Speculative Bookings for Holiday Travel

Everyone would rather pay a cheaper price for a trip if possible but sometimes you can’t plan too far in advance due to other limiting factors. Most people know if they will need to travel somewhere during the holidays and somewhat know their vacation days at work. Unfortunately, almost 99% of the time the travel industry (airlines, hotels and car rental companies) takes advantage of people who plan last minute. With a simple trick of creating speculative bookings, you can reduce your overall cost to travel during holidays.



I’ve always made flight reservations for popular US holidays such as Memorial Day, July 4th, Labor Day, Thanksgiving and Christmas in advance and usually 2-3 flights varying by 1 day and/or flight time to create flexibility. Most airline tickets are non-refundable and have change fees associated but here are 2 methods I’ve used to waive those fees:

-Book Southwest Airlines flights as they have no cancellation fees. You are able to cancel and then use those funds for a future flight within 12 months of the original purchase date of the ticket.

-Book Virgin America flights with your Virgin American Premium Visa credit card which waives cancellation fees. Again, the funds are placed into a travel bank account which can be used for a future flight within 12 months of the original purchase date of the ticket.

Tip #1: If you forget to make your speculative bookings for Christmas and New Year’s Virgin American has historically had last minute deals on premium seats (Main Cabin Select and First Class) which are often less than an economy ticket. I’ve even cancelled an Economy Class ticket and flown First Class as it was cheaper.

Tip #2: Always check to see when Southwest will be opening up their schedule to be able to book the cheapest seats by visiting here: https://www.southwest.com/html/travel-tools/



Most of the time during holidays you are spending time at a home with family/friends and not needing to stay in hotels. New Year’s is one of the holidays I prefer to travel to a new location each year. Booking a hotel in advance is key during these peak times. You can usually find a AAA rate which has very flexible cancellation policies associated with them. Another option is to use your points towards an award stay which can prove to be an excellent value if you find availability. I just made a booking for the 2016/2017 New Year’s at a value of $0.065 per SPG (Starwood) point which is 3x the normal value of a SPG point. Always double check the cancellation policy prior to booking a room. Some hotels have a 14 day minimum for cancellations such as Sheraton Maldives which caught me by surprise a few years ago.


Car Rentals

Always make speculative bookings and ensure they are non-prepaid rates. You can no-show and will never be charged for the bookings. It’s always nice to cancel the booking if you won’t be using it but there is no liability if you don’t. The prepaid rates might be 10-20% cheaper but I find having the flexibility is worth the extra money.


Now is the time to make some speculative bookings if you think you’ll be traveling during the upcoming holidays! Do you have any tips or tricks? Comment below…



You may also like...

Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.