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6 Questions To Ask Before Booking a Trip

Oh, the excitement when the time comes to book that well-deserved trip! Yet, it’s best to consider some important questions before booking any trip so that you’re completely happy with everything booked prior to securing a deposit and fully committing.

Why not get the ball rolling today? Ask yourself the following questions:

 1. What type of traveller am I? 

Solo traveller, adventure seeker, hiker/explorer, or rest and relaxation? You’re bound to fit into one of these categories and it’s a good idea to determine this so you can move onto booking the perfect trip. You could be travelling on a couple’s trip, a girl’s trip or a guy’s trip, and the type of activities and the types of destinations would be very different.

For every type of traveller you think of, our travel agency can find the best destinations to choose from rather than exploring tons of places that you’re not interested in, so it avoids any time-wasting so you can secure a booking in a place that you’ll love to visit. It’s better to know which one fits best for you and it’s the best place to start. The type of traveller you are will help us move to the next step, so we’ll look at the next question.

2. What is the best type of vacation?

The most popular types of vacations are vacation packages, but there are also FIT’s, cruises, backpacking trips, and road trips. The destinations and the options are going to be completely different for each one of these. For those travellers who want luxury despite restrictions in some countries, then a reputable resort is the best option for you. But, if you want to do a lot of sight-seeing and maintain distance from the public, a road trip is the best vacation.

More and more people are choosing road trips this year, for obvious reasons, and many travel agencies are noticing how this is becoming a choice for a higher percentage of people than usual.

Still, Travel Time – TPI always ensures they are helping their clients to choose the most highly reputable resorts or brands to stay at with an all-inclusive option. When more people are looking to travel abroad and take in some Caribbean sun, Travel Time – TPI will be ready to take care of the planning and booking of their trip.

For anyone interested in a vacation with lots of sight-seeing and tours then a FIT (Foreign Independent Tour or Fully Independent Tourist) could be for you. A FIT is a package vacation that combines:

  • air
  • hotel
  • transfers
  • possibly activities

This gives the traveller the option to sit back and relax while also ticking off their favourite locations and sights on their list with little hassle for the traveller.

Once we establish the best types of vacation to match the type of traveller, we’re ready to ask about destinations!

Planning The Perfect Trip
Planning The Perfect Trip

3. What is the best destination to consider?

This answer depends on who is travelling, and the purpose of the trip. For a maximum in relaxation, our agents at Travel Time – TPI always propose resorts from one of the travel agency’s partners who they know have a proven track record to be on top of any client concerns.

Travellers sometimes already have a destination in mind, perhaps for personal reasons. Some people have always dreamed of hiking the Inca trail in Peru or taking in a view of Paris from the top of the Eiffel Tower, walking along the Great Wall of China, or exploring the place of their family roots. Other people are happy with a relaxing vacation in any beach setting.

In cases where there aren’t any particular destinations in mind, we like to look at which destinations have offerings in line with the type of travel that someone is looking for.

Another factor is whether you’re looking for a place where you can get out and experience the local culture and interact with the locals- sometimes the language spoken in the destination should be one you’re familiar with, which would facilitate this type of travel.

If you’re looking for the perfect R&R vacation, the destinations that have the best in quality would be an all-inclusive resort with an emphasis on providing a great experience. For the more adventurous type of traveller who will want an active trip to take in the local landscape and get that perfect Instagram photo, well, you’ll want a specific biking and/or hiking destination.

For a relaxing trip, some great brands to consider include Sandals or Beaches Resorts, Playa Resorts, or AM Resorts. These are ideal destinations if you want high standards as they are known for taking care of their clients and especially during this pandemic, high standards and appropriate protocols in place should be one of your number one concerns as a traveller.

Many Destinations To Choose!
Many Destinations To Choose!

The best place to travel also depends on whether you’re going for a particular celebration. Travel Time – TPI regularly helps organize trips for weddings, honeymoons, anniversaries, family-moons (for those unfamiliar with this occasion it is a unique trip taken before the birth of a couple’s first child).

Whether it’s now during this COVID-19 situation or any other type of consideration, there are always risks (hey, there are even risks associated with staying home!) to take into account. The best option is to consider safety above all and do business with a brand that offers a very high level of care. Travel Time – TPI always recommends partner companies offering clients what would be recognized as the VIP experience that their celebration deserves and they consistently come back very satisfied.

Once there is a destination (or multiple!) in mind, it’s time to start checking out pricing. Pricing and timelines are often associated, and sometimes the timeline is fairly restrictive (if the goal is to travel for a specific occasion). The question begs to be asked, though, “how far in advance should I book my vacation?” and that’s the question we’ll look at next.

4. When is the best time to book?

If you could save money by booking your trip far in advance, you would probably be more than happy to do it, and if it means the whole vacation is organised months from the trip date, you can relax knowing it’s all taken care of.

Well, surprise! It does work out better to book in advance compared to booking everything last minute. Although for the spontaneous folk, they also believe that if they book last minute, that will give them their best prices. But can the best pricing also add up to the best value or the best experience? We find that neither is true in comparison to a well-researched vacation booked well in advance.

Booking any vacation the night or week before you leave can also limit your choices.

It’s fun to live in the moment but if you see a beautiful hotel advertised online that’s very popular, chances are it will be fully booked far in advance. This is especially true for the well-recommended brands that we offer at Travel Time – TPI. They are resorts that have a great reputation for looking after their guests and providing a high level of safety and planning to ensure everybody has a great time. These resorts are well known and space is in high demand and we know how disappointing it can be when the resort you want is sold out for your dates!

For the avid traveller, this is old news, as it’s obvious the best places sell out very quickly and no one wants to go searching for another accommodation or destination too close to the departure date.

The best time to book is well in advance. Just think, earlier is always better. Don’t leave it too late, get everything booked, reserved, and enjoy the pre-travel excitement months before departing. After all, isn’t the anticipation of the trip a huge part of the fun?

However, if you’re booking in advance, perhaps you’re thinking “A lot can happen in 12 months! What if I need to change my plans?” This is exactly the reason the next question needs to address the cancellation policy.

The Best Time To Book
The Best Time To Book

5. What is the cancellation policy?

Especially with the global pandemic, this is the one question that many people want to know and should know before booking any part of their trip. It is not something to think about only if something comes up or someone pulls out of the group trip or vacation.

Especially for those who follow our advice from question 4, those people who book in advance, this is also a piece of information they would like to know beforehand. And cancellation and refund policies can differ on flights, rental cars, lodging to even attraction tickets. And those policies can also vary by supplier which is also another situation where the cheapest price may not have been your best option.

So, whether you’re booking an all-inclusive package, a cruise, just flights and rental cars and hotels, how it’s booked sometimes will have very different terms with different suppliers.

No one puts all this time and effort into booking just to consider cancelling. It’s not nice when something happens that forces you to cancel your trip. It’s even worse when there’s no way to recuperate the cost invested in the planning process. This is exactly why the sixth and final question to ask is “Should I buy travel insurance?”

6. Should I buy travel insurance?

You’d be surprised at how many people avoid buying travel insurance and end up in a tricky situation where they wish they had bought any type of insurance policy.

In one of the worst-case scenarios, your kid gets injured on the trip and ends up staying a couple of days in the local hospital, your hotel and meals could be covered under the – “trip interruption” provision.

Our travel agents will recommend to every client who’s booking any trip, to get some form of travel insurance. Most people believe they have sufficient coverage through their credit card or another means, but typically any serious problems that happen while travelling are simply not covered by the complimentary offering of a credit card company, as if that’s any surprise.

Our agents at Travel Time – TPI typically travel abroad 2-10 times per year, and the number of times that we leave the country without travel insurance is zero. The same goes for any family members for whom we’re booking a trip. It’s the responsible thing to do.

Here’s a tip: Purchase travel insurance the same day you secure a deposit on your vacation, and you can then qualify for CFAR (Cancel For Any Reason). This is reassuring since you have the option to cancel for whatever reason you wish with no further questions or strings attached. This is a lifesaver, especially this year since it’s been such an uncertain year for travel.

At the same time, there are many travel companies (resorts, tour companies, airlines, etc) that now offer very flexible options for rescheduling a trip. Still, we do recommend getting travel insurance in all cases, as from our experience we know its always better to have all bases covered.

At least with insurance, you have peace of mind knowing you won’t lose everything. Just familiarize yourself with the terms and conditions of any policy.

There you have it, 6 key questions to ask yourself before booking that awaited trip of the year whether it’s a solo trip, a couple’s trip, a family vacation or a special occasion, save yourself a lot of time and money by asking these helpful questions and narrowing down your search before booking anything.


Are you thinking of your next trip?

Vacation Planning

Choosing the place you want to visit or the travel experience you want to have can be very exciting. But if you don’t know how to find the best option for you, Call us!

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