So You Want To Plan a Trip…

I’ve received a ton of questions this week about how Ben and I planned our trip to Italy. Planning a trip overseas can be overwhelming. Where do you stay? How do you know what to do when you get there? What about the language barrier? Here are my Top 10 tips for planning a trip overseas.

1. Determine your budget.

Determine how much you’re willing and able to spend on your trip. Remember to factor in the amount of money you’ll need for food, sightseeing, getting around, shopping etc. once you arrive.

2. Decide where you want to go.

Will your destination be a tropical island, or a snowy getaway? Are you interested in sight seeing or relaxing? This will also determine how much money you’re going to need to have on hand once you arrive. Ie laying on the beach isn’t as expensive as buying a mountain pass to ski all day.

3. Decide when you want to go.

Heading to Australia during your summer break may seem like a good idea, but it’s actually winter down under when it’s summer in the US. Make sure you’re aware of what the weather conditions are going to be like at your destination before you book your trip.

4. Figure out how you’re going to get there.

If you’re able to drive to your destination, and only need to book a hotel, I recommend Thier website has a great structure for comparing prices, ratings and areas.

If you need both a flight and hotel, my go-to booking agent is Expedia always has the lowest prices of any of the travel websites, and they have the wonderful option of booking a multi-city trip. For example, I was able to book a flight and hotel in Rome, then a hotel in Praiano and return via the Naples airport, which was closer to Praiano then Rome.

Whether I’m flying or driving to my destination, I always check out to double check the hotels I’m thinking about booking. Simply search for the hotel you’ve found on or Expedia:


Then check out the reviews:


I’ve never been steered wrong by this website. Of course, you’re going to get the occasional bad seed who bashes the hotel just because they’re the type of person who can’t be pleased in life, but generally you can get a really good feel as to if it’s going to be a good choice or not.

5. Research things to do.

If you’re going to Bora Bora, your list of things to do may be as simple as lay on the beach. If you’re planning on going to a large city with lots to do, make sure to do some research. I love reading travel blogs or checking out guidebooks at the local library to get ideas. Googling “Top 10 Things to Do in XYZ” always turns up some great ideas as well.

6. Look into transportation methods available at your destination.

Will you be traveling to multiple cities during your trip? A call to your hotel might help you determine how to get from point A to point B, but a quick search on the Internet will most likely answer your questions too.

When trying to figure out how we were going to get from Rome to Praiano, I simply Googled, “how to get from Rome to Praiano” and the answer popped right up.

My encouraging statement is – it’s often easier than you think!

7. If you’re planning on traveling Internationally, and need a passport, allow at least 3-4 months to acquire one.

Getting a passport takes a long time these days and, if you’re recently married, allow the same amount of time to get your current passport updated. I completely failed in that department, as my still valid passport still had my old last name on it, so I took along a certified copy of my marriage license, which worked too!

8. Exchange money before you go.

You’ll often get better exchange rates if you go through your bank to get the local currency instead of waiting until you’re at the airport. Make sure to do this at least a week in advance of your trip as most banks will have to order the currency. Often times they don’t keep a ton of it on hand!

9. Brush up on the local lingo.

Don’t assume everyone speaks your language. When I lived in Japan for a summer in college, nearly all the locals I interacted with knew enough English to get by. That wasn’t really the case in Italy. Having a pocket translator book and knowing a few key phrases helped immensely!

10. Notify your bank, family and friends before you leave.

Make sure someone will know where you will be at all times of your trip. Hand out copies of your itinerary to anybody who will take one and let your bank know that you’re leaving the country, if you plan on using your credit card, so they don’t suspend your account for suspicious activity.  

All in all, traveling overseas is one of the most rewarding things you can ever do in your life. At times, the thought of planning and actually DOING it may seem daunting, but you’ll thank yourself a million times over in the end. You only live once, see the world while you’re at it!

Have a good day!


What’s your best tip for traveling overseas?