What to do in Chepstow

Activities, attractions and tours

The ruins of a large, historic stone building with multiple arches and a tall, narrow tower.
An ancient stone structure with arched walkways and a grassy courtyard.
The ruins of a medieval stone structure with arched doorways and a tall bell tower.
The interior of an ancient stone structure with arched doorways and columns.
An ancient stone archway with a staircase leading into a lush green landscape.

Chepstow Attractions

Let Expedia help you experience the best that Chepstow has to offer! If you’re looking for fun itinerary ideas, we can provide you with a list of the top sightseeing attractions, as well as helping you to find unmissable activities. Whether you’re travelling with your family, planning a romantic trip with your loved one, or visiting on business, we’ll make it easy to plan an unforgettable holiday that checks all the boxes.

Activities and Tours

Chepstow is crammed with must-see places to visit and things to do. We can help you decide where to stay, and make it a breeze to explore the surrounding areas with our guides on where to go, what to see and when to see it. No matter how long your stay, it’s easy to find places of interest in Chepstow to make sure that you enjoy your experience to the fullest and don’t miss a thing. Leave the local knowledge to us and leave the hassle behind.

If you’re planning a visit, why not check out our handy guides to places of interest in the area? You can browse lists of things to do, learn about the most popular attractions, and get help with planning the details of your trip. Expedia makes it easy for you to check out all the top sights.

Chepstow Attractions

Expedia has something for everyone, so whether you’re planning to get active on a summer holiday, put a spring in your step with a romantic rendezvous, or pamper yourself with a leisurely winter trip, you’ll find plenty of attractions to keep you entertained. In addition to scheduling local tours, booking reservations and scoring advance event tickets, Expedia makes it easy to book your flight, hotel and rental car in advance, all on one consolidated travel itinerary, making for hassle-free travel and freeing you up to explore the sights of Chepstow.

Looking for things to do can be time consuming, but we can take the hassle out of planning your holiday. Whether you’re looking to get active in the great outdoors, sample the cuisine or catch up with the vibrant local culture, our guides to Chepstow attractions ensure that you’ll have a successful trip, whatever the season.

Things to do

From Barry Island: Gavin and Stacey Tour

From Barry Island: Gavin and Stacey Tour

CA $85
per adult
From Barry Island: Gavin and Stacey Tour
Cardiff: Gower Peninsula's Cliffs Scenic Day Tour

Cardiff: Gower Peninsula's Cliffs & Mumbles Scenic Day Tour

CA $160
per adult
Cardiff: Gower Peninsula's Cliffs & Mumbles Scenic Day Tour
The Wandering Bard's Mythical West Wales Tour

The Wandering Bard's Mythical West Wales Tour

CA $161
per adult
100% of travellers recommend
The Wandering Bard's Mythical West Wales Tour
Cardiff: South Wales Cliffs, Bays & Castles Day Tour

Cardiff: South Wales Cliffs, Beaches & Castles Day Tour

CA $161
per adult
Cardiff: South Wales Cliffs, Beaches & Castles Day Tour
The Wandering Bard's Valley Tour or the Swansea Bay Tour.

The Valleys tour or Swansea Bay tour. Please choose correctly.

CA $162
per adult
100% of travellers recommend
The Valleys tour or Swansea Bay tour. Please choose correctly.
Cardiff Bay Boat Tour

Cardiff Bay Boat Tour

CA $30
per adult
76% of travellers recommend
Cardiff Bay Boat Tour
The Dark Cardiff Guided Walking Tour

Private Cardiff Dark History Walking Tour

CA $312
per traveller
Private Cardiff Dark History Walking Tour
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Recommended things to do in Chepstow

Number of things to do
21
Cheapest thing to do on Expedia
Wales Coastal Way Road Trip Guidebook: Llŷn to St Davids: CA $25
Top 5 things to do
Half-day tours
With kids

What to do in Chepstow

Stay near popular Chepstow attractions

A historic stone cathedral with large arches and Gothic windows.

Tintern Abbey

9.6/10 (60 reviews)
Tour the ruins of an ancient monastery where Cistercian monks used to live, pray and study. See the remains of their former dwellings and church.
See properties

Where to stay in Chepstow

Find the best Chepstow areas and neighborhoods for the activities you enjoy most. Learn more about Chepstow
Learn more about Chepstow
Ancient stone ruins with overgrown grass and a grassy field.

Caerwent

Caerwent is noteworthy for its bars, and you can make a stop at top attractions like Caerwent Roman Town and Dewstow Golf Club.

 

Looking for fun things to do nearby? Check things to do near me to find and book the best things to do, fun activities, and top attractions wherever you happen to be.

 

 

Day trip destinations from Chepstow

A city street at night with a historic building in the background.

Bristol

A coastal landscape with a golf course, a lighthouse, and cliffs.

Newport

A river with a stone bridge, lush green fields, and distant hills.

Monmouth

A street lined with historic buildings, flags, and street lamps.

Cardiff

A bridge over a river with a sandy shore and greenery in the background.
Photo by Nicholas Mutton (Creative Commons Attribution-Share Alike 2.0)

Beachley

A historic church with ruins, surrounded by a small village with houses and a road.
Photo by Schwerdf (Creative Commons Attribution 4.0)

Tidenham

A stone church with a red roof, surrounded by green grass and a large tree.
Photo by Robert Powell (Creative Commons Attribution-Share Alike 3.0)

Oldbury-on-Severn

Frequently asked questions

Is Chepstow worth visiting?
Chepstow offers a unique blend of local charm, attractions and culture. Whether you're into nature, history or regional cuisine, there's a lot here to enjoy.
How do I spend a day in Chepstow?
Start your sightseeing with a visit to Chepstow Castle and Caldicot Castle. Then, tour different parts of Chepstow for local dining and some shopping.
What is the top tourist attraction in Chepstow?
Chepstow Castle is one of the top tourist attractions in Chepstow and should feature high on every to-do list of the area.
Is three days enough to stay in Chepstow?
Three days will give you time to tick off many city sights, such as Chepstow Castle, Caldicot Castle and Symonds Yat Rock. The average stay in Chepstow is two days. If you have the time to extend your vacation, Bath isn't far away.
What are some activities to do in Chepstow with kids?
Deciding what to do in Chepstow with kids has never been easier. Whether you're taking a trip with toddlers or teenagers, there are loads of family-friendly tours and attractions to keep them busy here.

What to do in Chepstow for adults?
Whether you're a culture enthusiast, avid foodie or outdoor explorer, there are loads of things to do in Chepstow for adults including Parva Farm Vineyard.
Are there free things to do in Chepstow?
From enjoying parks to wandering around vibrant neighbourhoods, it's simple to discover free things to do in Chepstow. If you're in need of ideas, ask for tips from a local tour guide. Chepstow Museum is a must for anyone wanting to save on their travelling adventures.