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Trip envy: 7 over-the-top Valentine’s Day trips we wish we could take this year

Feb. 14, 2021
13 min read
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Valentine's Day is just the right amount of time after Christmas, isn't it? January can be a drag, especially if you're on a new year health kick, summer seems a distant dream and after the year we've all had, I've had quite enough of Zooms, thanks.

Whether you're in a couple, throuple, single or whatever, Valentine's Day always seems like a nice excuse to drink some fizz, eat something fancy and have a saucy weekend away somewhere.

With travel not on the immediate horizon, planning a trip has become, for me anyway, a way to scratch that itch. So for a minute, imagine money was no object and you could go anywhere in the world, with anyone you liked. These dreamy itineraries that have been conjured up might help.

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The ultimate luxury Italian 'Grand Tour'

The concept of the "Grand Tour" began in the 17th century and was basically an excuse for posh English men to go on a debauched, extended "coming of age" holiday before settling down. Typically it started in Dover, England, and the terminus was Naples, Italy, but the trip also took in Belgium, the Alps, France and Greece — and what happened on tour, stayed on tour. The Italian leg of the journey was especially splendid and luxury vacation curator for the stars Merrion Charles has created an itinerary that draws inspiration from la dolce vita — with a romantic twist.

(Photo courtesy of Merrion Charles)

The 15-night (or shorter if you wish) itinerary allows guests to experience the country's most romantic landscapes, from the majestic Dolomites and the rolling hills of Tuscany to the magical Pontine Islands and then Rome. You'll begin with a helicopter pickup in Bolzano, South Tyrol, transporting you to a private 16th-century hunting lodge in the Dolomites that's super secluded. From there, you're taken by private chopper over northern Italy to Tuscany for four nights at the Conti di San Bonifacio hotel — a restored farmhouse located in the breathtaking countryside of Alta Maremma. Think hot air balloons, couples massages in the spa and more fine dining and wine than you can shake a stick at.

Inside the spectacular Villa Aquasanta. (Photo courtesy of Merrion Charles)

Next comes water. Five nights aboard the Blue Deer San Lorenzo Sea Lodge — a 74-foot catamaran — is the pinnacle of Valentine's Day luxury and comes with a private chef. Island-hopping between Ponza, Ventotene and Procida, stopping to try out the region's best eateries — it doesn't get better than this. Until you get to Rome.

Your last three nights will be spent at the magnificent Villa Aquasanta, lavishly decorated and with fragrant gardens to ... explore. If you want a bit more excitement, insider access is available to make sure you get to to the most sought-after museums, galleries and restaurants, including private tours of the Sistine Chapel, a private tour and dinner at Palazzo Pamphili and dinner at Pierluigi, the first fish restaurant in Rome, where it is impossible to get a table.

Prices start at $124,400 for two people all-inclusive with helicopter transfers from Bolzano to White Deer San Lorenzo on arrival and limousine transfers to Rome Airport from Villa Aquasanta (where the trip ends) on departure.

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Bhutan like never before

For a sprinkle of mysticism, but in keeping with our luxury theme, head to Bhutan in the Himalayas for a truly scenic "heli-adventure." COMO Bhutan is offering a six-night trip for couples after something a bit more transformational than your regular five-star resort experience. From the gravity-defying Tiger’s Nest Monastery to the Temple of the Divine Madman, this trip combines spectacular drives, unique nature walks and monastery visits — chock-full of mystery and romance.

The magical COMO Uma Paro. (Photo courtesy of COMO Hotels)

The trip includes stays at both of COMO's unique lodges, COMO Uma Paro and COMO Uma Punakha — the perfect base for exploring the kingdom's secrets. There are three distinct valleys and you'll be treated to five days of privately guided excursions through the Laya Valley — also known as the hidden paradise — tropical Punakha Valley and the emerald Paro Valley — by helicopter, no less.

After days spent exploring, couples can bask together in Bhutanese hot-stone bathhouses in the COMO Shambhala Retreat, or gorge on fresh local delicacies made with organic ingredients in Bukhari, COMO’s award-winning restaurant.

(Photo courtesy of COMO Hotels)

Prices start from $25,506 based on two people sharing and include four nights at COMO Uma Paro and two nights at COMO Uma Punakha on a full-board basis, including private transfers and all excursions with a guide. Flight transfers not included.

Scottish Highlands wilderness adventure

This is one for all the couples (or singles, self-love is a thing) of a heartier nature. The Scottish Highlands is not exactly known for its tropical climes, but it's dramatic, brooding and very romantic. This Valentine's Day experience, created by Wildnis Adventures, includes guided activities like scrambling and packrafting, and while camping might not be for everyone — imagine the, er, cuddling opportunities. Each night you'll be treated to open-fire feasts from a Michelin-standard chef washed down with the finest single malts the country is known for.

(Photo courtesy of Wildnis)

And if you've never been in a classic Land Rover Defender, you'll really enjoy that bit — very authentic. After being picked up from Edinburgh, the adventure begins in Loch Lomond and Trossachs National Park. After abseiling and climbing on the flanks of Ben A'an, you'll descend to Glen Finglas Reservoir, where a warming bowl of Cullen skink soup (traditional Scottish broth made from smoked haddock, potatoes and onions) awaits.

Other highlights include a sea kayaking trip in Arisaig on Scotland’s stunning west coast and braving a remote quarry to try a front abseil, a truly daredevil technique. Again, this trip is not for the faint of heart. But oh, how thrilling!

Prices start at $4,700 per person for a four-night expedition, including guiding, all activities, all meals, Land Rover vehicle hire and transfers.

Beyond the reef, Seychelles

Little more sings romance than the Seychelles. It's a paradise for lovers. If you fancy a total break from real life, this 21-day itinerary will blow your mind. It includes seven nights on Alphonse Atoll, four nights at Cosmoledo Eco Camp on one of the most remote atolls in the world and a three-night stay at Astove Coral House, where guests can follow in the fins of famed explorer Jacques Cousteau.

This trip, by Blue Safari, is also the ultimate digital detox, meaning you can fully connect with nature, the ocean and, of course, your other half. There is no mobile phone signal (sorry!) and Wi-Fi is extremely limited. This is not a WFH opportunity. In addition, the rooms at Alphonse Lodge, Astove Coral House and Cosmoledo Eco Camp are free of televisions — so essentially, "no news is good news."

(Photo courtesy of Blue Safari Seychelles)

So while you're not on Instagram, you can spend time hanging out with the trip's dedicated marine biologists and environmentalists and snorkeling to your heart's content, spotting shoals of fish in the hundreds, lemon sharks and green and hawksbill turtles. Magic.

Then, get ready for seven nights on the Two Oceans catamaran with luxury en-suite cabins, crew and a private chef who will create bespoke menus to your exact requirements while you sail around the Amirante Islands, exploring the African Banks, St. Joseph, Poivre, Desroches and the incredible Ste. Anne Marine Park.

This Valentine's Day trip is all about immersing yourself in nature in one of the most pristine places on the planet. The wide-open spaces at Alphonse Island and the remoteness of Poivre without any interruption from the outside world would be a true balm for the soul.

(Photo courtesy of Blue Safari Seychelles)

Prices start at $36,050 per person based on two sharing and include return inter-island flights from Mahe to Alphonse Island, full-board accommodation and all activities.

Wildlife Safari: Around the world by private jet

Imagine being whizzed across seven countries and two continents to experience wildlife you've only ever seen in documentaries — by private jet, with your amour? Until now, pretty unimaginable.

But luxury travel company Abercrombie & Kent can make this happen. This epic 24-day trip begins in Japan to observe snow monkeys in their winter wonderland before enjoying samurai performers and geisha. From there, you'll fly to the Philippines to see rare tiny tarsiers and whale sharks, then to Malaysia to feed Borneo's proboscis monkeys and to India to see the revered Bengal tiger in its natural habitat.

(Photo courtesy of Abercrombie & Kent)

After your Asia adventure, it will be time for the enchantment of Africa. You'll meet Madagascar’s playful primates, the lemurs, and enjoy a festive dinner with local musicians providing the entertainment. Then see endangered gorillas in Rwanda and then, of course, the "Big Five" in Kenya.

You'll fly in a chartered Boeing 757 with just 40 other guests with fully lie-flat, first-class seats with a crew-to-guest ratio of 1:7. All your accommodation is hand-picked and one of a kind and just think of the culinary journey you'll embark on.

(Photo courtesy of Abercrombie & Kent)

This trip will also be packed with meaningful ways to discover the world, from a private recital by the renowned Loboc children’s choir to a meeting a wildlife officer passionate about protecting the critically endangered orangutan.

Prices start at $172,285 per person all-inclusive, double occupancy and does not include transfer to and from Japan.

In love in St. Lucia

St. Lucia — the land of romance and rum punch. Despite its diminutive size, this Caribbean island is home to seriously lush rainforests, gorgeous beaches and some of the most spectacular hotels around. Enter Jade Mountain, real "no-expense-spared honeymoon territory." Every enormous suite — or sanctuary — has a glorious fourth wall revealing dramatic views of the Pitons and an iridescent infinity pool that blends into the horizon. There are no distractions like TVs and the entire space just screams: These rooms are where babies are made.

(Image courtesy of Jade Mountain)

Designed by architect Nick Troubetzkoy, Jade Mountain has a bit of an MI5 vibe, structurally. It's set into the hillside in layered blocks but doesn't damage the local aesthetic at all — it complements it. The themed sanctuaries are connected by walkways covered in flowers and complete privacy is paramount. Though Jade offers absolutely everything in the room from spa treatments to caviar and Roederer Cristal Champagne breakfast in bed, and lots of people choose to squirrel themselves away behind closed doors, Jade can also offer the Ultimate Bliss package with some extra special treats, as and when you want them.

(Photo courtesy of Jade Mountain)

If you stay for a week, pepper your stay with a private "castaway dinner" on the beach while being serenaded by a local musician, a visit to the island's mud baths with your own spa attendant, an early morning hike up the majestic Gros Piton with a gourmet picnic at the top, whale and dolphin watching, private cookery classes, rum tasting and, if you're feeling really frisky, the "Alchemy of Two" ritual.

The Kai en Ciel Spa promises to help you "celebrate the gift of being together" with role-playing, a hot tub, poetry, delicious treats and a couples massage with tantra vibrational oil. I'm blushing.

Before you're whisked back to the airport by helicopter, you can enjoy a private dinner cruise on Miss Babsie, a 42-foot catamaran, where the chef will create a bespoke menu while you're being, you guessed it, crooned at.

The package also includes a daily meeting with the resort sommelier to discuss your meals' wine pairings and an hour with the resort photographer.

(Photo courtesy of Jade Mountain)

Jade will create your "perfect itinerary," but as a guideline, prices start at $37,500 per couple for seven days all-inclusive in a sanctuary with helicopter transfers, unlimited spa treatments and the above excursions.

Deluxe diving at Kudadoo, the Maldives

Have you heard of having an underwater butler? No, nor had I. But if you and your loved one fancy the swankiest diving holiday ever, where your underwater concierge will take you diving whenever your heart desires, head to Kudadoo, a five-star private island in the Maldives. And it's adults-only — hooray!

Firstly, where you'll stay. The island has 15 overwater villas (with 15 matching butlers) with an open floor plan allowing plenty of natural light and an outdoor deck topped with an infinity plunge pool. In the evenings, try the Retreat, a two-story "architectural masterpiece" atop the lagoon, where you’ll find the infinity pool and world-class bar and restaurant.

(Photo courtesy of PADI Travel)

Now to your underwater shenanigans. Whether you're a novice or an expert diver, your butler will be on hand to guide you around the magnificent underwater world, introducing you to sea turtles, taking you on an underwater scooter to see sharks and visiting caves, shipwrecks, mantas and drift dives.

(Photo courtesy of PADI Travel)

The "anything, anywhere, anytime" concept, by PADI travel, also means you can jet ski like James Bond, ease your sore muscles at the Maldives’ first Himalayan salt chamber and dine 5.8 meters below the surface in the world’s biggest undersea all-glass restaurant. And remember, the dress code here is barefoot.

Prices start from $17,550 for seven nights per person, including island transfers and full board.

Bottom line

I hope these outrageous itineraries have given you a pop of inspiration. While some are eye-wateringly expensive and some may not include all the creature comforts you're used to, all should give you something to take away and think on for your next "treat yourself" trip — be it with a partner, alone ... or even with a pet. No judgment here!

Featured image by JOE MCNALLY 2008
Editorial disclaimer: Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, airline or hotel chain, and have not been reviewed, approved or otherwise endorsed by any of these entities.