How to be Your Own Travel Agent

Planning a travel adventure isn’t the mysterious process it used to be before the Internet made a wealth of information available to anyone with connectivity. Ideally, your planning should happen roughly four months before your trip to reap the best deals and guarantee availability. Here are my tips and tricks for getting the most out of your next trip, broken down into parts. I recommend that you read them in order, but feel free to skip ahead.

  • Step One: Establish your vacation vision / travel personality
  • Step Two: Purchase airline tickets
  • Step Three: If required, acquire visas / inoculations/medications
  • Step Four: Refine the pace/scope of your travel
  • Step Five: Research transportation at and between destinations
  • Step Six: Book your accommodations
  • Step Seven: Explore sightseeing/day trip opportunities and book ahead where necessary
  • Step Eight: Figure out what to pack


A big part of successful trip planning involves really thinking about what you would like to get out of the time (and money) you are spending.

Do you need luxurious relaxation? A romantic getaway to spice up your relationship? A long put off visit with far flung family or friends? A chance to cross something off your bucket list? The opportunity to get fit, improve your golf game, try sky or scuba diving or climb Mt. Everest? Would you prefer to spend your time in urban or bucolic adventures? Do you want to travel alone, with your significant other, a friend or a group? Are you on a really tight budget? In a lot of ways this is like the reflection high school seniors need to do when thinking about which colleges to apply to.

Be realistic about what amount of time is not just possible but optimal to do what you want to do. Must you travel between certain fixed dates or do you have flexibility?

A vacation isn’t really a vacation if you come home more exhausted and stressed than when you left. Long distance travel can take the wind out of your sails, what with last minute stuff to take care of at home, the stress of air travel these days and jet lag. If you are trying to visit three faraway countries in ten days — which is actually kind of crazy — you will need to plan differently than if you are spending three weeks in one place.

Figure out what kind of accommodations or mix of accommodations suits you and how much money you want to allocate.

Answers to the first two questions help to narrow down answers to this one. When Mr. D and I plan a trip we like to stay in intimate bed and breakfasts interspersed with one or two more expensive but non-chain hotels. This “high/low” approach stretches our budget, and allows us to splurge a little on the occasional once in a lifetime opportunity or a higher priced but more convenient option. If you are staying in one locale you might rent a place through, and if you don’t mind sharing a bathroom you can investigate hostels, which range from early ‘70s dormitory to really quite plush. Likewise, if you know that you have to have certain amenities or you will be miserable, be realistic about how that will narrow your choices and inflate your budget.

Once you have a destination, a time frame and a rough sense of the kind of vacation you want to have — do your research.

This is where the fun/time suck/savings start.


This is often the biggest expense of a long distance trip, so spending time getting a good deal leaves more money for other things. Round trip tickets are always cheaper, so plan accordingly.

A recent survey found that the optimal time to buy airline tickets is 151 days before travel. It used to be that last minute deals yielded the lowest fares, but with carrier consolidation and increased passenger travel that no longer seems to be the case.

The web has made buying tickets easy.

Sites like Travelzoo, Airfare Watchdog and Trip Advisor can inform you of hot deals in real time through e-mail alerts or Twitter. Aggregators like Kayak, CheapOAir and Expedia will search for flights and give results according to the filters you choose.

It pays to be flexible about not just dates and days of the week (Tuesdays are usually cheaper, for example) but airports.

Major American and European cities have multiple airports, generating large numbers of flights, both national and international. Sometimes different airports service different carriers. Sometimes it is cheaper to fly to a neighboring city and then to your final destination than it is to fly from your home city. Mr. D and I just experienced this flying nonstop to Milan from Newark Liberty at roughly half the price of flying from any Washington area airport. Even adding in the cost of getting to Newark from D.C., we were able to upgrade to Economy Premium for hundreds of dollars less than if we had flown from Dulles, Reagan National or BWI. Be creative when searching for flights!


The U.S. State Department website has all the information you need about acquiring a passport, arranging for visas, travel alerts and suggested inoculations, precautionary prescriptions, etc.

It can take a while to get these important aspects taken care of, so once you know where you are going it is wise to get started. Sometimes inoculations need to be spaced out and medical appointments aren’t always easy to get. Remember that insurance doesn’t always cover what is considered to be “elective” medical care. Travel health clinics catering to business travelers can often fit you in quickly, and have vaccines and medications on hand. I used Passport Health in the D.C. metro area and was very pleased with their speed and follow-up.

It may not be required, but it is foolish not to purchase travel insurance.

When traveling internationally, Mr. D and I always buy travel insurance that provides for medical care, medical evacuation and all manner of logistical support should, heaven forbid, something horrible happen to one or both of us while traveling. Some plans also cover lost luggage, cancelled flights, etc. The peace of mind we have far outweighs the minimal cost. Don’t leave home without it!


Once you have your round trip ticket booked, thereby knowing the start and end dates of your trip, break the intervening time into what I like to call episodes.

If you are only going for a week, you might only have one episode. You are ready to book your accommodation. If you are lucky enough to have more time, think about how many places you would like to visit, or, alternatively, how many different kinds of adventure you would like.

Keep an open mind.

You may find that your original ideas aren’t as interesting (or feasible) as an itinerary built around more in-depth web browsing.

Look at a map.

I know this sounds like a no-brainer, but I like to begin big with a map of the region and country that I am planning on visiting and work my way down to local areas. This gives me ideas about how feasible it would be to move from place to place, and sometimes suggests places to include in my visit that I wouldn’t have thought of otherwise.

Find out where other people have gone and how they liked it.

The New York Times has been running a wonderful segment called “36 Hours in _________”. See if your destination or places nearby have been featured. Another great resource is Trip Advisor, which allows you to search destinations and then look at reviews for places to stay, places to eat and things to do. Guidebooks like Lonely Planet can be useful, but even more fun is searching for YouTube videos about places you think you might want to visit. You’d be surprised how much you can learn about fun things to do, weather and traveler tips this way. Researching our trip to Vietnam last spring I came across several travel bloggers whose advice was invaluable and who I continue to follow, like Audrey Bergner at ThatBackpacker.

Pace yourself!!

Mr. D and I like to change up the pace of our travel, inserting longer episodes at strategic points to refuel and relax. Often these are midway through a trip and consist of spending four or five days in one place, preferably with a low-key non-urban non-touristy vibe, and sometimes with a tad bit more luxury.


Once you think you know what your episodes look like, research how to get from one place to the next. Do you want to rent a car? Fly? Take the train? A bus? A ferry? All of the above?

Driving in some parts of the world is downright scary — think Ho Chi Minh City, mountain roads in Peru or anywhere in Britain trying to remember what side of the road to be on. Renting a car may also involve getting an international or local driver’s license, so be sure to check. Hiring a driver can be very cost effective in some places.

Train travel is cost effective and allows you to see the countryside.

Europe has wonderful, fast, clean, reasonable train travel, making just about any place accessible. Trains in the so-called developing world can be a bit of a nightmare, but can also really make for memorable, authentic experiences. And don’t forget train travel in North America. We took the Starlight Express down the West Coast last fall and highly recommend it! The best resource for learning the ins and outs of train travel is the magnificent, invaluable website The Man in Seat Sixty-One. Check it out!

Taking public transportation in urban areas is a must as it saves money and gives a real flavor of what life is like in a city.

After riding the Hong Kong subway system, for example, D.C.’s metro system really seems shockingly outdated.

And don’t forget to just walk, walk, walk. There is no better way to get to know a new place.


Once you know where you want to go and how you will get from place to place, it’s time to book accommodations.

Trip Advisor, and all review hotels around the world, and you can book through these sites. (Be flexible. If I have my heart set on a particular place to lay my weary bones, I sometimes change my itinerary to accommodate its availability). Once you have really thought out how much time you wish to spend in each location, know how you will travel between them, and have secured your “must haves” you might consider non-refundable bookings, which can save you quite a bit of money. Paying at home also saves you the currency transaction fees that your credit or bankcard might charge you if you pay at the conclusion of your stay. And don’t forget about sites like and for apartment/house rental or bed and breakfast suggestions. Mr. D and I haven’t stayed in hostels, but this is also a choice to be considered, see

Decide whether you want to live like local or enjoy being a tourist.

When booking, Mr. D and I try to find bed and breakfasts or small hotels that are located in residential areas so that we can shop and eat at local haunts and minimize the need for expensive taxis. We prefer to spend our “splurge” money on either meals or “downtime” accommodations in smaller locales with beaches, magnificent hikes, gorgeous countryside, etc. But part of booking smartly is deciding where you want to allocate your precious dollars.


It pays to look at sites like and Trip Advisor to get ideas about tours and day trips that might make your stay more enjoyable.

You can book online in advance, or through your hotel once you arrive. Food tours and “hop on hop off” bus tours are especially helpful, especially if you are not familiar with the cuisine or the language of your destination, or if you don’t have a lot of time in a given locale to orient yourself.

Google the museums, theatres or attractions you wish to visit.

To avoid wasting time in long lines you should always check to see if special passes like the Firenze Pass (which gives you instant admission to any number of Florence sites) are available for purchase online or at a specific location. It may well be worth the extra money to avoid the hordes of selfies taking tourists at major sites by gaining immediate admission. If you need to reserve a specific time (for example at the Louvre) you can plan your itinerary around that if necessary.


You can Google “what to wear in _______________ in (fill in the month or season)” and find good advice for travelers, as well as look at YouTube videos to see what the locals are wearing.

Frankly, the most important thing to remember is that different destinations have different understandings of what is a) fashionable b) appropriately modest c) age appropriate. Please don’t wear tank tops and flip flops to religious sites even if it is 100 degrees out!

At least contemplate traveling carry on only.

Nothing is more exhausting than standing at the baggage carousel waiting for a bag that never arrives, or hoisting heavy luggage along cobblestone streets or up stairs. Even if you don’t succeed in fitting everything into a carryon size bag, trying to will help you to eliminate things you really don’t need. There are very few places in the world where you can’t buy toiletries or get access to a hairdryer. And remember, you are seeing different people every day so you can repeat and mix and match your clothes! You can see what I have packed for three-week trips to Asia and to Italy.

The best advice I’ve ever gotten on this subject is to place everything I want to take on the bed and then remove half of it.

Visit TravelFashionGirl for smart packing lists and tips and tricks for destinations around the world. While the audience for this site tends toward trendy twenty and thirty somethings, even mature travelers can adapt the advice to their own style. And the tutorial on packing cubes is a must for any traveler!


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