The October Break Edit: Where to Go With Kids (and Still Enjoy Yourself)
Because holidays shouldn’t feel harder than term time.
There’s something oddly high-stakes about October half term. Too short for a “big” holiday, too long to wing it with board games and oat milk hot chocolate — and always, always at the precise moment you realise the weather has turned and your house is full of muddy shoes and mismatched socks.
But half term doesn’t have to mean compromise. Done right, it’s a chance to pack your bags (and your favourite knitwear) and check into somewhere with real atmosphere. Whether that’s a coastal hideaway or a design‑led townhouse, the trick is to think small but clever. You want destinations that feel like a proper escape — with just enough adventure to occupy kids and enough comfort to keep grown-ups content.
Below, an edit of escapes that work beautifully in a one‑week window — from wild coasts to city streets, sunshine stretches to Alpine air — each with a place worth staying.
Cornwall (British Bliss on Home Soil)
Why Cornwall?
October in Cornwall is arguably its best-kept secret. With the summer rush long gone, you get the raw, windswept beaches and cliff paths all to yourself — minus the car park chaos. It’s the kind of weather that demands wellies, wool, and windblown cheeks, followed by fish pie and fireside board games. There’s enough adventure to keep kids occupied (rock pools, surf lessons, beach cafés), but also a deep exhale for grown-ups who just want to look at the sea and not answer emails.
Where to stay: Watergate Bay Hotel
A stylish, coastal all-rounder perched right above one of Cornwall’s most iconic beaches. It’s got serious atmosphere — sea views, Scandi‑ish interiors, a pool overlooking the waves — but remains effortlessly family-friendly. The kids' club is excellent, the restaurants are unfussy but good, and there’s even supervised surf sessions for confident kids. Ask for a sea-view room if you can.
👉 watergatebay.co.uk
Lisbon (City Energy + Family Flow)
Why Lisbon?
Lisbon is a masterclass in laid-back city charm. You’ve got your culture and colour — tiled buildings, trams, ancient ruins — but also a sense of ease that makes it highly doable with kids. October brings milder sunshine, which is ideal for wandering through Alfama’s cobbled lanes or hopping on the ferry for fresh seafood in Cacilhas. Add in custard tarts, quirky museums, and enough hills to wear out small legs, and it’s basically parent-approved urban exploration.
Where to stay: Martinhal Chiado Family Suites
A brilliant blend of style and function, Martinhal Chiado makes city breaks feel genuinely manageable. The apartment-style layout gives you space to spread out, snack, or sneak in a nap, while the on-site kids’ club means you can steal a grown-up dinner or slow-start morning. It’s polished without being precious — and it takes the faff out of urban family travel.
👉 martinhal.com/locations/chiado
Amsterdam (Culture Without the Eye-Roll)
What the area offers
Amsterdam is wildly underrated as a family city break. It’s compact, bikeable, full of water (always a win with kids), and packed with museums that actually engage — from the NEMO science centre to the Van Gogh Museum’s brilliant interactive exhibits. Autumn turns the canals golden, the markets are still buzzing, and there’s something wonderfully cosy about ducking into a brown café for apple pie after a brisk walk through Vondelpark.
Where to stay: The Dylan Amsterdam
A grown-up boutique hotel that doesn’t feel off-limits to families, The Dylan mixes canal-side calm with quietly luxurious interiors. It’s smart, serene and beautifully located — the kind of place where you can head out for pancakes in the morning, museums by midday, and still be back in time for a glass of wine by the fire. One to book if you want something intimate and design-led, without compromising on comfort.
👉 dylanamsterdam.com
Madeira (Big Nature, Little Fuss)
Why Madeira?
Madeira has the kind of raw, cinematic beauty that makes even a short trip feel like a real escape. Think cloud-draped peaks, subtropical forests, levada hikes, and cable cars rising over the Atlantic. October is ideal — still warm, still green, but blissfully quiet. You can start the day at sea level watching whales and end it in the mountains eating honey cake and grilled scabbardfish.
Funchal is the best base — historic, walkable, and close to most of the island’s adventures.
Where to stay: Savoy Palace, Funchal
A bold and contemporary resort with just enough polish to make it feel special — but without losing warmth. The design is glossy in all the right ways (marble, velvet, sweeping Atlantic views), and there’s a good kids’ pool, proper spa, and multiple restaurants. It's stylish enough for adults, big enough for children to roam, and perfectly placed for exploring the rest of the island.
👉 savoysignature.com/savoypalacehotel
South Tyrol (Alpine Air + Autumn Fairytales)
Why South Tyrol?
South Tyrol — tucked in Italy’s Dolomites — is where fairytale forests, storybook villages, and golden October light collide. It’s an easy win for families who want fresh mountain air, long walks, and hearty food without the ski-season chaos. Autumn is Törggelen season: roasted chestnuts, speck, local wine in mountain huts — plus castles to explore, gondolas to ride, and hiking trails that even little legs can manage.
Where to stay: Feuerstein Nature Family Resort
A modern alpine escape that’s actually built for families — think design-forward lodges, indoor and outdoor play areas, a forest kindergarten, and a spa with kids’ treatments. There’s childcare available (even for babies), daily nature activities, and a mountain lake just steps from your room. It’s warm, polished, and deeply kid-savvy without compromising on grown-up comfort.
👉 feuerstein.info/en
Puglia (Sunshine With Room to Breathe)
Why Puglia?
While the rest of Europe packs away its summer, Puglia tends to cling to sunshine just a little longer. October here still means long lunches under olive trees, empty beaches, and sleepy whitewashed towns that feel almost too photogenic to be real. Families can explore trulli villages, ride bikes through olive groves, take a pasta-making class, or just lounge poolside with zero guilt. It’s warm, unhurried, and feels like a proper reset.
Where to stay: Borgo Egnazia
More than a hotel, Borgo Egnazia is a Puglian fantasy village — with winding streets, creamy limestone, and beautiful rooms that somehow manage to feel relaxed, even with children in tow. There’s a spa, beach club, golf course, and four pools — plus an excellent kids’ club and daily activities for all ages. It’s elegant but easy, and ideal if you want the full Italian hit without long-haul effort.
