Cheltenham

Day Trips

Make the most of your day with our curated plans, packed with Cheltenham's hidden gems and unique experiences!

day 1
Exploring Cheltenham’s Regency Architecture
morning
:

Begin your day with a leisurely breakfast at one of the local cafes, savoring traditional English tea and pastries. Afterwards, take a peaceful stroll around the Montpellier District, where you can admire the stunning Regency architecture and charming terraces. Don’t forget to visit the Cheltenham Art Gallery and Museum to appreciate both local and international art.

afternoon
:

Enjoy a delightful lunch at a nearby bistro, sampling some local delicacies that Cheltenham has to offer. Post-lunch, venture to the beautiful Pittville Park to engage in a relaxing walk or a paddleboat ride on the lake. Spend some time at the Pump Room taking in the natural mineral water on offer, a nod to the town's spa heritage.

evening
:

As the sun sets, head to the iconic Cheltenham Racecourse to soak in the vibrant atmosphere of evening horse races. Dine at a fine restaurant nearby, where a variety of international cuisines will tempt your palate. Conclude the evening with a stroll down the Promenade, enjoying the lights and ambiance of this historic town.

day 2
Immersive Culture and History
morning
:

Start your morning with a visit to the historic Sandford Parks Lido for a refreshing swim or a leisurely walk around its grounds. Following the swim, head to Regency Square for a hearty breakfast at one of its charming cafes, fueling up for a day of exploration. Make your way to the Cheltenham Town Hall to discover its rich history and architectural beauty.

afternoon
:

After lunch at a quaint pub, visit the Everyman Theatre and take a backstage tour to learn about its history and ongoing productions. Spend the afternoon wandering through the Cheltenham Literature Festival’s bond with big-name authors if you are an avid reader. Wrap up your cultural exploration with a visit to the Holst Birthplace Museum, celebrating composer Gustav Holst's life and works.

evening
:

In the evening, catch an exciting performance at the Everyman Theatre, where a variety of shows from drama to musicals are often on offer. After the curtain falls, enjoy a delicious dinner at a restaurant known for local and seasonal ingredients. To cap off your day, explore the nightlife at local pubs or cocktail bars near the town center for a chill vibe.

day 3
Nature and Gardens Day
morning
:

Begin your day bright and early with a tranquil visit to the Cheltenham Botanic Garden, located in the heart of the town. Enjoy the vibrant flora and peaceful atmosphere as you stroll through the well-maintained pathways. Don’t forget to grab a coffee from the café on-site to enhance your serene morning experience.

afternoon
:

After lunch, take a trip to the picturesque Winchcombe, just a short drive away, where you can hike along the Cotswold Way for stunning vistas and fresh air. Make sure to stop at Sudeley Castle for a tour to learn about its fascinating history and beautiful gardens. The afternoon can also be filled with exploring the quaint shops and cafes in Winchcombe.

evening
:

Return to Cheltenham for an evening of relaxation at a local spa, where you can indulge in a soothing treatment after a day filled with activities. Dinner at one of Cheltenham’s Michelin-star restaurants will tantalize your taste buds with exquisite dishes prepared by talented chefs. Finish off with a nightcap at a nearby bar, enjoying the local craft beers or fine wines.

day 4
Day Trip to the Cotswolds
morning
:

Kick off the day early with a hearty breakfast before setting out to the picturesque Cotswolds countryside, known for its rolling hills and charming villages. A visit to Bourton-on-the-Water, often referred to as the 'Venice of the Cotswolds', is a must, where you can wander along the riverside. Stop by the local shops to pick up unique handmade souvenirs.

afternoon
:

Enjoy lunch at a traditional Cotswold pub, where you can savor hearty dishes made from local ingredients. Afterward, take your time exploring the beautiful village of Stow-on-the-Wold, famous for its antique shops and historic sites. This afternoon can also include a scenic drive through the countryside to appreciate the stunning landscapes.

evening
:

As you return to Cheltenham in the early evening, have dinner at a restaurant offering traditional Cotswold dishes, celebrating the flavors of the region. After dinner, enjoy a relaxed evening walk in the town center, maybe catching a local concert or live music performance if available. Let the peaceful ambiance settle you into a restful night.

day 5
Cheltenham Festivals Deep Dive
morning
:

Dedicate your morning to the Cheltenham Music Festival if you’re visiting during the summer, where you can partake in fun workshops. Alternatively, if it's the Jazz Festival time, enjoy soulful performances by local and international artists. Grab breakfast at a festival food stall to kickstart your day of musical enjoyment.

afternoon
:

Continue your festival experience with a leisurely lunch in a nearby park, enjoying the lively atmosphere created by fellow festival-goers. Engage in various activities, from interactive exhibits to engaging conversations with artists, adding depth to your festival experience. This afternoon is about immersing yourself in the creativity and vibrancy that the event brings to the town.

evening
:

As night falls, enjoy an outdoor concert featuring popular musicians in the heart of Cheltenham. Post performance, explore food and drink stalls that showcase local delicacies, immersing yourself in the festival culture. Wind down your evening at a nearby pub, reflecting graciously on the artistic experiences you had throughout the day.

day 6
Shopping and Spa Day
morning
:

Indulge in an energizing breakfast, then head to the High Street for a day of shopping in Cheltenham’s independent boutiques and well-known retail chains. Don’t miss the Promenade for a range of unique shops, perfect for picking up gifts or a new wardrobe. You can even explore the local farmers market for fresh produce and artisanal goodies.

afternoon
:

After your shopping spree, treat yourself to a luxurious lunch at a stylish café that prides itself on locally sourced ingredients. Following lunch, unwind at one of Cheltenham’s renowned day spas, indulging in afternoon treatments designed to rejuvenate your body and mind. Enjoy the spa's amenities, including a sauna or pool, letting the stress of the outside world melt away.

evening
:

Refreshed from your spa experience, enjoy a casual dinner at a vibrant eatery known for its eclectic menu. Afterwards, take a leisurely evening stroll through the Imperial Gardens, enjoying the serene atmosphere and beautifully landscaped surroundings. For night owls, visit local bars for live entertainment, reveling in the community spirit of the town.

day 7
Visit to Cheltenham’s Local Markets
morning
:

Start your morning exploring the Cheltenham Farmers Market, bustling with locals and offering fresh produce and homemade treats. Sample various foods while chatting with farmers and artisans about their products, immersing yourself in the community spirit. Finish off with a fresh pastry and coffee to fuel your day.

afternoon
:

After grabbing lunch from one of the food stalls, continue your exploration at the Cheltenham Flea Market where hidden treasures await. Wander through the stalls filled with vintage clothing, unique antiques, and handmade crafts. This afternoon is perfect for finding one-of-a-kind items while experiencing the charm of local entrepreneurship.

evening
:

Conclude your day with a relaxed dinner at an inviting restaurant that sources ingredients locally, allowing you to continue your local experience. Depending on the day, you might catch a weekly quiz night or themed event at a local pub, adding a fun twist to your evening. Wrap up with a dessert from a nearby café, celebrating the end of a wonderful day.

day 8
Art and Theater Day
morning
:

Begin your day with breakfast at a cozy café before diving into Cheltenham’s artistic side at the Everyman Theatre for a daytime production. The variety of shows will mesmerize you while providing a unique insight into the local culture. Take some time afterwards to explore the surrounding area filled with art installations and galleries.

afternoon
:

For lunch, consider a trendy café that promotes local art, creating a motivational atmosphere for artists and community members alike. Post lunch, visit the various galleries displaying a range of art forms, from contemporary to classic, elaborating on Cheltenham’s supportive art community. This afternoon is a wonderful opportunity to appreciate the creativity that fills the town.

evening
:

As evening approaches, return to the Everyman Theatre for a live performance that promises to be an unforgettable experience. Following the show, enjoy dinner at a bistro nearby that carries an artistic flair in both decor and menu. Cap off the night with a cocktail at a bar known for its unique mixology, celebrating the culture you’ve absorbed throughout the day.

day 9
Historic Landmarks and Nature Trails
morning
:

Kick off your day with a hearty breakfast before heading out to explore Cheltenham’s historic landmarks, notably the beautiful St. Mary's Church. Take a guided tour to appreciate its rich history and magnificent architecture. Afterwards, make your way to the tranquil Leckhampton Hill for some fresh air and spectacular views over the town.

afternoon
:

Enjoy a picnic lunch with local treats at the summit of Leckhampton Hill, allowing you time to soak in the beautiful surroundings. Spend the afternoon hiking through the nature trails, with opportunities to observe local flora and fauna in their natural habitats. Make sure to capture some pictures to remember your nature adventure.

evening
:

Return to Cheltenham in the evening for a well-deserved dinner at a local pub celebrating regional fare. Join in on any evening strolls around the town center to appreciate the vibrant energy of Cheltenham at night. Wind down your day with a quiet drink in a cozy pub, relishing the memories of your active day.

Discover Cheltenham

Read more in our Cheltenham 2025 Travel Guide.

Cheltenham Travel Guide