10 Steps to Planning Your Best Trip Ever

When I graduated from high school in 2009, I decided to take a trip to New York City. I have a cousin that lives in Manhattan and was working on her doctorate at the time, while teaching at a university. She had a nice apartment between Times Square and the Hudson River, which was a great, central location.

I had the best time! I flew in by myself and spent a week wandering around the city and going out to dinner at fancy places with my cousin. I got to see a three-story Barnes & Noble! As a bibliophile, this was amazing. After the first week in Manhattan, I was lucky enough to have my mom fly out and spend a long weekend with me. We went to the Empire State Building, Statue of Liberty, and Times Square.




Battery Park




This was taken at the Metropolitan Museum, if I remember correctly



Why do I bring up this trip from eight years ago? Because we’re going back in May!! I can’t begin to tell you how excited I am about this epic trip. I freakin’ love NYC; I want to live there some day, even if it’s only for a year. We’re also lucky enough to be able to go down to DC during this same trip and see my boyfriend’s sister, who lives nearby in Arlington, VA.

Let me give you a rundown first. We’ll be flying into LaGuardia–my parents, brother and his girlfriend, and Ryan (my boyfriend) and me–on Wednesday, staying in NYC til Monday. At this point, my family will fly back home, leaving Ryan and I to take the Amtrak from NY to DC and we’ll stay there til Sunday.

I’ve planned a lot of trips. I may have mentioned in my Ski Trip Destinations post, I’m essentially the “travel agent” of my family. I’ve planned most of our family trips, including finding the best deal on flights, rental cars, and equipment rentals (snowmobiles, skis, etc.). I also do the research on destinations and what to do there. I love planning trips.

I’m here to give you as much advice as possible, if you want to plan a trip and aren’t sure where to start. Without further ado, here are the 10 steps to planning the best freakin’ trip ever!

1. Choose Your Destination

Where do you want to go? This might be one of the most fun parts of the process. Do you want a beach destination, big city, secluded woods? Do you want to stay in your area or travel over state or country borders? As you can see, this step has a lot of questions to ask yourself.

2. Decide When You’ll Go

Now, this step is fairly dependent on your location. For example, you probably don’t want to go to Alaska in the winter, unless you’re looking a rugged and cold freezing adventure. You probably don’t want to go to Disneyworld in the summer when kids are out of school. This step goes hand-in-hand with Step 3:

3. Research

Another of my favorites (oh, who am I kidding, I love everything about planning a trip!). For this step, Google is your friend. I start by literally just googling my destination. One of the first few results will typically be the city or country’s tourism site, which is a great starting point. There you can find what the weather is like, what do expect in the area, and the history of that destination. Some places will even send you a free travel brochure or book through the mail or as a download. The Washington D.C.‘s tourism site sent me a cute and well-put together booklet about the city and surrounding area.

Now, two big factors to consider are weather and currency. You’ll want to be sure that you’re prepared for the weather during the time you’ll be there. We’ll be going to NY/DC in May, so I actually googled “weather in NYC in May” and found a site that gave me the information about what to expect (they said 60-70°F, fyi). So, now we know to take light jackets and warmer clothes–we’re from Texas, so in May, we’ll be expecting the temperature to be up in the 90s here.

Currency. This is fun. Obviously, if you’re going to stay in your country, this is likely not a concern. If your travel destination is in a foreign country, you should definitely see if they accept your country’s currency. When we went to Canada, it was a pretty even split of places that would or wouldn’t accept US Dollars. We exchanged currency at a bank in Canada, if I remember correctly. This is another thing to research. A lot of places, including banks, will give you an exchange rate that favors them. The best option is usually to purchase the currency at home and take it with you, at least in my experience. I used to be a teller at a local Texas bank. We would exchange currency, free, for bank members; and it was only a $5 fee for non-bank members. Check with your local banks.

Also, check on your bank or credit card’s policy for making purchases in another country. You definitely want to notify them that you’ll be traveling. I notified my bank when we were going to Seattle and Canada, but something was mixed up and the bank still saw my purchase in Seattle, canceled my card, and mailed me a new one–to my home in Texas, while I was in Seattle. Thankfully, I had a backup credit card and was able to use this during the trip. But this should emphasize the need to double check that your bank knows you’ll be traveling. While you’re checking on that, see if the bank charges a fee for making purchases in a foreign location. Most banks will charge 1-3% of your purchase amount, which isn’t much for a soda at the gas station; but if you’re paying a few hundred bucks for ski lift tickets or an expensive dinner, this can add up pretty quickly.

Step 4. What Can You Do There?

What does this destination offer? If you’re going to Hawaii, are you just going to hang out at the beach all day everyday or do you want to go snorkeling and waterskiing? The destination’s tourism site should give you good starting knowledge about what you can do there. When we go skiing, I’ll look up the area’s tourism site and see if there are any other ski resorts we should check out or if we should just stay on one mountain. For New York and Washington, D.C., I know there are hundreds of things we can do.

Did I mention tubing is an option?

I usually start with the tourist-y things. My dad, brother, brother’s girlfriend, and Ryan haven’t been to New York City before; so the first night, I’ve planned a bus tour that goes around the city so they can see everything. I’ve also planned for us to see the Statue of Liberty/Ellis Island, Empire State Building, and Times Square. My mom has wanted to see Cats since I was a kid, so I’m taking her to see it. My brother wants to see a Yankees game, so that’s in the itinerary. I’ll write a separate post about our trip, if anyone’s interested in some ideas about other things to do in NYC.

After you decide what tourist-y things you want to do, see what unique things the city offers. In Whistler, we went to the world’s coldest vodka tasting room (it was -25°F!), which was a great experience that we couldn’t have had anywhere else.

Step 5. What Do You Want To Do?

This pairs very closely with Step 4. I start with a master list of everything the city offers that sounds fun and is in our price range (there was a helicopter tour of Manhattan that sounded awesome, but was definitely out of our price range). I prefer to write the list by hand and then highlight things we actually want to do. For this step, make sure you think about how much time you have and your budget, which leads me to:

Step 6. Budget

Once you know where you’re going and what you plan to do there, you can start thinking about budget. This step includes the following everything we talk about in this post, and it’s a good idea to budget over. You know what they say: take half the clothes, twice the money!

Step 7: Getting There

Will you be flying? If you’re terrified of flying, can you drive or take a boat to get to your destination? How much will it cost to get you to where you want to go? One tip I have is, if you’re searching for the best flights online, make sure you’re “Incognito” or whatever your browser’s version of private browsing would be. When companies see you searching for flights multiple times, they know that you’re interested and start increasing the pricing. This is a real thing that happens, even though it’s not fair to the buyer.

Step 8: Transportation and Housing


Look up how you can get around in your destination. For all of our ski trips, we’ve had to rent two or three large SUV’s to fit everyone and our luggage or gear. In New York and D.C., we’ll be able to take public transportation, so I did some research and found the best option in NYC is to buy a Metrocard that’s good for seven days, which will cover the length of our trip.

For housing, we use sites like Airbnb or HomeAway. I usually look at hotels also, just to make sure renting the house really is the cheaper option–it usually is. Plus, it’s so much more fun to be able to hang out in the evenings with your trip mates.

Step 9. Food and Drinks

A good chunk of your budget will likely go to food and, depending on your preferences, may go to drinks as well. If you want to go the “budget-friendly” route and you’re staying at a place that has a kitchen, you can go grocery shopping and pick up the majority of your meals to cook there. We stop somewhere on the way to the house and pick up breakfast and dinner items, snacks, and drinks, like soda or beer. This lets us save money on eating out for expensive dinners or drinking at a bar. We’re usually at the ski resort or out and about for lunch, so we budget to eat lunch out somewhere.

I would suggest also looking at the menu of some restaurants in the area to get an idea of what to expect. Here at home, we can go out for dinner and spend $50 for two entrees and drinks, but the equivalent in New York City would be closer to $100, so that would definitely be a budget killer if you’re not careful.

Step 10: Organize and Have Fun!

I like to make an itinerary or even just a list of everything: how much we’re paying for flights, rental cars, prices for ski rentals or lift tickets, etc. Send it to everyone in the group so everyone’s on the same page about what to expect.

Have fun! This is your vacation, you should be excited and not stressed out. Word of advice: something will go wrong. It always does; in Seattle, my debit card was canceled, on my NYC trip in 2009, I was so exhausted from walking around the city after a few days, I had to spend two days just hanging out in my cousin’s apartment; in Park City, I tore my ACL! But one of the best things about traveling is that you’re out of your comfort zone and experiencing life! Roll with the punches–if you keep a good attitude, even a bad experience can be funny looking back.

I hope this list is helpful; if you have any questions, let me know.  🙂

P.S. If you’re feeling adventurous, you can always just scrap the list, buy a plane ticket and wing it!











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