How 2 plan a trip

Over the years I have planned out numerous trips for myself and my family. I’ve put together itineraries using an assortment of booking websites. Sometimes I booked directly with a hotel, airline, or rental agency, and other times I used third party websites like Expedia or Booking.com. I’ve also stayed at Airbnbs around the world from Reykjavik, Sydney, to Hawaii and more local destinations.

More recently I’ve booked directly more often than using third party sites. I have done so because for hotels, we’ve earned points that way, which you only typically earn when you book directly through them. If you book through Expedia, you will not earn loyalty points with that hotel chain (like Hilton or Hyatt). Through a variety of means, I’ve had mid-level status with Marriott, Hyatt, and top level status with IHG in the past few years. Further, through promotions, I’ve also held status with American Airlines. This certainly, in these times of seat selection fees even in business class, has helped save money on flights. Hotel statuses have netted room upgrades even when they were not an advertised benefit.

So what does that mean for planning a trip? I like to come up with three different options of well-reviewed hotels. Typically I’ll link to the TripAdvisor reviews just to get a general overview of the hotel. I’ll look at Google reviews as well and the reviews any travel/points blogger may have written as well. I’ll price out a “luxury” option, a “mid-range” option, and a “budget” option. I would consider each option a solid place.

For airfare, I generally search Google Flights first. My family has some flexibility, but dates are usually pretty concrete on when and for long we can travel. In Google Flights you can set price alerts for the dates and place(s) you want to fly to. Therefore, if there is a price drop, you’ll get an email about it. If local, I’ll also take a look at what Southwest is charging, especially as a family their 2 free checked bags per person benefit is helpful.

Airfare is a bit simpler, the luxury option is business (or first class domestically), mid-range is premium economy, and budget is economy. Super luxury is international first class, but there are only a couple airlines that still even offer that option. Sometimes, like with Qatar and British Airways, the first class seats might not be even as good as the business class seats. A Google search is your friend when it comes to reviews of different airline seats. Like Emirates, the A380 has an excellent business class, but they mainly fly Boeing 777s that have a completely different, and less-liked, seat. Before spending a bundle, do your research on business class flights.

Rental cars I typically use a third party site like Expedia or Orbitz. I haven’t found an advantage to booking direct and I rarely rent a car, so loyalty benefits are not much use to me. Even so, premium credit cards like the Chase Sapphire Reserve and AMEX Platinum offer rental car statuses as a cardholder benefit (other cards as well). These might get you a one-car type upgrade, but really won’t save you much I’ve found.

In sum, you should give yourself some options when planning a trip. Especially if you are traveling with family, you can run the costs of each option by them to see who is comfortable with what price point. Come up with a budget and remember some of these costs are pre-paid (like airfare) and others you may pay at check-out (hotels) or at car pickup. Some costs are spread out, but that also means you need to make sure you can afford the trip when you take it.

Enjoy your travel planning.

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