Executive Retreats: How to Plan for and Book the Ideal Place

The soft sound of birdsong fills the air. A shaft of sunlight pierces through the canopy of trees, illuminating the forest floor below with a delicate brightness. The whisper of a breeze carries the scent of fresh coffee and the promise of new ideas.

This isn’t a holiday — it’s an executive retreat designed to spark creativity and innovation.

Executive retreats offer leaders the chance to reconnect with one another outside of the office — the kind of deeply collaborative, in-person communication that creativity needs to thrive.

But finding the perfect combination of inspiring location and best-in-class workspace might send you down a few internet rabbit holes.

Instead, read on to find out how you can book the exact location your leaders need to get the work done and which 4 Ashore properties fit the bill.

5 tips for planning a perfect executive retreat

Executive teams should come away from a retreat with a renewed sense of clarity and purpose. But to achieve this goal, your planning needs to be on point.

You should consider everything from the technology available and how many workspaces are available, through to choosing a location surrounded by the elements that can help spark new ideas.

Here are Ashore’s top five tips for planning working retreats that just… work.

1. Decide on a budget

Yes, it’s not exactly inspirational, but deciding on a budget is an essential first step. Here’s what to consider:

Accommodation: Knowing how many nights your executive team plans to be away for is a good place to start.
Travel expenses: consider how far executives are willing to travel, and whether they’ll head to their destination by train or car (Ashore offers on-demand car rental for those who need it).
Materials and supplies: Ask the executive team if there’s anything specific they’ll need for the retreat.
Meals and refreshments: Ashore locations come complete with meal kits (and amazing coffee).
Activities: To cover any team-building exercises or other events like a brewery tour, pub lunch, or outdoor activities.
Fees: If you’re hiring a retreat facilitator or any speakers.
Miscellaneous: Adding a buffer of 15-20% to cover any unexpected costs is also a smart move.

2. Set clear objectives

Having a clear purpose for the executive retreat will help ensure your leadership team will meet this goal and explore the topic in detail.

Identify three or four key objectives, for example, setting next year’s goals, discussing strategic issues, or working to improve emotional intelligence. The goals are usually set by the executive team themselves, but your HR team can facilitate the discussion before the retreat takes place.

It’s also important to recognise that these aims may change as the retreat gets underway and the discussions deepen, so maintain enough flexibility to accommodate for that.

3. Stick to an agenda

Before any leadership retreats kick-off, it’s a good idea to create a loose schedule.

Use the objectives from step two when writing an agenda. Aim to strike a balance between time for discussion and the restorative free time that’s needed to get creative thoughts flowing.

An example agenda for day one of a three-day retreat might look something like this:

Morning session
Discussion of retreat objectives
Strategic planning
Afternoon session
Lunch
Device-free, outdoor time
Discussion (to cover one objective)
Evening
Free time/optional activities
Dinner
Pub quiz for team bonding and fun

Sometimes, organising for an experienced facilitator to come in for a day or more can help keep the team on track, especially if this is their first executive retreat experience.

Once back in the office, it’s also a good idea for leaders to deliver a short one-pager for their colleagues, or offer some informal feedback sessions. These could cover retreat outcomes like action items, next year’s business goals, and an overview of any new strategies.

4. Decide on technology needs

Is there anything more annoying than a patchy, slow internet connection?

Even in a remote location, senior leaders expect the technology they need to get the job done, including a fast and reliable internet connection.

Defining what’s expected from the outset means no frustration or disappointment when the 100 mbps internet turns out to be more like… one mbps.

Not all accommodation providers are set up with remote work in mind. But Ashore is different. All properties are personally chosen by us as not just the best homes with the best workspaces but in the best locations too.

Every Ashore property comes complete with:

Handmade Pegg Desks
Luxury Apple Studio Display monitors
Herman Miller chairs
Fast and reliable internet
Apple accessories including The Magic Keyboard and Magic Mouse
Charging cables

5. Find the right location

Great ideas are rarely born during PowerPoint presentations. While getting the technology right is one thing, choosing the right location is just as important.

Most of us can only focus on work for around four hours every day. A team walk in the breathtaking countryside (with a little snack break, of course) can help give executives the space they need to settle on a decision, whether that’s a new company direction or how to better encourage teamwork.

Another crucial concept is nature — the force that grounds us all. Tethering the experience in the elemental gives leaders the space and sanctuary they need to breathe out.

In fact, reconnecting with Mother Nature can decrease cortisol, the main stress hormone, by 21.3% for every hour outdoors.

The right combination of practical needs is also crucial. For some leaders, comfortable chairs and decent coffee machines might be non-negotiable, while for others they’ll want to know about internet speed and the number of workspaces.

Booking a location where ideas can thrive

Every Ashore location has something unique to offer, but they’re all connected by one clear thread: nature.

Heading into the great outdoors doesn’t just decrease stress levels. Research shows it also helps improve concentration and boost our capacity to effectively switch between tasks.

Nature might be crucial — but so is a comfortable working environment. Our carefully curated list of Ashore locations all come complete with best-in-class workspaces and amenities as standard. All properties are available for one of our signature packages: Ashore Reset, Focus, and Discover.

We also take the time to verify the internet access at each property, so you can be sure that your leadership team has everything they need to do great work, fast.

Here are some of our favourite properties, where participants can reconnect not only with the natural world but with their company’s missions and values.

The Residence - Gloucestershire

The Residence epitomises the electronic cottage concept, fusing rough-hewn stone and expansive views over ancient forests with modern tech and achingly stylish decor.

Perfect for startup retreats, the single workspace encourages collaboration as founders lay the tracks for future business success.

In between focus sessions, leaders can step beyond the private garden and into the heart of the Cotswolds. Amberley Castle and the market town of Stroud are both a stone’s throw away. Or they can pour a glass of something cold and enjoy the expansive views over the local vineyards.

Bedrooms: 3
Sleeps: 6
Workspaces: 1
Internet: 42 mbps download, 14 mbps upload
Choose from:
Ashore Reset: 3 nights, 4 credits (£1580)
Ashore Focus: 4 nights, 4 credits (£1580)
Ashore Discover: 7 nights, 6 credits (£2370)

Book The Residence

The Warren House - Suffolk

Step into real blue sky (and sea) thinking, at this exclusive clifftop retreat perched above the North Sea.

Bursting with natural light, leaders can work from two separate spaces when planning next year’s goals — or step outside, sink into the luxurious outdoor seating area, and find the inspiration required to solve business-critical issues.

There’s also plenty to do in between bursts of deep work. Leaders can connect with nature by taking a walk along the Southwold Coast Path, visit the local Adnams Brewery, or wander into Southwold to enjoy some local food.

Bedrooms: 4
Sleeps: 8
Workspaces: 2
Internet: Starlink
Choose from:
Ashore Reset: 3 nights, 2 credits (£790)
Ashore Focus: 4 nights, 3 credits (£1185)
Ashore Discover: 7 nights, 3 credits (£1185)

Book The Warren House

The Orangery - North Devon

The Orangery might look quaint from the outside — but it effortlessly blends old-world charm with the new technology that executive leaders require while discussing strategic plans.

From high-speed, near-gigabit internet to classic beams and a sunlight-filled orangery, this retreat offers the best of both worlds.

For leaders who love the outdoors, Braunton is home to the Museum of British Surfing and is located just 10 minutes from Croyde, one of the best beach breaks in the UK. Exmoor is nearby too, with its wild landscapes, standing stones, and dark-sky reserve that’s perfect for a spot of late-night stargazing.

Bedrooms: 3
Sleeps: 6
Workspaces: 2
Internet: Wifi 900 mbps download, 325 mbps upload
Choose from:
Ashore Reset: 3 nights, 2 credits (£790)
Ashore Focus: 4 nights, 3 credits (£1185)
Ashore Discover: 7 nights, 3 credits (£1185)

Book The Orangery

The Rapids - Herefordshire

As small corporate retreat locations go, it doesn’t get much better than this secluded property surrounded by woodland.

Located on the banks of the River Wye, it offers an immersive experience in more ways than one. After discussing strategy, leaders can kayak down the river, or relax on their own in the huge outdoor tub.

Located a one-hour drive from Cheltenham and Gloucester, this region is a popular mountain biking destination, with plenty of opportunities for exploring both easy and complex trails. River cruises are a more relaxed alternative, with plenty of time to let the ideas flow as you take in the sights.

Bedrooms: 2
Sleeps: 4
Workspaces: 1
Internet: 52 mbps download, 12 mbps upload
Choose from:
Ashore Reset: 3 nights, 2 credits (£790)
Ashore Focus: 4 nights, 2 credits (£790)
Ashore Discover: 7 nights, 3 credits (£1185)

Book The Rapids

FAQ: Executive retreats

Is there a difference between executive retreats and corporate retreats?

An executive retreat is usually targeted toward C-suite leaders and tends to focus on high-level strategic discussions and long-term business goals. A corporate retreat tends to include employees from all levels of the company and is more likely to focus on things like team building and creating a healthy workplace culture.

Why have an executive retreat?

Stepping into a different location at an executive retreat can help boost creativity and innovation, allowing for a deeper exploration of specific business issues. Having the dedicated time and space to focus on strategy can help the executive team align their goals toward this shared purpose.

What makes an executive retreat special?

A retreat’s location has the potential to make or break your executives’ experiences. Choose an executive retreat with a work environment that facilitates collaboration and innovation, but also offers private spaces for deep work. Location also matters — whether it’s a cottage nestled in the woods or a modern apartment with easy access to nature.

What to do after an executive retreat?

Once back at work, it’s a good idea to feedback retreat outcomes to your employees. This promotes transparency, trust, and alignment.