Top 12 Questions To Ask Yourself Before Going On Vacation

Top 12 Questions To Ask Yourself Before Going On Vacation

Are you thinking about planning an unforgettable trip? As you begin to design your dream vacation, the list of decisions to make can get a little overwhelming. There are so many elements to account for including choosing a destination and lodging, how to book the most affordable reservations, and what time of year to travel. If you have a destination getaway in your future, check out these 12 most frequently asked questions for travelers to help you avoid some of the most common travel planning pitfalls and plan your best trip ever. 

1. How early do I need to book? 

The short answer is: it depends. If you have fixed dates, are traveling during a holiday or to extremely popular locations, you might book as early as a year ahead of time. For most trips, however, having a rough plan with flexible dates six months ahead will give you time to learn about the specifics of your destination and to compare the travel pricing and reservation guidelines for your specific lodging. A good rule of thumb is to book international flights and hotels four months before your arrival dates, and around three months ahead for domestic locals. 

2. How important is travel insurance? 

Travel insurance is optional and some people feel like skipping it is a good way to save a little money on the overall vacation. However, imagine how much your vacation is worth overall. Flight cancellations or weather delays, lost baggage or illness can all derail your plans unexpectedly, and with trip insurance you can remain calm no matter what interruptions arise knowing your investment is secure. If you don’t use it, it’s a small upfront cost, but if you end up needing it, it will seem invaluable. 

3. How can I use my credit card to make my travel more affordable? 

Look for a credit card that offers frequent flyer miles on purchases you make on a regular basis, such as groceries or gas, and make this your primary card. Use it for all qualifying purchases leading up to the time you book your airfare. Just make sure you know exactly what the card terms specify for qualifying purchases and pay off the balance each month as you go so you won’t incur interest charges. Particularly if you have a major expense planned such as a new appliance or home renovation, getting flyer miles can soften the blow and get you closer to free travel for your dream vacation. 

4. How can I choose an affordable destination? 

It’s almost always more expensive to visit a popular destination. If you are totally open to new places, look for unique and off the beaten path locations that can be cheap AND a great adventure. Search for towns or resorts by picking the main theme for how you want to spend your time, looking for places to swim, hike, camp, or explore historical sites, museums or restaurants. If you have a specific popular (and overpriced) location in mind, search for places that offer similar amenities. Did you want the pricey resort because the brunch looks amazing? Find a small-town bed and breakfast that gets great brunch ratings. Are you dreaming of a world class beach? Find one farther away from a major metro area with less tourists. If you really have your heart set on a popular and expensive place, figure out when the off season for tourists happens and consider splitting your trip during that time with a nearby cheaper place and ending with a few days at your dream spot. It might take a little more research, but you’ll get all your important vacation activities at a fraction of the cost. 

5. Are there benefits to traveling with a group? 

If you are open to the idea of traveling with friends or family, boosting your numbers might lower your costs. Group discounts are often available for ticket prices to attractions or certain types of travel for groups as small as 10 people. Even smaller groups can offset the cost of a trip: a rental car and hotel rooms are cheaper per person when you’re splitting them four or six ways. Many popular destinations have travel groups you can join as a solo traveler or couple to get the group discounts without the hassle of organizing all those extra people. 

6. What days are best to travel? 

If you have flexible dates, you’ll save money on airfare and car rental fees by traveling on weekdays instead of weekends. Hotels and resorts often have higher room rates on weekends as well, but might offer discounts on packages that last more than a minimum number of nights. 

7. Where can I find the best prices? 

Often the direct websites for resorts or travel companies are NOT the cheapest place to book. Search sites like,,, and to comparison shop between companies and look at price trends across multiple dates. Using these sites can save you a significant amount of money on flights, car rentals, and hotels, and usually offer even more discounts when you bundle air travel and lodging together. 

8. What’s the most comfortable place for my large family to stay? 

Traveling with small kids, big families, or in-laws means you need extra space to keep everyone happy. Accommodating many people at a hotel usually requires paying for two adjoining rooms or shelling out for a big suite. If you’re looking for a more affordable option, consider renting a house or swapping your house with another family through where you can search tons of options and find all the comforts of home. Being able to buy a few groceries and cook in a full kitchen saves everyone money, and preparing meals together might just some of your best family vacation memories. 

9. How can I get the most value from our trip activities? 

Like any budget, vacation budgets work best when you plan them ahead of time. Arriving without a plan and a loose spending goal is a surefire way to waste your vacation in overpriced restaurants and unexpected expenses. Before you go, spend some time researching the area and make a list of all the possible activities and their costs. Call a planning meeting and ask everyone who will be traveling for one or two most desired activities for the trip. That should help you prioritize your time and money so you enjoy your splurges, and avoid disappointing impulse buys. 

10. Why do I need local classifieds for my planning? 

It sounds crazy, but the internet is giving new life to the art of trade. With enough planning time, you can find local buy-sell-trade or online classifieds for the area you’ll be visiting. Make a post requesting tickets to an event, discounts or gift cards for dining, or even a place to stay. You might offer some labor while you’re in town for childcare, helping someone move, or cooking someone a great meal. Maybe you have some specialized skills in design, computers, or crafting you can help them with before the trip. You could even bring a specialty from your home area to make a “local customs” swap when you arrive. 

11. How can I get free stuff? 

There’s no shame in looking for ways to maximize your vacation budget by taking advantage of included amenities and other free opportunities. If you’re heading to an urban area, look for free or donation days for museums and street festivals with free admission. In rural areas, look for national parks with free entrance or buy-one-get-one admission to historical tours. 

12. How can other people help make this trip great? 

Many people overlook the resources at their fingertips (or contacts list) that might make a trip better. Reach out to friends or family who live in interesting cities and combine your vacation with a visit to see them and save a few nights on your hotel costs. Call out favors from friends who can drive you to the airport instead of taking a shuttle. Ask to borrow camping equipment or a bigger vehicle that would make your travel more comfortable. Your friends and family want you to have a fabulous vacation, but they probably don’t know how to help. Don’t be shy to ask, just make sure to say please, and have a back-up plan if they can’t accommodate your request. Planning a vacation can be as much fun as the trip itself. If you have enough time to ask yourself these questions, you’ll maximize both your budget and your fun.