The 6 Steps To Planning A Trip: Tips & Strategies for a Perfect Vacation
It has taken us years to perfect the method of planning a trip.
Planning a trip can be both exhilarating and overwhelming. From choosing the destination to booking accommodations and creating an itinerary, there are numerous factors in the planning process to consider.
However, with the right approach and by using our strategic planning, you can ensure a smooth and enjoyable experience.
Here are some tips and strategies to help you plan the perfect trip.
The Right Way to Plan a Trip
6 Steps to Planning a Perfect Trip
Setting Travel Goals
How to Score a Cheap Flight
How to Plan a Trip
Booking Accommodations
Planning Your Daily Itineraries
Packing Wisely
1. Set Travel Goals
A. DECIDE YOUR “WHY” FOR TRAVEL
Embarking on a journey, whether it's a short weekend getaway or a long-term exploration, begins with setting clear and achievable travel goals. Traveling isn't just about visiting new places; it's about experiences, cultures, and creating lasting memories. In this section, we'll delve into the importance of setting travel goals and how to go about it.
Your “why” for travel could be anything exciting from trying new foods and visiting all of the National Parks in the US or it could simply be to relax. Whatever your “why” is, your destination should reflect that! Keep this in mind when beginning to travel plan.
For example, if live in the US, need some warm weather and a beach, take into consideration yourself, and with your travel partner…what else? Do you really just want to sit on a beach or at the pool for most of the day? (If yes, great! … aka Bahamas, DR, St. John) .. if not, maybe you’d also like a walk in a nearby jungle or volcano? (aka Maui, Costa Rica, Belize, Puerto Rico).
B. CHOOSE A TIMEFRAME
Time is a precious commodity when it comes to travel planning. Assessing how much time you can allocate to your trip helps determine the entire scope of your adventure. Whether it's a weekend getaway, a two-week vacation, or a year-long sabbatical, understanding your time constraints allows you to plan accordingly and make the most of every moment. With that said in our experience, Americans OVERESTIMATE the time they need to travel somewhere.
For example, if you live in the United States did you know it is only a 5 hour flight to Iceland from New York? Only a 4 hour flight from Denver to Belize? 3 Hour flight from Dallas to Mexico City? 5 hour flight from Boston to Azores?
Setting a realistic timeframe can start with looking at your vacation days from work. But don’t write off a bucketlist international destination just because you can only take 2-3 days off work.
C. DECIDE THE TYPE OF TRIP
Finally, define the type of trip that aligns with your interests, preferences, and travel goals. Whether it's a solo adventure, a romantic getaway, or a family vacation, choose a travel style that suits your needs and enhances your overall experience.
This also is when you decide who you are traveling with.
Maybe save Thailand to visit on your honeymoon, or Mexico City to check out with another couple instead of flying across the US to meet at each other’s house.
Your parents want to get together this summer? Sharing an Airbnb in Spain’s wine country might sound extravagant but not if you scored that $450 round trip ticket to Madrid and your shared villa only costs each couple $200/night.
Your “who” may greatly impact your “why”, “when”, and “where”.
2. How to Score a Cheap Flight
With so many tools out on the internet now, it is easier than ever to score the best deals on flights. With every search engine claiming to have found the best price, you may find yourself asking, “How do I know that I’m getting the best deal?”
A. MAXIMIZE SAVINGS WITH FLIGHT PRICE COMPARISON TOOLS
Flight price comparison tools streamline the process of finding the best deals by comparing prices from multiple sources in one place. Sites like Hopper, Skyscanner, and Google Flight help with compare prices across many airlines.
TIP: Not all airlines participate in price comparison tools. Check directly on sites for airlines like Southwest and Jetblue to see their flight options!
Many of the price comparison tools also offer the ability to send you a notification when prices drop or change.
One of our favorite resources for scoring cheap flights is by using Faredrop. Faredrop is a tool created by full-time travelers, Youtubers, and friends of Tripped, Kara and Nate.
HOW TO USE FAREDROP
Personalized Deal Alerts:
FareDrop's team of experts constantly monitors flight prices and sends personalized deal alerts tailored to your preferences and budget.
Exclusive Savings
FareDrop negotiates exclusive deals with airlines and booking sites, so that you have access to the lowest fares available.
Expert Advice: FareDrop's team of travel experts provides personalized advice and assistance throughout the booking process, helping you navigate travel itineraries and maximize your savings.
B. HOW TO USE CREDIT CARD POINTS FOR TRAVEL
There is a lot you can learn about using credit card points for travel, but we’ll give you the high level things that you should know when starting you point hacking journey.
Not only are travel credit cards great for flights miles, they also come with long list of perks like lounge access, travel insurances, and fee reimbursement that will make your travel experience that much better.
CHOOSING THE RIGHT CARD
Every credit card is different, with different perks to fit your lifestyle and spending habits. The first step to point hacking is to choose the right card for you. Some of our favorite travel credit cards include:
Read into some of these cards and check out which one will accumulate the most points based on your everyday purchases.
POINT HACKING 101
Almost every travel credit card will offer a sign on bonus. Meeting the minimum spending requirements within the specified timeframe can earn you a bonus of points or miles.
Depending on the card, you can earn enough points for a roundtrip to Europe by just meeting the minimum requirements.
Different spending categories will give you a different amount of points depending on the credit card you choose. Make the most of bonus categories like shopping and dining to earn extra points on your everyday spending.
Are you a foodie? Look into a credit card that offers you more points for dining.
Look for opportunities to transfer points to travel partners for higher redemption rates. This is especially beneficial if you are loyal to one or two specific airlines.
Frequent United flyer? Transfer your credit card points over to your United portal to be able to get the most out of your points.
AND just remember - no matter what any blog or blogger tells you (those are not affiliate links above by the way) the best travel card for YOU is the one that YOU spend the most on in the bonus categories. If you’re just getting started with points and miles, start with the Chase Freedom card and it will get you 60% of where you need to start out - all for free.
3. Create a Budget
We are firm believers that you can travel anywhere. No matter the budget. There is always a way to accommodate a budget; it’s all in the planning!
A. CREATING A REALISTIC BUDGET FOR YOU
A realistic travel budget doesn’t have to be rigid. It all starts with choosing flights and accommodations that work with the budget that you have set in place. Don’t feel like a tight budget has to hinder your travel experience. Traveling can be cheaper than you think.
If you’re looking to book long-term travel on a budget, check out Tim and Fin’s tips to budgeting for a multi-destination trip HERE!
B. WORKING WITH YOUR BUDGET
In our experience there’s usually the “expensive” way to do something and the “budget” way to do something. No matter what you spend, earth is earth. The Santorini sunset is still the Santorini sunset whether you have a private dipping pool or you’re standing on a crowded street (I’ll take the first please!). There’s very few places you also can’t enjoy just like the “luxury travelers” there just might be a different approach.
If traveling with a buddy or partner, be sure to have to conversation about budget beforehand. Being on the same page about budget will help you to stick to it and enjoy your trip without pinching pennies.
TIPS FOR A TIGHT TRAVEL BUDGET
Travel During Shoulder Season
Peak season means peak pricing. Traveling during the shoulder season of your destination will give you the best pricing on accommodations, flights, and activities.
Book In Advance
I’m talking to you, Travel Procrastinator. Booking your trip early will give you free range of places to stay and the best luck at scoring a cheap flight.
Short-term Rentals
Choosing Airbnbs or VRBO’s over hotel stays allows you the flexibility to cook your own meals. Or opt for a hotel that includes a kitchenette to lower the cost of dining out.
4. Book Your Accommodations
A. RESEARCH YOUR LODGING OPTIONS: HOTEL VS AIRBNB
When deciding on accommodation for your travels, one of the primary choices you'll face is between staying in a hotel or opting for an Airbnb. Each option offers its own unique advantages for everyone’s preferences and travel styles.
CHOOSING AN AIRBNB
Airbnb’s or other short-term rental stays offer two main benefits: privacy and independence. At a short-term rental you typically will have the place to yourself (unless disclosed that it is a shared space) and you will also typically have a space for cooking.
Airbnb’s are a great way to feel more connected to the area that you are visiting for a more authentic experience.
Airbnb’s are also a great option while traveling with more than 2 people. Now, for less than the price of two hotel rooms you can all share a kitchen and living space.
TIP: The Airbnb platform isn’t just for accommodations. On Airbnb, you can find experiences as well! Some of our favorite food tours have been found through Airbnb.
CHOOSING A HOTEL
Hotels are a great low maintenance option. At a hotel you will have cleaning services as well as dining which puts less pressure on you as the guest. Hotels are great for quick stays especially during travel days.
Whether you choose a hotel or a short-term rental, the biggest tip is to book early! If you have your eye on a place, book it up before someone beats you to it.
B. CONSIDER LOCATION
The location of your accommodation can significantly impact your travel experience. Consider proximity to attractions, public transportation options, and safety when making your decision. Choose a location that allows easy access to the sights and activities you want to explore.
This also accounts for travel days. You don’t want to be staying 50 miles from the airport for a 7am flight…
…and you don’t want to save $300 on your accommodation just to stay way outside the city, but pay for $40 ubers back and forth all weekend (creating a wash!)
5. Plan Your Daily Itineraries
A. DESIGNING YOUR DAY-TO-DAY
We are big fans of a mix of structured days and go-with-the-flow days while traveling. If you’re totally Type A, go ahead and schedule out your trip! It’ll make you feel better to have a sense of what is going on each day.
This could include:
Daily activities/excursions
Restaurant reservations
Transportation between activities
If you don’t feel like you need a schedule to adhere to, schedule out the basics and allow yourself to see where your trip takes you.
If this is your case, the basics that you should have planned are:
Nightly accommodations
Transportation (if you are traveling to different cities or countries)
Whether you choose to hardcore plan or hardcore wing it, be sure that whatever you choose to do fulfills the “why” of your travels.
B. CREATING A BALANCED SCHEDULE
Travel burnout is a real thing! Plan our a balanced schedule to ensure you have time to relax and enjoy the moment. We’re not saying don’t make the most of your trip! Just be cognizant of impending jet lag and hold ups that can lead to burnout.
Travel burnout can also come from planning rigorous activities too close to travel days.
For example: if you want to hike the Mahana Ridge Trail in Maui, don’t plan the hike the morning after a 19-hour travel day. Similarly, if you are planning your big hike, choose to have a low-key afternoon so that you’re not rushing or too exhausted to enjoy your other plans.
C. UTILIZING TRAVEL PLANNING TOOLS.
Where to even start? You might be feeling overwhelmed with travel planning. It’s time to start leveraging travel planning tools to help you make plans and stay organized. Some of our favorite travel planning tools are:
GOOGLE MAPS
Dowload the map of the area or region you will be in to have access to maps even without service or wifi. You can then pin places you want to visit or see to easily navigate while traveling.
GUIDE
This AI tool will generate an entire trip itinerary for you. You just answer basic travel questions like “when are you traveling” and “what are your interests” and Guide will create an itinerary for you based on the duration of your trip.
WANDERLOG
The Excel spreadsheet and sticky note method is old news! Wanderlog is an organizational platform that simplifies the process of planning your accommodations by allowing you to seamlessly add flights, Airbnb rentals, and more to your itinerary. While itinerary planning, you can add in hikes you want to do, places you want to see, and restaurants you want to dine at.
6. Pack Wisely
A. STARTING A PACKING LIST
Begin by creating a packing list to ensure you have all the essentials for your journey. The moment you plan a trip, you start thinking of things to bring. Write them down as they come to mind to ensure you have all the essentials for your journey! This is including clothing, toiletries, medications, travel documents, and any items considering the weather, activities, and cultural norms of your destination.
B. OPTIMIZING LUGGAGE SPACE WITH COMPRESSION CUBES
Compression cubes are game-changing tools for maximizing luggage space and keeping your belongings organized. You can pack day-to-day or choose to pack similar categories of items together in separate cubes to stay organized and easily access what you need during your trip.
THE TRIPPED PACKING SYSTEM
This system of packing was designed by travelers for travelers to ensure you have everything you need and nothing that you don’t for a streamlined packing experience!
The Tripped Packing System follows 3 main steps:
Pull - Pull everything you need for your favorite day, your most important day, and your travel day.
Push - Push past panic. Keep an abundant mindset. You will be able to take everything you want and need.
Pack - Choose a packing system, categorize your items, and double check.
By following these 3 steps, you will think about the entirety of your trip to be able know exactly what you need to bring.
Want To Pack Smarter?
For a guide to the right way to pack:
C. PACKING APPROPRIATELY FOR YOUR TRIP
As tempting as it may be to pack everything but the kitchen sink, resist the urge to overpack and instead focus on packing smartly and efficiently. Choose versatile clothing items that can be mixed and matched to create multiple outfits, and opt for lightweight clothing to minimize bulk and weight.
Between transportation and luggage fees, most times more luggage = more hassle.
This doesn’t mean that you have to go carry-on only.
But when you start dragging your heavy checked bag up the walk-up Airbnb in Paris, you’ll see what we mean.
Planning Your Perfect Trip
Believe it or not, traveling planning can be half the fun!
Deciding where to go and what to do can be stressful but by following these 5 steps to planning a trip, you’ll be off to the airport in no time.
