There are some places that we visit during our travels that stick with us. Destinations and experiences that engulf us and will continue to mesmerize us for years to come. I’ve recently been reflecting on places that I’ve stayed, where I’ve been hosted, and how they don’t only contribute to the overall experience but are an experience in and of themselves.

Perhaps it’s a consequence of welcoming guests into my home through Airbnb that I’m giving this more of a thought, but I’ve been lucky to stay at some truly special places around the world. But special is so subjective. This is my attempt to analyze what makes them special to me, and perhaps also to you.

What Makes a Place Memorable

Great hosts

I have been fortunate to stay at some excellent (read highly rated) resorts and hotels, but the places that stand out most to me are run by individuals who truly care about their guests and their surroundings. There’s something thrilling about experiencing a new destination through the eyes of a caring and passionate local.

Against the grain

I’m all about disruption and love encountering small businesses doing things differently. It might be my years of business travel that makes me abhor cookie cutter hotel rooms, but when planning a trip I look for unique accommodations and off-the-beaten path settings. Whether that’s a treehouse, yurt, or caravan, I know that the break with the status quo make for a memorable stay.

Nature element

I love cities but I have a soft spot for more rural settings. I think it stems from camping with my family when I was growing up, but being in a remote natural setting has an instant relaxing effect on me. Even if I’m staying in a large city, a bit of greenery like a terrace or garden goes a long way.


Although a few of my favourite lodgings have been completely private, many of them have not. The spots that I’ve remembered years later all had a great group of people staying at them. It’s the community that hosts are able to cultivate by appealing to a certain type of traveler and a knack for making everyone feel welcome. These aren’t party places but atmospheres of unforced socialization.

Great food

Food is the key to my heart. Many of my most memorable accommodations have had excellent food. Some didn’t have a kitchen or restaurant so I can’t fault them, but I always trusted my hosts to point me in the direction of tremendous food. Most at least had coffee, which is also critical for me.

Well designed

It’s always apparent when staying somewhere where the design and decor have been well thought out. I personally gravitate towards minimalist settings with touches of colour and local design elements. When assembling the list of my most memorable stays, it’s clear that most have this in common.

The Coolest Places to Stay

Puerto Escondido Travel Guide

Casa Kei, Mexico

Pepe opens his property in Puerto Escondido to travellers, who have their choice of six rooms including cabins and a third story room that has stunning views of the ocean and sunset. Originally planned to be Pepe’s home, he instead expanded his vision to welcome people from around the world. Pepe is a consummate host who effortlessly brings together a great group of people around the large communal table. It’s not uncommon for him to offer you a traditional Mexican breakfast or whip up a batch of margaritas. Property may be rustic to some, but have so much character.

Rabeang Pasak Chiang Mai Treehouse Resort

Rabeang Pasak Treehouses, Thailand

Just over an hour outside of Chiang Mai is the enchanting Rabeang Pasak. What began as a project for his family, proprietor Mr. Lee has built a half dozen treehouses welcoming travellers. These aren’t your basic treehouses either, they’re mind blowing. Multi level structures with bathrooms (some even have bathtubs), offering unparalleled views. Grabbing a rickety bike and exploring the surrounding jungle is a special experience. Some of the best homemade Thai food I’ve ever had.

La Posada de Cucayo, Spain

The Picos de Europa is a mountain range in a little explored region of northern Spain. Getting to rural village Cucayo will take you along winding mountain roads shrouded in fog, until you arrive at this one road town with a dozen or so stone buildings, some dating back to the 16th century. The town’s only guesthouse, La Posada de Cucayo, is run by a local family who have spent generations in the region. Breathtaking views, genuinely welcoming hosts. Unbelievable hiking. The onsite restaurant only serves up food from their farm or what grows in the region.

Curiocity Hostel Johannesburg Maboneng - Building

Curiosity Backpackers, South Africa

Johannesburg is in the midst of a cultural rejuvenation. For years, the city was branded as unsafe, particularly the central business district downtown, which left skeletons of former neighbourhoods. Maboneng, a neighbourhood development project, is bringing life back to the city centre and Curiosity is bringing travellers from the suburbs to downtown. Started by enterprising local Bheki Dube, Curiosity embodies Joburg’s transformation: youthful, hip, dynamic, sustainable.

Things to do in South Africa

Golden Gate Highlands National Park, South Africa

There were several excellent lodgings across my four week road trip through South Africa. What stands out most for me are the official accommodations in South Africa’s National Parks and the one that tops it is my stay in a Mountain Lodge at the Golden Gate Highlands National Park. Perched on a hill overlooking the vast terrain with the Drakensburg Mountains in the distance, our cottage was cozy and quaint. We spent hours sitting on the balcony, enjoyed our braai dinners, and putting on a fire inside when it got cold.

South Africa Road Trip Lesotho Maliba Lodge

Maliba Lodge, Lesotho

Staying at Lesotho’s only five star resort is an incredible experience. Situated in Tsehlanyane National Park at the base of mountains, Maliba offers a luxury twist on traditional accommodation. The spacious stone chalets with thatched roofs are spectacular boasting huge beds and gorgeous bathrooms. Food and drinks are first rate, and the outdoor dining area overlooking the mountains offers one of the best views I’ve ever encountered. Perhaps the most impressive element of Maliba is the service of its staff, who truly go out of their way to ensure you have a great stay.

Go Campers Van, Iceland

This one doesn’t fit as well into my criteria as the others, but I can’t exclude our accommodation on wheels from the list. When exploring Iceland, we rented a Go Campers camper van that we drove around the country’s infamous Ring Road. The adventure, comfortable van, and super service made this one of the most memorable travel experiences I’ve had to date. Parking the camper van in some unbelievably scenic camp grounds gave us the most spectacular settings for nightcaps and morning coffees.

The Coolest Places to Stay photos by Lauren Barth and JP Bervoets