Trip Planning Toolkit

How To Use This Trip Planning Toolkit- Updated February 2020

Trip planning can be both exciting and overwhelming. If you’ve never visited the destination before, it can be challenging to know where to start. If you’ve frequented your destination, you may want to find new and exciting things to do or explore a new neighborhood.

We’ve compiled our favorite  guides, tips, and tools that we’ve found over the years to create this comprehensive, but ever growing, Trip Planning Toolkit. Whether you’re an experienced traveler or getting ready for your first big trip, you can find resources to help you organize your travel planning process.

It’s time to start planning your next adventure!

We’ve broken down this guide into seven easy steps to plan your trip. Each tab covers essential information on how to: Pick Your Destination, Book Transportation, Plan Your Itinerary, Find Lodging, Pack, Prepare to Depart, and Maximize Your Trip Enjoyment!

Trip Planning Step 1: Pick Your Destination

Believe it or not, picking the destination for our next trip is often one of the hardest parts of the trip planning process! There are so many places that we want to explore, so once we decide we’re going to take another trip, we ask ourselves these questions to narrow down our options:

How much time do we have to travel?

When do we want to go?

What is our general budget?

What kinds of experiences do we want to have?

Our Favorite Destination Planning Resources:

• PlanIt Wandering Destination Guides- Read about our adventures to inspire travels of your own.
• Google Flights Explore– I use this tool especially when we are limited on time and budget as it allows you to search for flights from your home airport based on duration, price, and approximate time frame.
• The Blonde Abroad Destination Guides – Although this blog caters to solo female travel, their beautiful photography and comprehensive guides will inspire any traveler to explore their featured destinations.
• Roundup of Top Travel Destinations of 2020

Trip Planning Step 2: Arrange Transportation

Once we determine where we want to go, generally my next step is to research transportation options.

Pick your mode of transportation

Air Travel– Growing up, air travel was expensive and simply out of reach for any family vacations. In recent years, it seems air travel has become more cost-effective, especially if flying on a discount, no-frills carrier. 

Best for: When you’re traveling significant distances, are limited on time, can plan ahead (last minute fares can get expensive, and/or have flexible travel dates (flight prices can vary drastically from day-to-day).

Train/ Bus Travel– While the U.S. isn’t as connected as, say Europe, train and bus travel is still often a viable option for travelers. A train or bus ticket can cost a fraction of a plane ticket and allows you to take in the sights during your journey. (Just be warned that those sights are often interrupted by highways or industrial areas as many passenger trains share lines with freight trains.)

When traveling abroad, many regions, such as Japan or Western Europe, have excellent train travel options, and it’s often more convenient than flying. Be sure to research local options before settling on flight over the train.

Best for: When you’re on a budget, have more time to travel, are uncomfortable with air travel, or want to take in the view while in transit.

Car Travel– Road trips can be a lot of fun and give you the most freedom (both in schedule and mobility) of any of these options.

Tip: If traveling abroad, take some time to research local driving requirements and conditions to make sure you can legally drive there and will be comfortable doing so. Some countries require you to have an international drivers license or may have road conditions you aren’t prepared for. For example, when we rented a car in Iceland in January, the roads were icy and covered in snow drifts. Being from Michigan, we were used to those road conditions, but many other drivers were NOT and were putting themselves and others on the road at risk by not knowing how to handle their vehicle in the snow. Make sure you are a competent and confident driver before getting behind the wheel, especially on unknown roads.

Best for: When you have plenty of time, are on a tight budget, have a reliable vehicle, are traveling with group,  and/or are visiting destinations off the beaten path.

Research available itineraries and prices

If our dates our flexible, I use

Consider using points or miles to purchase your tickets

If you’re willing to put in a little time to learn the ins-and-outs of using frequent flyer miles or credit card points to purchase travel, you can sometimes find some great deals. We’re by no means points experts, but we recently cashed in some of our Chase Ultimate Rewards Points and scored two round-trip first class tickets to Japan and only spend $118 out of pocket. There are several blogs and online communities dedicated to points/ miles travel, and saving up points can take time and strategy, so if you’re curious about using them to fund your next adventure, we recommend you start planning now.

Book your tickets

For air travel, as a general rule, I avoid booking Basic Economy fares for three reasons: 1) many airlines don’t allow for any changes, so if we need to modify our flight, we have to book entirely new ticket. 2) You often can’t choose your seat. While that’s not a huge issue on short flights, longer or overseas flights can be miserable if you get stuck in a middle seat or near the restroom. 3) Some airlines will charge you extra for carry-on luggage, negating the price savings if you need to bring more than just a personal item.

Our Favorite Transportation Planning Resources

• Seat Guru– Once you’ve decided on your flight, you’ll want to make sure you pick a good seat
• Hopper
• The Points Guy
• Rome2Rio– Type in two destinations into their search engine to see what travel options are available between two points. We find that Rome2Rio provides more details options than Google Maps, and it includes prices and transit times.
• RoadTrippers– Enter your starting point and final destination, and their site will not only map out suggested routes, but also provide recommendations of places to stop along the way.

Related Posts:

• Destination Guides

Trip Planning Step 3: Plan Your Itinerary

Building a fun itinerary is my favorite part of trip planning! But if you’re not careful, it’s easy to get carried away and over schedule your trip.

Plan your trip around a couple of ‘Must Have’ Experiences

Plan a maximum of 1-2 experiences for each day. I find that, when I plan more, we usually end up feeling rushed as I’m constantly checking the clock to make sure we don’t miss our next activity. You can always add in additional excursions if you find you have extra time!

Read: How To Plan Your Must Have Experiences

Factor in your lodging location

If I’m not familiar with neighborhoods in my destination, I like to build my itinerary before booking lodging. That way, I can ensure we are staying in the neighborhood to put us in the center of the action.

Get a guidebook, but don’t stop there

• Blogs- Soon after reading my guidebook, I head online to peruse my favorite blogs to review their posts and advice about the destination in question. Luckily for you readers, we’ve compiled the blogs we use to plan each of our trips in our own Destination Guides.
• Pinterest- A quick search on Pinterest can turn up new or under-the-radar blogs, infographics, and tour companies specific to our destination and enable me to ‘pin’ them to read later.
• Friends and Family- Personal recommendations from friends, family, colleagues, or acquaintances can be a great resource when planning a trip! I particularly like talking to people who are repeat visitors or who may have lived in the destination in question. Chances are, they will have recommendations beyond the normal tourist traps.

Don’t try to plan everything

It may be tempting to schedule every moment of your trip to ‘maximize the fun’, but DON’T DO IT. You will run yourself ragged trying to stick to your itinerary.

• Avoid planning meals too far in advance- You won’t always know where you will be during meal times. If traveling several  timezones away, you might also find that your body clock is off, and you get hungry at different times of the day than when you would normally eat. The biggest exceptions to planning meals are if a) you want to visit a specific restaurant that requires reservations or b) if you’re traveling as part of a large group , which might also require reservations in advance.

Plot Out Your Itinerary

I like to plug activities, flights, etc. into a calendar so I can see how our plans are laid out. I enter flight, rental car pickups, hotel accommodations as soon as I decide what.This also serves as a way to double check that I’m not inadvertently overbooking us, or worse, planning for the wrong date.

Learn From Our Mistakes: While planning an upcoming trip to Costa Rica , I’d made lodging reservations for the first part of our trip (we wanted to stay in a specific Airbnb that was likely to get booked up) and then waited several weeks to book lodging for the second half of the trip. I got lazy and didn’t add the Airbnb reservation on the calendar and didn’t realize until after I’d made the second half reservations that we were due to check out of Airbnb one day earlier than I had thought! I had inadvertently left us with one night in between reservations where we had nowhere to stay! Fortunately, we found an overnight hiking trip (we get to stay in a cave behind a waterfall!) that fit our itinerary for the open night. However, had I not noticed the gap in reservations until later, we could have been in trouble! Lesson Learned: Always plug activities and reservations into a calendar to ensure there are no gaps or overlaps!

Leave Plenty of Buffer Time

Travel is inherently unpredictable at times, and your plans will get messed up. Flights will get delayed, tours will run long, directions won’t take you to where you want to go. Travel hiccups will happen, and it’s best to leave yourself some wiggle room to deal with them.

Plan A Few Backup Activities

I like to keep a list of ‘if we have time’ activities that didn’t make the Must Have Experience list, but are worth doing if there is extra time. But don’t feel like you need to fill every minute! Sometimes the best vacation memories are made in those ‘in between’ moments when you’re simply doing nothing but taking in your surroundings.

Our Favorite Itinerary Planning Resources

Although each destination is likely going to require some specialized research (blogs, guidebooks, etc.), we usually start our planning with these go-to web resources:

• Culture Trip– Provides great ideas for activities, attractions, and restaurant recommendations with a focus on more ‘local’ and off-the-beaten track options.
• Pinterest– Is a great way to find smaller blogs that list out itinerary ideas for just about every destination imaginable. Try searching for ‘Things to do in Destination’.
• Lonely Planet- Their guidebooks are some of my favorites, and the LP website offers some great content to help pinpoint activities and attractions.
• Thrillist– While targeted only at large cities, this site provides up-to-date information on upcoming events, recent openings, and other cultural activities.
• Eater– Since most of our trips revolve around food, we often head straight to Eater to find recommendations and maps showing the best places to grab a bite. Be sure to check out their travel tool for suggestions of great food around the world!
• Destination Guides–  Visit our destination guides and posts for a listing of destination-specific resources we used to plan each of our trips.

Essential Posts:

• How I Plan A Stress-Free Trip Itinerary: Tips to Avoid Overscheduling Yourself on Your Vacation
• How To Plan Your Must Have Experiences+ Free Printable Planning Template

Make sure your check-out, check-in dates overlap

If your trip involves multiple destinations where you’re changing lodging during your trip, be sure that you’re checking in to the new hotel on the same day you’re checking out of your prior hotel to avoid any gaps in your lodging.

For example, if you’re checking out of Hotel A on October 7, you’ll want to check in to Hotel B on October 7 as well. (Unless you have an overnight flight or train that you will be sleeping on.) I’ve accidentally booked Hotel B for October 8, only to realize we didn’t have anywhere to sleep on October 7! (We thankfully caught it on time!)

Trip Planning Step 5: Pack Your Bags

Bringing the right clothing and gear can make a huge difference on how comfortable you are during your trip. But that doesn’t mean buying a whole new wardrobe before every trip. Read our guides on how to curate your travel wardrobe and gear collection with all the essentials you need to enjoy your trip.

Check the weather

If you’re headed to a destination you’ve never been to, it’s a good idea to check long range or historical weather patterns to get a feel for the climate. Be sure to look up the actual city or region you’re traveling to rather than relying on general country-wide weather reports found in most guidebooks. Climate can differ drastically among regions within the same country or even the same region, especially if you’re traveling in the mountains or near water.

Make your packing list

Pick Your Luggage

Check the weather again

Trip Planning Step 6: Prepare to Depart

You’re so close to your much-deserved vacation, and there are just a few more steps to take before you depart to ensure a stress-free trip:

Confirm reservations

Double check that you have all of your essentials

Leave yourself extra time to get to the airport (if flying)

If flying, do yourself a favor, and give yourself plenty of time to get to the airport in case you hit traffic. Getting stuck in traffic and panicking that you’ll miss your flight is an awful way to start your vacation. (We’ve done this more than once.)

Bonus Tip:  If you’re parking your car at the airport, take a picture of the area (or marker) for when you return. I’ve tried writing the location down, but I’ve lost the slip of paper more than once. Pictures last longer. 🙂

Prep your home

Trip Planning Step 7: Bon Voyage!

You’ve planned and planned, and now it’s time to enjoy your vacation! These resources will help you avoid misadventures and get the most out of your trip!

Learn to accept the unexpected

We can almost guarantee that, despite careful planning, something will go at least slightly awry on your trip. Flights get delayed, an attraction might be closed, weather may not cooperate with your plans. While it’s ok to be a little disappointed when things don’t go your way, try not to let it derail your entire trip. Most trips can be salvaged if you’re willing to be flexible and find enjoyment (and even a little humor) in having to switch your plans.

Put your phone away

Smartphones can be a great asset while traveling, but try not to spend too much time staring at your phone. While it’s tempting to document your trip, share pics with friends, or even do some trip planning research on the fly, we recommend limiting screen time while you’re on vacation. When you’re staring at your phone, you end up missing the experience that you’ve planned (and paid!) for.

Stay Healthy

Nothing ruins a trip faster than getting sick! Protect your self from unwanted germs from fellow travelers by eating well, getting plenty of sleep, and staying hydrated. I also always carry disinfecting wipes with me to quickly clean airplane armrests, belt buckles, and other germ-magnets. Find more tips on staying healthy while traveling here.

Allow yourself to check out

While we’d love for everyone to be able to totally leave work pressures behind while on vacation, depending on your work and family responsibilities, taking a vacation might not necessarily mean that you can totally disconnect. However, it’s a good idea to set some boundaries and at least disconnect somewhat from work and/or family back home so you can still recharge on your trip.

Stay safe

Traveling often means stepping outside of your comfort zone, but we encourage our fellow travelers to not compromise their safety! We recommend reviewing this great list of 25 Important Travel Safety Tips from the Expert Vagabond, and we also abide by these travel safety rules:

• Don’t carry large sums of cash. We can always stop at an ATM if we need more.
• Listen to your gut.
• Don’t compromise safety to save money. If you’re on a budget, it might be tempting to save a few bucks by staying in a less than ideal neighborhood or try walking home after a night out. While those situations may work out fine, no amount of cost savings is worth risking your safety. Listen to your gut, and if it doesn’t seem safe to walk back to your hotel in the wee hours of the morning, just take a taxi.
• Give your itinerary to a family member of friend. We always send a copy of our Trip Planner to our parents before we depart so they know our itinerary and where we’ll be staying.
• If traveling alone, share your phone’s location with a trusted friend or family member. When I’m traveling solo for work, I turn on my Google Location Sharing settings so Mike can see where I am in case of an emergency. Find My Friends will also work if you’re an iPhone user!
• Avoid posting vacation pics and details on social media.

Essential Posts:

• Why I’m Taking Fewer Pictures On Our Next Trip: Stepping Out From Behind the Lens to Create Vacation Memories

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