Before You Go
Take photos of your passport, credit cards and important docs. Make sure these photo files can be accessed by your mobile phone or on cloud storage such as DropBox so you can have ready access it the information if your passport/wallet/mobile phone go missing.
Check your passport expiration date
Check the need for a Visa at Visahq.com
Obtain Travel Insurance. Your vacation is a substantial investment. It is wise to hedge against the unexpected.
Contact your credit card company to inform them that you are traveling and provide your intended destinations so your credit card is not suspended.
Mark your luggage with "fragile" designation. The luggage will be place on top of other bags and tend to be the first to come off the plane.
Place a dryer sheet in your luggage or a hotel bar soap in dirty laundry bag to mitigate odors
Ensure you have adaptors to the destination you are visiting
Organize your cords by velcro strap or an unused case such as sunglass or headphone case.
Wear your heaviest coat and shoes to save weight and space with your luggage.
Roll your clothes.
Place a rolled up belt within the collar of a dress shirt to preserve the collar's form.
Pack a power strip especially if traveling to a destination that requires a convertor.
WIFI and Mobile Phone
Download the WhatsApp mobile application for free messaging and phone calls. It's a lifesaver.
Use Foursquare to find local free WIFI hotspots and potentially passwords to public use WIFI
Contact your provider and obtain an international calling plan that has reduced rates on calls and data. DO NOT FORGET THIS STEP.
If you have an unlocked phone, consider a GSM chip. T-Mobile pre-buys are a good choice for Europe.
Purchasing Airline Tickets/ Search For Flights
Use Kayak or Skyscanner with your browser in Incognito mode. Incognito mode disables cookies and cached searches so Kayak or other tracking flight booking sites will assume that you are starting a de novo search rather than present the same information usually with notices of an impending rate hike to spur you to book. On the Chrome browser you can find "new incognito window" option under "File"
Check the direct sites of Jet Blue or Southwest Airlines that may not participate in the OTA system.
Use Seat Guru to find the best seats and leg room on the plane. The site will provide seat maps for your flight.
Money and Currency Exchange
When you arrive at your destination, use the ATM to get the best currency conversions.
Bring an extra credit card and store it separately. Assume worst case scenarios in the event your luggage is missing, carry-on is lost or your wallet/purse is stolen. Have back up systems in place.
Split cash into various places on your person and luggage.
Use a money belt if you are visiting popular attractions.
At Your Destination
Engage in conversation with locals. Ask them for their preferences for restaurants and local markets. Don't be shy. They want you to enjoy their town and will take pride in giving the best advice. You can be surprised how wrong Tripadvisor can be.
Make an effort to speak the language. Learn some commonly used key phrases. Find an app that can provide brief language lessons so you can learn while en route to your destination.
Smile and Be Friendly.
Rent a Car and don't be afraid to get lost (in the right neighborhoods.) You can see and experience more out of the destination by finding charming villages, beautiful pastures for picnics and simply being off the beaten path. Have a GPS Navigation device handy in case you get too lost.
Avoid Tourist Traps and Safety Precautions
Research before you go. Check local forums for good places to eat. Avoid restaurants located near major attractions with no locals eating there. Follow where the locals dine.
Put your wallet in your front pocket or button up your back pocket. Pick pockets can be prevalent when going through a turnstile, closing subway doors or very crowded areas where a bump would not be uncommon.
Lock up your valuables in the safe and keep track. Make sure you have precise counts of your money. Keep exact records. For instance, some hotel safes can be compromised by staff that may take $100 out of $1000 stash which can be overlooked by guests.