Meet Kayleigh | Hampshire Sommelier at The Chesil Rectory

Hampshire Sommelier at The Chesil Rectory - Kayleigh

Kayleigh is General Manager at The Chesil Rectory and Group Head of Wine across both the Chesil and The Three Tuns in Romsey.

With a passion for unusual grape varieties, local producers, and education, she’s redefining what it means to be a sommelier in the UK today.

My Role as Head of Wine

Hi, I’m Kayleigh, General Manager for the Chesil Rectory and Group Head of Wine for both the Chesil, and our country-pub The Three Tuns in Romsey.

My Head of Wine role focuses heavily on curating our Wine Lists to ensure there is something available for every budget and taste covering every corner of the globe, from Hampshire to Slovenia, South Africa to the Czech Republic and Tuscany to Austria. We do have a strong focus on Burgundy and Bordeaux, and I am in a very privileged position to be able to put some special, sought after bottles on my Secret Cellar list at very competitive prices, as well as By the Glass through the use of the Coravin preservation system.

Celebrating Hampshire Wines

We do strive to champion the fruits of our own UK soils, with an ever-expanding offering of Hampshire still and sparkling wine both from the bigger players on the scene such as Hattingley Valley and Black Chalk, to the new-kids-on-the-block The Heretics with their amazing rosé.

Wine Dinners at The Chesil Rectory

As well as offering a carefully selected wine-list to elevate the guest experience when dining at the Chesil Rectory, I also put together and host quarterly Wine Dinners with paired food and wine. Each one has a different focus – be it an amazing producer I want to highlight (such as Brian Bicknell and the Mahi wines of New Zealand) or a particular region (for example the Big Burgundy wine dinner we closed the 2024 season with). This gives guests the opportunity to meet wine-makers and sample their wines alongside a tasting-menu carefully crafted by myself and Head Chef Damian.

Brian Bicknell speaking at Chesil Rectory's Winemakers Dinner Winchester
Brian Bicknell chatting with guests and sharing stories at Chesil Rectory's Winemakers Dinner Winchester
Mahi Sauvignon Blanc 2023 and Tempura Asparagus with Sweet Chilli Dip at Chesil Rectory's Winemakers Dinner Winchester

Sourcing and Personalising the List

Curating the knock-out wine lists at the Chesil Rectory and the Three Tuns is a task I really enjoy as they both have very different audiences and thus the requirements for the lists change. I try to keep them fresh and interesting, and am often out and about at trade tastings in London searching for the next gem to bring to the people of Winchester and Romsey.

Guest Experience & Wine Philosophy

I don’t list the usual suspects like Prosecco or Marlborough Sauvignon Blanc at the Chesil, and some wines on the list may seem unusual, with native grape varieties or different wine-making techniques, but this is where the magic really begins. Between myself and my Sommelier Andrea, we interact with tables during service to enable our guests to feel comfortable stepping out of their comfort zone and trying something new. I love chatting to guests about wine and breaking down all the techy wine jargon into things they will understand and carry forward in their daily lives. I firmly believe that talking to the Sommelier shouldn’t be intimidating, it should be fun and enriching.

My Journey Into Wine

My background in Hospitality goes back nearly 15years (where has the time gone!), and I have held virtually every position Front of House – Hotel Receptionist to General Manager. Somewhere along the way, I discovered a passion for all things Wine and have pursued knowledge through the WSET pathway. I’m currently studying for my wine Diploma (like a degree in wine) and so far it has been the most challenging two years of my life, yet also the most rewarding. I never imagined 10 years ago that today I’d be using words like Flocculation and Remuage in every-day conversation but here we are!

Awards & Industry Recognition

In 2024 I was on the 30 Under 30 in Hospitality list celebrating the 30 individuals under the age of 30 in the industry making an impact; and in 2025 I was recognised in the Sommelier Edit Emerging Talent category – I’m very proud of these achievements as I truly believe it is harder being a Sommelier outside of London especially in todays cultural climate.

Judging at Prestigious Competitions

As well as my Head of Wine duties for the restaurant/pub, in my spare time I also judge for the International Wine Challenge (IWC) and the Sommelier Wine Awards (SWA).

With a 40-year legacy, the International Wine Challenge (IWC) is hailed as the world’s most rigorous and respected wine competition. Each medal-winning wine is blind-tasted by at least eight expert judges, ensuring impartiality and quality. Drawing over 500 influential figures from 38+ countries—including Masters of Wine, top buyers, and global industry leaders—the IWC sets a gold standard for excellence and opens doors to international recognition and trade for wines from 52 countries worldwide.

The Sommelier Wine Awards (SWA) is a unique UK-based wine competition dedicated solely to the on-trade—wines destined for restaurants, bars, pubs, and hotels. Since its launch in 2007, it has become the go-to reference for industry buyers looking to enhance their wine lists. Judged exclusively by top sommeliers, including Masters of Wine and Master Sommeliers, the SWA offers wines a direct route to greater visibility in hospitality venues. Under the guidance of Isa Bal MW, the competition not only highlights wines suited to real-world service but also champions values of support, sustainability, and inclusivity—aiming to uplift the entire hospitality industry while promoting excellence and diversity

Teaching and Inspiring Future Sommeliers

I have also undertaken training with our friend Erica at Enjoy Discovering Wine (my Diploma teacher) to enable me to teach WSET Level 1 and 2, which I thoroughly enjoy. There is something so amazing about standing in front of a class from different age groups and walks of life and sharing knowledge on a topic I feel passionately about. Seeing the penny drop, as wines they’ve perhaps enjoyed their whole lives start to make sense on a more technical level.

I recently decided to take the teaching forward a step, and spent the afternoon at Eastleigh College giving some Hospitality students a crash-course on the world of wine, tasting, and careers in the wine industry. This is something I feel passionately about – emphasising the integral role of the Sommelier/wine professional in UK hospitality, and ensuring those roles will be filled by the younger generations in time.

Hattingley Valley - bottle and glass - Wine tasting events in Winchester

Wine Dinners & Tasting Events

Join us for an unforgettable evening of wine dinners and tasting events, where carefully curated menus meet exceptional wines. Each event is a unique opportunity to explore hand-selected vintages, expertly paired with seasonal dishes crafted by our chefs.