How to Plan a Vacation From Start to Finish

How do you plan a trip from start to finish? 

When I told a friend about my travel blog we started talking about her dream vacation. She dreams of taking her teenage daughter to a horse ranch in Montana. 

When I asked her why she hasn’t gone yet she replied, “There’s so much to planning a trip like that. I wouldn’t know how to start!” 

Well hello blog post idea! 

  • Step 1. Find Inspiration
  • Step 2: Get specific on when, where, how much, and with whom. 
  • Step 3: Compare options and price points and start planning your itinerary. 
  • Step 4: Book transportation, accommodation, and activities.
  • Step 5: Go on your trip!

* This site contains affiliate links, where I get a small commission from purchases at no extra cost to you.

My husband and I LOVE planning our travels together!

I take for granted that not everyone loves trip planning. I plan trips I’m going to take years in advance! Even if I know I won’t be able to go on all of my planned trips, I love the process. The research, the digging to find hidden gems in a destination, and the execution when it all comes together – that’s my idea of a good time;)

So with my friend’s goal in mind I’m going to walk you through how to plan a trip, step by step, from gathering inspiration and conducting research to booking the trip!

Read More: Tips for First Time RVers: Everything You Need to Know

Find Inspiration For Your Travels

The biggest way I gather inspiration is with social media. You knew I was going to say that! But it’s true. The best resources for me are Pinterest, Youtube, and Instagram. 

I searched #montanahorses and here’s what I found on Instragram, Pinterest, and Youtube. 

I wrote down all of the options that I thought we should consider including specific towns in Montana, specific tours or ranches, and any activities my friend would be interested in. 

As I go through each option I’ll make notes about the type of accommodation, activities they offer, pricing, etc. This way I can reference later if needed.

Here are Example of Notes I Make When Researching

  • A retreat called Cowgirl Yoga at Big Sky Resorts in Big Sky, Montana
    • Geared towards beginner horseback riders and yoga enthusiasts. Not quite what we’re looking for. 
  • The Ranch at Rock Creek
    • This is a LUXURY destination with rooms starting at $2000 a night! 
    • If you had the budget, what a cool place!
  • Rocking Z Guest Ranch
    • Great for families and all skill levels 
    • “For the angler among you, the Little Prickly Pear Creek runs directly through our property and is a beautiful Fishing spot”
    • Free transfers to and from Helena, MT are set up for Sunday arrival before 1 pm and Saturday departures near 11 am. 
    • Rates around $2700-$3000 for 6 nights ALL INCLUSIVE
  • Flathead Lake Lodge: A Montana Horse Riding Vacation
    • Another luxury option with a higher price tag
  • Yellowstone Ranch Horses: Ladies backcountry Pack Trip
    • Looks promising but they don’t have any future dates listed. And this doesn’t look as kid friendly as some of the other options. 
  • Ride Like the Montana Wind at Bonanza Creek Ranch
    • Real working cattle ranch only for immediate or advanced riders, only 8-12 guests at a time, must be 21+. This option won’t work as her daughter is only 13. 
  • Nine Quarter Circle Dude Ranch near Yellowstone
    • For 13 year old + – just what we need!
    • Offers day riding daily, plus an all day and half day riding option for advanced riders
    • Also offers fly fishing activities – which was another activity my friend wanted to do in Montana
    • Family Season June 18 to Aug 26. $4000 for an adult and $2700 for children 6-14
    • Another good option for my friend!

Read More: How to Survive a Family Trip as an Introvert

You May Need to Widen Your Search When Travel Planning

Unlike other trips I’ve researched before, finding the best affordable Montana Dude Ranches proved to be a challenging task. 

In order to find a variety of budget options for my friend I expanded my search beyond Montana and included other horseback riding destinations like California, Wyoming, Colorado, and Arizona. 

I also added key words like “Budget” and “Affordable” when searching on Pinterest and Youtube. 

Be open to exploring off-the-beaten-path destinations. That’s how we found Townsend, Tennessee while researching our trip to the Great Smoky Mountains National Park

Get Specific

After doing preliminary research, narrow down what experience you’re specifically looking for.

Make a list of all of the possible options while answering these big questions:

  1. Who’s going? By myself, with a partner or family member, or a large group.
  2. What’s the best month or season to visit?
  3. Which region(s) am I most interested in and why?
  4. How much am I willing to budget for this trip? Is that budget aligning with the prices I’m seeing? If not, in what ways can I cut back?

Read More: How to Travel with Limited Time Off

Compare Options and Prices

Of the options above here are the top picks I found. The ranches below include lodging, meals, and horseback riding. Additional activities and gratuities may not be included. 

  • Nine Quarter Circle Dude Ranch (Most expensive option)
    • Location: Gallatin Gateway, MT near Yellowstone
    • Price: $4000 for an adult and $2700 for children 6-14 for 6 nights
    • Closest Airport: Bozeman, MT
  • Rocking Z Guest Ranch
    • Location: Wolf Creek, MT
    • Price: $3000 per person for 6 nights
    • Closest Airport: Helena, MT
  • Sweet Grass Ranch
    • Location: Big Timber, MT
    • Price: $2300-3000 per person for 6 nights 
    • Closest Airport: Bozeman, MT
  • Bitterroot Ranch
    • Location: Dubois, WY
    • Price: $1850-$2800 per person (4-7 nights)
      • They also have a backcountry pack trip option: $2400 per person 5 nights 
    • Closest Airport: Jackson Hole, WY
  • Rankin Ranch
    • Location: Caliente, CA
    • Price: $2135 per person for 7 nights in regular season, $1785 per person for 7 nights in off season
    • Closest Airport: Meadows Field, CA
  • White Stallion Ranch (Cheapest Option)
    • Location: Tucson, AZ
    • Price: $1974 per person for 7 nights
    • Closest Airport: Tucson, AZ

Book Your Trip

Before you book your accommodation I always double check the best prices to fly. 

For example, if you’re thinking about taking your vacation Saturday to Saturday, but you find there is a cheaper option if you were to go Friday to Tuesday, it may be worth considering. 

Where should I search for the best flight deals?

We use Google flights to find the best deal. What I love about Google Flights is that you can select multiple airports at once, use their price graph to find the very best deals, and see a list of unbiased listings. When you use Google Flights you book directly with the airline so you can be assured Google is listing the cheapest options because they aren’t pushing one airline or the other.

Since my friend lives in Maine I wanted to give her four airport options using the Hopper App. The Hopper App is a great tool to gauge the approximate price of flights to your destination. Although prices will depend on the airline and actual flight you select, it’s helpful to know the rough cost. 

Flight Costs:

Boston, MA to Bozeman, MT: $275-$500 pp (most likely the cheapest option)

Portland, ME to Bozeman, MT: $350-$600 pp

Manchester, NH to Bozeman, MT: $475-$775 pp

Bangor, ME to Bozeman, MT: $500-$800 pp (most likely the most expensive option)

Book Your Accommodation

And make notes of when check in and check out times are, any special items not provided by your stay, and anything not included that you’ll need to book separately. 

Book Your Activities

If there are separate activities you need to book, I suggest giving yourself a few days of wiggle room in your itinerary. For instance, if your flight is planned to arrive on Saturday, I would give yourself Sunday to relax and explore and plan your first booked activity on that Monday. 

One of our favorite activities while traveling is kayaking!

Go on Your Trip

Take lots of pictures and soak up everyday! I love to create a Snapfish photo book with all of the memories we made soon after the trip while it’s still fresh in my mind. 

Final Thoughts

Planning a trip doesn’t have to be stressful! In fact, it can be even more enjoyable than the trip itself. I hope these tips help you simplify your planning process and get you traveling more!