Southwest is a fantastic airline.  While it does not have the bells and whistles of a lot of the foreign carriers or have a first class cabin, they are efficient, friendly, and still have tons of customer friendly policies.  

Southwest is the last domestic carrier to offer free bags, no change fees and provide refunds (in the form of travel funds) for cancelled flights. 

One of the biggest perks of Southwest is that all flights booked with rapid reward points are fully cancellable without any penalties. 

For those who use timeshares, the above customer friendly policies are great in that you have a lot of flexibility to book fares at decent rates and potentially cancel them without a fee if other timeshare destinations become available. 

I wrote a longer article about Southwest here. 

Schedule Extension
​
As of November 3, 2017, Southwest has opened its schedule to August 6, 2018.  On February 8, 2018, Southwest will open their schedule until September 28, 2018. 

Summer Travel

With their schedule opened for the summer, now is the time to begin to solidify your summer travel plans.  Summer is a busy time of year for travel and flights can get extremely expensive quickly.  

With Southwest's customer friendly policies, the best option is to book flights with Rapid Reward Points.  You can book your flights and if your plans change, you can simply get all your points redeposited without a fee!  

Caution

During a recent booking session, I cam across an unknown policy with Southwest.  For Thanksgiving, we had flights booked to Cabo, Mexico.  We were on the fence on whether to take that trip or to book somewhere else.  Flights with decent rates came available to Costa Rica so I booked them with points.   

At that point, I have overlapping reservations to Cabo and Costa Rica.  I figured that I would cancel whatever flight we opted not to take once our accommodations were solidified.  Unbeknownst to me, Southwest's system will automatically cancel duplicate flights without notice and without contact if they overlap with the same travelers. 

After I completed our flights to Costa Rica, I woke up the next morning with cancellation e-mails from Southwest.  In a panic, I called Southwest and they explained this policy and why it happens. 

Frustration

This policy was new to me and I had no idea that Southwest's system would automatically cancel the reservation without a phone call or e-mail to tell you of the pending cancellation.  They just do it!  For me, I had booked with points, travel funds and gift cards so I had to recreate the bookings and find out where all the money had gone. 

This was frustrating and really wish that they would have simply called me to explain the policy before cancelling my flights. 

Despite this hiccup, Southwest is generally a pleasure to deal with and generally enjoy dealing with their representatives.  

Now that I know if this policy, I will make sure to not do this in the future. 

Conclusion

Since Southwest has such flexible policies, it makes sense to book your flights now and figure out accommodations.  If you need to change flights to a different destination or change dates by a few days, it is easily done with a couple of clicks or a quick phone call. 

Book your flights now.  Even though Southwest is a low cost carrier, this does not always mean that their fares or low cost.  During peak travel times during holidays, I have seen some very expensive fares. 

You should book early as even if fares drop, you can even call Southwest to get the difference in fare refunded.  This is yet another reason why Southwest is the best customer friendly airline left in the sky!

Where are you going this summer? Leave you comments below!

My family took an extended trip to Costa Rica for the month of July.  While I would have highly preferred to be able to stay in timeshares for the entire trip (mostly due to space and having a full kitchen), this was not doable for a few reasons.  

Costa Rica is a wonderful destination but they simply do not have a ton of timeshare options.  There are a few but not many high-quality timeshares which is an absolute must.

We did stay at the Breeze Private Residences for one week (review is here) which was a timeshare property but I simply could not find suitable timeshares in Costa Rica for the entire month. 

Planning Strategy

Booking a month vacation has its various challenges but doing it in a very cost-effective manner is difficult.  As I mentioned in other posts, I am a huge points and miles fanatic so I have plenty of points and miles available to use. 
​
Using Citi Thank You Points

For this trip, my family of four flew American Airlines to Liberia.  I used Citi Thank You points for our fights.  As a Citibank Prestige Credit Card holder, I was able to redeem my points for 1.6 cents per point.  This option just vanished on July 23, 2017 and points are now worth less.   

Southwest Rapid Reward Points

For our return flight, we flew Southwest Airlines.  I am a huge fan of Southwest as they are the last airline that offer customer friendly policies – free bags, free cancellations, free changes, etc.  Additionally, their customer service agents are generally friendly and helpful which is very noticeable when comparing it to other airlines. 

My wife and I both have a companion pass with Southwest so we are able to have our 2 kids fly with us for free.  We were each able to score the companion pass through the option of exchanging our Marriott points to Southwest points with the available Marriott travel packages.  Unfortunately, this option is now no longer available as of January 1, 2017.

With the above methods, my family of four was able to get free roundtrip flights to Costa Rica.  A good start.

Week 1: Playas del Coco

I was able to grab a fantastic deal through RCI for staying at the Breezes Private Residence Club.  I paid $278.99 for the entire week in a 2-bedroom unit.  This was an absolute steal as nightly rentals for this particular property were approximately $450 per night. 

The Breezes Private Residence Club is located in Playas del Coco and is a great area.  There are tons of restaurants and activities right out the front door.  I would highly recommend this destination and would definitely recommend the Breezes Private Residence Club.

Week 2: Arenal Volcano in La Fortuna
​
For week 2, we traveled to La Fortuna / Arenal which is located inland in the rainforest.  La Fortuna / Arenal was a very cool destination with the volcano as the centerpiece. 
​

For our trip to Arenal, we stayed at the highly rated Hotel El Silencio del Campo.  We chose this based on the Tripadvisor reviews which were stellar. 

The property generally lived up to those expectations but would say that the rooms, although spacious, needed a refresh.  The décor and bedsheets were older than I would like.  It was clean but definitely felt old and tired.  However, breakfast was stellar, they had hot springs on the premise, fruit trees galore to pick throughout the property and had an awesome view of the volcano when the weather permitted.    

Citibank Prestige 4th Night Free Benefit

For this stay, I again used our Citibank Prestige Credit Card in order to utilize our 4th night free benefit.  If you are not familiar with this benefit, it can be extremely rewarding in that you will receive the 4th night free on any hotel booking made through the Citibank portal.  This can literally save you thousands of dollars. 

​The Citibank Prestige Credit Card has done an overall of its card and has revised some of its offers but they have kept in the 4th night free benefit and made it easier to get by expanding the ability to book online.

For those of you interested, here is a link to the offer with 75,000 bonus points. A complete no-brainer to apply in my opinion. ​

For our stay in La Fortuna / Arenal, I paid about $200 per night for 4 nights and I will receive a $200 credit through Citibank’s 4th night free benefit.  This effectively gave us 25% off our stay in Arenal which is decent considering that there are no timeshares or points based hotel chains in this area.   
​

Week 3 and 4: Andaz Peninsula Papagayo Resort

For those of you in the miles and points world, there is a ton of buzz about the Andaz Peninsula Papagayo Resort.  The reason that there is so much buzz is because it is an extremely nice resort and is only a category 4 hotel in Hyatt’s World of Hyatt program.  

This is significant in that the Chase Hyatt Credit Card gives you a free night stay in a category 1-4 hotel each year upon paying the annual fee of $75.  Essentially, for $75, you can get a free night at the Andaz Peninsula Papagayo Resort where nightly rates are generally somewhere between $250-$1200 where the $1200 a night has been seen over Christmas.

Also, since the Andaz Peninsula Papagayo Resort is a category 4 hotel, you can use 15,000 Hyatt World of Hyatt points per night which is a very good deal.  The cash plus points rate of 7,500 points per night plus a payment of $100 per night is also a stellar deal.

I will be posting a full review on our stay so stay tuned.

Using my Chase Hyatt Free Night Certificate

We ended up staying at the Andaz Peninsula Papagayo Resort for a total of 16 nights.  I used my free category 4 certificate from my Chase Hyatt Credit card for the 1st night.

Using Hyatt Points or Cash

For the remaining 15 nights, we actually paid cash (a rarity as I almost always use points for our hotel stays!).  This was not expected as I had planned on using the points plus cash option for 15 nights.  If I had done this option, I would have used 112,500 Hyatt World of Hyatt Points and paid approximately $1500 for 15 nights. 

The cash plus points options is highly beneficial and would definitely recommend it.  $100 per night for this resort is almost unheard of and I would pay that in a second. 

Using Hyatt's Best Rate Guarantee

As I mentioned, I actually paid cash for the 15 night portion of our stay since I got a great rate with Hyatt.  I was able to use Hyatt’s best rate guarantee. 

Hyatt’s best rate guarantee provides that they will match any rate you find on other websites and give you an extra 20% off your entire stay.  I was lucky enough to find a lower rate for this time period and was successfully approved for the best rate guarantee.  As a result, my nightly rate for 15 nights was approximately $156 per night. 

The Hyatt best rate guarantee has been revised as of July 31st where instead of giving you 20% off the matched rate, they will give you a $50 voucher for future travel. While they will still match the lower rate, they will not give you the extra 20% off. 

Hyatt can make you jump through various hoops to get their Best Rate Guarantee but I have been successful in using it. This revision is really bad for the way that I use the Best Rate Guarantee. 

I am not happy about this change as this will likely affect my hotel choices going forward.  Marriott offers a 25% discount for its best rate guarantee and is much more accommodating than Hyatt but I definitely like Hyatt's properties.  

We'll see how this plays out before I switch my loyalties.  Despite preferring timeshares for our travels, I will actually be a Globalist (top tier elite status in Hyatt) this year so we'll see how Hyatt treats me going forward.  

As stated, I was able to secure a rate of $156 per night.  While higher than the per night cost of using the points plus cash rate of $100, I chose to pay cash instead of using 7,500 points per night.  If I used points, I would be redeeming them a rate of less than 1 cent per point (0.007) which is a horrible deal.  I generally get 2-3 cent per points and have received upwards of 6 cents per point for various redemptions. 

Therefore, I elected to pay cash.  The total bill was about $3,000 for 15 nights.  Higher than I would normally like to pay but still a good deal.  Rates for our room (the Andaz Suite) during our stay were approximately $600 per night so we did well.

Using Gift Cards for Further Discounts

In an effort to get even more of a discount for our stay, I ended up purchasing Hyatt gift cards through cardcash.  Cardcash is a second-hand reseller of gift cards.  They buy gift cards from people who do not want gift cards for a discount and resell them to people who can use them and make a profit of the difference. 

Cardcash has mixed reviews and there are definitely times when gift cards arrive with zero balance or the balance disappears after purchasing.  They offer a 45-day guarantee where they will refund your money if the cards value is not as described or disappears within 45 days.

I have had good experiences with Cardcash but I only purchase on the day that I will be using it.  I purchase it and immediately apply it to my room.  This limits the chance of getting a bad card or having your balance disappear.  I did receive one bad card and my order was refunded within 48 hours of purchase. 

For this stay, I was able to get Hyatt gift cards for a discount of 16% through Cardcash.  Their discounts fluctuate but I was able to purchase $3,000 worth of Hyatt gift cards for about $2520. 

Using the Chase Ink Card for 5x Points

One of the added benefits of using Cardcash is that purchases through Chase Ink Credit Card are coded as utilities which generate 5x Chase Ultimate Reward points.  Therefore, by purchasing $2520 worth of Cardcash gift cards through my Chase Ink credit card, I received 12,600 Chase Ultimate Reward Points. 

Chase Ultimate Reward Points are very valuable and can transfer into multiple travel partners including Hyatt or can be redeemed for about 1.25 cents per point or for 1.5 cents per point if you have the Chase Sapphire Reserve Credit Card. 

Final Tally and Summary

As you can see, I used multiple different strategies to get a month of vacation in Costa Rica. 

For our flights, these were completely free using Citibank Thank You Points and my Citibank Prestige Credit Card to redeem for American Airlines for our flight to Costa Rica and used Southwest Points for our return flights.  Our kids fly free with us on Southwest since my wife and I both have the Companion Pass at the moment which we achieved by redeeming Marriott travel packages.

For the first week, we used a timeshare and rented it through RCI’s Extra Getaways for a purchase price of $278.99 for the week in a 2-bedroom.  No timeshare presentation required even though I did attend one ( I am The Timeshare Guru so I kind of needed to do it).

For the next 4 nights, I used my Citibank Prestige Credit Card to take advantage of the 4th night free benefit.  The total cost for these 4 nights was $800 minus the $200 credit for a total of $600.

For the following 16 nights, I used my annual free night certificate for my Chase Hyatt Credit Card and paid cash for the remaining 15 nights.  I was able to get a great rate using Hyatt’s Best Rate Guarantee.  I was able to purchase discounted Hyatt gift cards for a further discount of 16% off our entire stay so the total was $2520 for 15 nights which is $168 per night which includes the resort fee and taxes.

By purchasing the gift cards, I was also able to get 5x Chase Ultimate Reward Points by using my Chase Ink Credit Card for Cardcash.  Therefore, even if I valued these points at only 1 cent per points, this equates to another discount of approximately $126.

Here are the total numbers for accommodations for our month of travel:

1. Week 1: $278.99
2. Week 2: $600.00
3. Week 3 and 4: $2394.00

Total: $3,272.99

Conclusion:

The above is an actual real world example of how I utilize timeshares, frequent flyer miles, hotel points, credit card points and perks, hotel best rate guarantees and gift cards to maximize my travel.  This can be complicated but it is doable. 

As you can see, we saved multiple thousands of dollars off of retail prices and traveled in luxurious accommodations for an entire month!  

I will be doing a detailed review of the Andaz Peninsula Papagayo resort in an additional post as this is definitely a property to check out (even though it is not a timeshare).

The intent of this blog is to explain timeshares and how they can be a great tool for your travel arsenal.  As you can see in the above, it is not the only tool that I use but they can be very useful and affordable.  

My goal is to show you how to incorporate timeshares in your travel plans and demystify timeshares, their costs and how they can work to your advantage.  Timeshares are simply one tool among many to travel well and affordably.    
​
What are your thoughts on the above?  Did I miss any strategies that I could have implemented?

If you find this useful, please share this post across your social media channels!  Your support is highly appreciated!  

Southwest is one of the best airlines out there thanks to its extremely customer friendly policies.  Southwest still offers 2 free bags for any type of fare as well as having 100% availability for redemption of its Southwest Rapid Rewards points. 

I have discussed why Southwest is great for timeshare planning here. 

Instead of rehashing the entire post, this is merely to inform my readers that the new scheduled has opened up as of today for travel up to January 7, 2018.  This is an important schedule update since you can now book travel for Thanksgiving, Christmas and New Years. 

Booking with Southwest Rapid Reward Points is a fantastic option since they are fully refundable.  If you have points, book now and continue to monitor the flights as Southwest will refund your points if the airfare cost goes down.  

My advice is to book now and look for accommodations later.  There is little risk in doing so if you are booking with points.   

As us timeshare owners know, planning for a vacation using a timeshare can be difficult as exchanges to prime resorts and weeks can be difficult.  While request first, deposit first and ongoing searches can help with getting the desired week, the issue then becomes airfare.  Airfare can make or break a reasonable vacation.  There have been plenty of times that I was able to exchange into a very desirable resort only to find out that the airfares for the particular week were astronomical and quickly derailed that plan. 

Southwest Airlines is the last airline that still has consumer friendly policies.  Southwest actually allows you to cancel, change or revise your reservation for no change fees.  This is drastically different that the other major carriers who charge significant penalties per ticket to make these changes.

If you book with cash, Southwest will allow you to change or cancel your flight for any reason and you will receive a refund for the full amount of your flight in travel funds.  Travel funds are essentially vouchers where you can use the value of the travel funds to book trips for a year from the initial date of the reservation. 

For timeshare planning, this is very helpful since you can make reservations before a the timeshare week is confirmed and if the week does not get confirmed or you end up booking a timeshare in a completely different destination, you can simply cancel the airfare and use the travel funds for another destination.  This flexibility is why Southwest is essential when dealing with timeshare planning.

An even better method is to use Southwest Rapid Reward points.  Rapid Reward points are Southwest's frequent flyer program.  You can reserve flights using Rapid Reward points and you are still given the same flexibility as with cash.  However, when you use Rapid Reward points for flights, first, they are free, and second, in the event you need to cancel, the points gets redeposited immediately so you do not need to worry about travel funds.

Travel funds can be difficult to keep track of since they are tied to confirmation numbers.

By using Rapid Reward Points, you can book speculative airfare for multiple trips for the same time period and see if and when a certain timeshare week becomes available.  You have the ability to book flights in advance without worrying about a confirmed week knowing that you can cancel it at any time for a full refund of points.

Southwest has recently expanded its operations to various international destinations and these consumer friendly policies still apply. 

One issue is whether Southwest services your area.  If so, you are in luck.  These policies and their free bag policies make Southwest a clear winner.

The other issue becomes on how to acquire the Rapid Reward Points.  The fastest and easiest way is to apply for a Chase Southwest Credit Card.  They currently are offering a sign up bonus of 50,000 points!  Depending on where you travel and if wanna get away fares are available, this can get you 3-4 round trip flights.  

I recently used points for my family of four to travel to Montego Bay, Jamaica for about 15,000 points round trip per passenger.  That is an absolute steal! 

In other posts, we can explore more about how frequent flyer points and hotel points are essential to acquire in order to make timeshare vacationing easier and more affordable.  In addition, free flights are great and can save you thousands of dollars.  Everything is better when its free!

Make sure to follow me on Twitter and Facebook.  Also, subscribe below!