How to Plan a Startup Retreat (and 5 Perfect Places to Host One)

You have a million and one priorities to juggle, and on top of it all, your leadership team has just asked you to plan a retreat.

Now, you have to find a location that will be convenient and organise an itinerary that keeps everything moving smoothly.

It’s okay to feel overwhelmed—this is a big task and one you’ve probably never done before.

To help, we’ve created this mini start up retreat guide. It explains the purpose of startup retreats (so that you can organise yours around specific goals), how to choose a location for your retreat, and tips for making it effective.

We’ve also listed five Ashore locations in the UK you can use for a small start-up retreat—they’re the perfect places for your team to unwind, recharge, and be productive.

Are startup retreats worth it?

Short answer: Yes.

Startup retreats offer an escape from the distractions and monotony of working from home. They allow teams to unwind, collaborate, and bond. The exact outcomes of a startup retreat all depends on the goal(s) you set and how well you plan for it.

That said, here are the most significant benefits of a startup retreat:

Fun and relaxation

A startup retreat can be a time for employees to recharge. It serves as a break from the intense and fast-paced work culture of most startup environments.

Instead of working alone for hours, focused on their objectives and looming deadlines, they can come together, brainstorm without pressure, try out new meals, go for group walks, and get involved in new activities.  This change of scenery and break in routine work wonders in elevating one’s mood.

According to environmental psychologists, changing scenery to a location surrounded by nature (like the ones offered by Ashore) can improve mental health by reducing depressive and anxious thoughts.

Team bonding

Startup retreats allow employees to interact in person rather than async through a screen.

As stats from TravelPerk hybrid work trends show, having a sense of belonging is the most significant benefit of physical meetups with colleagues.

While virtual games and get-to-know-me sessions can help remote teams build rapport, nothing beats exploring places and sharing experiences in person. Apart from how memorable and fun such experiences are, they allow you to learn more about your colleagues' personalities in ways virtual interactions won’t.

Work productivity

A startup retreat produces happy, relaxed, and bonded employees. And this impacts how they show up at work—in the best way. They’re energised and motivated to show up everyday as their best self.

Apart from that, a retreat environment can be mentally stimulating, making it the ideal place to brainstorm on a new project or design a pitch deck.

Research from Nature, a science journal, shows that virtual communication can stifle creativity due to the hyper-fixation on screens and lack of external factors that can stimulate the production of better ideas.

The pressures and distractions in our homes can stifle creativity and innovation. It’s hard to think of something new with the kids playing in the background or when you know you still need to get groceries for dinner in an hour.

It can also be helpful to ideate with others in an undisturbed space designed for a productive working retreat. A team is made up of different strengths. Some will be the idea generators, others executors.

Having your people in a serene and spacious space with the right tools can take a product or project from idea to reality. This was the case for Canny, a small startup that has used its various retreats to organise a team hackathon, film a product launch video, and hold its annual planning meeting.

If you have a task you’ve been putting off, or your startup’s pitch deck needs some work, you can borrow from this playbook and use your retreat to tick it off your team’s to-do list.

Career growth

Not all startup retreats are for only working or relaxing. You can organise a retreat to bring employees together for a training or workshop or even send just one away to do it on their own. This type of retreat encourages focus and full participation from participants in the training. Maybe it’s an online certification an individual can complete without distraction or maybe your Head of Customer Success is onboarding new joiners, training them on the company’s clients and the processes the team follows.

This setup lets them learn in a relaxed and focused environment, plus they’ll appreciate your investment in their growth and development.

Joint strategic planning

Your startup retreat could be a time when the founders and C-suite members come together to work and unwind. You can even treat it as a leadership retreat.If that's the case, it can be used to review the startup’s business model, develop the next quarter's goals, or even kickstart a new project before launching it full-scale.

Such retreats are effective as they create an enabling environment for startup founders and stakeholders to work together on a single goal without distractions.

Factors to consider when choosing a retreat location for your startup

The location is the basis of a successful or unsuccessful retreat. This goes for a startup retreat, corporate retreat, or any other.

Aesthetics and proximity to the company headquarters or employees' residences are only some of the points to consider when choosing the location. Working with the right partners like Ashore and considering the following factors can make your location scouting process easier.

Number of participants:

When choosing a location for your upcoming retreat, you need to know how many people will be attending.

For a small group, a property that can house everyone at once is ideal. Larger groups can book multiple hotel rooms instead or opt for properties with multiple residential buildings like you'd see at a farm stay.

Retreat duration

A startup retreat runs for a day to as long as two weeks. But three to seven days is the best. Ensure the accommodation options in your preferred location are conducive enough and suit your budget for however long you wish to stay.

For instance, with Ashore, you can enjoy our three to seven-day listings in three packages:

Ashore Reset offers a three-night stay to reflect, relax, and explore.
Ashore Focus offers a four-night to dedicate time to a project in a relaxed space.
Ashore Discover offers a seven-night stay for creative work and strategic thinking.

Accessibility

Your choice of location has to be accessible enough for participants wherever they’ll be coming from.

Will they be able to get there by train or will they need a car? Do you need to arrange a taxi service from the train to the property? Will you all travel together from a set starting point?

Check to confirm that trains or cabs are available to transport your team members to and from the retreat venue.

Depending on where most retreat participants reside, you can opt for a venue in another city, country, or continent.  For distributed teams, a central location where everyone can converge will be ideal. This way, more people get to participate without the issue of distance or flight costs. But it’s usually more cost effective to hold your retreat somewhat locally within a few hours of participants.

Facilities

The choice of location should come with facilities that align with the retreat's overall aim.

For example, a retreat featuring a design sprint should be in an environment that encourages brainstorming and creativity. A retreat meant for full relaxation should have nature nearby.

And of course, any retreat where work is done should have a strong internet connection and a suitable work setup.Ashore properties come with workspaces, a stand-out feature in our listings, kitted out with custom desks, chairs, and Apple monitors.

Five perfect locations for your startup retreat from Ashore

If your startup is small or you're only sending a group of people, you can use an Ashore property to host your retreat.

Catering to groups of 4-8 people and based in the UK, these properties are in a serene environment with surroundings great for sightseeing and trying out outdoor sports like golfing, tennis and surfing, and they all come with a standard workspace.

Here are our top five UK startup retreat locations:

The Warren House - Suffolk Coast

The Warren House, an isolated cottage located on the coast of Suffolk,  is excellent for a relaxed retreat vibe all year round.

It has a natural landscape providing an impressive view overlooking the sea, and its proximity to the Adnams Brewery means you can add a beer tour to your activity list for the retreat. It’s also a walkable distance from the town of Southwold and the pub for group evening walks.

Bring your team along to enjoy co-working during the day, and engage them in water sports, golfing, tennis, and bird watching to unwind.

Capacity: Up to 8 people.

Bedrooms: Four

Workspaces: Two

Workspace 1 specs: Apple studio display, Herman Miller Mirra II  and the classic Pegg desk, magic keyboard, trackpad II, laptop stand, universal adapter

Workspace 2 specs: Apple studio display, Herman Miller Mirra II  and the classic Pegg desk, magic keyboard, trackpad II, laptop stand, universal adapter

Internet: Starlink internet connection. 105 Mbps download, 34 Mbps upload

Amenities: watch room, large freezer, microwave oven, sound system, dishwasher, private garden with a large sitting space and a barbecue setup.

Pricing

Ashore Reset: 3 nights, 4 credits (£1580)
Ashore Focus: 4 nights, 4 credits (£1580)

Ashore Discover: 7 nights, 6 credits (£2370)

The Worker’s Cottage - Sandringham Estate

The Worker's Cottage

Situated in Great Bircham, The Worker’s Cottage is a renovated space within the Sandringham estate, a property once owned by the late Queen.

From this countryside listing, you can visit the Sandringham House Museum & Grounds,  Houghton Hall and enjoy afternoon tea sessions at the Bircham Windmill.

Capacity: Up to 6 people.

Bedrooms: Three

Workspaces: Two

Workspace 1 specs: Apple studio display

Workspace 2 specs: Apple studio display and classic Ashore Pegg desk

Internet: 62 Mbps download

Amenities: Dining space, private parking, patio with garden views, rainfall showers, private bath cabin, well-equipped kitchen.

Pricing

Ashore Reset: 3 nights, 4 credits (£1580)
Ashore Focus: 4 nights, 4 credits (£1580)

Ashore Discover: 7 nights, 6 credits (£2370)

The Grainstore - East Sussex, Lewes

The Grainstore

This 145-square-metre luxury holiday home is an eco-friendly property that offers a collaborative workspace for meetings and work sessions during the day.

The Grainstore, located in East Sussex, Lewes, is an hour's train ride from London, a 20-minute drive from Brighton’s train station, and a 10-minute drive from the Lewes train station.

It comes with free parking for up to five vehicles and a complimentary local wine on the first night. Go on hill walks, visit Stanmer Park, the Railway Land Wildlife Reserve and other fun places within Lewes when you book this listing.

Capacity: Up to six people.

Bedrooms: Three

Workplaces: Two

Workspace specs: Apple studio display and classic Ashore Pegg desk

Internet: 63 Mbps upload

Amenities: solar panels, heated floors, hot tub, smart TV, private courtyard, and an open plan kitchen space.

Pricing

Ashore Reset: 3 nights, 4 credits (£1580)
Ashore Focus: 4 nights, 4 credits (£1580)

Ashore Discover: 7 nights, 6 credits (£2370)

The Orangery Braunton - North Devon

The Orangery

This listing is a pet-friendly cottage featuring an Orangery and a private garden with a barbecue setup.

It also has a well-equipped kitchen, making it great for group cooking. Within this location, you’ll find the different surfing spots of the North Devon Coastline, which you automatically have access to as an Ashore guest.

At The Orangery, Braunton, residents can try golfing, cycling, and visiting the Croyde or Putsborough Woolacombe beaches.

Capacity: Up to 6 people.

Bedrooms: Three

Workspaces: Two.

Workspace 1 specs:  LG 34” UWHD curved monitor, Herman MillerNevi sit-stand desk, Herman Miller Mirra II, magic keyboard, trackpad II, laptop stand, universal adapter

Workspace 2 specs: Apple studio display, Herman Miller Aeron and the classic Pegg desk, magic keyboard, trackpad II, laptop stand, universal adapter

Internet: 900mbps download, 325 Mbps upload

Amenities: Private garden, sun deck, Kamado Barbecue, boiling water tap, fireplace with log burner, and a large dining room.

Pricing:

Ashore Reset: 3 nights, 4 credits (£1580)
Ashore Focus: 4 nights, 4 credits (£1580)
Ashore Discover: 7 nights, 6 credits (£2370)

The Residence, Amberly - Gloucestershire

The Residence at Amberly, Gloucestershire, provides a scenic view over the vineyards in the heart of Cotswolds and is excellent for a holiday retreat. It’s close to exciting spots like Minchinhampton Golf Club, Tetbury, and Nailsworth for boutiques.

Capacity: Up to six people.

Bedrooms: Three

Workspaces: One

Workspace specs: Apple studio display, Herman Miller Aeron and the classic Pegg desk, magic keyboard, trackpad II, laptop stand, universal adapter

Internet: 42 Mbps download, 12 Mbps upload

Amenities: private outdoor garden, courtyard, and dining area.

Pricing:

Ashore Reset: 3 nights, 4 credits (£1580)
Ashore Focus: 4 nights, 4 credits (£1580)
Ashore Discover: 7 nights, 6 credits (£2370)

Tips for having an effective startup retreat:

Once your location is sorted, you can focus on other aspects of retreat planning.

The following tips will help ensure the overall success of your startup retreat:

Be clear on the purpose of the trip and stick to it

The two biggest reasons startups go on a retreat are to brainstorm or unwind; sometimes, it’s a mixture of both.

So, whatever the reason for your upcoming retreat, communicate it to your employees at least one month ahead.

This way, you’ll give them enough time to prepare, share any reservations about the trip and build excitement towards the retreat. Focusing on the purpose will help your planning move faster and achieve the retreat's goal.

These goals could be:

Refine brand messaging
Prepare for an upcoming pitch
End a business period and plan for a new one.

Give participants space to explore

Between the numerous work sessions and team-building activities lined up for the retreat, participants should have free time to do what they want.

Your employees can be encouraged to use their free time exploring the local community, going for walks together, and taking the time to reflect on their own.

The retreat should not feel overly regimented; otherwise, participants get bored, irritated and tired, defeating the goal of your offsite.

Cover all bases while planning

Accommodation, venue, food, sleeping arrangements, cleaning, transportation, and activity schedules should be sorted out and communicated to employees before the retreat commences.

This way, you can address any issues or questions they have ahead of the trip and ensure the entire team returns from the event feeling fulfilled.

Make your startup retreat a success with Ashore

Hoping to use any of our recommended locations in this piece for your next team retreat? Or are you looking for a space that works for your time off?

Sign up on our website as a member, or book a call with Stephanie.