May 9

Travel Series: Top Trip Booking Tips

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Now that you’ve found your trip inspiration and sketched out the perfect itinerary for a wonderful vacation, it’s time to lock it down. It takes a lot of work to go from travel idea to flights booked, accommodations arranged, ground transportation organized, restaurants reserved and activities confirmed. Here are our top tips for finalizing your travel plans…


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Book hotels first

Unless you are booking many, many months in advance, it’s not always easy to book the exact trip you planned. Sometimes things aren’t available or they fall out of budget. As soon as we confirm that all of our accommodations are available on desired dates, we book all hotels in one sitting before booking anything else. After that we book travel, and then everything else.

Book online for speed but don’t be afraid to call

We try to book as much online as possible, but because we often book pretty late, we sometimes have to call or email to check on availability (if we plan something more than two months in advance we are way ahead.) When we find somewhere that’s so amazing that we have to stay there, it can be hard to find out online that they don’t have rooms available for our desired dates. Calling and offering to be flexible can often mean the difference between getting into our number 1 choice versus having to settle for second best. It’s not uncommon for us to even offer to change rooms when staying for longer periods of time. While you have them on the phone, another thing you can try is negotiating for extra benefits at the hotel during your stay. A complimentary breakfast or a spa voucher isn’t out of the question. Think about it – by calling and offering to be flexible you are helping them fill room inventory that might otherwise have been difficult to fill. More importantly, you are booking directly with them which means they don’t have to pay a commission (often 20%) to companies like or

Everyone loves to save a dollar when possible, so here are some of our favorite tips to save some money when booking:

Travel dates and times can impact costs significantly

Tuesdays and Wednesdays are traditionally the least expensive days to fly. We’ve also found that flights before 8am are typically less expensive too. An added bonus is that you’ll have less of a chance of a flight delay due to a late arriving plane. That’s because these early flights are the first of the day, meaning the plane most likely spent the night at your departure location.


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Compare all in costs rather than advertised prices

Staying at hotels can be luxurious but you definitely end up paying a premium. After you factor in hotel taxes, overpriced meals at the hotel and tips for hotel staff, you’ll be paying way over the list price. More and more often we are finding ourselves staying in airbnb’s and b&b’s as we find the experience to save us money and offer a more unique trip.


When we first started traveling frequently we would book the cheapest flight that we could find on booking sites like Kayak. Now airlines use the cheapest rate as a marketing tool to get you onto their site, while they nickel and dime you for baggage, more legroom, priority boarding, meals and so many more items. You should even consider travel costs to and from the airport.

Loyalty has it’s benefits

After a while we found we were flying the same 1 or 2 airlines all of the time so we decided to commit to Delta by getting a Delta Credit Card. The minimum benefits for airline credit cards often make up the difference in price, most typically include a free bag per person on the booking ($100 roundtrip value on Delta for the two of us) and earlier boarding. At the highest level of benefits you can get free upgrades to premium economy and first class, as well as free lounge access (which we use a lot when traveling).


When considering making yourself loyal to an airline, think about where you will be flying from and to most often. Big city dwellers like those in NYC and LA have a bunch of options, while others should have a pretty clear choice. We picked Delta because it’s one of the biggest airlines in the world and it’s the biggest in Charleston, so we knew we’d be flying it often.


Outside of airline credit cards, the list of rewards programs in travel are endless. At a minimum you should signup for free mileage plans with airlines. Even if you don’t fly often you might earn enough miles to upgrade a seat every once in awhile. If you do want to explore a travel card but can’t commit to any single airline, American Express Platinum is a great card for travelers which offers access to lounges, amazing perks at Fine Hotels & Resorts and 5X points on travel and a lot more.

ITA Matrix is great

One of our favorite booking tools is ITA Matrix. While you can’t book directly through ITA Matrix (you have to then find the same flights on the airline’s website), it’s a great visual tool with lots of filter options. It’s especially useful when planning multi-city flights.



Non US traveling is a whole other beast

When traveling to and from Europe or in Europe, be wary of the potential for strikes.
Europeans are famous for going on strike. One week it’s pilots, another week it’s train conductors, the next week it’s air traffic controllers and then there’s always the question mark of how “legal” Uber is any particular city. There are certain things you can’t avoid but when flying between Europe, we will book a flight on a U.S. airline, if possible.


We’ve found American Express Travel to be extremely helpful for booking rental cars, especially in Europe because you can specify automatic transmission. We used it pretty much on every trip (Ireland, Iceland, Hawaii, Europe and more).


Europe has an amazing network of trains so when traveling in Europe make sure to consider this awesome way to get around. Three of our favorite things about train travel are: train stations are normally found in city centers compared to airports which are much further away, no cost for luggage, and you can show up 10-15 minutes before a departing train compared to 1-2 hours before a flight. If you are new to booking trains, checkout (formerly Captain Train) it’s what we use every time to book trains in Europe.


So that’s it, these are all of our booking secrets. Now that you have your trip all confirmed you should be all set for a little while. The next step is to start thinking about what and how you are going to pack? Tune in next time for the next article in the travel series.

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