Skip to main content

How to plan a vacation without the stress: A step-by-step approach

A step-by-step guide to to planning the vacation of your dreams

plane taking off with ocean in the background
Oleksandr P / Pexels

Planning a vacation? I know the feeling – it usually starts with a spark of excitement, a growing list of dream destinations, and endless scrolling through travel blogs and Instagram photos. Then comes the deep dive into flight searches, hotel comparisons, itinerary planning, and second-guessing every possible choice. Are you packing too much into one day? What should you even bring? Before you know it, what started as an exciting idea begins to feel like an overwhelming project. Don’t worry, though! I’m here to walk you through how to plan a vacation step-by-step so you can get the most out of your time and planning.

Step-by-step guide for stress-free vacation planning

1. Choose your destination

Bali beach
Dimitri Dim / Pexels

Deciding where you want to go is the first step in planning any vacation. Are you dreaming of relaxing on a tropical beach in Bali, exploring the historic streets of Rome, or hiking the trails of Patagonia? Maybe you’re picturing yourself sipping coffee in a Parisian café, snorkeling in clear waters in the Maldives, or chasing the northern lights in Iceland

Recommended Videos

In this first step of the process, consider factors like your budget, travel restrictions, weather, and the kind of experience you’re hoping for.

2. Set a budget

man holding credit card looking at computer
Sora Shimazaki / Pexels

Once you have a destination in mind, it’s time for everyone’s favorite (or not-so-favorite) part, setting a budget! Knowing how much you’re willing to spend will guide your choices for flights, accommodations, activities, and dining. Be sure to factor in hidden costs like travel insurance, local transportation, and tips. When you have a realistic budget, you can be sure you won’t return home financially stressed. 

Remember to keep your budget in mind when you’re choosing your destination. For example, a week in Bali might cost significantly less than a week in Switzerland, so plan accordingly.

3. Pick your travel dates

person rolling luggage through airport
Josh Sorenson / Unsplash

Your travel dates are crucial to the entire experience of your vacation. If you’re looking to save costs, flexibility with your travel dates can help save you money on flights and accommodations. Plus, traveling during the off-season or shoulder season often means lower prices and fewer crowds. Use travel tools like Google Flights to check for the best deals and plan accordingly.

4. Book flights and accommodations

Person standing on an airplane
Kelly / Pexels

After finalizing your dates, it’s time to set your flights and accommodations in stone! I recommend booking early to secure the best rooms and rates. You should also consider package deals or loyalty discounts at this stage.

Mark Wolters of Wolters World suggests carefully reading hotel reviews and checking the fine print before you book your accommodations to avoid unexpected charges, such as resort fees. It’s also a good idea to double-check for additional taxes that might not be included in the initial price. You don’t want to end up blowing your budget by not considering the additional unexpected fees that can sometimes come with hotels. 

5. Plan your itinerary

Person sitting on floor with world map
Vlada Karpovich / Pexels

An itinerary helps you make the most of your vacation. For itinerary creation, I use Jotform, which has a bunch of templates that can help you stay organized. 

Research popular attractions, local events, and must-try dining spots when filling out your itinerary. For example, if you’re heading to New York City, you might want to plan visits to iconic landmarks like the Statue of Liberty and Central Park but also leave time for a spontaneous Broadway show. When you’re making your itinerary, I recommend not overloading your schedule. Always leave room for spontaneous adventures and relaxation!

Here’s a sample 5-day itinerary for a city trip:

  • Day 1: Arrival and city exploration
  • Day 2: Guided tour of historical sites
  • Day 3: Take a day trip to a nearby attraction or scenic location
  • Day 4: Enjoy a leisurely morning at a café, followed by visits to museums or galleries
  • Day 5: Final stroll around the city, last-minute shopping, and departure

If you’re planning a beach vacation, your itinerary might look like this:

  • Day 1: Arrival and beach relaxation
  • Day 2: Water activities like snorkeling or kayaking
  • Day 3: Explore nearby towns or islands
  • Day 4: Spa day and sunset dinner
  • Day 5: Morning swim and departure

These are just examples; you can adjust the sample itineraries to suit your destination and preferences.

6. Take care of logistics

Hand holding two U.S. passports
Image Credit: / Global Residence Index

Logistics are often overlooked but are essential when learning how to plan a vacation. Make sure you double-check passport and visa requirements and book the necessary transportation. According to the U.S. Department of State, some countries (including most of Europe) require that your passport expiration date is at least six months away, so make sure your passport is in order before traveling internationally. 

You should also download essential apps, such as maps, translation tools, and ride-sharing services, to help make your trip smoother. 

7. Pack smart

a man wearing headphones while packing clothes in a suitcase
Vlada Karpovich / Pexels

Packing smart can save you time and unneeded stress during your trip. Make a packing list tailored to your destination’s weather and planned activities. Don’t forget essentials like travel documents, chargers, medications, and a travel first-aid kit. If you’re heading to a tropical destination, lightweight clothing, sunscreen, and a reusable water bottle should be at the top of the list. 

The TSA’s travel checklist recommends packing items in layers (shoes one layer, clothes one layer, electronics one layer). And don’t forget that liquids, gels, and aerosols packed in carry-on must follow the 3-1-1 rule.

3-1–1 rule:

  • 3.4 ounces or less per container
  • 1 quart size, clear, plastic, zip-top bag
  • 1 bag per passenger

8. Prepare for emergencies

Passport with stamps
Agus Dietrich / Unsplash

You should always be prepared for unexpected emergencies. Keep copies of important documents, share your itinerary with someone you trust, and have a plan in place for emergencies. Knowing the location of nearby hospitals or consulates can also be helpful. 

Kelly Baker
Kelly is a writer who loves good books, baking homemade bread, playing the piano, and spending time with her family.
10 must-know solo travel tips for a stress-free adventure
How to make the most of your solo travel experience
Person rolling luggage through the airport

I’ll never forget my first solo trip. I couldn’t help but wonder, would I get lonely? Would I feel safe? But as soon as I stepped out into the world on my own, I realized how freeing solo travel could be. Solo travel teaches you to rely on yourself, embrace spontaneity, and fully immerse yourself in new experiences. That said, traveling by yourself also comes with its challenges. There’s a learning curve, but it’s worth it. If you’re planning your next vacation, here are the solo travel tips I wish someone had shared with me before I packed my bags.
Solo travel tips

Solo travel doesn't have to be a daunting prospect, just follow this advice to make your trip the best it can be.
Research your destination thoroughly
Before you set off, do your homework. Dive into the culture, customs, and quirks of your destination. Learn phrases in the local language like "hello," "thank you," and "help" – mastering the local slang might just earn you a few smiles! You should also check travel advisories and scour reviews from other travelers. You’ll want to know which areas are safe, the best ways to get around, and if you’re traveling internationally, where your country’s embassy is (just in case).
Plan, but not too much
Have a bucket list of fun experiences you want to do? Great – but don’t pack your schedule tighter than your suitcase. Leave space for the unexpected, like a random street fair, a hidden cafe, or a spontaneous invite to explore a local spot. Flexibility can be where the magic happens in solo travel.
Pack light and smart
When packing, stick to versatile clothing, bring only the essentials, and use packing cubes to keep things organized. And don’t forget the essentials – a power bank, universal adapter, first aid kit, and digital and physical copies of your important documents.
Stay connected
Before you go, ensure you have a reliable way to stay connected. This might mean purchasing a local SIM card, renting a portable Wi-Fi device, or arranging for an international data plan. Staying connected helps you navigate unfamiliar areas, keep in touch with loved ones, and access important information on the go. Apps like Google Maps, Google Translate, and currency converters can be lifesavers during your travels. Don’t forget to download offline maps and guides in case you lose internet access.
Share your itinerary with someone you trust
While solo travel is about independence, it’s always smart to let someone know your plans. Share your itinerary, accommodation details, and contact information with someone you trust. A quick “I’m safe and having a blast!” text can ease your loved ones’ nerves. Apps like Find My or WhatsApp location sharing can add an extra layer of safety.
Choose accommodations wisely
Your accommodation can make or break your trip. Look for highly rated places (especially those recommended by other solo travelers). Hostels and guesthouses are perfect for meeting people, while private Airbnb spots can offer quiet comfort.
Own the solo dining experience 
Eating alone? Bring a book, journal, or your phone to keep busy, or sit at the bar and strike up a chat. Joining food tours or cooking classes is another fun way to combine good eats with good company.
Stay safe
If you’re going to listen to one of these solo travel tips, pick this one! Safety should always be a top priority when you're on your own. Keep your head on a swivel, be mindful of your surroundings, avoid flashing valuables, and trust your gut. If something feels off, it might just be. Consider keeping a photocopy of your passport in a separate bag and storing emergency cash in multiple locations. It’s also a good idea to have the contact information for local emergency services saved on your phone.
Make friends (but set boundaries)
Traveling solo doesn’t mean being alone 24/7. Join group tours, attend events, or use apps like Meetup to connect with locals and other travelers. Remember, always trust your gut when meeting new people, and don’t feel pressured to share personal details if you’re uncomfortable. 

Read more
Tumi vs. Rimowa: How do the two luggage brands compare?
What you need to know to choose the right suitcase
Man carrying luggage in both hands

Whether your existing luggage is worn down or you don’t even have any yet, you’re going to need somewhere to stow your belongings for your next trip. There are a ton of great luggage brands on the market, but at some point, you’ll narrow your choices down to one or two options. If that’s the case, and you’re currently weighing Tumi vs. Rimowa luggage, well, you’ve ended up here. And trust me, I’ve been there, scrolling through luggage websites online and wondering which suitcase to splurge on.

Both Tumi and Rimowa have incredible reputations, so choosing between them isn’t easy. A head-to-head between these two brands makes a lot of sense because they are similar in many ways. Of course, there are some differences, too, and that might help you make your decision on which to choose for your next luggage set. We’ve got the lowdown on Tumi vs. Rimowa right here, so let’s discuss. 
Tumi vs. Rimowa luggage: Who wins?

Read more
How to pack for a week in a carry-on (without sacrificing the essentials)
Avoid the dreaded overstuffed carry-on with these tips
An overhead view of a man packing a suitcase

Packing a carry-on for a longer trip seems intimidating, but it’s definitely doable. My first time was for a week-long conference in Seattle, where I was determined not to drag a big suitcase. It worked. Since then, I’ve refined my system, and now it’s my go-to for work trips, beach vacations, and city breaks. Over the years, I’ve learned how to make the most of the space without sacrificing the essentials, and now I’m sharing the formula that never fails. Here’s how to pack for a week in a carry-on.
Choose the right carry-on bag

The first step is picking the right carry-on bag. Look for one that meets airline size restrictions, typically around 22 x 14 x 9 inches. Hard-shell suitcases are great for durability and keeping everything secure, while soft-sided bags often have more give for squeezing in a few extra items. Spinner wheels can make navigating airports a lot easier, so consider that feature, too.

Read more