"IF YOU FAIL TO PLAN, YOU PLAN TO FAIL"
Ol' Ben Franklin said it best. In the initial steps of planning, there are a few approaches including contacting a travel agency, winging it or researching and planning. Both a travel agency and winging it are the least time consuming (initially); however, each come with their own risks. A dictated itinerary may not capture everything you wish to see and accomplish, and further, it offers the least flexibility. Winging it is a beautiful concept and can work with lesser-demanded locations or off-season travel; however, there’s the risk of experiences and accommodations being fully booked and worse, you return back home only to realize some experiences were missed. The safest and most tailored approach is getting your hands dirty and researching and planning the heck out of your trip to ensure you achieve the best experience and nothing is unintentionally missed. Research and planning starts online, and I hope to be a source of information for your travel needs.
Guidebooks also provide you with a wealth of information; both Lonely Planet and Rough Guides have worked well for me. Additionally, TripAdvisor is a well-established online travel review source. Whichever avenue you choose, the information learned will allow you to accomplish what you’re after, for your specific time frame. Cross referencing is huge, thus if multiple sources recommend a spot, it's likely a winner.
Regardless of where you visit, safety is priority #1. An approach that has worked well over the years is creating an itinerary noting down: dates and the locations you plan to visit, flight information and accommodations with contact information such as websites and phone numbers. Before departure, provide this information to family and friends so in the case of an emergency, loved ones will know your location and have the means to contact you. A final perk to this itinerary is after you return, if family and friends ask about what you did and where you stayed, this spreadsheet of goodness is only a click away.
Finally, try to get a sense of the safety levels of the cities you plan to visit. If you’re unable to achieve this before through research or discussion, simply get a logical snapshot when you arrive. We know what's required to remain safe and sound in our home country, but this can change when we travel. The majority of countries I've visited have been completely safe, but it's best to be prepared. As an example, in countries where theft is an issue, I've been asked to not place a mobile (cell phone) on a table, while dining outside. Reason being because thieves can steal the phone and run and unless you're Usain Bolt, you’ll be unable to catch them. In one of the proudest moments of traveling, I was catching a bus at midnight outside of a station and threw my bags in the luggage compartment and headed inside. About 10 mins later, I needed something from my bags and proceeded to the luggage compartment only to realize that my bags were gone, stolen. These points are not to deter traveling; moreover, they're simply suggestions to be smart and be aware. Research the (modern) pulse of the country and its cities, and know in advance what you’re getting yourself into.