The Trials and Tribulations of Travel Planning with Timeshares: "Fail to Plan is a Plan to Fail"

As my father tells me, Fail to Plan is a Plan to Fail. 

If money was not an issue, travel planning would not be an issue at all.  You choose flights, irregardless of costs, and choose accommodations, irregardless of cost.  Unfortunately, I do not have that luxury and most people do not as well.

Exchanging your timeshare can unleash tremendous value and you can end up staying in properties that far surpass the quality of your own timeshare or those available to you through the internal exchanges.  While there are opportunities to make great exchanges, availability for specific weeks and destinations can be extremely hard to come by and may never become available. 

The issue with vacation planning with timeshares is that you need to plan very far in advance.  Some timeshare systems allow you to reserve weeks 2 years in advance of the actual week.  Most people do not plan ahead and typically only plan vacations a few months in advance.  As I will detail below, if you plan to exchange into prime weeks, this strategy may not work very much and you will quickly become disgruntled with timeshare ownership with the claim that your desired week, destination or resort never becomes available.  The goal of my site is to help you avoid this fate and get the maximize value out of timeshare ownership.

Further complications with travel planning with timeshares involve airfare if you are traveling to a destination outside of driving distance from your home.  Airfares fluctuate and destinations during prime travel weeks can easily far exceed the budgeted amount for the vacation.  I personally use frequently flyer miles to get airfare for free but frequent flyer miles can be even more complicated than timeshare exchanging and having availability with free airfare along with the desired week and resort can be next to impossible. However, I have successfully navigated this system for many years and it is doable with diligence, planning, patience, flexibility and websites such as mine!  In order to get the two goals to meet up requires a ton of time, work and flexibility.  My goal is to give you some tips on how to navigate timeshare exchanging in order to get the desired weeks.

I will also detail some basic tips on how to get frequent flyer miles and use them to get airfare for free!

TIP ONE:  PLAN AHEAD, WAY AHEAD AND BE FLEXIBLE:

The first tip is that you must plan ahead. One of my vacation rules is to always have a trip planned.  This keeps me motivated to work and keeps me excited to see new destinations and spend quality with my family.  Generally, I plan one year in advance and put in a Request First with Interval International or an internal request with one of my timeshare programs. (i.e Hyatt, Marriott, Hilton, etc.) I put in a request with various top quality resorts around the world that I would like to travel to.  You need to make sure that you choose the specific resorts that you want and not just put in a destinations.  There are some crummy timeshares out there so you need to make sure that you choose the high quality luxurious ones.  I make sure that the potential destinations have decent flight paths from my home airport so that I can make sure to only have one stop and to make sure that there are no overnight stays.  We travel with young children so an overnight stay or more than one stop can be more difficult than desired.  

Request First with Interval International is a great tool and highly recommended since their system will constantly check their system and automatically confirm you into the desired resort for the specific week.  I always make sure to use E-Plus which provides three free exchanges for a one-time fee of $54.  This is absolutely necessary for added flexibility as without E-Plus, the reservations are non-cancellable except for a large fee for cancellation as well as the re-booking fee.  I will discuss E-Plus in more detail later but this is an absolute must to give you the needed flexibility to change destinations  Many times I change destinations because nicer resorts become available or fantastic airfare deals become available. 

SECOND TIP:  HAVE A PLAN B

The second tip is that you always need to have a Plan B.  Most hotel reservations allow you to make reservations and cancel up to 24 hours before check-in.  Once I put in a Request First, I also review hotel options in the desired areas of travel.  I will make a few speculative bookings for the desired weeks so that there are options for accommodations in the event that the timeshare accommodations do not come through.  Booking directly through the major chains is preferable as they generally make it easy to reserve and cancel your reservations with a few clicks.  While I highly prefer timeshares for many reasons, you need to make sure that there are viable hotel options.  One of my favorite ways to have a Plan B is to use hotel points to reserve a week in the desired location.  I can reserve a hotel room that is fully cancellable with hotel points so that the week will be free in the event that the timeshare option does not become available.  I will explain in later posts how to arm yourself with hotel points so that you too can have this option.   

THIRD TIP:  USE INTERVAL GETAWAY ALERTS:

As discussed in this post (Getaway Alerts), I explained how to use Getaway Alerts on the Interval International App.  I routinely populate various dates and times and become alerted when a desired resort and destination becomes available.  As discussed, many times it is economically beneficial to reserve a week with cash instead of using your deposited weeks or points.  In addition, there are some fabulous deals with Interval Getaways so a deal at a great resort may end up dictating the ultimate destination for your vacation. A great deal for accommodations may open up the budget for an increase in the price of airfare.

FOURTH TIP:  USE HOPPER TO TRACK AIRFARE

The fourth tip is to populate the airfare searches using Hopper.  Hopper was discussed in this post here and is a great way to easily monitor airfare.  Since at this stage, you will not necessarily know the ultimate destination, you can put in multiple itineraries and Hopper will constantly monitor the cost for the flights.  If one destination is significantly cheaper than another, you can opt in to booking the airfare at that time.  Once you book airfare, you are generally locked in to the destination as change fees can be as high as $200-$300 per ticket so you need to make sure things are lined up with the timeshare or have a reasonable Plan B that you are prepared to use in the event that the timeshare availability does not become available. 

Once your airfare is locked in, I would revise the request first to make sure that only the resorts in your request are for the destination desired.  While you will have 24 hours to cancel it free of charge, if you miss this window, it can be problematic. 

FIFTH TIP: USE  SOUTHWEST AIRLINES IF POSSIBLE

Alternatively, if you are in destination that is serviced by Southwest, I highly recommend booking tickets with Southwest. Southwest is the only airline left that allows changes and cancellations free of charge.  Southwest even allows you to receive travel credits if the price of the airfare goes down.  Southwest will give you travel credits to use at a later date in the event your flight cost went down from the date you originally booked.   However, there are a few issues with Southwest that should be understood.  Southwest only opens its flight schedule for approximately six months in the future.  Therefore, if you confirm into a resort a year in advance, you may not be able to book airfare with Southwest until six months from the trip.  You will also be subject to the price of the trip once it opens up.  While Southwest is known for its low fares, the prices for some trips and high demand weeks can be extremely expensive.  The second issue with Southwest is relating to cancellations. Southwest does allow cancellations but the do not provide refunds.  They provide you with a travel credit that must be used within one year from the initial reservation date.  They also require you to keep the reservation number in order to access those travel funds.  This does require a bit of record keeping and organization.  The best method for Southwest is to use their Rapid Reward Points.  Instead of booking with cash, you can use Rapid Reward Points and if you needed to cancel or change destinations, the points are immediately redeposited to your account.  I will explain this in later posts but for the purpose of this post, Southwest is a great airline to use when timeshare planning.

SIXTH TIP:  USE AUTOSLASH

As discussed in this post here (autoslash), Autoslash is a great tool for rental cars. You can make reservations using Autoslash without any credit cards and they will track your rental to ensure that you receive the lowest price on your car rental.  Since it is conceivable that you have many potential destinations for the trip, you can make multiple reservations for the same week.  Do it as far in advance as possible and autoslash will do the rest to make sure that the cost of your rental car is the lowest. 

SEVENTH TIP:  CONTINUE MONITORING AIRFARE, HOTELS AND TIMESHARES AFTER CONFIRMING

Going through these various steps seem exhausting but once you get a system in place and have alerts set, it becomes on autopilot and just requires monitoring.  The key is that once everything is booked, that you continue to monitor everything to make sure that there are no unintended surprises.  I try to book my airfare 330 days in advance which is when most airlines open their schedules.  When I book this far in advance, airlines continue to make schedule changes throughout the year.  Many times, the reserved flight path changes, times are altered or non-stop flights all of sudden require a stop. These can completely derail all the travel planning put forth above and could require a complete re-do of everything above.  This is why is is highly beneficial to continue to monitor all these items to make sure everything is on track. You do not want to be surprised on the check in date that your flight now requires an overnight stay.  Also, while schedule changes with airlines can be problematic, most if not all airlines allow you to re-book or cancel your flights for no charge or fees if the airline make a schedule change that impacts the travel time by greater than two hours.  In other posts, we can discuss schedule changes and how to use them for your advantage but for the purpose of this post, you need to monitor your airfare.  Airlines will generally inform you of schedule changes but those e-mails may go to spam or simply be missed.

In writing this post, I realize that travel planning can be daunting and difficult.  Working with timeshares adds even more complexity.    These tips are meant to allow my readers to begin using these tools and becoming informed on how these tools can help  alleviate these issues and obtain the desired weeks and resorts within a reasonable budget.  I highly recommend that you subscribe to my Guru Deals below so that you can be alerted to various exchange opportunities, travel deals, flight deals and other opportunities to allow you to travel to luxurious destinations for a fraction of the retail cost.  Travel planning as described above may not be for everyone so when airfare deals become available, I will try to include some options for timeshares and see how you can easily book quality weeks for reasonable costs and avoid all the steps above!

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