How to Plan a Trip

Its no secret I love to travel.  Right now I’m on a 3 week back to back travel spree…for work but who cares.  I have the wanderlust bug and I’m lucky to have a job that lets more indulge it.  I truly enjoy the whole trip planning process and am not happy unless I’m gearing up for my next vacation.

Today I’m sharing my tips on planning a trip thinking out loud style.  Thank you Amanda for hosting, check out the full post here.


  • Decide where you want to go.  Silly for a first point I know but trust me, you want to have a general idea of where you want to go.


  • Research the best time to go.  When I say best I don’t mean peak season.  We went to Italy in January and while it was cold and not as lush with floral as the spring/summer we got to stay in some amazing accommodations for less than 1/2 of the cost during peak season.  The crowds at major attractions were minimal or non-existent and we didn’t have a difficult time getting a table at all the places we wanted to eat.  I’m not saying don’t go during the best times of the year (hello Oktoberfest I’m looking at you) but there are some cities where it may not matter so much and could save you money at the same time.


  • Figure out how you are going to get there.  Does it make more sense to drive or fly?  What is the difference in cost?  When we travel to Disney the flights are stupid expensive so we drive, but when we went to Carolina we used points for my flight and Joe’s was covered through the company.  About the same distance to drive as it would have been for Disney but different costs.

driving in italy

  • If you are flying will you need a rental car or can you walk/public transport everything?  Some cities have fantastic public transportation (New York, London, Rome, Amsterdam to name a few) and others do not (Houston, Atlanta, Orlando).  Make sure you are able to get around without spending a fortune on cabs and such.  San Francisco is a great example of good public transportation but you can also supplement that with bike rentals!  Another fun way to get around the city when available.

san francisco

  • What do you want to do when you are there?  I bet there is a reason you chose to go to said city, so what are 3 things you for sure have to do while you are there.  Pick a few MUST DO things and loosely plan your day around that.  I 1000% believe in getting “lost” in a city and finding awesome random things but there is a reason you chose to go there, make sure you do what you came to do (Pineapple fountain in Charleston, check, Big Ben in London check, Pasta in Bologna check).


  • My favorite part…figure out where you are going to stay.  I use for all my travel, have never stayed at a chain hotel (internationally) and have loved every hotel.  You can also find bed and breakfast places, apartments, hostels, even a castle (my uncle stayed in one in Scotland!) but I do prefer the more traditional hotel route.  I try and find a place to stay close to public transportation, near food/shopping and at a price point I’m happy with.  I do book my hotel at the same time I book my flight but check back often to see if the price changed.  Almost all websites will adjust the price if you find a lower one somewhere else.  Nowadays there really is not much if any advantage to booking direct…but that’s a whole ‘nother topic for a whole ‘nother day 🙂

florence hotel room

  • Have an idea of where you want to eat.  Have a few places bookmarked but also allow room for flexibility.  For my travels I always look places to eat up on yelp.  I want to find trendy/funky places to eat and that’s not always easy when you are walking by.  For me food is a major part of travel so I do my research and plan my day around where I’m going to eat.  Now I know not everyone is like this but having a few places bookmarked will help when you are ready to eat and don’t see anything nearby that you like.  Nothing is worse than being starving at 7pm and have no idea where you are going to eat and settling for some crappy chain restaurant (sorry, #truth).

steak in florence

  • You hear all the time things like “travel like a local” and that’s a pretty vague term.  How I interpret this is by going to city websites/facebook pages and finding local events/festivals/shows to attend.  When I was in Savannah I walked around a local farmer’s market, when in Bologna we found another local market, in San Francisco I went to a food truck festival.  Its great to see the tourist destinations but going to local activities adds some extra flavor to your trip and can often times be some of your best memories.

italian candy market

  • Ask around for recommendations.  When I plan pretty much any trip I ask my friend/family/co-workers/strangers if they have been to said place and what they recommend.  When talking to the agent at the United Club 1 day before our trip to Italy she gave us some great recommendations some of which we took and really enjoyed.  You never know where or from whom you will find your next great adventure!


  • Above all, get ready to have fun!  Make some memories and enjoy yourself!  Things always come up and plans don’t always happen 100% like you want (which is why having a lose plan instead of a minute by minute works best) but as long as you have a marvelous time that’s what counts!!!


CHIME IN!!!  What are your travel planning tips?  Where are you going next?  Do you like a structured trip or fly by the seat of your pants?


2 thoughts on “How to Plan a Trip

  1. So I plan a lot like you do, except tip #1. I usually start my planning by having no idea where I want to go. I start by finding great deals & then determining if that would be a good time to visit the place if it’s one I’m interested in, if that makes sense. It’s usually how I end up getting good deals. I would definitely rather travel in shoulder or off season. Give me eh weather before crowds any day.

    Liked by 1 person

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