How to Plan an Awesome Vacation (Spoiler: Wine is Involved)

Yippee!!  For many people, it’s time to start thinking about vacation!!  Time to start researching places, flights, accommodations, things to do…putting together this year’s adventure of a lifetime!  I  cannot wait to get started…who is with me?  Anyone????  

Ok, ok, so I get it…trip planning can feel like the equivalent of an avalanche barreling down on you at a 100 mph.   But boy, I do love to plan a trip and, like any good type-A personality, I have a process for adventure planning.  By the time we are airport bound we have a game plan to be excited about and fewer things to be stressed about.  

Going on vacation is supposed to be fun and (IMHO) so should planning the vacation!  It should be the big anticipation builder that gets everyone excited.  So grab a glass of wine and let me share a few of my tips & tricks that should make planning your next vacation (at least a bit more) exciting!


I created a Vacation Planning Workbook to help you plan your perfect getaway.  Grab your free guide below, add a glass of wine and plan away!  

Vacation Planning Guide Download


Step 1: Choosing Your Trip  

So the world is a pretty big place, which brings up the question, how on earth (pun intended) do you pick what corner should be explored?  So the first thing to decide, in conjunction with your vacation sidekicks, is what type of trip you want to have.  This is a big topic for us each year when we start to plan vacations.  We spend a lot of time chatting about what we want to experience with our trips which helps to narrow down the target locations.  Exploring all the options can be pretty fun!     

I pulled together a list of questions that are good vacation exploration conversation starters.      

arrowQuestion 1: What type of trip are you planning?    

  • Family vacation
  • Couples trip
  • Boys or girls trip
  • Romantic getaway

arrowQuestion 2: What is the length of the trip?

  • Weekend/long weekend
  • Week
  • Two weeks or longer

arrowQuestion 3: What types of location(s) is preferred?   

  • City
  • Small town
  • Mountains
  • Beach

arrowQuestion 4: What regions of the world are preferred? 

  • Africa
  • Asia
  • North America
  • South America
  • Central America
  • Caribbean
  • Europe
  • Middle East

arrowQuestion 5: What are the weather and timing preferences?  

  • Warm weather
  • Cold weather
  • Spring
  • Summer
  • Fall
  • Winter  
  • High season
  • Low season   

arrowQuestion 6: What type of accommodations are preferred? 

  • All-Inclusive Resort
  • Cruise
  • Hotel/Motel
  • AirBnb
  • Adventure accommodations: camping, camper car, tree house, boat, etc.

arrowQuestion 7: What types of experience(s) are you interested in?     

  • Road Tripping
  • Chilling in one place  
  • Adventures seeking: Hiking, biking, yoga, boating, paragliding, etc.
  • Relaxing: spa, pool, reading, etc.
  • Cultural activities: Museums, historic monuments, theatres, etc
  • Foodie experience: food tours, unique local cuisine, cooking courses, wineries, distilleries, microbrews
  • Educational experience: Learning a new skill or hobby such as a foreign language or organic farming
  • Fashion & Shopping: Checking out the latest in the fashion world

arrowQuestion 8: What is the budget?

  • Luxury:  Going all out of this trip and expenses are not a primary concern.  
  • Comfort: Travel in relative comfort but no need to be extravagant.
  • Budget: Watching the dollars and it’s more about the experiences.

Being on the same page with your travel sidekicks for what you want out of your vacation is important.  These are the types of questions that will impact the destination you choose and the itinerary you create.

Tip to Make it Fun: One fun idea is to host a tapas and wine evening with your fellow travelers, print out this list and have everyone fill it out.  Then compare and see what commonalities everyone has to help pick a destination!  

Right now, I am planning 3 different types of trips:

  • Norway: This trip is to celebrate my hubby’s 50th birthday.  He prefers adventurous and active vacations (most people need a vacation from his idea of a vacation). Since his birthday is in February he wants to ski in a new and exciting location. His travel style is minimalist, off the beaten path, authentic experience with local people and culture.  Because we travel a lot and want to stretch our travel dollars as far as possible, we tend to vary between budget and comfort.  
  • Ireland: This trip is for my sister and brother-in-law to celebrate my sisters 40th birthday.  They want a road trip that will allow them to see all the well-known sites of Ireland in a zippy and sporty convertible.  One of their hobbies is making beer so they want to take a tour of pubs and sample plenty of pints.  They want this trip to be between Comfort and Luxury budget because they don’t travel as much and are celebrating a big birthday milestone!  
  • Amazing Beach Destination (TBD): This is a girls trip that will be a long weekend to celebrate the 40th birthday of one of the best friends of my sister and me.  She wants a relaxing and gorgeous beach location that is a new destination for the 3 of us.  She doesn’t want to think too much and come home feeling recharged and refreshed for life with her toddler.  Our budget for this trip is comfort.

So you can see how planning the details of these from accommodations, transportation, food, and activities will be very different.  If I tried to plan any of these vacations without this info it would likely just turn into wasted time.  But now that I know, I am full steam ahead to present viable options to the travelers.  

Step 2: Verify Travel Document Requirements

If this is your first trip abroad, check out this earlier post on Tips for Traveling Abroad the First Time

So once you pick the destination of your adventure, if traveling abroad there is the (not so minor) detail of travel document requirements.  While it has not happened to me, I have had several friends get to the airport only to discover they could not get on the plane because their international travel documents were not in order.  Literally a vacation killer!  

Both the US and Canada enjoy some of the highest travel flexibility in the world. However, you should still always verify the requirements before booking your dates to ensure you have plenty of time to get your documentation together.        

arrowPassports: Of course if you don’t have one…get one.  But in addition, many countries have a time frame for accepting passports that are close to expiration.  Usually, this timeframe is within 3 – 6 months of expiration.  However, it does vary by country so make sure you double check the expiration date on your passport and the window of acceptance of the country you are visiting.

arrowVisa: Especially important if your trip is for an extended period but even if a shorter trip it is always a good idea to check out the requirements.  If a visa is required make sure you take into account the timing and requirements of the foreign government before purchasing airfare.  This is a helpful website for checking the visa requirements by always double verify with official government websites for latest information.  

arrowImmunizations: Check the requirement for immunizations for any country you are traveling to so that you get them timely and have the medical to take with you as proof.  This US CDC site that is easy to use when determining what vaccinations you may need.  

Step 3: Creating a budget

If you are not high rolling on this vacation, consider creating a budget.  Ok, so for some maybe  a bit over the top type-A, but I find it to be a stress saver for:

  • Managing expectations on how much money will be spent and how it will be spent.
  • Providing transparency to everyone funding the trip which can be especially important if you are traveling with people who will be splitting costs.  
  • Alleviating financial anxiety while on vacation.    

Tip: Making a budget can double as a tiebreaker.  In the past, when torn between destinations a budget helped us make the final decision.   At least I find this to be a better decision-making method than a rousing game of Rock, Paper, Scissors.  

So what to include in a budget?  Well, this CPA (that would be me!) is more than happy to help out with that (you could call it my expertise :-)!   

arrowArrival and Departure Transportation: Cost of airplane tickets, train tickets, or gas if driving your car.  

arrowDestination Transportation: Some typical expenses can include rental car and gas, public transportation passes, or even train/plane tickets if you are location hopping.  

arrowAccommodation: Cost can vary vastly depending on where you are staying, but also can have a big impact on your vacation experience.  Typically this is where the balancing act between cost and desired experience can be the most tricky.  So check your options across hotels, AirBnb, hostels/guesthouses, campsites, campervan etc. to determine where and how to stay for your vacation.  

arrowEntertainment: Cost of places you want to visit, events you will attend, or activities/experiences you want to have.  These can add up quickly so if you are in a situation of picking and choosing knowing cost could help with making a decision.   

arrowFood & Alcohol: This is one expense area that can sneak up on you since eating is pretty much required regardless of which corner of the earth you are in.  Especially if you are on a budget this is also one area where you can have the most control. For example, opting for an AirBnb with access to a kitchen can really help control costs by cooking some meals as opposed to always eating out.  

arrowCell Phone Plan: If traveling internationally it is likely that you will need access to your phone and if you are outside of a major city, relying on wifi could be tricky.  For more information on cell service when traveling internationally, check out this earlier post.

arrowSouvenirs: Plan for any shopping or keepsakes you want to bring back with you.  I have this one in here because there is nothing I love to say more than “Oh this…I got it at this great little boutique in Paris”.  I just need to know if I am planning to spend $100 or $1000 on this adorable piece of something before my “shopping spree” begins.

Tip: If you are traveling with others and splitting expenses there are some great apps that keep track of split costs and allocates to each party, eliminating stress over who owes what.  At the end of the trip, it is much easier than digging through a pile of receipts.  I have used both Splitwise and Share-a-Bill apps and can recommend either since they function similarly and are easy to use.

Step 4: Booking a Flight

Booking a flight can be one of the most stressful parts of the trip.  Forever in search of the perfect combo of price and itinerary, hours can be spent hunting the perfect flight.  

arrowTrip Timing:  Having flexibility in your trip timing can be a big price saver.  So if you have flexibility take into account:  :

  • High Season vs. Low Season: Not arriving at the peak of high season will help to minimize cost not only with the plane ticket but often with the whole trip. Plus you don’t have to battle all the crowds!
  • Day flexibility:  Fares can vary drastically by day and most sites will let you compare prices on flex days (or if they don’t find use another site).  There have been many times we have saved several hundred dollars just by flying a day earlier or later than our initial plan.   

arrowFinding Affordable Flights:  Ok, so this might be the task that is the most dreaded (me included) but can save some serious $$$ in the travel budget.  A new discount air tracker is always popping up, but some of our favs right now are:

  • Google Flights: So easy to look at pricing months out, easy to compare price by destination, and they aggregate across most of the airlines.  Plus they have this cool “I’m feeling lucky” feature that will randomly select a place (I love seeing what they come up with).
  • Momondo: One of the most popular flight and pricing aggregators currently out there, another great option for flight searches.
  • Kiwi: We just used this site to book our Norway trip and we ended up paying 50% less than originally budgeted by being flexible on which days of the week we flew.
  • Airfare Sale e-Mail lists: Ok, so this is possibly one of the coolest ways to stumble upon an unexpected trip or even find an awesome fare on a planned trip (like we just did with Norway!).  I totally recommend signing up for them:
    • Scott’s Cheap Flights: My current fav, so easy to use and I love to see what places drop into my inbox daily.  I currently use the free subscription but am likely going to upgrade to the premium because the cost is nothing compared to the potential savings.
    • Delta Flash Sales, Air Canada Destination Offers (or whichever airline you hold frequent flyer miles or can use credit card miles).  I had a friend just book tickets on Delta to Turks & Caicos for 8,000 points round trip (that is seriously nothing!)
    • TPG, The Points Guy: Not only great tips on airfare but general tips on maximizing your travel dollars and experience.

While we mostly travel on Delta and Air Canada and have status perks, we are not so loyal to them or their partner programs that we will pass up an awesome airfare on another airline (some travel-holics are stringent about it, but not us). So which camp you fall into is totally up to you, both have perks.

Step 5: Booking Accommodations

Choosing your type of accommodation has a huge influence on your vacation and just like buying a house the most important thing is location, location, location to keep you close to your activities and desired experience.   

  • Do you want the option to cook or no freaking way…you are on vacation it is someone else’s turn to cook!  
  • Have maid service each day or do you own tidying up?  
  • Sharing a room with others or opt for a bit of privacy?
  • Be easily accessible to your activities or commuting a bit isn’t a problem.

We don’t go all out on accommodation expense since we are not there to hang out in a room.  To fit into the flow of our vacation, the items most important to us are location, cleanliness, and price.  Like airfare, there are tons of sites/apps to find a place to stay. There are the traditional ones such as Expedia, Priceline, Trivago, or Kayak that are great for hooking you up with a hotel/motel/resort.  

But, to be honest, we rarely stay in a traditional hotel/motel setting when traveling.  There are too many unique experiences to have so I rarely use those sites for finding accommodations.  Instead, apps/sites we love are those that allow us to discover hidden gems:

arrowAirBnb: We love AirBnb because unlike any hotel or resort it allows you to live amongst the locals.  Plus you can customize your vacation including experiences, pricing, amenities, and accommodation type.  By renting a house, private room in a house, or shared room in a house you get an experience that is more authentic, local tips & tricks from your host and save money.  We have never had a horrible experience (sure some were better than others) with AirBnb and as early adopters of the concept have been using it for years.  

AirBnb Tip: Always read the property description and rules for any place you are considering reserving.  Read at least a sampling of the reviews that were left by previous travelers.  These are the best ways to ensure that you are aware of what your experience will be like.  Also, always leave a review after your stay.  AirBnb is a social platform that relies on feedback to make sure that future travelers have a great experience too.  

arrowBooking.com: So amongst the plethora of hotel/motel aggregators and booking sites things I love about this site include:

  • I have never found another site that beat their pricing
  • Once your account is set up booking is super easy (account setup is easy too),
  • Just in case it is needed, the cancellation is generally crazy flexible.  The site is super clear about the property cancellation policy before you book and they even send an email reminder when the cancellation deadline is coming up (seriously cool, right?).
  • Not only does booking.com have hotels and motels they have smaller local accommodations as well such as B&Bs, hostels, and guesthouses.  

By pairing AirBnb with Booking.com, we get the full range of accommodations available to us.

Tip: Before booking a location use Google street view to check out the neighborhood.  This is great for getting a sneak peek at the surrounding area for your home away from home.

Un-Ordinary Vacation Tip: Some of the best vacations can be adventure accommodations such as a camper car to hop from place to place, camping in really cool places, staying in a tree house, or renting an airstream on a beach.  If you are at all interested in checking out vacation with a bit of a twist check out the options on AirBnb, people have come up with some really inventive ideas!

Croatia Camping
Camping on the Adriatic Sea in the Croatian Dalmatian Islands. Note to self: zip the tent and hide the mess next time 🙂

Step 6: Destination Transportation

Whoo Hoo!  Vacation is booked, flights, accommodations, and you have lots to see and do.  You just have to figure out how to get from place to place.  Of course, your need for transportation is going to depend on your vaca itinerary.

arrowPublic Transportation: I love a city with good public transportation…LOVE, LOVE, LOVE.  It makes it so easy-peasy to get around a city quickly, efficiently, and affordably.  These days navigating public transportation almost stress-free.  Most large cities have their own public transportation apps, so between those and Google Maps this can be a no-brainer way to move around a city.  Before leaving read up on the city’s public transportation options and how to buy passes once you arrive.    

arrowBicycle: Sightseeing on a bike is becoming a bigger and bigger trend in the US, but it has been popular in destinations like Europe for many years.  I also love a city with a bike rental system.  These systems allow you to rent bikes for short-term periods either for free or minimal cost.  You can pick up and drop off a bike at stations around the city (a concept the same as a bus or metro stop).  If you are up for a bit of exercise, the weather is great, and you want to see the sites from behind handlebars, check to see if this option exists in your destination.  Most cities will have an app for the bike system so using it is simple.

Tip: If you love the idea of exploring a place on a bike but your destination does not have a rental bike system, then look for local bike shops that rent bikes.  

London Bike
Zipping around London on a city bike!

arrowRental Cars: For hopping from town to town the first option that comes to mind is renting a car.  Before renting a car abroad read up to find out if an International Drivers License is required in the country(ies) you will be visiting.  It is always helpful to read up on driving laws as there are always differences and they are not always posted (or even if they are, not easily decipherable).  Our preferred sites for getting the best deal on rental cars are RentalCars.com and Kayak.  Also, to get the best rates it is advisable to book in advance.

arrowBuses, Planes or Trains: Other options for town hopping in some destinations, such as Europe, are buses, planes, and trains.  Often very affordable if purchasing a “local” ticket there is also usually lots of flexibility with timetables.  My favorite is to tour an area by train.  Not only is it relaxing, it is a bit romantic/nostalgic to sit back with a glass of wine and watch the passing countryside.  If in Europe my fav app/website to use for booking is GoEuro, which allows you to compare prices and times across all three transportation methods.

Nice Train Station
Hopping the train from Code d’Azur to Paris

arrowScooter/Vespa: Ok, so this might be a bit personal but I am Vespa OBSESSED.  O.B.S.E.S.S.E.D.  So obsessed I bought one for home because it makes me feel like I am on vacation when I am zipping around on it in the summer (not the best transportation option for winter since I live in Canada).  However, if you are in a destination, such as Europe, where scooters are a common transportation method and you are comfortable driving one, do it!

Tuscany Italy Vespa
My first time driving solo on a Vespa and in Tuscany, Italy. After all, isn’t Italy the perfect place to learn to drive a Vespa?

Step 7: Things To Do (Explore!  Explore!  Explore!)

Rarely on vacation is the problem boredom and a question of what to do (or if it is you should definitely be re-thinking your vacations).  Instead, it is tough decision making on what won’t make the cut.  At least that is usually how I feel!  The excellent news is that there are so many great ways to get feedback and suggestions from those who have already “been there, done that”.  This type of feedback can remove some of the guessing game and make the decision process a bit easier.

arrowSocial Media: Find travelers with similar interests to yours and discover their “can’t miss” suggestions:

  • Blogs: Awesome resources for more in-depth information and pics on places to see and do.  Most bloggers also usually include tips and tricks that are sooo helpful to know before you get there.  
  • Instagram: My favorite social app for travel purposes, especially now that you can follow hashtags.  Follow travel Instagram accounts and hashtags for your destination to get lots of amazing pics and plenty of ideas for places to add to your itinerary.     
  • Facebook: Use the “Looking for Recommendations” capability to get feedback from people in your network who have already made the same voyage.  I am usually surprised at how many of my peeps have already traveled to the same place and have great ideas.   
  • Pinterest: Search for your destination, then create a beautiful board to pin all of the things you would like to do.  What is really great about Pinterest is that you will continue to get suggestions on new items for your board.    

arrowOfficial Tourism Websites: A great way not only to check out the best things to do, but also a great resource for price checking activities (including finding the free options).  

arrowTour Companies: For activities you can’t do on your own or would be a better with an experienced person check out local tour companies.  I do highly suggest reviewing cancellation policies and checking reviews before purchasing.  Tripadvisor is great for checking out reviews and selecting a tour company.

arrowOther Apps: Some great apps that I like for checking out suggestions on things to do are Culture Trip and Google Trips.   

So now you should have a list of all the awesome and cool things you want to do.  If you need to narrow it down you now have the budget and time information you need to make decisions.   Even for things that don’t make the final cut there is good news!  Your adventure will still be exciting and now you have Instagram and Pinterest to live vicariously through for the missed items.    

Old School Travel Tip: Even with the easy access to fantastic travel information online I do still love to buy the travel book (Fodors, Frommers, Lonely Planet, etc.) for a few reasons. First is that it is a great souvenir that makes me happy when I see my bookshelf with all the books from my travel destinations.  Also, it is nice to have a book with you to follow along with on your trip, especially if you are in areas where wifi is not always reliable or accessible.    

Do It All Tip: Since there is never time to do it all, there are two “typical tourist” activities we like to do!  Insert image of a person with a camera around neck, phone on selfie-stick, following a person waving a flag here.  But potentially embarrassing tourist activities aside, we find these great for getting a city overview (confession: it is pretty fun too)  

  • Bus Tours: On the first day, take the tourist bus to get a good overview of the whole city.  This is perfect if you only have a short amount of time in a place or to map out the places you like best and want to go back later on your trip to explore more in-depth.      
  • City Pass: If there are a lot of popular attractions you want to visit, many cities offer a “city pass” or a “city tour” that you can purchase.  This often gives you access to the most popular attractions at significant discounts.
New York City Bus
Playing tourist on the NYC Blue Bus with my sisters! It was my youngest sister’s 21st birthday and we took her to NYC for the first time. Since our time was limited we wanted to make sure she saw it all!

Step 8: Create an Itinerary

Now that all the pieces of your trip are done, you are ready to organize into an itinerary. An itinerary for helping to make sure you are doing items close to each other on the same day (as much as possible), deciding which days to purchase any advance tickets, and prevent from wasting ½ of each day in the “So what do you want to do?” ritual.    

But my best vacation tip:  Be flexible!  Give yourself some space for that “can’t miss” place you discover, or for the plan that doesn’t go perfectly and requires some an on-the-fly revision.  Take this bit of advice coming from a self-confessed Type-A personality who loves a well-made plan!  Now…go have a fabulous adventure!


If you have not downloaded the Vacation Planning Guide to help you plan your getaway now would be a perfect time!   

Vacation Planning Guide Download


bon voyage

P.S. If you have any trip planning hacks you want to share with me, I would love to hear them!  Leave in comments below or send me an email.

P.S. x2  As you get a bit closer and it’s time get the final details done, check out these blog posts for tips on making sure all goes smoothly as possible.  

Packing Tips and Tricks

Tips and Tricks for Packing a Carry-on Bag

Tips for Traveling Abroad

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