The Most Worthwhile Luxury Destinations for Vacation-Starved Entrepreneurs

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Being an entrepreneur can be a grueling lifestyle. Some entrepreneurs boast of not taking vacations in a bajillion years and never disconnecting (#hustle). I’m not that type. I love to travel the world and break often. For me, it’s all about sustainability and longevity. That’s why my wife and I travel as often as possible. We love experiencing new cultures, people, places and foods (especially foods) and have visited each of the places on the list below. Whether you are looking for an intimate, relaxing getaway or travels full of adventure, this list of luxury stays has you covered.

Kauai, Hawaii

The Hawaiian Islands usually makes the list when it comes to luxurious destinations rich with unrivaled experiences and cultural traditions. Each one has its own vibe, and some are more tourist-oriented than others. Among the less traveled islands, Kauai beckons with cascading waterfalls, lush gardens, long beaches and secluded hideaways. The selection of hotels on Kauai is small, with a few bed-and-breakfast options, a few major chains and even fewer boutique options. 

My wife and I love the Koa Kea Hotel & Resort, as it sets the bar high. Situated between the top two beaches on the island, Poipu State Beach and Kiahuna Beach, it’s closer to the ocean than any other resort. The best snorkeling and surfing is right on the hotel’s beach. 

In addition to the luxuries you’d expect to find at such a well-appointed resort, they have an array of unique options, including waterfront couples massage, one of the best menus on the island at the Red Salt Restaurant, oceanside fire pits and a lava-rock hot tub. And if you’re a foodie, I cannot stress how good Red Salt is, from the fresh fish entrees to the sushi bar (the Miso Butterfish melts in your mouth), to fresh morning breakfast muffins and papaya with lime on every table. You’ll be completely floored each time you eat. 


For a departure from all the buzz, there’s The Lodge at Kukui’ula, where you’ll find beautifully appointed bungalows, cottages and villas with endless opportunities. Imagine spending your morning at their organic farm and then drifting off in the afternoon to the Hi’ilani Spa to indulge in massages, acupuncture or aesthetician services, private sanctuary rooms, outdoor showers and plunge pools for the ultimate in relaxation. Nearby, a sprawling, plantation-style open-air lounge called The Clubhouse offers access to golf courses, tennis courts, Makai Pools and more. Come here in the evenings to wrap up each day with perfectly crafted cocktails and toasted marshmallows while the sunset glows in the distance.

Mahe and Praslin, Seychelles

Seychelles is an archipelago of 115 islands in the Indian Ocean off East Africa, where you’ll find an abundance of exotic beaches, coral reefs and nature reserves. It’s home to rare animals, such as giant Aldabra tortoises, and is known for its fascinating Creole architecture and colorful covered markets overflowing with fresh foods and local wares. Royal and celebrity couples are known to honeymoon here — Prince William and Kate Middleton, Gabrielle Union and Dwayne Wade and Amal Alamuddin Clooney, to name a few — certainly a testament to the caliber of privacy and delights found in the Seychelles islands. 

When visiting, definitely make plans to take advantage of five-star accommodations at The Savoy on the island of Mahe, with elegant suites and perfect terraces overlooking palatial grounds and tropical gardens. You’ll be able to experience a vast variety of local and international food, wine, cocktails and brews in any of the seven indoor or outdoor restaurants and bars, some of which are poolside, all of which are delicious. 

Only a 15-minute helicopter flight from Mahe, you’ll be treated like royalty with legendary butler service in waterfront villas with private pools at the Raffles Seychelles. An oasis for well-traveled patrons, you can break away from ordinary vacations and be submerged in opulence and adventure in the heart of the island of Praslin. Indulge your senses and nurture your spirit with multiple award-winning, island-chic restaurants, a magnificent spa and wellness center and exotic excursions. If you really feel like balling out, get yourself a villa with a private pool and you can lounge around your hotel room all day. 

Manuel Antonio, Costa Rica

As the premier destination of the Central Pacific region, Manuel Antonio offers idyllic coastlines with soft white sands, gentle turquoise waters and endless landscapes to explore. Manuel Antonio National Park brings you up close to the colorful wildlife of the rainforests and allows no more than 600 visitors per day. Other local attractions range from nighttime jungle walking tours and canopy safari zip lines to spice tours and butterfly gardens. The hotels you’ll find here are boutique-style accommodations, usually not more than 20 rooms, and sit on the jungle hillside.

Hotel Makanda By The Sea has been designed as a posh and lavish getaway with gourmet fare and exotic elements in the architecture. Whether you are honeymooning or just wish to vacation like honeymooners, you’ll find every detail of your stay reflects paradise. A detached spa complex created with only natural elements, the Shanti Spa awaits to envelope you in serenity with rejuvenating massages, private yoga sessions and a wood steaming room to relax your cares away.

Mallorca, Spain

Mallorca (Majorca), the largest of Spain’s Balearic Islands in the Mediterranean, is known for lavish beach resorts, romantic sheltered coves and fascinating limestone mountains. Tourism here is full of culture, with art and cartography dating back centuries; music and dance festivals that vary from traditional Ball dels Cossiers to modern jazz; and unique adventures like visiting an ostrich farm or swimming with the sharks at the Palma Aquarium. There’s no shortage of luxury hotels in Mallorca, like the five-star Castell Son Claret, which resides in a 15th century castle nestled in the Tramuntana foothills. Hundreds of acres of lush parklands and glorious panoramic vistas gracefully combine for a world-class experience that includes Michelin Star dining. 

Reykjavik, Iceland

Iceland has epic waterfalls, notorious volcanoes and glaciers that rank among some of the largest in the world. And while you could spend a lifetime exploring this beautiful country, we strongly suggest at least four days. Reykjavik, on the coast of Iceland, is home to the National and Saga museums, tracing Iceland’s Viking history. Spend a day wandering through this unusual city, and take in the striking local architecture of concrete churches and glass domes that offer sweeping views of the sea and hillsides. 

The next day, you can escape the hustle of the city with a drive to the Hotel Husafell. Ranked on National Geographic’s Unique Lodges of the World list, any time of the year is the perfect time to be a guest. In the summer, guests can play golf under the midnight sun. In winter, a concierge will call your room in the early morning hours to come outside so you can enjoy the northern lights when the skies light up several times a week, and their thermal pools are available to soak in any time of year.

For an adrenaline rush that can’t be had anywhere else, spend a day snowmobiling nearby. With expert guidance, you can ride along the snowy expanse of an Icelandic glacier before exploring into an ice cave that draws you to the blue heart of Langjökull for a one-of-a-kind experience. 

If you’re a fitness fanatic, you can’t leave the country without dropping into Crossfit Reykjavik, home of Annie Thorisdottir (CrossFit athlete, entrepreneur and overall badass). Before you leave this magical country, you’ll want to take time to be awestruck by the island’s volcanic activity with a day at the geothermal Blue Lagoon spa, near the village of Grindavik, listed as one of the 25 wonders of the world. Submerge yourself in the purifying waters and come home renewed.

Yes, it’s absolutely imperative for entrepreneurs to work their asses off, but as hard as you work, you should vacation the same. Enjoy your travels, and share your stories with me on Instagram.  


Andrew Medal

Andrew is the founder of Action & Ambition. He's a tech entrepreneur and angel investor.

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