Wimbledon, Winston, and Whiskey: A client’s dream trip becomes reality
What started as a “once-in-a-lifetime” dream to attend Wimbledon 🎾 in London … turned into a once-in-a-lifetime adventure for Barb and Dave. (Let’s just say, their itinerary ends with some very royal treatment.)
When they booked their first discovery call with Whitney, they were unsure what else they’d like to do while venturing across the pond for Wimbledon. But in just 30 minutes, Whitney helped uncover their deeper travel passions, turning their trip into an itinerary even better than they could have hoped for in summer 2025.
And the best part? This wasn’t a checklist trip that any tourist would experience, but instead, an adventure curated to their individual passions, including:
🏴 An immersive exploration of the history of Winston Churchill and WWII in London
🚂 A stunning scenic train ride from London to Edinburgh
🫖 Tasting local flavors, from hearty pub meals to Scottish whiskeys
🛌 Winding down each day in comfortable boutique hotels…
🏰 And the final stage experiencing an upgraded stay at a castle-manor in the Scottish highlands
From Wimbledon to Walking in the Footsteps of London’s WWII
Barb and Dave knew one purpose of this trip – to experience Wimbledon. But as the discovery call progressed, it became clear that this was Barb’s dream. Turns out that Dave didn’t share the same enthusiasm for hours and hours of watching tennis 🙃…
His passion? To dive deep into the history of Winston Churchill and WWII in one of the very cities where that history went down. Within minutes, Whitney suggested a slight adjustment to their plan - while Barb watches Wimbledon to her heart’s content, Dave will be soaking in the history he is so passionate about while walking the very streets it happened.
Fun fact: During WWII, Churchill famously took refuge in the underground war rooms beneath London, directing Britain's war efforts in secrecy. Now, visitors like Dave can step inside these preserved rooms and see where history was made.
And from there, the drizzly British sky was the limit. What else could we add on to this trip that would make it a truly memorable experience?
A Ticket to Quality Time and Scottish Memories
Even though they didn’t know how to express so at the start of the call, it was apparent that what really matters to this couple is immersing themselves in the culture and enjoying each other's company (except during Wimbledon 😅)
And the rest of the trip’s activities hit all those desires, starting with a relaxing train ride to Edinburgh that paints a picture of the lush British countryside leading into one of the world’s most picturesque cities. Winding cobbled roads, cozy alley pubs, and robust history around every corner make Edinburgh an ideal spot for the couple to enjoy time exploring.
After a day of exploring Holyrood Palace and learning about Scotland’s various clans, Barb and Dave finally make their way to their last stop – The Fife Arms, a stately manor nestled in Scottish countryside that makes you feel like royalty. Far more than a turn-of-the-century hotel, it is a haven for history buffs, whiskey enthusiasts, and visitors looking for a relaxed environment to soak in nature. (Did you know? The Fife Arms has an extensive art collection, including works from Picasso!)
Some of the memories to be made here include:
🥃 A cooking class with a local food writer to make local dishes and pair them with several varieties of Scottish whisky
🛻 Exploring the rugged moorlands by guided rover tour and taking in the sights of stunning mountains and ruined villages
🍻 Sipping a pint at the pub, The Flying Stag, while chatting with locals and travelers alike and listening to local bands
Talk about ending the 10-day trip on a high note! Every step along the way was carefully curated to the interests and passions of both Barb and Dave, giving them both unique memories that simply can’t be captured in a photo. That is the heart of what we do at Undiscovered Sunsets – to infuse the passions of each traveler into every moment of their trip, from the room they wake up in to the food they taste and the sights they see.
And it can all start with one simple dream, like Wimbledon.
Undiscovered Sunsets was a long time in the making, even if I myself didn’t realize it. During my time at the University of Northern Iowa, I studied abroad in New Zealand. Upon graduating, I bought a one-way ticket to France, lived with a French family and studied with classmates from Turkey, China, Russia, Germany, Italy, and everywhere in between. In 2010 I began teaching English as a foreign language. This job quickly took me to China, where English teachers were in high demand and within three years, I began working in a 5-star hotel, speaking Mandarin throughout most of my day. In total, I lived abroad for 7 years.
I consider Undiscovered Sunsets to be the perfect mélange of my personal experience traveling the world and my professional experience working in the hospitality industry.
I look forward to designing your next adventure!
