How to Plan an Amazing Vacation in 8 Steps

Good morning, friends!  Natty Guy and I recently got back from a trip to Portugal.  Whenever we travel, we often get asked if we took a tour. Almost 10o% of the time, the answer is no, we travel on our own.  That always sparks a new set of questions.  How did you know where to go? How did you know where to stay?  How did you get around?

I won’t lie.  Independent travel can be quite a bit of work – especially if you research to the degree that we typically do.  But, it can reward you with a much more authentic and rewarding vacation experience as well as the satisfaction of forging your own way in a foreign country.  This post will walk you through everything you need to know to plan your OWN amazing vacation!

Plan an Amazing Vacation

Inspiration to Plan an Amazing Vacation

We get travel inspiration all over the place!  Initially we each had dream counties that we wanted to visit.  Italy for me, Germany for him.  Now that we’ve checked our most obvious places off the list, inspiration comes from other sources.  These include: other travelers and their recommendations, The Amazing Race TV series, reading travel books and magazines, following photography and travel blogs, etc.

What’s your dream?  Shopping in Paris and visiting chateaus?  Beach bumming in Thailand?  A safari in Africa?  Let’s work now on getting you there!  If you are limited by budget, once a plan is in place you can use point travel tricks (among others) to get you there and let you stay on budget.  For today, let’s just get that plan in place!

8 Steps to Plan an Amazing Vacation

1. Decide upon your destination and how much time you have.

  • See inspiration notes above!

2. Decide where to travel within that region.

  • Do you want to visit just one main city or are there multiple towns/areas that interest you?  Note, these don’t always have to be in the same country.  We planned one trip that started in Amsterdam, visited Belgium and ended in Germany.  In Europe particularly, things are pretty close!

3. Determine an itinerary.

  • Easy, if you are going to stay in just one place.  For multiple stops, look at Google maps to determine distances and see if any of your dream spots are outlying or inconvenient in some way.  Those may need to be eliminated from the plan.  Once you get a good travel route in place (noting that it may make sense to fly in and out of 2 separate cities), determine how many days/nights you want in each location.
  • Try to minimize 1 night hotel stays.  While on occasion they make sense as a resting way-point, stacking more that one or two 1-night stays into a trip can leave you pretty exhausted.
  • Remember to include your travel time in planning.  It always takes a little bit longer to pack up, get things in the car (or to the train station), travel, etc.  Never hurts to pad your times a little bit.

4. Book your flights (or tour).

  • Once you have your travel plan in place, book your tickets.  Again, be sure to consider whether in makes more sense to fly into one location and out of another.  We often use this practice which saves tons of time in back-tracking to our original landing city.
  • At this time, also check that your passport has 6 months validity remaining and for any visa requirements or immunizations that you may need to receive.  I recommend going right to government websites for this information as it can change frequently and a guide book may be out of date.  Check again a week or two before your trip.
  • NOTE: While this post is geared toward independent travel, depending on your dream destination a tour MAY make more sense.  The African safari option comes to mind as one instance.  Even if you don’t use a tour for the whole trip, for the logistics of getting to/from and around various game preserves, this may be the better option.

5. Determine how you will get from Point A to Point B.

  • Options to consider include flights, trains/buses, rental cars or car/driver and occasionally ferries.  If you are going to be in very large cities only, the inconvenience of having a car may be too great and train travel could be the best option.  For exploring rural areas, a rental car or car/driver can offer much more flexibility.  In Asia, flights are pretty cheap and distances long so this air travel may be the best option.

6. Book lodging.

  • We tend to stay in traditional hotels while in larger cities but have used pensions/guesthouses in smaller, rural areas.  Other options include home rentals, hostels or AirBNBs.
  • Location is everything for us!  I use Google Maps to see where the heart of the area is (for us, it’s usually the old/historic town center) and see what options are within a short walking distance.  From there, we turn to TripAdvisor, friends and other review sites to see what seems to be a good value (experience in combination with price).  If you are a sports fanatic and want to go to lots of soccer matches in Spain, you might want a location close to the main stadium.  A beach bum likely wants to be close to the water.

7. Determine a Rough Daily Plan

  • This is where I lose some people.  “I’m on vacation…I don’t want to plan, I just want to go with the flow and have everything happen organically.”  Well, that is all fine and well but you will likely end up wasting a lot of time and missing some of things you might have hoped to see.  Can’t tell you how many times we’ve been privy to conversation like:
    • What do you mean Versailles is closed on Mondays – it’s not open all the time?
    • Oh, the Last Supper is in Milan?  I really would have liked to see that but we’re leaving early tomorrow.  I had no idea it was here.
    • What do you mean you can’t wear shorts in the Vatican?  I signed up for this tour – you can’t tell me I can’t go in!
  • Things to investigate include:
    • The top (and lesser) sites.  Rank them by your interest in them and also note what neighborhood they are in.  When you rough plan a day, try to see everything you have an interest in within one neighborhood so you don’t keep zig-zagging back and forth across the city.  If you have a special interest (sports, food/cooking, nightclubbing) check out what might be available in the area you are visiting.
    • Note days that venues are closed, daily hours, free days or evenings (cheap but very crowded) and whether advance tickets are needed.  Even if not needed, getting advance tickets can often save you a lot of time standing in line.  Note any dress codes at religious sites.  Do your homework!  Good guide books usually have this information listed and if the book is a bit out of date, I’ll double-check by going the site’s actual webpage.
    • Check out any local events going on during the time you will be visiting. You may even want to plan your trip around one of these events.  When we visited Germany we planned to end up in Munich during Oktoberfest, which was an amazing experience.  With advance planning we were also able to attend the Rhein en Flammen wine festival on that same trip.  Equally spectacular.
  • Lock down any thing that is both on your “must do” list and needs advance reservations.  Get those events cemented in place!
  • Schedule free or down time.  The plan above should be your guide but shouldn’t prohibit you from all spontaneity if a unique experience presents itself.  Build in the time to take advantage of those moments without having to forgo all your originally planned sites.  For us, 1 major site and 1-4 smaller sites seem to make for a good day.  It allows for some unexpected finds along with plenty of cafe time and general strolling time.

8. Determine Your Local Transportation Plan

  • In large European cities metros and buses are both plentiful and efficient. On our most recent trips we’ve been using Uber a lot with great results.  In Asia tuk-tuks are common.  Wherever you are, determine your best options for getting to the sites/areas you want to visit.  Check to see if it’s more efficient to buy a re-loadable travel card or day pass than individual tickets.

9. Pack  up and enjoy knowing you’ve planned an amazing trip!

Stay tuned for a vacation planning printable for use in organizing your dream trip!  I’m hoping to have it completed this month.

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6 thoughts on “How to Plan an Amazing Vacation in 8 Steps”

  1. Hey Elizabeth good post. I’m pretty good at planning our trips but they are small within our state. A European vacation would be a dream and you give lots of good tips to use. Looking forward to printable that will help out in the organization.

  2. I really love this post. I’m not a huge fan of the tour trips either. I wonder what we did before Google Maps! Happy weekend, and thanks for hosting the link up.

    1. Crazy to look back on what travel was like in the pre-internet days! Travel agents, fold-out maps and only word of mouth for recommendations! You have a great weekend!

  3. So many great tips! My husband is really good at figuring out things to do and how to get there on trips, especially when we’re in larger cities or abroad. We do enjoy doing a tour or two, tho!


    1. Hi Carrie! Yes, tours definitely have a place! Sometimes city tours can give a great overview and a better sense of the lay of the land!

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