August 8, 2018 0 Comments Reader Questions

Reader Question – Best Vacation Deals


One of our readers from Fullerton, California asked us “Where can I find the best deals on vacations?” Thanks for the question Chelsea. While this may seem like a simple question, it is pretty complex. Let’s break apart what we look at when taking a vacation.

3 Questions

#1 – Travel Method – Are you driving? Flying? Taking a cruise? If you are driving, you have to figure out the costs of gas, rental car, wear and tear on your car, etc. If you are flying, are you paying cash or miles? If miles, what are the taxes & fees? (Flying to Mexico & Bahamas on miles still costs ~$83 & ~$118 respectively. Flying in US only is typically $11.20 round-trip on miles.) If you are taking a cruise, what are the gratuities and excursion costs you will pay in addition to your cruise? If you will be traveling by public transportation, how much will the subway, Uber, etc cost?

#2 – Housing – Will you be staying in a hotel? Airbnb or VRBO? Cruise? Friend’s house? If you are staying in a hotel, are you paying cash or on points? Are there resort fees or parking fees? Downtown parking areas can get pretty high, like the Ritz Carlton Central Park, NY going for $75 per day. If you are staying in Airbnb or VRBO, is parking included or do you have to park in a nearby lot and pay that fee? If at a friend’s house, plan out what would be fair to offer (cash or nice gift) for letting you stay there.

#3 – Activities/Food – What type of activities will you be doing? Safari? Theme parks? Massages? Diving? Tours? Events like concert and/or sporting event? Activities like Zip-lining or rafting? If you are on a cruise, what excursions will you take? Will you enjoy fine dining restaurants? Are meals included in your housing?

When planning our trip we may come across a good deal for one of the 3. For example, on 12/25/14, we saw flights from New York to South Africa for $330 roundtrip; thus point #1 was very cheap. We booked on priceline, with the ability to cancel within 24 hours. We then researched #2 and #3. If we were going to South Africa, it was mainly for a safari, so we researched all-inclusive safaris and found that it made sense for us to take the trip.

Another example would be our DisneyWorld/Jamaica trip. You can read about that trip here.

So, back to Chelsea’s original question, “Where can I find the best deals on vacations?” The question back to her would be, what “deal” are you interested in? Cheap flight? Cheap housing? Cheap activities? Also, are you interested in a particular location? Are you flexible with your dates or are they set?


Cheap Flights – If you have airline miles available you can get some great flights (economy/business/first class) and just pay taxes and fees. There are also great offers available for reduced price flights. For example, Alaska Airlines offers a free companion for their Visa Credit Card holders, where the companion just pays taxes and fees. If you are looking for cheap cash flights, we recommend using Google Flights.  Using this site, you can also put alerts on flights to be notified of price changes.

Cheap Housing – Building points with hotel programs (by stays, hotel credit card sign-up bonuses, hotel credit card) can get you free stays. Hilton and Marriott/SPG also have a 5th night free policy on award redemptions. Airbnb or VRBO can be very economical, but make sure to read all of the reviews, and generally speaking, you get what you pay for.

Cheap Activities – Sometimes the opportunity presents itself to get a free activity. For example, you can read our Jack Johnson Trip Report about how we built a trip around a concert in another state.


While this was a long answer to a short question, hopefully it gives you some insight into the 3 things we think about for a vacation. If we are able to get cheap flights, free hotel, and free activities (i.e. Jack Johnson concert trip) then we have a winner. We also offer a Travel Consulting service where we review your travel goals and provide recommendations and extra tips on how to get there.

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