When you hit the road over 100 days a year, people start to take notice. Below are some of the frequently asked questions, tips and thoughts to get the most out of your travel experience.

How Far in Advance Should You Book Travel?

This is a tricky question, it really all depends on where you are going and if it is a peak travel time. Best rule of thumb is 21 days out domestic so you get the best airfare rates and 2-3 months for international travel. If you are going to a destination that has a peak season (Caribbean during winter or Europe during summer) it can be to your advantage to add some extra time to plan your excursion to get a better deal.

::BONUS TIP:: Hotels.com will offer a price match guarantee, which is a pretty sweet deal if you book far enough in advance and notice that the hotel has a lower rate than what you paid, all you have to do is call them up and they’ll refund you the difference. We have used this strategy a few times and saved over $300 on an international trip.

What is the Best Day of the Week When Booking Airfare?

Surprisingly enough there is not magic day to book airfare. Sunday, Monday & Tuesday seem to be the best time of the week to look for deals. Most Airlines do their sales first of the week and sometimes will scramble to price match one another, so from Sun-Thurs there are always some type of fare sale going on. Just like the question above if you can schedule your departure 21 days out you can usually save some big bucks and if you are going last minute airlines will fire sale seats to fill the plane. My best advice is to plan ahead and check fare fluctuations over 2 weeks to compare for the best price. Sometimes it may be cheaper to alter your travel days to save mega bucks, for example if you fly out on a Thursday rather than Friday and return on Tuesday instead of Monday you can see significant prices in airfare.

::BONUS TIP:: Sign up for an airline loyalty program with your choice airline. You will get their fare sale alerts weekly and can sometimes get deals through email that are not posted online. For example we like to fly Virgin America when possible and every Tues/Weds I get a sale on tickets via email and sometimes I get better deals (special promo codes) than if I looked online. American Airlines also releases fare sales via email on Mon/Tues.

How Can You Avoid Extra Fees?


We get asked this question a lot and the answer is not so black and white. Yes you can get free bags on Southwest Airlines but their fares are often higher than other airlines who charge for bags. So its best to check rates/fees for a few airlines and see who has the best deal. One airline to lookout for is Spirit, they have low fees but then upcharge for seats, bags and carry-ons. Most airlines offer free soft drinks but will charge for alcoholic beverages and almost all airlines upcharge for meals, so if you do a little research then you can save a lot when it comes to hidden fees.
::BONUS TIP:: Credit card and frequent flyers can almost always get free checked bags, upgrade offers and change fee discounts. We have a Virgin America Credit Card because they are one of our favorites to fly, we get free checked bags and no change or cancel fees on bookings made with the card. This is hands down one of the best airline cards out today because you can loose huge if you have changes to your airfare in fees.


Mini bars, wifi and parking can all be fees to look out for when booking a hotel. If you are on a budget it may be best to grab some snacks on your own and use your smart phone to browse the web. There is little relief as some chains offer free wifi and others give free bottled water. Most Vegas Hotels often have hidden charges referred to as “resort fees” and these are mandatory no matter if you use the services you are paying for. Its always best to read the terms before confirming your booking to avoid fees.
::BONUS TIP:: Another way to save on fees is by joining a hotel loyalty program and stay at a particular chain to gain status. We have multiple loyal accounts with Omni, Hilton and SPG – these always ensure we get the best deals with the least amount of fees.

Car Rentals:

It’s all about reading the fine print. While it may be convenient to bring the car back on an empty tank you could end up paying big time. All rental car companies charge abnormally high rates for fuel per gal for cars returned less than what they were rented out with. Turning in the car too early or later than your agreement could also cost you so its best to look at the contract before signing.
::BONUS TIP:: Tired of being pressured into buying “insurance”? Most major credit cards will cover you for Collision Damage Waivers or CDW’s so check with your credit card company – this will save you big and will be less of a head ache. Try booking your car online which will also save over the counter. We always use Budget because the rates are really good for a chain, the service is good and we can save money by booking online over going to the counter. An added bonus…Budget has a program called FastBreak with will allow you to get your car without going to the counter, making your travel quick and easy!

What Are Your Rights When Your Flight is Delayed or Canceled?

Let’s face it, flight delays and cancellations suck big time and can be a drain on your getaway. Depending on what’s going on every airline has a different policy, but most will rebook you on the next available flight and sometimes on another carrier if the delay/cancellation is the airlines fault. If the delay/cancellation is weather related you will be allowed to rebook another flight with a voucher or get a refund.
::BONUS TIP:: If your delay is in your home base, hold out for a voucher. Airlines will often try to give out vouchers for free flight to compensate passengers who will give up their seat to another passenger. Its all about what you are will to do for them and what they will offer you. Best way to do this is to casually approach the gate counter and quietly offer your seat for a voucher or first class upgrade.

Vacation Insurance, yes or no?

This all depends on where you are going and the time of year. For example if you are traveling to the Caribbean during hurricane season, it may be wise to purchase travel insurance. It is always important to look at the risk factor vs what your trip cost when deciding to buy Trip Insurance. Most airlines will cover you if the trip is delayed over weather. Also look at your hotels cancellation policy most will let you off the hook with no penalty if you cancel within 48hours. So for the most part I decline the extra cost of insurance.
::BONUS TIP:: Most travel reward credit cards will offer some type of Trip Insurance at no additional fee, its just a perk of being a member. For example certain American Express cards cover major medical/weather events if you book the entire trip on their card. Also did you know that your home owners or renters policy covers your goods when traveling? Depending on your policy if you take your camera or laptop and it gets stolen, your home owner/renters insurance will cover it. Read your policy and you may be pleasantly surprised.

How Do You Score an Upgrade?

This is another question we get asked all the time. Upgrades aren’t as hard to score as one might think and if you work it right, it could even be for free. Below are a few ways we’ve found upgrades:


Join a loyalty program and start racking points is one way to score a upgrade for very little out of pocket expense. Once you hit enough miles you can book a reward ticket for just the taxes or use those miles to upgrade the coach ticket you already purchased.
Another way to score and upgrade is to call or check online a few hours before departure and see if first class seats are still available. Most airlines will drop the prices last minute to fill extra seats on the plane, thus giving you a sweet upgrade for a fraction of the cost. We do this all the time with American Airlines and Virgin America and get our first class upgrade for about half the full fare rate. Even if you can’t go first class a lot of times you can get extra legroom for a nominal fee.


Loyalty programs is the fastest way to an upgrade at hotels. Hotels will offer their loyal customers speedy check-in and complimentary upgrades – so this is the best way, hands down. You can also use loyalty points for a free nights stay or upgrade. Arriving late in the day can sometimes help your cause as well, as hotels will often try to fill their open rooms quickly.
Another way to score and upgrade is to make sure you book directly through the hotels website and if you are traveling lets say on your anniversary make sure you tell the hotel about it. Its not guaranteed but sometimes the staff will either bump you up to a nicer room or give you a bottle of champagne to help you celebrate. In life its all about the little victories so it never hurts to mention a special occasion and see what happens.
::BONUS TIP:: Sign up for a hotel reward credit card or travel rewards card such as Amex or Chase Sapphire. You will usually get a signup bonus which will equal a free nights stay (on hotel credit cards) or enough points on a travel card to transfer to a hotel loyalty account to get an upgrade.

Car Rentals:

At the rental-car desk, asking for an upgrade might work, but make sure you’ve weighed your options: A higher-class car could mean higher gas costs, which can quickly negate any benefit. In any situation, even with the airlines, it never hurts to ask; when you do, dress nicely, be specific with your request, and above all, be polite.