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How to Book Last Minute Travel

How to Book Last Minute Travel
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How to Book Last Minute Travel


So you didn’t book a trip. And now you wish you had. Is it too late? Not according to my travel experts, here are there tips on how to book last minute travel.


This is the first year I have ever booked last minute travel, and I did it all wrong. After I wrote the story about Giving the Gift of Time I was inspired to surprise my family with a trip to the British Virgin Islands. I knew nothing about the destination but have an outsized sense of my ability to “make things happen.” While visiting Caneel Bay on a press trip I had heard about the Soggy Dollar Bar on a nearby island. The only way to get there is by boat, they have a clothes line to dry your soggy dollars, and they invented the cocktail the Painkiller. I have been obsessed with sailing the BVI’s since. Other than the Soggy Dollar, I knew nothing about them.


Book Last Minute Travel


On a wild hair I cashed in a gazillion Amex points and turned them into Delta miles and booked six tickets to wherever I could get into, turned out to be St. Thomas. Then to get home I had to fly from Tortola to San Juan home, no problem I thought (though I had zero clue where Tortola is or how we would get there) I spent $400 per ticket for some island puddle jumper. I had flights. I thought, how hard could getting hotels be? According to travel expert Tim Burke of TMB Travel Concierge, booking flights first is usually a big mistake. Tim says “you can ALWAYS get flights, you might not like the route or the price, but you can get flights, hotels are another story.” Never mind that he is also my agent who helped me book the flights, when I am high on my travel superpowers I can be very persuasive. Also, after being a guest on the Moet VIP boat during the America’s Cup races, I was pretty sure I was a sailing expert. See photos.


Book Last Minute Travel

Book Last Minute Travel


Turns out that the rest of the world also thought that the BVI’s was a great place to spend Christmas break (though I still can’t place them on a map-research is not my strong suit-I refer to them by their nickname). There was not a hotel, villa or campsite to be found. Though a PR firm had reached out to me and offered a stay on Scrub Island, when we went to confirm, they said “oops-they’re full-sorry about that.” So I reached out to every PR firm on the planet, every hotel was full. So I got on VRBO and started madly sending out requests. My dream for a perfect getaway had turned into “I will stay anywhere-beds not necessary.” Just as I was about to give up and turn the miles into a trip to South Carolina and give up on my fantasy of surprising my family with a huge magical trip to a place I knew nothing about, I got an e-mail from someone with a yacht for rent. He had had a cancellation and if I sent him money RIGHT NOW we could have it. After chatting with him on the phone and making sure he was legit (I’m not insane) we booked the boat. I’m still not sure how many bedrooms it has or where the crew sleeps, I don’t care, Christmas magic reigned!


How to Book Last Minute Travel


Since I booked flights with no plan for where I was staying, I was now stuck with an extra two days before we can get on the boat, with no place to stay. I scoured the internet, too ashamed to crawl back to my travel agent and admit that I have no real travel superpowers. I found nothing, zero, nada. Ok, I found Bluebeard’s castle and the most expensive suite at the Ritz, but a room that was nice but not Presidential was nowhere to be found. I called Tim in tears. He jokingly suggested a campsite on St. John, and then found us two beachfront rooms at a small hotel on St. Thomas that did not turn up on any of my internet searches. We scored two rooms at the super cheesy Bolongo Bay Beach Resort. It has great reviews, a swim up bar, and beds.


How to Book Last Minute Travel

Don’t be me. Take the advice of my travel experts and plan your last minute trip the smart way:


Don’t do internet searches. I googled advice about booking last minute travel, none of the articles recommended using a travel expert. They all said to to search Orbitz or Expedia and to look on Tuesdays for the best deal. Apparently no one does actual journalistic research anymore. Unless your internet search brought you here, then internet searches are freaking brilliant.


Use a travel expert. I know, you think you’ll find deals online. You think you can do it yourself. But you just can’t Nemo. According to Jolie Goldring of In The Know Experiences you should, “Work with a travel consultant as we have the hotels and hotel wholesalers updating us on their inventory all the time. We also have direct access to critical on-property relationships such as sales and revenue/reservations managers who can push things around and make openings possible unlike a hotel call center.” Case in point, while I was struggling with this trip (while at a tennis match, don’t judge) a girlfriend overheard me and said that she had “lost her Christmas reservation” at the Breakers in Florida and the hotel was sold out. They were considering canceling the trip. I sent her to my agent Tim, voila, they have a suite and their vacation was saved.


Try to pick your timing (if you can).  Jolie says, “14, 30 or 60 days are big time cancellation points. During festive season (Christmas and New Years) it can be as strict as 90 days. But again having access to a professional travel consultant will provide better exposure to what’s being made available last minute at your favorite resorts and destinations. If hotels receive cancelations they email that info to their travel industry partners so we can pass hot open space onto our clients. According to USA Today you should book two to four weeks before travel. Hotels, cruise ships and airlines can quickly determine whether they are filled to capacity (especially during peak season). In an effort to boost tourism and fill their complement, these companies often slash prices 14 days in advance of booking. If you are within this time frame, do not give up, you have travel superpowers, you can make this happen.


Be flexible. We are leaving on a Monday, flying out Sunday was twice the price. Also be willing to fly from random airports. A travel expert can help you navigate this, please do not try to do this yourself, it will make you crazy. Jolie says, “Last minute doesn’t have to mean last resort however I do recommend having an open mind about the destination if you’re hoping to travel super last minute during a busy holiday time.”


So we were super flexible, super lucky, and had some professional help. I told the kids by giving them each a carry on bag with their name on it. I told them I had just bought them some new ski gloves. When they opened the bags they found these notes. JJ found “Virgin” first and asked why I was being so passive aggressive on Christmas morning. I shouted “IT’S A WORD PUZZLE!!” When they sorted it out there was some screaming and shouting.  This is our last Christmas break before Macie goes off to college and all I wanted was to spend time together, as a family. So I’ll be offline for a week, unless the amazing Bolongo Bay has wi-fi.


Wondering how to reach these magical travel experts I speak of? Here is their contact info. Tell them I sent you. I don’t recommend anyone lightly, these two have proven themselves to me and to many of my readers, I can’t recommend them highly enough.


Jolie Goldring
Luxury Travel Consultant
IN THE KNOW EXPERIENCES, a Virtuoso agency

Direct 203.629.7013
Fax 203.286.1224


Tim Burke, CTC
TMB Travel Concierge
Independent Affiliate of Travel Experts, A Virtuoso Agency
2029 Wyandotte Suite 102
Kansas City MO 64108
PH: 816-423-8045


This is not an ad, a sponsored post, or otherwise. This trip is costing me a fortune and these are really my trusted travel experts. Don’t be so skeptical.


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