When my younger brother got engaged a year ago, I did the supportive, sisterly thing and started asking the important questions.
“Where are you going on your honeymoon? Do you need any help planning?”
After putting me on hold for a few months while they handled the (supposedly) more pressing first steps of choosing the date, venue, photographer, guest list, deejay, and wedding party, my brother came back and asked my opinion on a promotion he had found on a travel deal website. The site was offering 50% off a seven-night stay for two people at an all-inclusive resort in St. Lucia for $2,800, excluding airfare. My brother was twenty-three at the time and had never researched or booked his own travel, so he was a bit lost on how to decide whether or not it was actually a good deal.
Sites like Groupon, TravelZoo, and CheapCaribbean.com regularly offer amazing-looking deals on travel, and it’s easy to get swept up in the excitement. (“A four-night trip to Paris for $199, including airfare? M, where’s my credit card?!”) Before you reach for your wallet and submit for days off from work, however, it’s important to consider all sides of the deal to make sure you’re truly getting a bargain. Doing a little research can make all the difference between jetting off on a fabulous, low-cost vacation and wasting your precious PTO on a cheap but disappointing trip.
To assist my brother with his honeymoon decision, I sent him a list of the factors I consider anytime M and I are contemplating booking all or part of a trip through a deal site or promotion. I’ve adapted the questions here so that hopefully they will be helpful to you, too. While it may look like a lot of work, checking off all of the questions below shouldn’t take much more than a half-hour, or perhaps less the more often you do it. It’s time well spent to ensure that you’re getting the most out of your money and experience!
1.) Does the deal cover the dates I want?
This is hugely important. The travel deal is worthless to you if you can’t use it when you want or are available to go. If you have specific dates in mind, make sure they’re covered. If you are more flexible, make sure that you want to visit the location during the timeframe of the deal. Prices tend to fall outside of prime tourist months, such as winter in Europe or peak hurricane season in the Caribbean. While I am a big proponent of off- and shoulder season travel, you may not want to pick up that TravelZoo deal to visit Greece in March if your dream is to bask on a warm, sunny Mediterranean beach. Decide whether it’s worth the extra money (and often extra crowds) to experience your destination in prime season. If the timing of the deal looks good to you, move forward.
2.) Is airfare included?
As any traveler knows, transportation – particularly airfare – is a major cost of travel. If flights aren’t listed as part of your deal, do some light searching to get an idea of how much you can expect to spend. Does that number fit into the budget when added to the total cost of the deal you’re considering? A four-star hotel room for $30 a night may not be as great of a bargain for you if the flights to reach it will add thousands to the total cost. If the flight costs seem reasonable and budget-friendly, move forward.
3.) Does the hotel or resort look like somewhere I’d like to stay?
If lodging is included in the travel deal, do some research to see if the featured property or properties are truly what you want and worth your money. TripAdvisor and Google are a great place to start; I tend to look for a rating of at least 3.5 (ideally 4) stars out of 5. I also like to read a few one-star reviews to see how reasonable people’s complaints were and if the disappointments they mention would have been dealbreakers for me. Keep in mind that people are most frequently motivated to comment when they’ve had an experience to one extreme or another, so take individual reviews with a grain of salt. That said, it shouldn’t take long to find some common themes that can help shape your decision.
Sites that include traveler-submitted photos, again like TripAdvisor, also help provide a more realistic picture of the place you’re considering and aid in comparing it to similar locations and competitors. Is the water really as gorgeous as the website would suggest? Is the food as upscale and delicious as it seems? Doing a little digging can give you a good sense of the deal’s value by setting accurate expectations. If everything checks out, move forward.
4.) What food and drinks are included?
When I was a tour director in Alaska, one of my guests’ most common misconceptions was that meals on the land portion of their cruisetour were covered just like on the ship. As a result, many were dismayed at the additional, unexpected, and often un-budgeted cost of feeding themselves, especially with how expensive restaurants can be in Alaska.
Keeping in mind your own travel eating habits, such as splurging on fine dining or a tendency to skip a meal like breakfast or lunch, try to get a good idea of how much extra you’d be spending on food. Most all-inclusive resorts are quick to label themselves as such, but answering this question may require some digging for other hotels, tours, and vacation packages.
For hotels, check if breakfast is complimentary. For tours and vacation packages, look at the itinerary to determine how many meals are included and how many are on your own. If you’re considering a resort that is not all-inclusive, I suggest checking their website for the menus of any onsite restaurants to determine how pricey (and appetizing) the food might be. Particularly in places where it is not quick or easy to find dining options outside the hotel, resort food prices can be steep and quality can suffer because guests have nowhere else to go. If it looks like food costs will not be prohibitive when added to the price of the deal, move forward.
5.) Can I afford to enjoy myself?
Especially if you’re on a tour, cruise, or resort vacation, it’s wise to look into the prices of optional excursions and other amenities to make sure you know how much these “extras” could add to the total cost of your trip. It might not be worth booking a deal for an inexpensive resort stay if you get bored sunbathing but don’t have the budget to do anything else. On the other hand, finding a bargain might leave more room in your budget for fun, allowing you to take advantage of activities you otherwise might not have been able to afford. Check out how much that snorkeling excursion will set you back, or if it’s going to be cost-prohibitive to upgrade your included car rental from a manual to automatic. If you feel confident you’ll enjoy your time, move forward.
6.) How do I get to where I’ll be staying?
We all know that transportation costs can add up, but after booking flights it can be easy to forget to factor in the price of getting away from the airport. M and I once learned that the hard way when we mistakenly flew into the wrong airport and had to take a two-hour private taxi ride to our destination. Ouch.
Especially if your hotel or resort is far from the airport, I advise having a plan in place before you land so that you can be on your way as quickly and cost-effectively as possible. Check to see if the deal includes airport transfers or car rentals (or the option to add them); if not, you will need to consider the cost of public transportation (often the cheapest option), a cab, or a rental car to get you to your actual destination. This shouldn’t be a big expenditure if planned ahead, but it’s worth adding to your total cost when evaluating the deal. If your airport transfer won’t break the bank, more forward.
7.) Are there any restrictions?
Watch out for the fine print. Sometimes hotel or tour deals don’t cover weekends, or there may be a surcharge to book services outside of a Sunday – Thursday window.
Are there taxes or fees that are not included that would significantly increase the price? (Resort fees can be a real budget buster.) Is there an additional charge for solo travelers, odd-numbered groups, or children that would apply to you? Are there any advertised services that are not included in this deal that would have been included if you paid the usual price, like a hotel breakfast? Will you be surprised by any additional charges upon arrival, such as paying a premium for top-shelf liquor or extra pillows?
Make sure that you have a full picture of your expected cost so that you’re not sticker-shocked by what might have been left out of the deal. If everything looks copacetic, move forward.
8.) Is the booking website reputable and safe?
Anytime a travel deal looks too good to be true, it’s wise to double-check that it isn’t. If you’re not booking directly through the hotel or tour service’s website, do some quick research to make sure that the selling vendor is legitimate. One of the easiest ways to do this is to type the name of the vendor into Google and add “reviews” before searching (ex: “TripMasters reviews”). As you can see if you actually complete the TripMasters search, you should get directed to links to forum discussions, TripAdvisor pages, or organizations like the Better Business Bureau. If there’s no web presence to be found apart from the vendor’s website, or if anything looks suspicious, be cautious.
I always try to book through the actual resort, destination, or airline if the deal is available there, but there’s nothing wrong with booking through a third party if they’re reputable and having a good sale. (We booked a TripMasters deal through TravelZoo to explore Prague and Budapest last year and had a great experience.) If you’re sure you’re not getting scammed, move forward to the last question!
9.) Above all, do I feel good about it?
Trust your gut! Does this deal get you excited to set off? Are you already creating a packing list and souvenir book of photos in your head? If by this point you feel that the price listed is a good value for the location and experience, then go for it – and have a blast! If not, let the deal pass by, but don’t worry. Another sale will come around soon, and the next TravelZoo Top 20 is due on Wednesday 🙂
How do you decide if a travel deal is worthwhile? I’d love to hear any tips that I missed, or any stories of great bargain finds that led to amazing experiences!
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This article was originally posted on February 14, 2018, and was last updated on February 15, 2021.
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