My Life In Travel: Holly Rubenstein

My Life In Travel: Holly Rubenstein

On her podcast ‘The Travel Diaries’ Holly Rubenstein chats to a range of guests – from Stanley Tucci to Poppy Delevingne – about the travel experiences that have shaped their lives. As a travel journalist, she’s also been to many of the most desirable destinations in the world. Holly took some time out of recording series six of her show to share her favourite places and most memorable trips...

The last place I travelled to was Saint-Tropez on the Cote D’Azur. It was my first trip abroad post-Covid, and I stayed at Airelles Chateau de la Messardiere, a hilltop castle set within glorious landscaped gardens, overlooking Pampellone Bay. It’s one of the most magnificent places I have ever been to – the setting, the décor, the pool overlooking the sea. Plus, it has its own beach club, Jardin Tropezina, which is such a perk for a Riviera hotel. Being chauffeured to a striped sunbed and retreating to the beach club restaurant to tuck into fresh fish was a bit of a pinch-me moment. Saint-Tropez Old Town is so pretty – I loved sitting in cafés in the square watching the locals play boules. I also had a spectacular lunch at Cheval Blanc Saint-Tropez, right by the sea. It was a good reminder that the perfect beach holiday needn't be a flight away – my husband and I took the train from London.

The most memorable place I’ve been to is Ascona, a village on the northernmost tip of Lake Maggiore, the second largest of the Italian lakes, but across the border in Switzerland. Despite its many charms, it remains largely untapped. I stayed at Hotel Eden Roc Ascona, the only five-star hotel on the shore of Maggiore, with one of the best views – lush green mountains plunging into the water, framed by palm trees and vibrant hydrangeas. We hired a swanky Riva yacht to visit the nearby Brissago Islands (they can also be reached from Ascona by a 20-minute direct ferry). In its heyday, the larger inhabited island, Isola Grande, was a haven for artists, musicians and writers including author James Joyce. These days, the majestic Palladian villa at its heart has a café, restaurant and a few bedrooms. It’s three degrees warmer than anywhere in the vicinity, so the islands are almost subtropical, which explains why a show-stopping botanical garden has flourished there for more than 100 years.

At The Chapel

I’m a bit of a hotel addict so it’s hard to choose just one that really stands out. However my favourites include Post Ranch Inn in Big Sur, California; Kasbah Tamadot in the Atlas mountains of Morocco; Al Maha in the Dubai desert; and The Hoxton Williamsburg in Brooklyn, New York.

For a staycation I always go to Bruton in Somerset. I’ve stayed at Number One Bruton the last couple of times I’ve visited, which is home to the now Michelin-starred restaurant Osip. I also loved staying at The Newt, which has become a hit with the travel community, as well as Babington House about 15 minutes away. When I’m there, I love having brunch at At the Chapel and walking around the grounds of the Hauser & Wirth art gallery. 

This summer we had an unforgettable stay in the new beach lofts at Watergate Bay Hotel in Cornwall, where I coincidentally stayed next door to Stanley Tucci – we have a laugh about that on his episode of The Travel Diaries. There are so many outstanding hotels in the UK – I’d love to go back to Wilderness Reserve in Suffolk. Each property there has such character, and the setting is bliss. Chewton Glen in Hampshire is also a classic – I stayed in one of the treehouse rooms, with a wraparound balcony complete with wooden hot tub which was so much fun. Last Christmas before lockdown, we had a great little break at The Mitre, a boutique hotel with great interior design, an excellent riverside restaurant, and views of Hampton Court Palace. Another fantastic pub with rooms is The Old Coastguard in Mousehole, Cornwall. 

Al Maha
Post Ranch Inn

For a city break, I love going to Amsterdam which is so easy now thanks to the direct Eurostar route. I stay at The Dylan or Soho House Amsterdam, both of which have beautiful canal-front locations near my favourite neighbourhood – ‘The 9 Streets’ with its quaint bridges, individual clothes and homeware shops, quirky cafés and trendy restaurants. Pluk Cafe is the most Instagrammable restaurant in Amsterdam – try the unicorn horn-topped miniature cakes and doughnuts. Dinner at Momo is also a must. For years, it’s been one of the city’s best-known fashionable hotspots, serving up mouth-watering Japanese and South American fusion cuisine. Another gem is De Kas. It’s not on the tourist trail, but the 20-minute taxi ride from the city centre is worth the journey.

The most romantic place I’ve ever been to is Islamorada, an island in the Florida Keys. We stayed at Casa Morada, a minimalist bay side boutique hotel set among lush palms and greenery, looking out to the balmy waters of the Gulf of Mexico. My partner organised to take me out on their sailing boat and proposed as the sun set. When we returned to our room, the hotel team had filled our room with rose petals and candles. 


A few years ago, I took a two-month road trip around the US. It was the most memorable travel experience of my life. We flew into Denver, Colorado, then drove through the Rocky mountains, stopping in Marble and Durango, before heading into the deserts of Utah and Arizona, covering Monument Valley, the Grand Canyon, Lake Powell and Zion National Park. From there, we drove south through Sedona to Scottsdale, Arizona, before finally hitting the California coast.

For our honeymoon, we drove up to California wine country. We stayed at Beltane Ranch in Sonoma, a quintessentially American upscale B&B on a working ranch with vineyards, which Lucy Williams picked as her hidden gem on her episode of The Travel Diaries. We also spent our wedding night at Beaverbrook in Surrey. 

Airelles Chateau de la Messardiere
Le Riad Yasmine, Marrakech

The most magical place I’ve ever been to is Inns of Aurora, a collection of inns overlooking the magnificent waters of Lake Cayuga in the Fingerlakes in upstate New York. Aurora is a quintessential all-American village – our inn was all-white clapboard with a wraparound porch and flag outside, with its own resident innkeeper cooking home comfort snacks. It was so peaceful, wholesome and charming.

For a family holiday, book a beachfront villa at Six Senses Zighy Bay on the Musandam Peninsula in Oman. Calm and warm seas, golden sand, great restaurants and pools, and every activity under the sun – what more could you ask for?

If I had just two nights abroad, I’d go to Versailles. I’ve never been and have always wanted to go since first watching Midnight in Paris. The cast walk around the palace gardens and it’s just so romantic. The most exquisite hotel has recently opened in its grounds, Airelles Chateau de Versailles, which means you can have the gardens to yourself after hours. That's on my bucket list.

Islamorada, Florida Keys
Six Senses Zighy Bay

One of my most memorable holiday meals was at the Armani Hotel Dubai. They serve the best sushi. You sit outside on the terrace, overlooking the famous Dubai Fountains. I’d also recommend the chocolate soufflé at San Ysidro Ranch in Santa Barbara; and Terra Restaurant at Waldorf Astoria Maldives where you dine in nest-like bamboo pods. 

If I had to live in one hotel, I’d choose Royal Mansour in Marrakech. Commissioned by King Mohammed VI, with a reportedly unlimited budget, the idea was to create a ‘medina within the medina’ to celebrate the historical crafts and skills of the Moroccan people. The hotel is made up of a series of three-floor riads, packed with ornate plasterwork and tiling, carved cedar wood, sumptuous fabrics, and decadent design. They even have their own butler and rooftop swimming pool – so it’s no surprise I would happily move in tomorrow.

Miami has a special place in my heart. Being half American, I’d regularly fly back and forth to Miami to visit my family when I was younger. I love the art deco architecture, weather and beaches. One of the best ways to experience Miami’s Cuban culture is through its food. The most famous restaurant is Versailles, which is a family-owned no-frills spot with authentic Cuban dishes where local families congregate for late-night meals.

The Loft, Amsterdam

My holiday packing essentials include Antler packing cubes, slippers (nothing beats your own, in my opinion) and my Ugg slides. I also have to travel with ear plugs, an Amazon Fire Stick because there’s something comforting about some Netflix when you’re away, bikinis, a large cashmere scarf (ASKET has some gorgeous ones right now that are 100% recycled wool), my Papier journal, and magazines. In my wash bag, I’ll always have Nuxe Huile Prodigieuse Multi Dry Oil; La Roche-Posay Anthelios Age Correct SPF50 and Estée Lauder Advanced Night Repair Eye Supercharged Complex

I’m looking forward to staying at The Gilpin in The Lake District, and Lucknam Park in Bath. Then I’m heading to Italy’s Dolomites which has the most beautiful landscape and a disproportionate number of excellent restaurants – many with Michelin stars. We’re staying at two magical hotels: Forestis, and Rosa Alpina. I’ll be sharing all the details on my Instagram and on the next season of the podcast.

My bucket list is so long. I save everywhere I want to visit on a Google map and I'm currently at over 1,500 destinations. I know, it’s ridiculous. Australia, New Zealand, Japan and South Africa are still very much at the top of my bucket list. I’ll find a way to get there some day. Nearer to home, Slovenia and Lake Como have been on the list for a while, and here in the UK, I can’t wait to visit The Scarlet in Cornwall and Gara Rock in Devon.


Season 6 of The Travel Diaries is available to listen to here. Follow @HollyRubenstein

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