Middle Age Miles

Southwest 3-Day “Tropical Travel” Sale to International Destinations + Stack with Southwest Vacations Black Friday/Cyber Week Promo?

From today (November 20) through Thursday, November 22, Southwest has a “Tropical Travel” fare sale to its international destinations in Mexico and the Caribbean. These winter sale dates could be your gateway to escape the chilly US winter in favor of the tropics!

In addition, you might be able to stack the “Tropical Travel” sale with the Black Friday/Cyber Week promotion from Southwest Vacations to get the sale fare plus $250 off on an international flight + hotel package!

Relevant Links

The links to Southwest’s regular site and the specific page for this fare sale are here:

Link to Southwest regular site

Link to Southwest “Tropical Travel” fare sale page

Link to Southwest Vacations Black Friday/Cyber Week promotion

Details & Analysis

In this week’s Southwest sale, they’ve focused on their international tropical destinations in Mexico and the Caribbean. Travel dates for this promotion are January 8 through March 6, 2019, and April 23 through May 16, 2019.

That said, the biggest downside to this sale is that the sale fares are generally only available for travel on Monday through Thursday. That will make it a lot harder for most people to use this sale. The best way to use this sale may be to take a long weekend, departing on a Thursday and returning on a Monday (but be careful about the limitations on the dates of the sale for flights to Cancun, Cabo San Lucas/Los Cabos, and Puerto Vallarta (see below for more details)).

The other significant downside to this sale is that the sale fares are valid only on non-stop flights. Many of the US cities that have Southwest flights to Mexico or the Caribbean are in Florida or other parts of the South, so opportunities to use this sale to escape the cold may be limited. That said, though, we see some flights from chilly locations like:

  • Baltimore (BWI) to Cancun and Montego Bay;
  • Chicago Midway to Cabo San Lucas, Cancun, Montego Bay, and Punta Cana;
  • Denver to Cabo San Lucas and Cancun; and
  • St. Louis to Cancun

Unfortunately, there aren’t any non-stop flights from our hometown of Dallas or our family’s home airports in Albuquerque and Little Rock that are part of this sale.

Stack with the Southwest Vacations Black Friday/Cyber Week Sale?

We’re also seeing a new Black Friday/Cyber Week sale from Southwest Vacations. This sale offers $125 off US vacations with the promo code SAVE125DOM and $250 off international vacations with the promo code SAVE250INT, when you book a flight + hotel package on Southwest Vacations. For this sale, booking is from now through December 3, and travel dates are from now through June 7, 2019.

That means that the international portion of the Southwest Vacations sale overlaps with the “Tropical Travel” sale. We would expect that if you book an international flight + hotel package on Southwest Vacations between now and Thursday, it would pull the “Tropical Travel” fare sale prices for your flights to save you money, plus you will be able to apply the promo code SAVE250INT to save an additional $250 off of your package.

Southwest Vacations Black Friday/Cyber Week sale

More Details on the “Tropical Travel” Sale

Be sure to note that you have only 3 days, until Thursday, November 22 (Thanksgiving), to take advantage of this Southwest sale. But even though the sale runs for 3 days, you’ll want to act sooner than later before all the good prices and routes are gone!

Here are the most important details of Southwest’s “Tropical Travel” sale:

  • Must purchase tickets form November 20 through November 22 at 11:59 pm (in the time zone of the originating city for your flights)
  • Travel dates for this sale are January 8 through March 6, 2019, and April 23 through May 16, 2019
    • However, these fares are generally only valid for travel on Monday through Thursday
  • There are several other restrictions on the days of the week for travel using this sale:
    • Travel to Cancun, Cabo San Lucas/Los Cabos and Puerto Vallarta is valid only on Sundays through Wednesdays
    • Travel from Cancun, Cabo San Lucas/Los Cabos and Puerto Vallarta is valid only on Tuesdays through Fridays
    • Seats and days are limited and won’t be available on some flights that operate during very busy travel times and holiday periods
  • And here are two terms and conditions of the sale that loosen these restrictions:
    • Travel is valid daily to/from Mexico City; Liberia, Costa Rica; and San Jose, Costa Rica
    • Sale fares may be available on other days of the week, but that’s not guaranteed
  • Sale fares are valid only on non-stop service

In addition to booking new flights with this sale, remember to check any existing Southwest reservations to see if they have decreased in price.  If the price has dropped, you can either cancel and re-book at the new price, or select change your flight and then re-book to the same flights with the new lower price.

Under Southwest’s generous cancelation and change policies, if you cancel before your flight, you will receive Southwest credit for your previous fare, which you can then use to re-book.  Similarly, if you change and then re-book to the same flights, you will receive credit for the difference in price (whether in dollars or Rapid Rewards miles). Southwest does not impose any fees for canceling or changing future flights.  However, note that travel funds (such as the credit for canceling and re-booking at a lower fare) expire 12 months from the original ticket purchase date.

Until very recently, there was a huge advantage to cancel-and-re-book as opposed to changing, in that if you changed your flight, it would lock in the reservation and become non-refundable going forward. Now, however, flights remain refundable if a change is made to the reservation.

When you book your Southwest flights, be sure to use a credit card that maximizes your points earning for airfare, like the Chase Sapphire Reserve (referral link), the Amex Personal Platinum (referral link), the Citi Prestige or Premier, or the US Bank Altitude Reserve.

Here’s a look at a sampling of departure and destination cities and fares. We like that you can fly from Fort Lauderdale to Grand Cayman for $71 and back for $145. If the sale dates work for you, you can take that round trip for only $216!

Full details of this week’s Southwest fare sale are shown here:

Will you be taking advantage of Southwest’s “Tropical Travel” fare sale to book an international trip to a sunny destination? Where are you going? Please share with other Middle Age Miles readers in the Comments!


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