How To Plan A Trip From Flights And Hotel To Travel Guides!

How To Plan A Trip From Flights And Hotel To Travel Guides!

How To Plan A Trip

From initial planning to pre-departure, how to plan a trip in 5 easy steps while navigating travel in a post-COVID world!

COVID has placed tremendous pressure on today’s travel scene, redefining the way we are conducting business and transforming one’s approach to vacationing. Regardless of purpose, navigating how to plan a trip from flights and hotel to travel guides can be a challenge for novice and experienced travelers alike, especially under today’s new rules.

Dying for an adventure? Us to!
Uncertain about how to plan a trip during post-COVID days? You are in good company!
Can this post help? We sure hope so!

This article provides a wealth of resources and pro tips, while walking you through, step-by-step, how to plan a trip. From initial research to pre-departure preparation, we will draw on our experiences from the field while factoring in the updated rules of todays travel.

Let’s get underway!

How To Plan A Trip, Step 1 – A Plan Is Hatched

Just where should one get started as they gear up to travel? With a plan, of course! I like to begin by charting out the following:

  • Purpose of the trip
  • COVID safety considerations
  • Location, duration & dates
  • Who all will be joining you?
  • Budget
  • Mode of transportation e.g., flying, driving, going by train, camper van

How To Plan A Trip, Step 2 – Let’s Get Booked & On Our Way!

  • Research options
  • Book key items e.g. flights, ground transportation, lodging
  • Determine travel Insurance needs
  • Ground transportation options
  • Staying fueled while in route

How To Plan A Trip, Step 3 – Upon Arrival

  • The art of the rendezvous
  • Eating out

How To Plan A Trip, Step 4 – Staying Organized, Up To Date & Connected

  • Lists are a travelers BFF
  • Travel Apps of interest

How To Plan A Trip, Step 5 – Pre-departure Preparation

  • Some last minute ideas that take you through the home stretch

How To Plan A Trip, Step 1 – A Plan Is Hatched

My dear friend and I look forward to our traditional vacation every January with great anticipation. And by January, we are both ready!

We can’t wait to meet up in a warm, sunny location to escape the long days of winter! Oh, to feel the sand between our toes and spend precious time catching up.

She travels from New York, and I from Portland, Oregon, therefore a lot of planning goes into our logistics. Furthermore, I have more flexibility when it comes to flying longer distances. To this end, I generally organize many of the details of our overall trip, with her input of course, and she rewards me by buying my meals once we arrive!

COVID Safety Considerations

This year, COVID has made our planning even more complicated! We discuss our hesitations, concerns and anxieties, reflecting on past experiences regarding how to plan a trip. Tapping into travel blogs and the free online travel guides proves invaluable as we get deeper into researching our adventure.

My friend and I are both genuinely concerned about our health and the health of those around us. Online safety tips go a long way to inform us of rules that may impact our trip. Furthermore, sites such as the CDC State & Territorial Health Department provide a lot of useful information in support of our planning.

Air Travel In Today’s Post-COVID World

Historically, travel plans that involved flying began months in advance as a way of saving money. However, now days, you can find inexpensive flights and flights and hotel packages.

While inexpensive flights are super sexy, what about the financial ramifications of having to change or cancel flights? Search engines such as Expedia, Priceline, google flights, and Kayak are a great place to compare options however when ever possible, I recommend booking direct.

When at all possible, book direct!

Although a great place to research deals, there are good reasons to avoid booking through OTA’s.

often the same deal can be found when booking direct and you get all the customer service feel goods!

Loosing out on airfare due to change in plans is certainly a concern for my friend and I! Therefore, prior to committing to fly, we review cancellation guidelines and are pleasantly surprised! Many airlines have implemented flexible refund policies to encourage air travel. This goes a long way to alleviate the stress around loosing airfare due to a change in plans.

For Those Staying Grounded…

In the event that you are keen to stay grounded, going on a socially distanced adventure and planning a ‘staycation’ may just be the ticket!

Working remotely and the kiddos are home schooling? Then why not take advantage of the situation, head out on a road trip and rent a vacation home?

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Many vacation homes provide modern conveniences, flexible workspaces for those operating virtually, and allow pets. In addition, having a full kitchen at your discretion allows you to prepare meals in the comfort and safety of your home away from home. Researching vacation rental information on sites such as Airbnb and VRBO is a wonderful place to begin. I have stayed in a host of Airbnb’s throughout the US, as well as Internationally, and yet to be disappointed.

For the serious road tripper, perhaps renting a home on wheels is your preference! The camper van craze isn’t just for those seeing a nomadic lifestyle! Check out camper van rental options on sites such as Outdoorsy and USACampervan!

How To Plan A Trip, Step 2 – Let’s Get Booked & On Our Way!

My friend and I conclude that we are indeed comfortable with flying. With this decision made, we set our sights on vacationing in sunny St. Petersburg, Florida for the white sand beaches, sunny weather, and East Coast location (shorter flight for her)!

Alas, our plan is hatched and we turn our attention to booking our flights!! Weee!

Researching & Booking Flights

Since we will be rendezvousing at the Tampa airport, we will do our best to land around the same time. We begin comparing flight options using google flights. Why do we love google flights? It provides multiple options on our preferred airlines, United for me, Delta for her.

Fantastic flights are found within our budget. We review COVID updates and cancellation policies for our desired airlines, United Airline and Delta Airlines. All looks good, so we pull the trigger!


Lodging is an important decision and one that is typically predicated on the purpose of your trip.

The corporate traveler may choose a location close to clients and conveniences they require to conduct business. In contrast, the vacationer may be more selective based on tempo and what leisure activities they wish to partake in.

As for our trip to Florida, my friend and I love taking in the sights while walking to nearby restaurants, bars, and city attractions. For this reason we will rent a car and choose to stay centrally located.

To save some cheddar, I try booking all or part of our lodging on points. I am part of the Marriott Bonvoy loyalty program. Why do I love Marriott? One of the reward programs gives you access to staying at over 30 brands, offering a range of accommodations. Free nights at locations of my choosing? Yes please!

I source our location and eureka, I’m able to score 3 nights on points!

Not part of a rewards program? To help better inform your hotel selection, guest reviews on TripAdvisor, ratings found on hotel websites, and insights shared on travel blogs can go a long way to help inform decisions. Furthermore, filtering hotel rates to see other discounts on offer. For example, AAA members and military are often extended fabulous discounts.

Every little penny helps!

Maximize loyalty & rewards programs for amazing benefits!
Free Nights At Your Favorite Hotels
Flight Upgrades
Rental Car Discounts
Purchasing Points

now that’s money in the bank
Need Travel Insurance?

Now that flights are purchased, this is the perfect time to assess travel insurance needs and research options. There are benefits to travel insurance and policies that can be reviewed via 3rd party vendors as well as through the airlines directly .  

Prior to buying travel insurance, be sure to compare coverage against new airline refund policies.

They may overlap!

saving money is fun!
Ground Transportation Options Abound

In the US, travelers are spoiled by the variety of transportation options they have. Not only are there a number of rental companies to choose from, rideshare has come a long way, as has public transportation.

During our time in Tampa, my friend and I have chosen to rent a car during our entire stay as we want to have wheels at our discretion throughout our entire visit. For longer trips, however, we may choose to rent cars on a daily basis or not at all at destinations with decent public transportation.

Did you know, most CC companies provide converge on rental cars? Furthermore, many auto insurance companies slide this service in as part of your general coverage. Be sure to check into both benefits and if all looks good, save money and bypass purchasing extra converge through car rental agencies.

Why not leave the driving to others? Sounds good to us!

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Traditionally, taxi’s have been the key option for leaving the driving to someone else. However, in additional to Taxi’s, rideshare companies such as Lyft and Uber have really come on the scene and changed one’s ability to hop from one place to another. Simply download each app, respectfully, put in your payment information, enable you GPS and you are good to go.

Not only will the drivers know where to pick you up, you set you destination and no cash exchanges hands. Efficient and more secure!

Staying Fueled While In Route

When it comes to food options, staying fueled is critical and during COVID days, finding food (and healthy food at that) may be a challenge.

Airlines often have limited meal options and many restaurants are closed or operating under reduced hours. One solutions is to pre-pack healthy snacks to stay nourished between stops.

Most airports have posted up-to-date restaurant information as a way of keeping passengers informed. As for airlines, they offer special meals upon request prior to departure. Check out United Airlines, for example!

How To Plan A Trip, Step 3 – Upon Arrival

Excitement mounts as you set your sights on arrival at your destination! Whe’re here, now what?

The Art Of The Rendezvous

Ahhh, the art of the rendezvous! In the case of me and my friend, we have traveled together extensively and have learned a lot of valuable lessons along the way. One such lesson is that airport maps are an awesome resource to help us get from point A to B. It’s all about easing stress and understanding an airports lay of the land can sure help!

For those traveling solo, or as a team, an additional strategy is staying organized, up to date and connected with the use of Apps (See Step 4!).

Going back to our Tampa example, I arrive an hour earlier thus will grab the rental car, swing around, and pick my friend up once she lands. Every hour saved is one more hour at the beach! To plan this timing, I will use the Delta Airlines app for flight arrival updates.

Eating Out

While my friend and I both eat healthy, we also have a few dietary restrictions. To this end, I have booked us lodging that offers room service with a variety of options.

As for venturing out, we will check in with the hotel concierge or ask locals for recommendations. To research additional options, I like to use Yelp as it has a variety of filters to choose from, guest reviews, photos, a map view for directions, and contact details.

COVID tip once at your destination: Every state has different rules and regulations regarding eating out. With rules changing often, details posted to restaurant websites may not be up to date. Mitigate frustration by calling ahead of time to confirm their hours, seating options, if they take reservations and if they are serving from a full or limited menu.

How To Plan A Trip, Step 4 – Staying Organized, Up To Date & Connected

Packing lists are a travelers best friend and are a fabulous way to stay organized! With a variety of online lists to reference, your destination, duration and dates can inform what you bring, and how much.

My goal when I travel, regardless of trip duration, is to only carry on what I bring. As a result, this saves money on baggage fees, keeps me from overpacking, mitigates issues around lost luggage, and makes logistics much more manageable.

My philosophy is, if I can’t carry it, I’m bringing too much! Experiences from the field have taught me:

  • For longer trips, mix and match your outfits and bring items that can be hand washed. This will save on valuable packing space, especially if you like to shop along the way as I do!
  • Only bring items you can’t purchase upon arrival.
  • I never leave home without flip-flops, a multi-functional coverup / scarf / wrap, compact plastic poncho, swim suit, high fuel grab-n-go snacks (such as nuts), and passport.
  • Travel in your heaviest clothing, such as boots, jeans, jackets, and sweaters, that would otherwise take up a lot of packing space.
  • Think through how much cash you need on hand and plan accordingly. While in the states, I always have a little cash for tips and incidentals. For international travel, I review airport maps to locate currency conversion stations and ATM’s and often wait until I arrive to convert or withdraw money as needed.
Travel Apps To The Rescue!

In addition to lists, Travel Apps are an awesome way to stay organized, up to date and connected!

So which are the top apps to consider? If you check out any “best travel app” review, you will find the following on the list!

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TripIt organizes reservations and creates master itineraries that can be shared with friends and family. Users simply forward reservation confirmations to be automatically added to a master itineraries.

While TripIt may not be the best option from a collaborative perspective, it auto-syncs with calendar apps such as Apple iCal, Outlook, and GooglePlay. Available on both iOS and Android, TripIt has a free version or you can upgrade to a TripIt pro subscription and access additional features.


Ah, the great open road! If you enjoy road tripping as much as me and my friends, you may find RoadTrippers a handy app! Enter where you want to start and finish and in short, discover destinations along the way.

Available on both iOS and Android, RoadTrippers offers a free version or you can upgrade to a RoadTrippers Plus subscription. The paid option allows you to plan longer trips, collaboratively. Furthermore, you can select from a list of offline maps to explore while off the grid.

Sygic Travel

Sygic Travel is one handy app that maps out day-by-day itinerary details. The free version of this app catapults driving details by displaying itinerary information on a map. To this end, if you will be going to remote locations with spotty service, the ability to download maps ahead of time may just do the trick putting your mind at ease!

In addition to offline maps, Sygic provides readymade travel guides for over 10,000 locations. Upgrade to Sygic GPS Navigation to stay apprised of traffic, find the best parking spots, and avoid speeding tickets.

New App On The Block – GOeConcierge

Released in 2021, GOeConcierge is a digital organizer created by our team of travelers, for the traveler. Designed to streamline organization, collaboration and expense reporting, this powerful, multi-purpose goodie combines the power of 3 apps in one.

In addition to the organizational features, GOeConcierge provides users with the ability to track and log mileage, as well as customize expense report templates, making this app truly unique!

Ideal for individuals and groups alike, you can try this ‘new app on the block’ free for 14 days or choose from a number of subscription options.

Exploring A Broader Selection Of Travel Apps

Don’t just take our word for it! With a myriad of options to explore, once again, blogs and articles to the rescue!

Below you will find a host of “best travel app” reviews that may be of interest:

For software alternatives and reviews, check out independent software marketplace, SaaSHub.

Options are awesome!

How To Plan A Trip, Step 5 – Pre-departure Preparation

Here we are, the home stretch!

As mentioned above, lists are a traveler’s best friend, and we love providing you with this list of last-minute preparations!

24 to 48 hour prior to departure, we recommend:

  • Pack early then review! To avoid forgetting items you may need, check the weather forecast, go over your lists one last time and review your pack job so you can grab that umbrella, sunglasses or scarf prior to take off.
  • Have you packed items that will help keep you safe and comfortable while traveling during COVID?
  • Download itineraries, get checked into flights, and secure seats.
  • Call your bank and credit card company prior to departure to avoid security locking.
    • If traveling internationally, check to see what their currency conversion rate fees and cash withdrawal options are.
    • Ideally you would use credit cards that gain reward points.
    • If renting a car, inquire what insurance coverage the CC provides. Often CC companies will provide rental car insurance which you can cross reference with your own auto insurance. Avoiding the need to purchase insurance through the rental car company can save you a lot of expense, additionally ensuring that you have the coverage you need in case of emergency.

And lastly…

  • Put yourself in your trip and think through any last details you may have overlooked. For example, currency. Are you traveling with enough cash? If not, where can you access it? Most airports do a fabulous job posting these details to their services page on their website.

We’re Curious … How You Are Preparing For The ‘New Normal’ Of Travel?

As the hospitality scene comes out of it’s post-COVID slumber and re-awakens as a redefined industry, just what will the ‘New Normal’ of travel look like?

Our team at GOeConcierge is interested in your opinion. What do you think the ‘New Normal’ of travel will look like and how will these anticipated changes impact you? If you have dusted off that wheelie bag, dipped your toe in and tested the waters, what have your experiences been so far?

About the author

Simply put, Tamara lives for travel and travels to live! With 25 years of bleisure travel under her belt, it is only fitting that she founded HospitaliYAY LLC, a 2020 start-up described as the perfect intersection between technology, travel, and hospitality.

Tamara and the HospitaliYAY team bring their unique tech and travel expertise to the eConcierge suite of products designed to help novice and experienced alike travel like a pro!

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