A Grown-Up Getaway in Chester

Find your Thrill

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If you're looking for a weekend of excitement, elegance, and just the right amount of mischief, Chester delivers in spades. Start your adventure the easy way by hopping on a Transport for Wales train—relax, enjoy the ride, and arrive right in the heart of the action. From the roar of the racetrack to rooftop dining and paddleboarding on the River Dee, this itinerary is all about experiencing the best of the city — with a little adventure, a splash of luxury, and plenty of Instagram-worthy moments.

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Day 1: Champagne, Speed & Sophistication

Morning to Afternoon – Place Your Bets at Chester Races

Feel the thrill of the turf at the iconic Chester Racecourse, the oldest in the country and arguably the most stylish. Whether you’re in the grandstand, a private box, or enjoying a picnic on the lawn, the atmosphere is electric. Dress to impress, grab a glass of fizz, and soak up the glamour of a day at the races — where the people-watching is just as good as the horse action.

Evening – Dinner with Flair

After the final race, keep the indulgence going with dinner at one of Chester’s top spots:

Tucked away just outside the city walls, Porta is the kind of place you stumble upon—and never want to leave. This laid-back, low-lit tapas bar is all about big flavours in small plates, with a buzzing atmosphere that feels straight out of Barcelona. Perfect for a spontaneous bite or a long, lazy graze with friends, Porta serves up thrills in every mouthful—think sizzling chorizo, jamón carved to order, and crisp glasses of Spanish wine.

Brasserie Abode – If you prefer modern British dishes with a stylish twist, this chic brasserie inside Abode Hotel is ideal for laid-back luxury dining, with cocktails and views to match.

Day 2: Paddleboards & Paranormal

Morning – Glide into the Day on the River Dee

Ease into the morning (or shake off the night before!) with a paddleboarding session on the River Dee. Whether you’re a complete beginner or a confident boarder, it’s a refreshing way to see the city from a different angle — with a few giggles and wobbles thrown in for good measure.

Lunch – Skyline sips

Ready to take your Chester adventure to the next level? Rooftop Social is where the thrill kicks in—think sky-high views, street food with swagger, and an Aperol Spritz in hand as you look out across the city. This buzzing rooftop hangout serves up bold flavours, banging playlists, and a vibe that turns up as the evening rolls in.

Afternoon – Towering Views or Ghostly Whispers

Climb to new heights on a Tower Tour at Chester Cathedral, where you'll be rewarded with stunning panoramic views across the city (and a bit of a workout too!).

Or, if you prefer your thrills on the spooky side, join a Chester Ghost Tour and uncover the eerie secrets lurking in the city's ancient streets and shadowy corners.

Evening – Tapas & Toasts

Wrap up your weekend with a relaxed evening at Salt House Tapas. This buzzing city-centre favourite serves up delicious small plates with big flavour – perfect for sharing, grazing, and swapping race day stories over sangria or Spanish wine.

Where to Stay – Rest in Style

Rest your head in one of Chester’s welcoming hotels, all within easy reach of the action:

Crowne Plaza Chester – Centrally located with fantastic views, a spa, and all the comforts you’d expect.

DoubleTree by Hilton (Chester) – A luxurious retreat just outside the city centre, with a spa and beautiful grounds.

New Blossoms Hotel – A charming city-centre stay with heritage appeal and a prime spot for exploring on foot.

From race day glamour to riverside adventures, fine food to ghostly tales, Chester is the ultimate playground for adults ready to escape the ordinary.

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Included in this itinerary

£
Chester Cathedral Tower Tour
Chester Cathedral Tower Tour
Dee Kayaking 2
Paddle the Dee
Abode 03
Brasserie ABode Chester
Chester Racecourse 03
Chester Racecourse
Chester Ghost Tours 01
Chester Ghost Tours

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