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Top Holidays

Winged Boots Team Travels

  • Inspiration
  • By Natalie Baker
  • Published 19 October 2023
  • Revised 30 January 2024

Top insights from our team of travel professionals

Explore the globe through the eyes of luxury travel experts as we reveal the destinations that captivated our hearts this year.

Holiday like a luxury travel professional with these insights from the Winged Boots team. See where they spent their holidays and arrive to yours equipped with the insider knowledge to maximise your trip.

Lauren Godfrey, Head of Marketing

"2023 was a special year for me; I took my baby daughter on her first holiday to Crete. We stayed in Daios Cove in a Junior Suite with Individual Pool. The resort was quiet and the staff were incredible – they were so friendly and accommodating with Lilah. The resort is great for families, as well as couples, with a few adult-only restaurants as well as a separate adult-only area in the main buffet. The hosts actually let us sit in the adults section in the evening so that the children in the family area wouldn’t wake our sleeping baby. The food was delicious, and there was so much choice; the strawberry tarts in the evening were standout! The beach has silky soft sand and calm waves, while the main infinity pool is lined with comfortable loungers and cabanas, which offered some much-needed shade.

We booked airport transfers through Daios Cove, and they were on time and extremely comfortable. They provided car seats for Lilah and when we were returning home, we had a concierge stay with us and carry our bags until we checked in for the flight. We used the same car service to take us to and from the local town Agios Nikolaos – where we had a delicious Greek feast by Lake Voulismenni – and our drivers were reliable and super helpful with restaurant recommendations.

One small thing to consider is that some restaurants and the beach are not accessible for prams and wheelchair users. There is no lift or ramp, instead the route is via steep stairs built into the cliffs. We carried Lilah and our bags during the day to make use of the beach club and some facilities but at night we didn’t want to risk carrying the pram in the dark and have a tumble… or worse, picking her up and folding the pram in case she woke up and stopped us having a glass of wine!"

Sophie Azeem, Administration Manager

“We went to Chicago in May and stayed at the Sonder apartments in the South Loop, which was perfect for us as it was just a short walk to many of the city's main attractions and plenty of places to eat. There's so much to do for all kinds of travellers: Exploring Millennium Park, the grand architectural wonders, and the Art Institute left me in awe – and definitely made us feel like we'd earned that delicious Chicago favourite of deep-dish pizza at the end of the day! Don't miss the magnificent Lake Michigan and Navy Pier. For a dose of culture, take in a show at the iconic Chicago Theatre. It's a city of endless discoveries.

Later in the year, I travelled to Rome, which – well, what can you say? It is an amazingly cultured city with beautiful architecture, and the food is out of this world: hard to beat for a city break. Late Spring/early Summer is a great time to explore Rome. The weather is gorgeous, the city's gardens are in full bloom and with fewer tourists, you can visit iconic sites without the crowds. Plus, you might stumble upon unique events like "May of the Monuments", when usually off-limits architectural gems open their doors to the public. It's a rare chance to wander through historic buildings and hidden courtyards, unveiling Rome's secrets in a new light. May is an ideal time to explore the Eternal City."

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Louise Silverman, Personal Travel Manager

"This year has been jam-packed with incredible travel experiences. Kicking things off in the Seychelles, I stayed at the Four Seasons Resort Seychelles on the main island of Mahé. With stunning views, luxury villas, lots of amenities and services for families, large secluded villas with private pools, and plenty of privacy – it's a wonderful choice for anyone looking for laid-back luxury in a versatile environment equally suited to couples, friends, and families. Similarly, Constance Ephelia is another great choice for families that want a big resort with lots to do, offering several restaurants, two separate beaches, zip wiring, bicycle hire, and much more...

Then it was on to the pure paradise that is the Maldives – islands which, let's face it, need little introduction. I stayed on Conrad Rangali, which consists of two islands: one adult-only and one family-friendly option. You'll find a choice of several restaurants, including a fabulous underwater venue, two fantastic spas, complimentary non-motorised watersports, including snorkelling on the resort's own reef. It truly is out of this world. I then moved on to the Hilton Amingiri: a new resort with a big kids club, an in-resort art school, an overwater restaurant and an overwater adults-only cocktail bar simply made for sophisticated sundowners. It boasts spacious villas, all of which have private pools and complimentary bicycles so that you can make your way around the whole resort on two wheels.

My next trip was to Dubai, where I stayed at the uber-glam Atlantis The Royal, one of the glitziest new hotels on the Palm in Dubai (and that's saying something). The infinity pool on the 22nd floor, some of the best restaurants in Dubai, and the first Nobu on the beach combine to make this the hottest place to see and be seen. Once you've had your fill of people-watching or making use of the myriad services and amenities, retire to your sumptuous room. I particularly loved the beautiful marble bathrooms, which you could really feel had been designed with self-indulgence in mind.

Finally, I rounded things off in crowd-pleasing Croatia, where I stayed in a private villa in the coastal town of Slano. Located about 33km from Dubrovnik, it is a small, pretty old fishing village with a few family-run restaurants, a harbour, and a lovely bay overlooking the stunning coastline and the many islands bobbing away in the Adriatic. Dubrovnik's Old Town was simply spectacular. Sequestered inside a large, ancient fortress, it is quite literally bursting with history and offers lots of atmospheric cobbled back streets and churches to explore, as well as a smattering of high-end restaurants and boutique hotels."

Jadeene Burrage, Senior Marketing Executive

“I got married this year, and we celebrated with a once-in-a-lifetime trip to South Africa and Mauritius that began with a safari – something I have always wanted to do. We started with an overnight stay in Johannesburg before flying to Hoedspruit, the gateway to Kruger National Park. We stayed at Thornybush Game Lodge, where our private butler and lodge staff took five-star service to new heights.

The Luxury Suites have a private terrace with views over a dried riverbed and any animals that may be wallowing there, as well as a freestanding bath, outdoor shower, and luxurious décor. Sunrise and sunset game drives meant that our expert rangers found the Big Five on the first day. Plus, thanks to our concierge Claire, the lodge organised a honeymoon dinner in the private library. Thornybush also features a swimming pool and spa to fill your downtime and help you recuperate after all that action which packs the days here.

We then swapped searching for wildlife on the grasslands for sunning ourselves while gazing over turquoise seas in mesmerising Mauritius, where we stayed at Constance Prince Maurice. While here, we took a private boat tour around the picture-perfect beaches, including Flic En Flac, where talcum powder sands and wet and wild watersports await. Our adventure-seeking side loved La Vallée Des Couleurs Nature Park where we enjoyed quad biking, luging and the longest zip line in the Indian Ocean. Back at the hotel, we made a reservation at Le Barachois for our final evening. Here, a candle-lit pontoon leads you to a floating table among the mangroves where you can dine on haute cuisine made with locally sourced ingredients. It was the most perfect way to end the trip of a lifetime.” 

Claire Baker, Luxury Travel Concierge

“This year, I was lucky to take three and a half weeks exploring Hong Kong, Bali, Fiji, and Singapore.

In Hong Kong, I stayed at The Ritz Carlton, which has the most amazing view from the club lounge: A must if you visit the city. For me, it's Hong Kong's dynamic fusion of Eastern and Western cultures, stunning skyscrapers, lush natural escapes, and world-class culinary scene that make it a unique and irresistible destination for travellers seeking unforgettable experiences. Having travelled all over the world, there's nowhere with quite the same energy.

While 'glam packing' around Bali, I stayed at the ultra-luxurious Jumeirah in one of their new pool villas, which were absolutely incredible (and certainly put the 'glam' in 'glam-packing'). I loved being able to explore the whole island and take in more of its diverse landscapes and cultural experiences than I would have staying in one place, so I would really recommend this concept to anyone looking to combine luxury with a touch of adventure.

Then, it was off to the sleek skyline of Singapore, where I immersed myself in its rich tapestry of cultures, from vibrant Chinatown to enchanting Little India. The city's blend of tradition and modernity creates a distinctive, thrilling atmosphere that appeals to discerning travellers wanting the best of both worlds. Marina Bay Sands is a must for its breathtaking rooftop pool alone. Floating above the citys, it offers a serene escape and the perfect backdrop for some spectacular, social media-worthy snaps.

My favourite, however, has to be Fiji. When we landed, we hopped on a helicopter that took us to Qalito, or Castaway Island, and was pure barefoot paradise and the closest likening I have found to the Maldives. After a day of sunbathing, swimming, and snorkelling in the swimming pool-like waters that wrap around the island, the balmy evening is all about tropical fun (anyone for a bit of crab racing?!). One of the most special things for me was listening to the local tribes singing traditional chants. It was something I won't be forgetting in a hurry and just added to the overall experience. All I can say is that it's definitely worth travelling the distance.

I'm not quite done for the year yet though: I was inspired by Jadeene's wonderful trip to South Africa and Mauritius, so I'm off there myself in a couple of weeks! Can't wait!"

This year, I was lucky to take three and a half weeks exploring Hong Kong, Bali, Fiji, and Singapore.

Daniel Ox, Ocean Holidays Co-Founder

"Our stay at Anantara Dhighu Maldives Resort over Christmas 2023 was nothing short of magical. Set in a secluded corner of the island, our Sunset Beach Pool Villa offered breathtaking views of the Indian Ocean. The direct access to the beach and private pool in the garden meant we could enjoy some peace and quiet in seclusion away from the rest of the resort, while still being able to keep an eye on the kids while they swam or played on the beach. We loved that we could literally walk straight out, get in the water, and snorkel right off the shore.

Exploring the underwater world was a highlight for the whole family, especially at the dedicated snorkelling island. You can actually walk to the island across a sand drift in 1ft of sea water or you can hop on a two-minute boat ride from the main reception area. There is also a small bar and sun loungers if you want to hang out on the island for the day. The kids couldn't get enough, while we enjoyed an evening ritual of a sunset stroll followed by a drink at the island's bar. Don't forget your camera because the photo opportunities as the sun dips below the horizon are simply stunning.

As for the dining options, they are pretty incredible and there really is something for everyone. The buffet breakfast is vast, with worldwide cuisine on offer (if you fancy curry for breakfast) and there are lots of patisseries, fresh smoothies, and crepes made to order too. Our favourite restaurant had to be Sea.Fire.Salt: a kind of dry-aged steak and truffle mac 'n' cheese affair with really high-quality produce, all capped off with amazing ocean views. It's an upscale restaurant but still has a laidback, beachy feel so I would say it's perfect for a romantic evening or a special celebration without feeling formal.

One of the most unique things was that Anantara Dhigu has a scheme wherein you can hop over to neighbouring islands and make use of their fabulous restaurants too. We did this one evening, catching a two-minute-long boat ride to the nearby 'adults only' island where we had a great meal at the Japanese Teppanyaki restaurant. If you reserve the chef's table, your food is prepared right in front of you and the chefs put on a bit of a show - just make sure to book beforehand. 

There is a watersports centre where you can book any of the available activities and tours, such as swimming with wild dolphins, sea fishing and much more. We took out the complimentary kayaks which was great exercise and so much fun, as well as being a great way to take in the surroundings. Circling the island takes about 25 minutes, depending on heat and health!

Whilst we were there my son took part in the Football Escapes program where he got to train for two hours every morning with a professional footballer Rio Ferdinand, which was quite surreal but he absolutely loved it! Parents got to take part in a match against the staff - more serious than I thought it would be and parents got pretty battered! Speaking of the staff, everyone was very kind and so thoughtful. Nothing was too much trouble and there were some really nice touches and special surprises, such as dressing our bedroom with rose petals and leaving some sweet gifts on the children's pillows at night.

Accessing the island was a breeze with a quick boat ride from Male Island. While we missed the thrill of a seaplane, the shared transfer provided a comfortable and efficient journey. Overall, Anantara Dhighu is ideal for families seeking a relaxed Maldivian getaway, with snorkelling adventures and unparalleled hospitality. For avid snorkellers, Anantara Kihava may offer a more immersive experience, but Dhighu remains a perfect choice for first-time visitors or families looking for an unforgettable escape."

Inspired by our team's travels? Call our team of personal travel experts on 0203 816 0985 or enquire online and let’s start planning your dream trip (now that you're armed with all that insider information).

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