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Plan Now, Enjoy Later.

Updated: Apr 9, 2021

But Olivia... I like to be spontaneous.

If I had a penny for every time I heard this from a client I would have, like, $20. But you must know this one secret in the travel industry, planning a trip one year or more in advance can seriously pay off. I am not only talking about family reunions, or the once-in-a-lifetime safaris, or even the super-in-demand cruises that book up the moment they go on sale, like the Ritz Carlton Yachts. THOSE you absolutely need to start at least 12-months in advance.

I am also referring to everything and everywhere.

What?! Yes.

While social distancing is a part of our norm, hotel rooms will be limited as many need to be empty for 72 hours between guests as part of new health and safety protocols. So occupancy will be significantly less - and they will book up quickly and well in advance of what you might be used to. Additionally, for special destination hotels, availability is often already limited and often times has a "wait-list", like Giraffe Manor in Kenya. Furthermore, some destinations, like the Galapagos and Faroe Islands, restrict access with visitor limits. Start booking too late, and there’s nothing anybody can do to help. Not even me - and that is saying something. I mean, I got a client into the Ferrari Factory within 6 days, not the normal 6-month waitlist (for owners). But, the more you plan ahead, the less we have to work to make magic happen.

Other factors, like the size of a group or room and bed configuration can complicate things when planning a trip less than one year in advance. Many places only have a few villas with more than two or three bedrooms. Therefore, big group trips or specific bedding configurations are something you always want to book well in advance. Multi-generational groups or other larger groups traveling together are usually interested in the same seasons, summer and holidays, making it all the more competitive.

Example: My favorite last-minute traveling family called me looking for a 3-bedroom house on the beach at a famous resort in the US...for the END OF JUNE. They asked on June 8. Of course, there was nothing. Especially now that people who might have traveled abroad for summer trips are forced to stay in the lower 48.

The same is true for sought-after cruise itineraries, maiden voyages and / or specific cabins. Another item to keep in mind, for many cruises, the tours and excursions oftentimes sell out before the cruise itself does. Therefore, better to get your cruise and cabin reserved as soon as you think you want to take a cruise and reserve your first choice of activities. For itineraries that have the possibility of rough water (Antarctic, Galapagos, North Sea, Bering Straights, etc), the best cabins - those in the low midship area which are the most stable - will sell first. Bottom line, all cruises should be booked 12+ months out.

Here is your blueprint.

1. Twelve+ Months Out: Like putting in the foundation of your house, you survey the region(s) you want to visit; allocate time in each region like building the foundational perimeter; reserve accommodations, which is like installing the footings. You'll get the best chance at the hotel or villa of your choice with the best possible selection of available room-types.

This is very, very low risk when working with a professional travel advisor. They will make sure you have the most flexible cancellation options. You can always change your mind and cancel, but you can't make hotel inventory "appear". It is essential, however, to go over cancellation policies with a fine-toothed comb, now more than ever. Same goes for "packages" like safaris, and cruises. For any kind of travel with a lot of moving parts, the earlier you start, the better.

If you are hoping to use all of those points you've been saving up for your flights, grab them 330 days before you want to go. They book fast in any given year, in the coming seasons, they will go faster because the number of flights actually taking off will be dramatically reduced. Keep in mind, point-based tickets are among the most flexible, so you can usually put the miles back into your account for a modest charge.

Key takeaway: If there is anything on your must-do list like a rare experience, famous guide, destination restaurant, or other element to your trip that you would be disappointed without, get that locked down now with your professional travel advisor. This is the opportunity to get your non-negotiables in place*, before losing any more time or getting forced into a timeframe that doesn't jibe with your priorities.

2. Six - Eight Months Before Departure: to follow the dream home analogy, now comes the framing. These are the elements that make your trip feel like a trip - the moving parts...guides, event tickets, drivers or rental cars.

This is when you'll need to start reserving any entry tickets to special exhibitions, sporting events or shows. If you are buying airline tickets outright, this is also the time to put an alert on Kayak or similar to start watching airfare prices.

Key takeaway: The earlier you get a bead on flights, the more options you have.

3. One - Three Months Before Departure: time to decorate your dream home! Now is the time to reserve easier restaurants, general entry tickets, firm up any transportation like transfers and train tickets, shop, order foreign currency if you wish, and review any change cut-offs or cancellation policies for items you've reserved.

Key takeaway: The devil is in the details. Too often this is where people realize they have messed up timing and it is too late to make significant changes. If you are working with your professional travel advisor, this is where you kick back, relax and look forward to your adventure.

A quick note on travel in the C19 era:

* Before making any deposits or payment, make sure you fully understand ALL booking and cancellation policies. Right now, the flexibility is fantastic. If you don't work with a professional travel advisor, book directly with hotel properties, airlines, both international and internal, and on the ground suppliers who are accredited and respected. Be wary of using third-party booking sites - they have many loopholes and clauses that can leave you exposed to financial loss. Have you googled "covid-19 refunds"? I have personally been on both sides of this issue and it was very hectic, frustrating and even scary.

The Net Net

Oscar Wilde once said, "You can never be overdressed or overeducated". I subscribe to an abridged idea - you can never plan too early. The earlier you plan, the more flexible you can be as your needs evolve. Having a plan helps you and your travel advisor to be proactive instead of reactive, it allows you to be efficient and judicious with your travel budget, and it gives you something to look forward to. As much as you might dislike waiting for an upcoming adventure, research shows this period of anticipation is just as good for our well-being at the actual trip. According to a recent study at Cornell University, humans find more joy in counting down the days to travel and the experiences that come with it than they do buying some kind of new material possession.

So plan now. Enjoy later!


Olivia loves hotels and is passionate about the transformative power of travel. She started Nash Travel Management because her goal is to make your bucket list come alive! She is one of fewer than 250 agents worldwide who is a certified Virtuoso Wanderlist Advisor and is a charter member of Virtuoso's Sustainability Community.

Olivia holds degrees from The Ohio State University, New York University and an MBA in Marketing and Strategy from Vanderbilt University. She, her husband, and two daughters reside in Nashville.

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