today, that habit has evolved into the tsipouradika, with hundreds spread across the city.

You don’t order in the usual way. Each small bottle of tsipouro arrives with a plate, starting simply and becoming more substantial as you continue. It might begin with anchovies or pickled vegetables, then move on to grilled octopus, sardines, or dishes like spetsofai, depending on what’s fresh that day.

Beyond that, in Volos, the centre is compact, the waterfront is part of daily life, and everything is within walking distance. In May, it starts to feel alive again without being busy, especially in the early evening when locals head out after work.

Pelion

Just beyond Volos, the Pelion peninsula offers a different pace again, and it’s one that works particularly well in May. Villages like Tsagarada, Portaria and Makrinitsa sit among dense greenery, with stone houses and views that stretch out towards the Aegean.

This is one of the few places where you can move between mountain and sea within the same day. Mornings are cooler, suited to walking through the villages or along old paths, while afternoons can shift towards the coast if the weather allows. It’s not about ticking off long lists, but about having the option to change pace easily, which is what makes it appealing this time of year.

Kalamata

Over the past decade, this coastal city has evolved. Known historically for its olives and agricultural trade, it now has a richer gastronomy scene, while still holding onto its relaxed feel.

The city stretches between its old town and a long beachfront, and in May both begin to feel alive again. The sea is just starting to warm, the promenade is in use, and restaurants are fully open without the pressure of peak season. It also works well as a base. Places like Kardamyli and the Mani peninsula are close enough for day trips, which adds variety without needing to move around too much.

Thessaloniki

For those leaning towards a city break, spring suits this one. Built around its waterfront, Thessaloniki is compact and easy to navigate, with most of the experience centred on food and neighbourhoods rather than traditional sightseeing.

The White Tower and promenade set the tone, but areas like Ladadika and Ano Poli give the city its character. In May, the humidity has not yet set in, making it easier to walk between places, and the café and bar scene is fully active. It is a social city, where dinners start late and plans tend to shift as the day goes on.

Ioannina

Further north in Epirus, the landscape changes. Set on Lake Pamvotida with mountains surrounding it, this lakeside city feels more enclosed and slower than coastal destinations.

Its Ottoman and Byzantine history is visible in the castle quarter, while the small island in the lake, reached by boat, adds another layer to the experience. May is one of the best times to visit, before the summer heat arrives and while the surrounding hills are still green. It is quieter than the other destinations on this list, which is exactly what draws locals to it.

Main Image by Monemvasia Winery