Late Breaks in September 2026: 3 Places Worth Booking Now

September breaks Prague Czech Republic

September is one of my favourite times of the year to go on holiday. The start of the new school year means there are fewer families with children about, so things are a little less crowded and queues are much more manageable. The brutal midsummer heat has lost its edge (without disappearing altogether) and entering shoulder season means prices start to tail off – so more value-for-money, specially for the solo traveller. Here’s my 3 recommended places to visit for a late summer  September break.

Affiliate Disclosure
This post doesn’t actually contain affiliate links. If you book through them, I won’t earn a penny. They are my gift to you 😉

Table of Contents

Malta

Why visit Malta in September?

A September holiday in Malta still feels like proper summer holiday: the sea is warm enough to swim in, and the Sliema promenade is no longer wall-to-wall tourists. The island is small enough to cover properly in a week and with enough layers of history (Knights of St John, Baroque Valletta, Neolithic temples) that you won’t run out of things to explore.

Where to stay in Malta

  • Casa Ellul (Valetta): a Small Luxury Hotels of the World property is an understated, design-led, no-chandeliers kind of place.
  • The Xara Palace, Relais & Chateaux (Mdina): inside Mdina’s walls, in the old “silent city,” for a quieter base with real history under your feet. And stunning views to boot! Sadly, no pool onsite, but they have an arrangement with a local spa.
  • The Phoenicia Malta (Valetta): grand without being showy, just outside the gates of Valletta. Good for anyone who wants a proper pool and garden to relax in after a hard day’s exploration.

Where to eat in Malta

  • Guzé Bistro (Valletta): Mediterranean cooking in a 16th-century townhouse. Dinner service only
  • de Mondion at The Xara Palace (Mdina):  the fine-dining option, rooftop views over the old capital. A must if you’re staying in the hotel.
  • La Pira Maltese Kitchen (Valletta): traditional Maltese fare, including rabbit and aljotta fish soup, this place is down-to-earth and unpretencious. Make sure to leave room for dessert

What to do in Malta

Slovenia

Why visit Slovenia in September?

Grabbing a September holiday in Slovenia trades the lake-side crowds of Lake Bled for something closer to what postcards promised: mist on the water, empty rowing boats, Ljubljana’s cafés with tables free again. It’s compact, easy to self-drive, unfussy, and less manicured than either of its neighbours Croatia or Austria.

Where to stay in Slovenia

  • Grand Hotel Toplice (Bled): old-world lakefront glamour with a private beach (warning: Lake Bled is COLD). Part of Small Luxury Hotels
  • Vila Bled (Bled): Tito’s former summer residence, now a hotel. Part of the Vila Bled Estate, it has grand gardens and walking distance to the lake.
  • April 1550 Boutique Hotel (Ljubljana): A contemporary boutique hotel, complete with secret garden, in the heart of Ljubljana. Ideal as a base to explore the city before or after a few days in Lake Bled.

What to eat in Slovenia

What to do in Slovenia

Prague

Why visit Prague in September

By September, Prague has turned the corner on the stifling mid-30s heat of July and August. Evening as now long and cool enough for sitting out with a leisurely drink followed by a proper dinner. If you’re happy to walk a little, you can happily get lost for hours in the old streets, and you get to skip July’s queues for the astronomical clock. Don’t forget to immerse yourself in the city’s rich musical history (Mozart, Smetana, Dvorak and Janacek all have connections with the city).

Where to stay in Prague

  • Golden Well Hotel (Malá Strana “Lesser town” near the castle): a small boutique hotel (only 17 rooms and a couple of suites) with terrace views over the castle and over the rooftops 
  • Aria Hotel Prague (also in Malá Strana): a music-themed boutique hotel, is a wonderfully over-the-top place to stay. It’s not cheap, but it’s the place to stay if you want to treat yourself.
  • Augustine Hotel (also in Malá Strana): is in a former 13th century Augustinian Monastery of St. Thomas, and compared to the big chain luxury hotels, it really holds its own as a 5 start destination. Good value (albeit on the pricey side), there’s usually a deal or 2 to be had on their website.  Easy walking distance to the castle.

What to eat in Prague

What to do in Prague

  • Cross the Charles Bridge over the Vlatava River at first light (before tourists, coaches of day-trippers, and jobbing caricature artists overrun the place).
  • Spend a morning walking around Prague Castle and St Vitus Cathedral, then in the afternoon descend through the fairytale Nový Svět lanes.
  • Spend an afternoon in Vinohrady or Žižkov districts to escape the tour groups down tree-lined streets full of local life.

Summary

Even now at the beginning of August, it’s not too late to book a last-minute getaway. Try a September holiday, and I’m sure you’ll be hooked like I am on taking your summer break at the end of the season!

I’m actually off to Mallorca this year. I would suggest it as a top favourite, but then I’d have nothing to write about afterwards 😉