Planning a trip can feel overwhelming—there are so many details to consider, from choosing a destination to booking accommodations and figuring out transportation. If you’ve ever thought, I want to travel more, but I don’t know where to start, you’re not alone. Learning how to plan a trip in a way that feels simple and stress-free can make all the difference.
While I’ve always had a knack for organizing, trip planning wasn’t always easy or enjoyable. The more I did it, though, the easier it became—and now, I genuinely love the process. Long before I started this travel blog, I found planning trips to be exciting and fun, which ultimately led me to create Life of Whimsley.
I know not everyone loves planning—and that’s okay. If it doesn’t come naturally to you but you want to get better at it, just remember it takes time. The more you do it, the easier it gets—even if you never end up loving it.
In this guide, I’ll walk you through the foundational steps of how to plan a trip, from choosing your destination to making the most of your time while traveling. We’ll cover key considerations for U.S. versus international travel, and I’ll share insights from my own planning process along the way. Let’s dive in!
Step 1: Choose Your Destination
Picking a Destination
Before diving into travel details, the first step in how to plan a trip is choosing a destination that aligns with your interests, budget, and time frame.
It sounds simple, but sometimes deciding on a destination is the hardest part. Maybe you have a place in mind, but after researching, it doesn’t seem like the best fit. Or perhaps your destination has already been decided for you, and now you need to figure out your plan.
If you’re still deciding, here are a few questions and considerations:
- First-time traveler? Start with destinations that are easy to navigate and match your interests. Consider places with good infrastructure, English-speaking locals, or well-established tourism industries.
- Seasoned traveler? Maybe it’s time to push your comfort zone with a new type of adventure.
- Factor in seasons & weather: Ideal times to visit may vary, and these two factors are closely connected. We almost always travel during shoulder season. (Fun fact: April is my favorite month to travel abroad!) I don’t like being uncomfortably hot, so we avoid destinations during their peak summer or rainy seasons.
- Consider your budget, travel time, and trip length together: Your budget will likely influence how long you can travel, but time constraints matter too. For example, Japan might be on your wishlist, but if you only have five days, the long flight and time difference could make it a less ideal choice.
- Flight deals: Often, seeing an amazing flight deal is what helps us decide where to go—sometimes to places we hadn’t even considered.
Key Things I Research Before Traveling
- Resources I use: Pinterest, travel blogs, guidebooks, Google, and recommendations from friends or family who have been to the destination.
- What I focus on:
- Best areas to stay: Walkability, safety, quiet vs. lively, nearby food, and activities. I also do a quick search on hotel or vacation rental prices to get an initial sense of potential costs.
- Transportation: How easy is it to get around? Will we use public transport, or need a rental car, or hire private transfers?
- Top attractions & hidden gems: The number of things to do can help to determine how long to stay.
- Local customs & etiquette: Should you tip? Is there a dress code for certain places?
- Best times to visit: Consider shoulder season or off-peak travel for fewer crowds and lower costs.
- Weather: Research average temperatures and any extreme seasonal conditions (hurricanes, typhoons, etc.).
- Major events: Know if national holidays, festivals, conferences, or other events will impact pricing and availability.
Avoid over-researching! Get informed but leave room to be surprised and delighted during your trip too.
U.S. vs. International Considerations
- U.S. trips: Easier domestic flights, no passport needed for U.S. Citizens, fewer language barriers.
- International trips: Factor in visa requirements, vaccinations, currency exchange, and cultural differences. Pro tip: Double-check your passport’s expiration date! Many countries require it to be valid for at least six months beyond your travel dates. Avoid last-minute stress by staying on top of this before booking your trip abroad.
Step 2: Set Your Budget & Trip Length
Budget Considerations
Your budget determines where you can go, how long you can stay, and what type of experience you’ll have. A crucial part of how to plan a trip is understanding how far your budget can take you. Not all destinations are equal—$2,000 in one place may stretch much further than in another.
- Major expenses: Flights, accommodations, activities, food, and transportation.
- Hidden costs: Visa fees, travel insurance, baggage fees, currency exchange rates, SIM cards, and international data plans.
Trip Length
- Weekend getaways vs. multi-week trips: Domestic trips are often shorter, while international trips typically require more time to justify the travel effort.
- Factor in travel time & jet lag: Some destinations take multiple days just to reach (Looking at you, Australia!). If possible, we always try to return home on a Friday or Saturday to allow time to reset before heading back to work.
U.S. vs. International Considerations
- U.S. trips: Shorter flights and time zone changes make weekend trips more feasible.
- International trips: Long-haul flights mean you’ll want at least a week to make the most of your time.
Step 3: Decide on Your Travel Style
Ahead of planning the logistics, consider how much structure you want in your trip. Some travelers love spontaneity, while others prefer a well-organized plan.
I typically fall somewhere in the middle—having key logistics booked but leaving room for flexibility. Everyone has their own way of traveling, and deciding on your travel style early will shape how you plan your trip.
Types of Trip Planning Styles:
- Figure-it-out-as-you-go: Book flights and accommodations, but plan activities spontaneously. Perfect for seasoned travelers who thrive on flexibility or those who love to wing it.
- Semi-planned: Book flights, lodging, and key activities, leaving room for unplanned exploring.
- Fully planned: Structure everything in advance to maximize time, perfect for destinations with limited availability for popular attractions.
How Much Planning Is Too Much?
No matter how you like to travel, having a loose itinerary helps you make the most of your trip without feeling overwhelmed. It also leaves room for flexibility when things don’t go quite as planned (because, let’s be real, it happens).
Figuring out your travel style early on makes a big difference—it helps you know how much planning you actually need and when to start. For international trips, I usually start planning 3-6 months ahead, while domestic trips can be anywhere from a week out (if we’re really feeling spontaneous) to three-ish months if it’s a more popular destination or we snag a great flight deal.
There’s no one-size-fits-all approach, but keeping a rough timeline in mind can make planning way less stressful.
Step 4: Book Flights & Transportation
When learning how to plan a trip, figuring out flights and transportation is one of the most important logistics to sort out early.
Finding the Best Flights
- Flight search tools: Google Flights, Skyscanner, ITA Matrix, and Hopper.
- Consider weekend flights carefully: While they may be cheaper, they can also mean higher hotel and rental car costs.
- Tips for cheaper flights: Be flexible with dates, book in advance, and use airline or credit card miles.
- One of the best ways to find flight deals is to use a service that does the searching for you. A membership can easily pay for itself with the savings you get on just one trip—and it saves you the hassle of constantly checking for deals.
flight deal alerts recommendation
I personally use and love Going. Their annual membership delivers curated flight deals straight to your inbox, and you can set up alerts for specific destinations you’re eyeing.
Use this link for 20% off your membership!
Getting Around Once You Arrive
We’ve been on trips where we’ve used nearly every form of transportation—flights, rental cars, public transport, private transfers, ride shares, trains, ferries, and walking! The best transportation option really depends on your destination.
Here’s what I consider when planning how to get around:
- Study a map of your destination before your trip. Get familiar with major attractions, distances between key locations, and your accommodations’ proximity to transit options. This helps determine whether a car rental, public transport, or a mix of both makes the most sense.
- Use public transportation when possible. If we can avoid renting a car, we do—it saves money and removes the stress of driving (and parking!) in an unfamiliar place. In most major cities, public transport is efficient, affordable, and well-connected. Plus, many destinations have apps to help you navigate routes easily.
- Research ride share availability. Not every location has Uber or Lyft, especially internationally. Look into the most common ride share apps in your destination, check their reliability, and download them before your trip.
- Consider a private transfer for airport arrivals. If you’re arriving in a completely new place or the airport-to-hotel transfer seems complicated, booking a private transfer can be a game-changer.
Private transfer recommendation
I personally use Welcome when traveling abroad. They monitor your flight arrival and adjust for delays, so your driver is always waiting when you land. It will likely cost more than public transport, but skipping the hassle of navigating a metro system upon arrival makes it worth it.
U.S. vs. International Considerations
- U.S. trips: Generally, the U.S. is more ride-share and car-friendly, and last-minute transport bookings are easier.
- International trips: More reliance on public transportation like trains, metros, and taxis. Ride share availability varies—some places have Uber, while others rely on local apps. If renting a car, check if you’ll need an International Driving Permit (IDP) and be aware of local driving laws.
Step 5: Find the Perfect Place to Stay
For me, deciding where to stay is probably the most time-consuming part of planning a trip. Between researching neighborhoods, reading reviews, and sometimes battling indecision, it can be overwhelming—especially for multi-destination trips. However, choosing the right accommodation can make or break your experience, so it’s worth putting in the effort.
Hotel, Vacation Rental, or Something Else?
- Hotels: Ideal for shorter stays, offering more amenities and flexible cancellation policies. Many also provide luggage storage, which is a huge perk if you arrive before check-in or have a late flight out.
- Vacation Rentals (Airbnb, Vrbo): Great for longer stays, larger groups, or unique stays in more remote areas. If laundry facilities are a priority, vacation rentals are usually the better option.
- Hostels & Guesthouses: While these aren’t our style, they are budget-friendly options, particularly for solo travelers or those looking to meet others on the road.
How I Choose Where to Stay
- Compare hotels vs. vacation rentals. Sometimes hotels are the better deal, while other times a vacation rental makes more sense. Consider what works best for your budget and needs.
- Prioritize location. Being centrally located can save time and money on transportation. I always research walkability, nearby dining options, and public transit access.
- Read reviews carefully. Reviews often reveal crucial details that listing descriptions don’t—like how comfortable the beds are, potential noise issues, and the overall cleanliness of the property. Use your discretion to recognize when someone is complaining versus offering up helpful information.
- Check the cancellation policy. I always try to book accommodations that are fully refundable in the event we need to cancel. I think of it like a little insurance policy—letting you adjust plans without extra hassle.
- Book flights first, then lodging. Flight prices can be more volatile, so I lock those in first before committing to accommodations.
Step 6: How to Plan Your Itinerary (Without Over-Scheduling!)
Planning an itinerary is all about balance. Early on in our travels, I made the mistake of booking too much—only for us to end up exhausted. Over time, we’ve learned that the best trips leave room for spontaneity while still ensuring we don’t miss the must-see spots. It’s all about having a plan without feeling like you’re stuck to a schedule.
How I Structure an Itinerary
- Identify must-do experiences. Start by listing the key attractions, activities, or restaurants you don’t want to miss. If reservations are required, book them in advance.
- Map it out. Look at where everything is located to avoid unnecessary backtracking. Group activities by area to maximize efficiency.
- Schedule flex time. Allow blocks of time in your day for wandering, relaxing, or discovering something unexpected. Some of our best travel memories have come from unplanned moments.
- Prioritize energy levels. Plan heavier sightseeing, more active experiences, and longer travel days earlier in the trip when you have the most energy. Save slower-paced activities and shorter travel days for later in the trip.
- Check local customs and opening hours. Some attractions have ideal times to visit due to crowds, while others may be closed on certain days for cultural or religious reasons. A little research ahead of time can help you avoid surprises and make the most of your trip.
Reservations vs. Going with the Flow
I always aim for a mix of planned activities and free time. Here’s how I decide what to book in advance:
- Book ahead: Popular tours, restaurants with limited seating, or timed-entry attractions like museums or historical sites.
- Be flexible: Leave time to discover things along the way, local recommendations, or just enjoying the atmosphere of a new place.
Our ideal travel day? We’re early birds, so we love starting the morning exploring, taking a break in the afternoon to recharge, and then heading out for dinner in the evening.
Ultimately, the best itinerary is one that enhances your trip rather than overwhelms it. Give yourself the freedom to explore while still ensuring you experience what you came for!
Step 7: Pack Like a Pro
Packing is an art—and something I’ve gotten better at over the years. I have a list of my favorite packing tips you should check out, but here are some key takeaways:
Essentials for Every Trip
- Comfortable walking shoes, travel-sized toiletries, and a reliable day bag.
- Packing cubes = game changer!
Special Considerations for International Travel
- Power adapters & converters (double-check voltage differences!).
- Passport, visas, and digital copies of important documents.
- Local SIM card vs. international data plan.
- Backpack-style luggage can make it easier to move between destinations and navigate public transport.
U.S. vs. International Considerations
- U.S. trips: No passport required for U.S. Citizens, standard outlets, and typically easier access to replace forgotten items.
- International trips: Different customs, baggage restrictions, and power adapters needed.
Final Prep & Travel Day Tips
By this point, you’ve put in so much planning that you’re probably just ready to go. I get that—I’m the same way! Here are a few last things to help things go smoothly:
Before You Go
- Make a packing checklist and prep gradually so you’re not scrambling last-minute.
- Double check you have all your entry requirements and documents (passports, visas, vaccinations).
- Notify your bank & set up travel-friendly credit cards.
- Download offline maps & key travel apps.
- Learn a few key phrases if you’re heading abroad.
Smooth Travel Day Tips
- Front-load longer travel days while you have the most energy; save shorter travel days for the back half of your trip.
- Arrive early for flights or train rides, especially for international travel.
- Stay flexible—things don’t always go as planned!
Travel Planning Gets Easier Over Time!
Whether you’re exploring a new U.S. city or heading abroad for the first time, following these steps will help make travel planning smoother. Learning how to plan a trip effectively can save time, reduce stress, and help you make the most of every adventure.
Think of travel planning like a muscle—the more you use it, the stronger it gets. Over time, you’ll fine-tune what you prioritize, and you’ll develop a better sense of what’s worth spending time and money on.
I believe in striking the right balance between planning and spontaneity. While over-planning can take the fun out of a trip, putting in the effort upfront makes the actual exploring so much more enjoyable.
A lot of stress while traveling comes from unrealistic expectations—whether it’s about costs, crowds, or logistics. When things aren’t well-organized, you end up wasting time figuring things out instead of experiencing the destination. That’s why understanding how to plan a trip in a way that works for you is so important—it allows you to travel with confidence and ease.
That’s why Life of Whimsley is all about planful travel, made joyful.
Ready to start planning your next adventure? If you have any questions about the tips I shared or need help with your itinerary, drop a comment below or send me a note — I’d love to help!
With joy,
Bri
P.s. Be sure to check out my favorite travel resources for everything I use when planning our trips!
