Create a Travel and Credit Plan

Oh no, you might have lost me...
         I understand, goals and plans are made to be broken.  Often we forge again with a plan only for an unforeseen obstacle to get in our way.  Perhaps there's no better picture of this reality than in most of our financial lives.  Yes, yes, the wise man would save up money expecting to replace his tires every few years, but so often we neglect the savings plan for the "wearing/flat tires" in our lives.  I can assure you that I dislike budgeting and all such saving plans even though I know the wisdom of it (and do some of it).  

          However, when it comes to seeing how to maximize what percentage back I can get from my purchases (or freebies) and when I dream of where to fly on my miles and where to stay on my points, that's when planning gets exciting.  Of course, you can stumbling into this and still make some points/miles but you could waste valuable time and/or credit inquires that slow your vacation possibilities.  I would propose there are only a few things in life more important than a good vacation with your family or traveling to see your family/friends on a regular bases.  It is also very rewarding to fly someone to see you, points/miles can make excellent gifts. 
Staying in an executive suit on a FREE upgrade because my wife has the Citi Hilton Reserve card with complimentary Gold Status is just part of having a good plan to save money and use credit cards to your benefit. 
Food/snacks/drinks can be expensive during your travels, that's why gold status, platinum status, or elite status means savings for you.  Often with upgrades you receive  free food and drinks on your journey.  These executive lounges are in most high end hotels and most airports.  We ate so much in Venice, Rome, and Curacao in executives lounges that it saved us from buying lunch or dinner.  
This is your LARGE cappuccino in Europe.  Yes, they want 3 euros or more for this 3 sipper.  Saving money for vacation still needs to be done the old fashion way for taxis, food, and souvenirs.   Although, there are ways to get your car rentals on points and reimbursements for travel on cards such as Barclay's Arrival and Miles by Discover.
If you want to go to see Ludwig II's castle, it takes planning.  These views are possible on the cheap, take a look at the region around Munich, Germany in this short video...
Know your travel plans (if possible)

          There is a big difference between flying within the continental United States and anywhere international.  Even though Europe might be closer to the USA, it can still cost more miles/points if you want to travel business class (or winter/summer).  Where do you live?  What are airlines have the closest "hub cities" to your proximity?  For example, when I want to gather American Airline miles through Citibank I know I must fly out of Chicago.  When planning overseas trip, Delta might be my next choice (points are often harder to gather and they lower the values of their Skymiles too often lately) but I need to fly out of Minneapolis.  Continental USA and sometimes the Caribbean are cheapest flying Southwest through their Rapid Rewards program out of Milwaukee.  You need to be familiar with your surroundings and aim for the points/miles of how to fly there first.  

Rule #1 - Know what airline you want to fly and how many miles/points it would take to fly you and each member of your family during the season you want to travel.  Aim for these miles/points credit card sign up bonuses first and learn any programs/shopping portals that you earn more bonus miles throughout the year.  Off-peak flying usually requires less miles, such as, American Airlines off-peak time frame to Europe is October 15-May 15th each year.  Each country/Hawaii has it's own off-peak time frame.  Hawaii, for example, has off-peak dates of January 12-March 13 and again August 22-December 15 each year.  Here's American airlines Award Chart, but know the airline you choose. 

Rule #2 - Know which bank miles/point card will transfer to your airline to boast up your account.  For instance, American Express Membership Points can be transferred, often at a bonus percentage to British Avios, Hawaiian Airlines, and Virgin Atlantic Airlines.  If you sign up for the 50,000 Membership bonus that happens throughout the year, sometimes targeted, sometimes for everyone, then get 30% bonus to transfer them to an airline you want to fly, you'll be ahead of the game.  Note: Chase Ultimate Reward points are the only points that transfer 1:1 to Southwest Airlines.

Rule #3 - Know the hotel you want to stay in and learn which cards give you the best bonus offers AND hopefully an Upgrade to a higher status.  For example, the Citi Reserve card or the American Express Hilton HHonors Surpass give you free Gold elite status (think free internet and breakfast, room upgrades if available) and how to gather extra bonus points.  Note: Upgrade in status cards almost always come with an annual fee up front.  Such as the Chase Hyatt, US Bank Club Carlson Cards, and these Hilton cards mention above).  

Rule #4 - Know which bank or airline rewards cards that can transfer to your airline or hotel you want to use.  In addition, diversify as much as possible with some Chase Ultimate Reward(UR) point card(s), AMEX Membership points card(s) and any other points that transfer between airlines and hotels easy.  The AMEX SPG cards are good for Starwood hotels and transfer at 20,000 to 31 different airlines, including American Airlines, with a 5,000 bonus.  That's a 25% bonus, so these points are worthwhile.  Chase UR's transfer to Hyatt, Southwest, Virgin Atlantic and several others. Also, Hawaiian Airlines miles and Virgin Atlantic Flying Club miles transfer 1:1.5 to Hilton but take a few weeks to completely transfer over.  

Rule #5 - Know your finances and do not neglect your credit needs just for points/miles.  In other words, if you, and I hope this is not the case, carry a balance on your credit cards sometimes, it is wise to start a home business or apply for some business credit cards on your current business.  Capital One business cards, in my experience, show up on your personal report, but US Bank business cards often do not.  This is my personal favorite card for carrying balance needs.  First, US Bank does not like to see a lot of inquires on credit reports and they definitely like good/excellent credit scores.  Flexpoints are wonderful if you use them for flying.  You can often get 17,500 bonus for opening the card or more and after you complete the $2,500 minimum spend in 5 months, you will have 20,000 Flexpoints which are equal to a flight up to $400 in value or just $200 in value for merchandise, etc.  Often, once you've had their account for 6-12 months they offer 2,000 bonus points for 0% balance transfers for 18 months over $1,000 with a 3% fee (they mail the offers, they are not automatic).  This means if you transfer $1,001.00 from a personal card to your Flexpoints business card you will spend $30.03 to do so but receive 2,000 Flexpoints worth up to $40.00 in flights.  If your financial needs include carrying a balance for virtually 0%, then this card should not be forgotten.   NOTE: This card has an annual fee, your financial needs and credit score probably need a 1-2 cards you never cancel, then carrying a $0 annual fee card is wise.