Sierra Obermark

San Diego Office

At the age of three, armed with coloring books, goldfish, and my Winnie the Pooh backpack I boarded a plane to Denmark with my parents and my life of travel began. Although I don’t remember much about that first trip other than walking a turtle on a leash, finding a hedgehog, and going to Legoland, it sparked my lifelong love affair with the world.

Since then, now armed with camera, sketchbook, and Hufflepuff backpack, I have been fortunate enough to travel all over Europe, North America, Australasia, and more.

Whether wandering the rolling, sheep-covered hills of Scotland or the bustling, colorful markets of Istanbul I am constantly fascinated by the landscapes, cultures, and peoples of the world. I will never forget the peaceful excitement of strolling along the canals in Venice nor the local festival I stumbled upon on the Schloss Sommersdorf castle grounds in Germany.

I am always looking forward to the next adventure and my greatest joy is to share the world with others as it has been shared with me.

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Travel nuggets

  • When viewing the Northern Lights in winter, bring a bandana or extra-large scarf for your face!

  • When diving in St. Lucia, bring drops to keep your mask clear.

  • The best gelato I have ever had is on the Ponte Vecchio in Florence.

  • Instead of walking along the roads in Paris during the day, walk along the river. The waterfront bars, skate park areas, and boat views give a new perspective to the City of Light.

  • Explore new islands in Greece. There are so many more than Santorini and Mykonos waiting to be discovered!

  • If your bag is over the airline weight limit when going, you packed too much! Just think of all the weighty items you are going to be bringing back with you!

  • Pack for beach, biking, and city walking when planning a trip to Puglia. There is more to explore than you can imagine.

  • Get an Oyster Card when traveling in London, it makes public transport straight forward.

  • Don’t be scared off by thoughts of bad weather in Ireland, without the rain, the country wouldn’t be nearly as beautiful and green. Make sure to pack a reliable jacket!

  • Highland Coos are amazing creatures. Be on the lookout for opportunities to view them, but don’t jump the fences!

My hot picks

Ard Na Sidhe Country House, Ring of Kerry, Cork, Kerry and the South, Ireland

A relaxing oasis on a lake, perfect for enjoying the scenery that Ireland is famous for.

Belmond Cadogan, London, United Kingdom

Expertly located in Chelsea with homey touches and a high level of service.

Belmond Castello di Casole, Tuscany, Italy

The best way to experience the Tuscan countryside: perched upon a hilltop with miles of land to explore.

Casa Angelina, Praiano, Amalfi Coast, Italy

A way to experience the beauty of the Amalfi Coast away from the hustle and bustle.

Eremo Della Giubiliana, Ragusa, Sicily, Italy

An idyllic location that blends centuries of history with local countryside feels.

Grace Santorini, Auberge Resorts Collection, Santorini, Greece

An amazing location with luxurious cave-style dwellings and the most excellent service.

JK Place Florence, Florence, Tuscany, Italy

A perfect encapsulation of Florence’s history with added modern luxuries and a food and wine list to die for.

Poseidonion Grand Hotel, Spetses, Greece

The only luxury hotel on the island of Spetses, it blends tradition and indulgence in the best way.

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