How to Plan a Trip


When it comes to travel one of the most difficult parts is planning it! Where should you go? When should you go? Where will you stay? What will you do? And let’s not forget, how will you pay for it?! Well, if you know us at all you know that’s the easy part! We’ll use credit card points! The rest of it can be a headache, but it doesn’t need to be! Today we’re going to share with you how to plan a trip!

Decide Where to Go

The first step in planning a trip is deciding where to go! Do you have a place you’ve always wanted to go?  Hawaii?  Italy? Greece?  Those are some of our favorite places and you can read our guides on how we made it happen for us.

I have a huge list of all the places I’d like to go and I add to it all the time.  To begin, start a list for yourself. The more points you have the more ways you have to make that trip happen.

When can you go? That definitely changes the places I can go to.  I don’t want to go to Australia in my summer because it will be their winter. Summer is always a great time to vacation but also there is more demand then so that can change things.  Even award flights go for more when there is high demand.  I don’t know about you, but I want my points to stretch as far as possible!

I find that Europe is great in the spring and fall.  The weather is nice and it is less crowded.  During the winter, I always want a warm destination.  For this reason, I tend to look at Mexico, the Caribbean, and Hawaii.  Asia is stifling in the summer, so winter or early spring is the time I choose to go there.

So make your list and jot down the best time to go there after doing some research.  Keep that list handy and add to it as you talk to others or read about destinations.

Making Plane Reservations

The next step in how to plan a trip is finding the right award ticket for your travels. This can sometimes be challenging.  I have spent many hours looking at award travel in order to find what meets my needs.  I will start with flights out of my home airport of Denver and then start looking outward. Positioning to another airport makes it much easier to find flights.

For instance, I am flying to Chile soon and could not find award travel on a flight I liked out of Denver.  Now I am flying to Atlanta on my own dime (cheaply) and then taking a Delta flight to Santiago, Chile using points. Coming home, I found a flight from Santiago to Denver using points again.  It is on Copa Airlines though and I’ve heard mixed reviews.  These are all business class seats because they are long flights.

When looking for award travel it is often easier to look in one-way segments.  I may book one way with one airline and my return with another airline. I do this quite often.  It allows me to use different miles and also try out other airlines.  I just love getting on the plane of a new airline that I haven’t tried before to see how their business class compares to my favorites.  Truth be told, in my opinion, most compare pretty well because I just love the business class!

At The Airport

Hopefully, you have a credit card that gets you into a lounge.  Lounge access makes travel so much nicer.  A nice cold beverage, snacks, and comfy seats in a quieter atmosphere are the beginnings to a nice trip!  The opportunity to shower during a long layover doesn’t hurt either!

Turkish Airlines airport lounge Istanbul

Istanbul Airport Lounge – lounges are a great way to travel!

Getting From the Airport

Another step in planning your trip is figuring out how to get to and from your hotel. Getting from the airport to your hotel is pretty easy if you travel domestically.  I usually just rent a car and AutoSlash is amazing for finding a great deal.

International travel is a different deal.  Personally, I prefer to not rent out of the country.  If I am with my husband, we just take a taxi to the hotel.

I must admit to feeling a little more vulnerable when in foreign countries and so, occasionally, I will book a shuttle through GetYourGuide or Viator to pick us up at the airport – especially at a new destination.  And especially when we are just women traveling. It just feels safer.

There’s something comforting and reassuring about someone anticipating your arrival and seeing your name on a piece of paper when you are unsure of where to go.  When I went to Vietnam we booked a service that helped us through our visa on arrival and then took us to our hotel.

Always check to see if your hotel has a free airport shuttle.  Unfortunately, with international travel, that doesn’t happen as much as domestic.


Where to Stay

Our next step on how to plan a trip is deciding where to stay! The ideal situation is for you have hotel points as part of your points portfolio too. Free stays and free flights are my perfect scenario!  Many of my stays are with points or annual free nights from the hotel cards I do have.


Hotel suite

Pure joy when you get upgraded to a suite!


Unfortunately, sometimes I travel where there are not many branded hotels.  Perhaps you don’t have hotel points. In this case, I like to use  Their prices are competitive but, best of all, I get credit for my stays there.  After 10 stays, I get a free room equivalent to the average cost of my 10 stays.  This definitely cuts the sting of having to pay for a room once in a while.  I am all about getting rewarded in some way! is another way to find a good hotel room.  Their site is easy to use and can help you find an affordable room in any country you travel to.

Airbnb is another great choice if you are traveling with a group.  It is difficult to find big rooms in Europe for more than 2 people so Airbnb has been a huge choice for us when we travel as a family.  I have had some pretty amazing houses/flats I’ve stayed in through Airbnb!


Another step in how to plan a trip is deciding what to do! I am a huge fan of free walking tours when I first get to a new destination. I like Sandemans. Basically, you just tip the tour guide what you think the tour is worth.  I generally try and do one the first day I arrive somewhere to get the “lay of the land”.

Another great way to plan out activities is VisitaCity.  Their site gives you sample itineraries for various cities.  You can add or subtract to the itinerary and map out a nice plan.  They will show you a map of how to get everywhere and how long it will take.  I have used this in Spain, Portugal, and Athens and really liked it.

That being said, nothing beats a good tour.  Especially, if you want to get outside of your main city.  I am a huge fan of Viator Tours or GetYourGuide.  Whenever I go to a new place, I start researching all the best tours and usually book one or two.  Some of my favorites are biking all over Barcelona,  a Lisbon neighborhood walking tour, and relaxing on a catamaran in Santorini.

Learning to cook the cuisine of the country you are traveling in has proved to be a great way to spend time in a new country.  Cookly offers cooking classes all over the world.  Not only do you get to hear about the country from the instructor and meet interesting people, but you learn recipes you can recreate at home to remember your adventure.  I have made pizza in Florence and it was the highlight of my trip there!

Three women with pizzas they made

Take a cooking class when you travel!

How to Pack

I used to be the queen of a million clothes changes on a trip.  My husband used to roll his eyes but still lug all my luggage all over the world.  Of course, we brought it back and I hadn’t worn half of what I brought.

When I started traveling more without him, I got sick and tired of pulling heavy suitcases while I was running to get on a train.  I finally became a carry-on girl!  Believe it or not, one swimming suit works for my whole trip.  And the invention of packing cubes really made it a no-brainer to pack less.  I can’t tell you how liberating it is to pack for a week no matter how long many weeks I am staying.  It is possible to wash out clothes in a hotel sink and I have learned that it is all about the experiences I have not the clothes I wear!

What to Pack

Here is a sample of what I tend to pack on a trip of 1 week or longer:

  • 2-3 joggers. I love these ones (need to include the link)
  • 5-6 t-shirts.  My favorites are from here because they don’t wrinkle!
  • Underwear for 4 days (maybe 6 for 2 weeks – I wash them in the sink)
  • Bathing suit
  • 2-3 shorts or skirts
  • Sweater for layering
  • Tennis Shoes
  • Sandals
  • Comfy walking shoes
  • Umbrella
  • Tiny toiletry bottles
  • Maskcara makeup because it can go through security
  • A great travel pillow! Trtl is our favorite.

Bottom Line

A little planning ahead can go a long way in how smooth your vacation goes. If the stress of planning a trip is too much then use these tools! Hire a booking service, book tours ahead of time with a company! Then, just show up and enjoy your vacation. Hopefully, with these tips, you now feel confident in how to plan a trip!



a pinterest graphic about how to plan a trip

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