How to Plan a Whole Year of Travel in 7 Steps
Plan the year, not just the next trip. Mapping your time off and your trips together is how you fit in more travel without burning out or overpaying.
If you’re Type A like us, congratulations! You’re going to find the best travel deals and opportunities by planning your year of travel now.
Travel planning can feel overwhelming and full of decisions: where to go, what to do, and when is the best time. It can become a job in itself!
This blog will help you to outline the perfect year of travel so that you only have one last thing to do… go!
Crafting the Perfect Year of Travel
7 Steps to Planning an Entire Year of Travel:
- Set Travel Goals
- Maximize Vacation Time
- Plan Around World Events
- Begin to Book
- Make Your Itineraries
- Plan the Budget
- Prepare Documentation
1. Set Travel Goals
A. DEFINE YOUR TRAVEL GOALS AND INTERESTS
Before diving into the details, it’s imperative to define what exactly you are looking to get out of your travels. Prior to booking a flight, take a moment to define your travel goals and interests.
Are you looking for relaxation? Is adventure and cultural immersion calling your name? Maybe you’re looking for a combination of these!
Understanding your goals and objectives will guide the selection of destinations and activities for your itinerary.
B. DECIDE A TIMEFRAME
Not always do you have full autonomy over the timeframe of your travels. Sometimes the timeframe for your travels are decided for you:
- You may have a special event, like a destination wedding, that has you traveling in a specific month.
- You have limited vacation days and need to capitalize on pre-decided holiday time.
If this is your case, it is important to understand how to utilize your time to get the most out of your travels. This may mean planning shorter but more frequent trips to be able to fulfill your calendar of travel.
Deciding how long you are able to travel for will have a large impact on the destination that you choose.
For example, if you live in the United States and only have a long weekend to travel, Japan wouldn’t be the best choice as you would spend the entire vacation in the air.
C. RESEARCH SHOULDER SEASONS
The age old question of travel: do you choose crowds or do you choose weather?
When a location is in its prime season for weather, this is when you will see the majority of crowding. It makes sense, right? People want to visit a destination when the weather is going to be its best. This spike in tourism is considered peak season. Peak season comes with a rise in flight prices, accommodation prices, and of course, crowding.
On the other hand, do you want to visit a destination when the weather is at its worst? Frigid temperatures, flooding, and hurricane season all would be considered off season for a destination.
The resolution? Traveling during “shoulder season”. Shoulder season is when prices and crowds aren’t off the charts, but the weather is also reasonable enough to visit.
2. Maximize Your Year: How to Add More Trips and Vacations
A. STAGGER SHORT TRIPS VS LONG VACATIONS
While it would be nice to be able to take month long vacations multiple times a year, for most of us, it just isn’t always possible. To be able to still get your travel fill, add a good mix of long vacations and shorter trips to your travel calendar.
This could be the difference between a two week trip around coastal Europe this fall and a long weekend road trip through the Utah National Parks. Both are incredible trips, but one is better suited for a busy work schedule.
A good balance between long vacations and short trips will also help with travel burnout. While this may sound impossible, frequent long travels can become an exhausting jet-lagged blur.
When looking at your year, stagger your trips so you don’t wind up with the only two long vacations only a few weeks apart.
B. UTILIZE HOLIDAYS AND PTO
Get the most out of your year by planning around your work holiday calendar. Most workplaces close for the federal holidays, and many of those fall on a Monday or a Friday, so a few PTO days next to each one turns a long weekend into a real trip.
The average US worker gets around 10 days of PTO. Spend them next to holidays and those 10 days can turn into five or six week-long breaks a year.
Request time off as early as you can. The best weeks go fast, especially in summer and around the holidays.
HOW TO STRETCH YOUR PTO AROUND HOLIDAYS
- Monday holidays (MLK Day, Presidents' Day, Memorial Day, Labor Day): take Tuesday to Friday off for 9 days away on 4 PTO days.
- Thanksgiving: take Monday to Wednesday off for 9 days on 3 PTO days.
- Fourth of July, Christmas and New Year: check which weekday they fall on this year and book the days in between.
- Shoulder season: put your longest trip in spring or fall, when flights and hotels cost less than in peak summer.
3. Plan Around World Events
A. CHOOSE WHETHER TO MISS OR JOIN
Timing is everything when it comes to planning your year of travel. You may be timing your trips around specific events, whether that be choosing to miss the crowds of these events or to be a part of them!
Big events like the Olympics, a World Cup or a stadium tour can double hotel prices in a city. If you want to be there, book early. If you do not, plan that destination for another month or the shoulder season.
We went to the Paris 2024 Olympics, and it was worth it, but only because we planned it around the event. Check what is happening in your destinations before you book.
4. Begin to Book
A. REVIEW YOUR GOALS
What are your travel goals for the year? In the mix of travel planning, it is important to go back and check in to make sure these goals are being met!
Your goals may include something like:
- Take your longest trip yet
- Travel to a new continent
- Do a food tour in a new city or country
- Take a backpacking trip
- Travel on a strict budget
Whatever your travel goals are, keep these top of mind when deciding the when, where, and who of your travel calendar.
Do your travel goals line up with your travel partner’s? If not, you may opt for more solo trips this year! Find people with shared travel goals? Maybe it’s time for a group trip!
B. BE OPEN-MINDED
One of the major lessons of travel is flexibility. Learning to be flexible when traveling or having the opportunity for flexible travel can mean the difference in hundreds of dollars.
WEEKDAY TRAVEL
Generally, the busiest days to travel are Fridays and Sundays. Not only are the weekends the busiest days to travel, they are also typically the most expensive days to travel. Airports are busier, flights are more expensive, and accommodations have less availability. If you have the flexibility, traveling on weekdays like Tuesdays or Wednesdays, can make a huge difference.
FLEXIBLE DESTINATIONS
Flying can be one of the largest expenses when traveling… but it doesn’t have to be! Having a flexible mindset when choosing your destination, can give you a similar destination with a vastly different cost.
Do you have your heart set on Costa Rica for April 26? Your round trip flight could be around $650. As luck would have it, you could fly to Panama on April 25 round trip for $350.
Yes, yes, we know Costa Rica and Panama are not exactly the same, but a destination in a similar region for half the price? We’ll take it.
C. BOOK IN ADVANCE
Now that you know the when and where of your trips, it’s time to start the booking process. This is one of the biggest perks of beginning travel planning early. Booking well in advance ensures that you’ll have the top choices and top deals.
In many cases, reservations can fill up quickly especially if traveling during peak seasons. Luckily, many reservations open up 6-12 months ahead of time to give you adequate time to snag your spots.
BONUS NICHE SPECIFIC ADVICE
CAMPING
Camping spots are a particularly competitive accommodation to reserve. Especially if planning to camp around National Parks, it is crucial to reserve your spots early. Making reservations in January for your June National Parks road trip will be key to getting a great stop, or a spot at all! You can make reservations for National Parks campsites at Recreation.gov.
USING POINTS
When it comes to point hacking your travels, there is a a crucial strategy that often separates the savvy from the spontaneous: booking early. As a flight or accommodation becomes more desired, the point value can fluctuate. By booking early, you get the best rated deals for flights and accommodations when booking with points. Some deals may also be limited in quantity, by booking ahead, you will have a better chance at getting first dibs on your rewards.
5. Curate Your Itineraries
A. BOOK COMPETITIVE DETAILS NEXT
Ok, the flights are booked, now the real fun starts.
As you plan your year of travel in advance, continue to book the most competitive aspects of the trip next, for example:
- In Maui, rental cars are competitive
- In National Parks, camping spots are competitive
- In Almafi, hotel rooms are competitive
- In Tahiti and the Maldives day tours are competitive
B. OUTLINE YOUR ITINERARY
Travel excitement is real. It can be easy to get excited when planning and become overzealous with your itineraries. Especially with close proximity destinations like countries in Central America or Europe, you want to do it all. And you can! We’re not saying to not make the most out of your trip, but be cognizant of jet lag and travel times that can prove to make quick turnarounds difficult.
This being said, everyone’s travel preferences are unique to them! Our recommendation would be two full days per location minimum. This gives you time to adjust to any time differences, get a general lay of the land, and find a favorite place in this location. For larger cities, this number of days could even be doubled.
Staying in in a location for a single night can be perfect for certain situation but often, you’re dealt with the hassle of a later than preferred check-in time and an earlier than preferred check-out time. Allowing two nights in a location gives you one full day to enjoy your destination.
C. BOOK ACCOMMODATIONS
When deciding your accommodations, take these travel needs into consideration:
- What is the distance from the accommodation to your transportation (airport, bus station, train station)?
- How many people does the accommodation sleep?
- Would you prefer a kitchen to be able to cook meals?
- What area would you like your accommodation to be in?
- What is the budget you would like to stick to?
Once you have decided the answers to the questions above, you can begin to narrow down the search. Most accommodations fall into two categories: hotels/hostels and vacation rental properties such as Airbnb or VRBO.
HOTELS AND HOSTEL STAYS
Hotels are great for short term stays. Many will offer accommodation perks like room cleaning, continental breakfasts, and amenities such as a pool or hot tub. Another great perk of hotel or hostel stays is that they are planned to be located in highly accessible areas.
VACATION RENTAL STAYS
Vacation rental properties can be a perfect fit for both short and long term stays. These can be very unique stays anywhere from a rental room in someone’s home to an entire beach front stay to yourself. Vacation rentals offer more independence than hotels. Sometimes these stays come with the ability to meet your host which can be a great cultural experience.
6. Estimate your Annual Travel Budget
An unlimited travel budget? That is the dream!
If this isn’t quite your case, then it is important to set a budget when travel planning for the year. A good budget planner is key to keeping on track while you plan the year. Full-time travelers and owners of Tripped Travel Gear, Tim and Fin, created the ultimate budget planner for long term travel.
Even if long term travel isn’t in your plans for this year, their budget planner can be catered to any length of trip!
7. Prepare For Travel
Before we go any further, go double check that your passport isn’t set to expire within the next year
Did You Know: Although a passport has an expiration date, a passport is not longer valid to travel with within 6 months of the passport’s expiration in most international destinations.
Okay, are we all set?
Passports are crucial for international travel, but there are a few other documents that must be acquired prior to heading out on your travels.
VISAS
A visa is a permit that is required to enter certain countries. They are issued based on the type of travel and duration of trip, particular to each country.
Be sure to check:
- Does your destination require an entry visa?
- Does your destination require a visa for the length of time you’re visiting?
- How long does your visa last once issued?
Depending on the country, the visa application and issuing process can be extensive. Some visas even can require an in person interview. Another perk of planning your travel early is less stress around a late visa!
IMMUNIZATIONS
Unfortunately, illnesses are a part of travel… we’re looking at you Bali Belly! To help from coming back with something more serious, certain countries recommend immunizations prior to visiting or carrying medications while traveling. Check out the CDC’s recommendations prior to traveling to stay up to date.
PACKING
Did you know there’s a RIGHT way to pack a suitcase? Whether you’re trying to avoid baggage fees by going carry-on only, or are wanting to maximize space in your suitcase, we have the Ultimate Packing Guide for you!
For a guide to the right way to pack:
DOWNLOAD THE TRIPPED PACKING SYSTEMYour Year of Travel
People are traveling more than ever. In this year of travel, it’s about checking off your bucketlist and going further than you’ve gone before.
This year will be full of epic destinations, exciting deals, and unforgettable trips. All thanks to YOU for starting your year off by planning the ultimate year of travel.
Packing for this trip? Shop Tripped Travel Gear, the packing cubes and organizers we designed.
