Chester is a city that invites exploration through its centuries-old architecture, lively streets, and scenic waterways. But what truly sets Chester apart are the unique tours and experiences designed to give visitors a deeper connection with this charming city. Whether you’re interested in uncovering the stories behind Victorian graves, sampling local cuisine, or paddling along the River Dee, Chester offers options that suit every taste and energy level. We especially love the Guided Overleigh Cemetery Tour for its intimate look at Chester’s Victorian past, and the Chester Food & Drink Tour for those eager to taste local flavors while soaking in the sights.
If you’re visiting Chester and want a well-rounded experience, you’ll find tours that combine history, food, and outdoor activities. With options ranging from 90-minute cemetery strolls to full-day excursions into North Wales, there’s truly something for every traveler.
Quick Overview
Our top picks include a guided cemetery walk that offers a fascinating look at Chester’s Victorian-era graves, and the food and drink tour that highlights local cuisine and hidden culinary hotspots. For outdoor lovers, kayaking adventures on the River Dee—like the River Dee Kayaking Tour or the Kayak Rolling Clinic—offer a chance to experience Chester from a different perspective. If you’re after a full-day trip, the Snowdonia and Chester Tour from Manchester combines mountain scenery with historic villages.
1. Guided Overleigh Cemetery Tour in Chester
This guided cemetery tour is a quiet journey through Chester’s Victorian past, hosted by a knowledgeable Green Badge guide. For just $13.71 per person, you get an engaging 1.5-hour walk through Overleigh Cemetery, opened in 1850 and designed by the notable architect T.M. Penson. The cemetery’s grounds are filled with around 25 significant graves, each telling stories of Chester’s past residents—famous Victorian architects John Douglas and T.M. Lockwood, archaeologist Professor Newstead, and even the discoverer of 47 spider species, Dr. Arthur Randall Jackson.
What makes this tour stand out is the personal storytelling and the focus on individual lives, not just names on stones. The guide expertly links these stories to Chester’s broader history, making the past feel alive. The cemetery’s design is also worth noting—its layout, lodges, chapels, and ornamental lakes reflect 19th-century tastes. Guests often comment on how Caroline’s storytelling makes the city’s history feel personal and relevant.
The tour runs from 4:00 pm, making it a perfect late-afternoon activity—just bring comfortable shoes and a sense of curiosity. The only possible drawback is the grounds’ upkeep, which some visitors note could be better maintained, but that doesn’t detract from the storytelling.
Bottom line: If you enjoy history and quiet walks, this cemetery tour offers a meaningful way to connect with Chester’s Victorian era.
2. Unique Chester Food & Drink Tour plus Sightseeing
For a full immersion into Chester’s culinary scene, the Food & Drink Tour is hard to beat. Over four hours, you’ll visit seven carefully selected food stops, each offering regional specialties and expert drink pairings. Starting at Chester’s Town Hall, the tour guides you through a mix of restaurants, hidden spots, and local favorites, covering everything from street food to regional cheeses and spirits.
What sets this tour apart is the combination of tasty samples with engaging storytelling about Chester’s history—like visiting a secret spot in the Roman Gardens or hearing tales about the famous Rows. The tour also features exclusive visits to local chefs and owners, giving insight into Chester’s vibrant food scene. Guests rave about the quality of the food and the knowledgeable guides, as well as the chance to learn about regional ingredients firsthand.
For around $116, you gain a lot of value in both food and cultural insights. The tour concludes at Chester Market, where you can continue exploring on your own. It’s ideal for food lovers or those keen to combine culinary discovery with sightseeing.
Bottom line: If you want a memorable, flavor-rich experience that also dives into Chester’s history, this tour is a delicious choice.
3. Chester: Kayak Rolling Clinic on the River Dee
In need of a confidence boost on the water? The Kayak Rolling Clinic offers a personalized, one-on-one lesson tailored to your skill level. Held on the River Dee, this 1.5-hour clinic is perfect if you’ve ever wanted to learn how to roll a kayak but weren’t sure how to start. The session includes all necessary equipment, and you can use either a closed cockpit rigid kayak or bring your own.
What makes this experience stand out is the focus on individual coaching—your instructor will help you master the roll in a safe environment. It’s suited for those with some paddling experience who want to improve their technique or absolute beginners eager to conquer their fear of capsizing. Reviews highlight how effective and encouraging the instruction is, making it a popular choice for anyone looking to build their kayaking skills.
The clinic’s flexible scheduling makes it accessible, but check availability beforehand. It’s a fun, skill-building activity that leaves you feeling accomplished—and ready to paddle with confidence.
Bottom line: For paddlers wanting to learn or perfect their kayak roll, this clinic offers expert guidance in a relaxed setting.
4. Chester: River Dee Kayaking Tour with Guide
If you’re after a guided adventure, the River Dee Kayaking Tour is a great way to see Chester from a different angle. In 1.5 hours, you’ll paddle under the Queens Park Bridge, past the city walls, and along the scenic riverbanks. It’s perfect for beginners and those with some paddling experience alike, thanks to the stable, easy-to-handle boats.
What makes this tour appealing is the combination of relaxed paddling with interesting commentary from your guide about Chester’s history and wildlife. You might spot local birdlife or learn about the river’s role in the city’s development. The tour is designed to be safe and accessible, with all equipment provided. Reviewers appreciate the friendly guides and the opportunity to explore Chester from the water with minimal fuss.
It’s best suited for people looking for a gentle introduction to kayaking or wanting a peaceful break from sightseeing. The tour is weather-dependent, so check the forecast.
Bottom line: This guided trip offers a relaxing way to enjoy Chester’s waterways and learn about its history from the water.
5. Chester: SUP Skills Tour with Instructor
For those wanting to try paddleboarding, the SUP Skills Tour combines instruction and adventure in a two-hour session. Led by experienced instructors, you’ll learn proper paddling techniques while exploring the river under Chester’s historic skyline. It’s ideal for beginners or intermediate paddlers looking to improve their skills.
What makes this tour stand out is the social aspect—paddling with others while receiving tailored advice. You’ll also enjoy spotting birdlife and enjoying the tranquility of the river. The session focuses on skill-building, so it’s great if you want to boost your confidence on a paddleboard.
The tour is suitable for most fitness levels and provides all necessary equipment. Reviewers mention how friendly and clear the instructors are, making it easy to pick up new skills.
Bottom line: If you’re interested in paddleboarding and want professional guidance, this tour offers a fun, social way to enhance your skills.
6. Chester: Whitewater Kayaking Session with Instructor
For thrill-seekers, the Whitewater Kayaking Session provides an exciting experience navigating grade 2 rapids in Chester. This 2.5-hour class is led by an experienced instructor who will guide you through the basics of whitewater paddling, including safety and technique, while tackling the Chester Weir rapids.
What makes this experience stand out is the chance to paddle through the city’s rapids, offering a rare combination of urban and outdoor adventure. Reviewers point out the adrenaline rush and the expert instruction that makes even beginners feel confident tackling the white water.
It’s best suited for those with some paddling experience or active travelers eager for a challenge. The session provides all necessary equipment, but check availability in advance, as spots are limited.
Bottom line: For adrenaline junkies and adventurous paddlers, this session delivers high-energy fun in a safe setting.
7. Snowdonia, North Wales, and Chester from Manchester
Looking to combine Chester with a broader exploration? The Full-Day Trip to Snowdonia and Chester offers an 11-hour journey through some of North Wales’ most iconic sights. You’ll explore the historic town of Conwy, with its impressive shoreline castle, and visit Betws-Y-Coed, a charming mountain village. The day also includes breathtaking views of Snowdonia National Park.
This tour is ideal for travelers who want a comprehensive day trip without the hassle of planning. It includes transportation, guided visits, and plenty of opportunities for photos and sightseeing. Expect a mix of history, natural beauty, and local culture.
The price is around $174, which reflects the full-day experience and transport logistics. It’s perfect for those short on time but eager to see more of Wales’ spectacular scenery and historic sites.
Bottom line: For travelers wanting a scenic, all-in-one adventure, this day trip offers an excellent blend of mountains, castles, and charming villages.
How to Choose the Right Chester Tour
When selecting the best experience, consider your interests and physical activity level. Are you passionate about history? The Overleigh Cemetery Tour offers a quiet, storytelling walk through Chester’s Victorian past. Want to indulge in local flavors? The food tour combines tasting with sightseeing. For outdoor enthusiasts, kayaking options like the River Dee Tour and whitewater session deliver adventure and a whole new view of Chester.
Budget-wise, the cemetery tour provides excellent value at just over $13, while the food tour is a more premium experience at $116 but includes multiple stops. Outdoor activities vary in price, so check availability and skill level requirements.
Booking early is advised, especially for kayaking and full-day trips, to secure your spot in these popular experiences. Think about your fitness level, interests, and how much time you want to dedicate to Chester—then pick an experience that matches your style.
Final Thoughts
Chester offers a range of tours that go beyond the typical sightseeing. Whether you prefer delving into history, tasting local dishes, or paddling along the river, there’s something for every traveler. For history lovers, the Overleigh Cemetery Tour provides a thoughtful look at Victorian Chester, while foodies will enjoy the food and drink experience. Outdoor enthusiasts can choose between a kayaking guided tour or a whitewater adventure.
No matter your interests, Chester’s diverse offerings ensure you’ll find memorable experiences. We recommend booking early—these tours are popular, and the best times tend to be during spring and early summer when the weather is most reliable. Whatever you choose, Chester’s unique blend of history, nature, and local life will keep you coming back for more.