How to plan your dream trip

Do you ever feel like there’s never enough money for that dream vacation?

You’ve been talking about visiting a certain country or continent for years, but the thought of planning it and paying for it has you stuck in the ‘one day…’ loop.

I used to struggle with it too – but over the last few years I’ve figured something out.

For close to 20 years, I dreamed of visiting my distant cousins in Africa, but the cost of a $2000-5000 flight scared me off. I always thought… “one day.”

Then, I turned 40 and realized that if I didn’t make it a priority, I’d blink and be 60 and still have not taken my dream trip to Africa.

I don’t want anyone else to be held back from taking their bucket-list trip because of money the way I was!

Getting started with Rewards Points

I remember when I stumbled upon ‘travel hacking’.

I was pretty sure that I would never be able to pull it off. After all, I have low monthly personal expenses, didn’t trust myself with credit cards, and I am not super nerdy about planning trips.

And for the first few months, I really struggled learning the ins and outs of points and miles for cheap flights.

  • Cash back?
  • Points?
  • Miles?
  • How many do I need for Africa?
  • How do I get them fast???

It wasn’t until I sat down to actually plan my dreamAfrican Adventure‘ that I finally figured out what I was missing.

recycling in Ethiopia Africa
travel blogger and rewards points for free or cheap flights to Africa
work remotely and travel the world using points and miles for Africa

Where would you go with a free flight?

Best business credit card for travel

Now, years later, I’ve taken many more free trips, made mistakes, learned more tricks, and I have even gone back to Africa again.

I’ve also taught others to do the same…

  • My wedding clients, James and Laura, were in the throws of planning their dream wedding and they were able to harness that spending to earn enough points and miles to go First-Class, around-the-World on their honeymoon for two weeks (including hotels!). They have taken many more trips since.
  • A wedding photographer friend, Lori, paid over $2500 for economy seats with her husband when they went to New Zealand. After my yelling at her (It’s what I do… ha), she has not paid for a flight since! Hawaii, Spain, Seattle, Florida, California…

I want you to know that I understand how it feels to dream about a specific country to visit. And it’s totally possible to learn how to quickly earn points and miles, and more importantly how to redeem them so you can travel more.

5-days in Ethiopia with a free flight stop over and layover in Addis Ababa and Lalibela

how I planned my dream trip using points and miles

Planning a dream vacation, epic honeymoon, or a big family vacation after years of staycations is no easy feat.

So, how do you actually start the long process of planning a dream trip using credit card rewards points and frequent flier miles?

The first step to planning any rewards trip is to get an idea for where you want to go, who flies there, and what layover options does it provide.

Planning a dream vacation is similar to planning a regular one… is starts with a dream and some basic research.

When I went to Africa the first time, I paid $82 for my International flight and used Chase Ultimate Rewards Points for flights within Africa as I went along. Those were great because I could buy those flights last minute.

For my second trip, I paid $84 for my flight’s taxes & fees + $125 to change my flight when I decided to do an extended layover. 

This is how I planned my flights to Africa using points & miles….


Where do you want to go?

For me, I was dreaming about Africa, but Africa is 3X the size of America, so where specifically did I want to go in Africa?

Well, I have relatives in Zimbabwe that I’d met before, so I wanted to visit them for sure. After that, I wanted to go visit my Mom’s cousin in Livingstone, Zambia because I knew her really well too. Other than those two countries, I didn’t have any real plans. 

Cape Town was naturally on my mind, and I did have one of my past Grooms plan out a 5-day locals itinerary for me, as he has a travel planning company that does exactly that.

What I ended up doing was going on a Photographer’s Safari in South Africa because I found out some photog pals of mine were going to be there at the exact same time as my trip! Yes, please!


Who Flies there? How?

This is where I do a little recon on which airlines fly to Southern Africa and look into the layovers, connections, routes, etc. 

For my first trip to Africa, I drove from Rochester, NY to Boston to visit friends for a few days. Lufthansa had a flight from Boston to Frankfurt, where I could visit more friends. From there, I took a Lufthansa flight from Frankfurt to Johannesburg. Jo-berg is a huge hub in South Africa for nearly all flights in Southern Africa.

Hot tip: you can ask the airline for an extended layover. The Frankfurt connection was already a long-layover of 14 hours, so I just asked them to put me on the next day’s flight so I could visit my friends nearby. It’s a great way to see another location and stretch your legs/shower/etc.

Reality check: My friend’s in Boston gave me a stomach bug and I flew out of Boston a day late! This ruined my sneaking in a free trip to Germany en route. Thank goodness I had that layover already built in though.


Economy or First Class?

Long-haul flights are brutal, as airlines reduce seating width and legroom. There are a lot of travel hacks for enjoying the ride in economy airplane seats, but nothing beats a first class or business class seat on an overnight flight to a destination far far away. 

When I went to Singapore, the best part of the trip was the first class flight from Chicago to Japan!

My goal for Africa was first-class because of these long flights. It didn’t work out for me, but I earned plenty of miles for it and ended up taking like five more trips that year because I had extra points. Win.


Need a hotel or Rental Car?

While earning and planning for rewards points, it’s helpful to know if you want to stay with friends & family or if you might need hotel points & rental car options. 

I’ve never been much a hotel person until I learned just how easy it is to get tons of points using travel hacking and sign-up bonuses.

Airbnb is run by a bunch of imperfect humans that aren’t business people (unlike hotel chains) and I’ve been screwed too many times.

–>> Now, especially right around a flight arrival/departure, I always stay in a hotel.

When my parents and I flew to England a few years ago, we spent three hours trying to find our Airbnb in Chester. UGH. We had been up all night on the red-eye flight from Toronto to Manchester, spent time in the airport getting the SIM cards and rental car, met up with family for lunch, and were EXHAUSTED.

The Airbnb owners gave us TERRIBLE directions with a map that was unreadable. We even stopped locals on the street to try to have them decipher it for us. Three hours.

It took three hours for us to figure out that we needed to find this odd alley behind the building we were staying at to find the parking spot and key. Then we get into the apartment building and needed another treasure map to show us which door was actually ours.

We finally get into the Airbnb, tired, smelly, hungry, angry, and there are no frikken towels in the bathroom.

So, now I stay at hotels often!

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after you spend $3,000 in purchases on the Card within your first 3 months of Card Membership.

We can both get rewarded if you’re approved! Learn more…

how to plan a honeymoon using points and miles
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How many miles do you need?

Now that you’ve decided where you want to go and how you want to get there (in style, by the way), now it’s time to figure out how many points & miles you’ll need to make your dream trip happen.

Airlines have award charts and that’s a great place to start. Hotels have an option to see the rates based on points as well. Rental cars are a different story and you can actually use points to pay for that too if you want.


Pick a Travel Credit Card

The next step is to strategically choose a new travel credit card that gets you a bonkers awesome sign-up bonus. Sign-Up bonuses are the key to earning credit card rewards points and airline miles fast.

–>> If you don’t know what signup bonuses are, download my Free Flight Guide and I’ll tell you all about them.

I take a 1-2 punch to getting a lot of rewards points fast:

  1. A general travel card that allows you to transfer the points into ANY airline, hotel, or rental car.
  2. The Airline brand card for your possible flight route.

This last trip to Africa was through just one sign-up bonus on a business United Airlines card {referral link: I can be rewarded too, so thanks!} + a few Chase Ultimate Rewards points. I flew from Toronto to Harare, Zimbabwe via Addis Ababa. You heard that right… just one sign-up bonus! The flight taxes/fees was a whopping $84!

Earn 50,000 bonus miles with United Explorer Card.

I can be rewarded too if you apply here and are approved for the card.

Find cheap flights

Planning your dream trip doesn’t have to be painful. Yes, redeeming points and miles and earning them fast can be a part-time job, but it doesn’t have to stress you out.

The key is just to start. I started with a cash back card, then I moved to an airline card, and then I learned all of this fun stuff and now I go crazy opening a lot of different cards and closing them as well.

Where will you go with a free flight?? Chime in below in the comment field or DM me on Instagram @aparallaxlife.

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