When travel planning becomes an art form: meet the women who make the most of their holiday allowance

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The Stylist web team
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Still haven’t got around to booking your Easter mini-break? Grab your passport and get inspired by three women who are obsessive about planning their holidays…

Photography: Pixeleyes

Gemma Crisp

Stylist’s acting executive editor

“I’m infamous in the Stylist office for always going to Europe for the weekend. When my husband and I moved from Australia in 2013, I made him promise we’d travel at least once a month – my record so far is 17 times in a year. I always go away over the bank holidays to stretch my annual leave and book those flights as early as possible – if we haven’t organised our Easter trip by October, I start panicking. I've already booked flights for nine of 2017's breaks. I have a long list of destinations stored on my iPhone notes which I update with recommendations I find via magazines, websites and apps like G Spotting, Lost In and Seasonal Cities. I also follow travel accounts on Instagram – @petitepassport and @tinyatlas quarterly are current favourites – and travel blogs like Hand Luggage Only and Culture Trip on Facebook. I don’t think I’ll ever run out of places I want to visit.”

Gemma’s 2017 travel calendar

January: Brussels, Belgium
“A weekend visit for a friend’s birthday – the novelty of arriving in Paris or Brussels after a two-hour Eurostar journey never gets old.”

February: Sydney, Australia
“I flew back for a week to celebrate my birthday with my twin sister. I booked the flight five months in advance and got a great deal using an app called Hopper, which sends notifications when cheap flights go on sale.”

March: Bath, UK
“I’ve been before for a hen party but didn’t see much so I’m going back to do it properly. I’ll be perusing the city guide on for tips.”

April: Bordeaux, France
“My husband and I are planning to visit the new Cité du Vin wine museum and do a day trip to Saint-Émilion.”

Early May bank holiday: Glasgow, Scotland
“I love edgy cities – I also love animals so we’re doing a side trip to the Isle of May to see the puffins.”

Mid-May: Soho Farmhouse, Oxfordshire, UK
“After booking my first trip here in January, I can’t wait to see what the fuss is about.”

Late May bank holiday: Cefalù, Sicily
“We booked flights to Palermo at the end of November – I saw Cefalù on an Instagram feed a couple of years ago.”

June: Montreal, Canada and New York, USA
“Montreal intrigues me due to its mix of French and Canadian influences. We’ll stop in New York en-route back to London.”

July: Tudela, Spain
“I booked this in January after seeing Hotel Aire de Bardenas ( in an article on – we’re staying in an architectural cabin in the middle of a wheat field in the Navarre desert.”

August: Lisbon, Portugal and Hamburg, Germany
“This will be my third visit to Lisbon, staying in the same Airbnb in Bairro Alto as before. I’ll also take advantage of the bank holiday – Hamburg is currently at the top of my list.”

September: Crete, Greece and Brindisi, Italy
“I’m meeting my parents in Crete for a few days of village-hopping along the coast. A friend is celebrating his birthday at a villa near Brindisi so we’ll spend a few days there on the way home.”

October: Tbilisi, Georgia
“The Georgian capital is my current travel obsession – I’ve heard it’s the new Berlin.”

November: Paris, France
“I have a self-inflicted rule that I must visit Paris at least once a year. I love wandering around the grittier neighbourhoods like Pigalle, Belleville and Butte-aux-Cailles.”

December: Sri Lanka
“With no family in the UK, my husband and I always go away over Christmas – we like to alternate between hot and cold climates.”

Caroline Villamizar Duque

Group creative director at luxury lifestyle group Quintessentially

“I have been known to plan my holidays two years in advance. I mostly book up to a year ahead; the flipside is that a lot of my work travel only has a week or two’s notice – some memorable trips have been to Senegal, Belize, Zanzibar and Myanmar. I love to plan (almost as much as the trips themselves). I am an app junkie and use, TripAdvisor and Skyscanner to research. I keep a list of places to visit in my Wunderlist app so I don’t lose track of where I want to go, and spend hours sourcing quirky one-off boutique hotels via Mr & Mrs Smith and i-escape, and researching remote destinations such as Misool island in Indonesia and the Bijagós islands in west Africa – some of the best fun I’ve had has been in off-the-beaten-track places. Quite often my holidays are timed around work trips for me or my husband, and my friends also plan group holidays together. I keep running lists of where I’ve been from previous years so I can ‘transport’ myself back there at any given time.”

Caroline’s 2017 travel Calendar

January: Palm Beach, Florida and Colombia
“I started the year in the US with family – most of them live there so I’m there a lot. Then I flew to Cartagena in Colombia to meet my husband and spent 10 days there with a side trip to the jungle and beaches in Tayrona National Park and finished up in Bogotá.”

March: Dubai, UAE
“I’m often in Dubai on business but I make sure I stay in nice hotels (this time, I spent five nights at the One & Only Royal Mirage) and usually extend around a weekend so that I have a chance to explore.”

Early April: New York, USA
“I’ll be there for a week, staying at an Airbnb in the Meatpacking District with Quintessentially’s creative director.”

Mid April: Hvar, Croatia
“I’m happy to revisit certain places – we went to Hvar last year. A friend has opened Hidden House (, a small boutique hotel in Stari Grad, and it was so amazing we’re going back this Easter.”

Early May bank holiday: Nantucket, USA
“I’m staying at Greydon House (, a new 20-room boutique hotel. I found the place on and then sense-checked it with a client who spends summers there.”

June: Forte dei Marmi, Italy and New York, USA
“We’ve booked a weekend with friends at their place in Forte dei Marmi in northern Tuscany, plus I have another work trip to New York.”

August: East Hamptons, USA
“My mother has a place here so we go once or twice a year. We usually book dinner at The 1770 House ( well ahead as it gets really busy in summer – that’s where I tell friends to stay when they visit.”

September: Côte d’Azur, France
“I’m organising an event here and am hoping to stay on for a couple of days – I’ve got my eye on Orion Tree Houses (, an eco-retreat B&B in the hills behind Nice.”

October: Monte Argentario, Italy
“My husband and I eloped to Il Pellicano ( where the jetset used to stay in the Sixties, and try to go back there every year – it doesn’t always work but this year we’re going back for our anniversary.”

November: Kuala Lumpur and Borneo, Malaysia
“At the end of the year I’ll be visiting my husband working in Kuala Lumpur and we’ll do a side trip to Borneo. It’s next on my list to start planning.”

December: Mozambique
“I’m hoping to go on a safari in Mozambique over Christmas but it’s not booked yet.”

Kirsty Ames

Media consultant

“I like the idea of travelling somewhere new every year but often it’s hard to find the time – when you put something in the diary, you are more likely to make it work which is why I plan ahead. Plus it’s an excuse to research that destination which I love. I subscribe to newsletters from travel sites such as Black Tomato and Travel Dose. I love going somewhere hot when it is cold in the UK so I usually choose at least one long-haul destination in winter. To find hotels, I use Design Hotels, Suitcase, Doris and Dicky, Splendia, Jetsetter and i-escape (which gives pros and cons for each hotel so you really get a sense of what it is like). I also search Instagram to get a more realistic portrayal than press photos. For restaurants and bars, I search for local blogs and cross reference using The Fork and Culture Trip. My family and boyfriend laugh at me for planning so much but they reap the benefits of great restaurant reservations and the best rooms in boutique hotels. Next on my agenda is a trip to Japan in 2018.”

Kirsty’s 2017 travel calendar

January: Paris, France
“I’m starting a swimwear line with my friend so we went to a trade show in Paris. We stayed at Hotel Monterosa ( in Pigalle and found some great bars such as Lulu White ( Usually I read up on neigbourhoods and decide where I want to be before I start looking at specific hotels.”

February: Trinidad
“My father is from Trinidad and I have been to carnival for the past three years – this time in a group of 13 people. It takes a lot of forward planning so I started in July. We ended up in The Normandie ( staying four people to a room but it was worth it.”

March: Porto, Portugal
“I read about Porto in Suitcase then kept hearing that it was a great city because it is affordable and small enough to walk everywhere. I’m going with eight girlfriends so we’ve rented an Airbnb apartment in the centre.”

April: Mexico City and Yucatan, Mexico
“Mexico has been on my list for years. My sister and I want to make sure we see as much culture as possible. We got flights via air miles to Mexico City and I had seen some gorgeous hotels on i-escape in Mérida, which looked like a great city, so we’re going there afterwards. Bacalar Lagoon was recommended to me so we are driving the 300km there so we can see as much as of the country as possible before going on to Tulum for a couple of beach days.”

July: Mallorca, Spain
“I've been trying to plan a trip here for the past couple of years but summer can get quite hectic with weddings so I started planning this at the end of last year. I was originally inspired by a Condé Nast Traveller article – we're staying in Deià because I love the look of a rustic restaurant on the beach.”

August: St Tropez, France
“I’ll be spending a long weekend at a villa in the hills above St Tropez with a group of friends.”

September: Rhode Island and New York, USA
“I’m using a wedding here as an excuse for a trip to New York. I’m currently looking at flights and deciding whether I can add a trip to somewhere else nearby or, possibly, Toronto. I use Kayak to search for the best prices and keep an eye out for any good deals on Jack’s Flight Club.”

December: Tobago
“My family spends Christmas here every year with two other families – I’m staying for two weeks.”

Main image: Iconic A6 Travel Planner in pink, Fox and Star (