Planning a vacation should be just as enjoyable as taking one, but let’s be honest—sometimes it feels more like a part-time job. From deciding where to go, to figuring out what to pack, the process can be overwhelming. But fear not! With a few best practices (and a touch of humor), you’ll be on your way to creating the perfect getaway. Plus, we’ve included a downloadable Travel Planning Checklist for you to use!

Best Practices for Planning the Perfect Vacation

 

Start With Your “Why”

Why are you taking this trip?

• Is it to relax, explore, or reconnect with loved ones?

Knowing the purpose of your vacation can help shape your destination, itinerary, and activities.

Choose Your Destination Wisely

• Research seasons: Avoid monsoon seasons and overcrowded tourist hotspots.
• Consider your budget, travel time, and vibe—are you after city chic, tropical bliss, or mountain serenity?

Set a Realistic Budget (And Stick to It)

According to Pacaso.com, "On average, a vacation costs $1,986 per person, per week in the US. However, costs will vary based on a number of factors like destination, time of year and type of accommodations." Nobody wants to stress about money while sipping a margarita. Budget for:

• Flights
• Accommodations
• Meals
• Activities
• Souvenirs (because, of course, you’ll need that overpriced magnet)

Pro Tip: Research the past trips you've taken. See if you can find an average amount you spent on previous travels, or begin with 5%-10% of your yearly net income for vacations.

 

Pro Tips to Make Planning Easier

Embrace Technology

• Use travel apps like Google Maps, TripIt, or Hopper to book flights and stay organized.
• Bookmark key locations, like restaurants, museums, and attractions

I keep several different saved lists in Google Maps. Some are labeled "Places I want to hike," "Adventures for the family," "Scotland," and more. When I come across places that peak my interest, I save them to a Google Map list. This way I don't 1) forget about it 😝 and 2) it helps in planning where we want to go on vacations.

Marry a Partner Who Loves to Plan (or Befriend One)

Let’s face it: not everyone enjoys creating spreadsheets and itineraries. If planning stresses you out, delegate! And finding a partner the loves to plan is the ultimate hack!

• Find a partner or friend who lives for color-coded calendars.
• If all else fails, consider a travel agent or concierge service.

Prioritize Experiences Over “Doing It All”

I have to admit, I get caught up in this very easily. Researching locations, reading the blogs and stalking Instagram feeds, makes you want to do and see it all in the short amount of time you are there. Remember:

• You don’t have to see everything. Pick 2-3 must-do activities per day and leave room for spontaneity.

Pack Like a Pro

• Roll your clothes instead of folding to save space.
• Use packing cubes to stay organized.
• Don’t forget the essentials: travel-sized toiletries, chargers, and an outfit for unexpected weather changes.
• Order a Travel Well Box, so you can pamper your trip!

Check Travel Requirements Early

• Is a passport or visa required?
• Do you need vaccinations or travel insurance?

Avoid last-minute stress by preparing months in advance.

Make Dining an Experience

• Plan a mix of high-end dining and casual, local eats.
• Always ask locals for recommendations—they know where the real gems are.
• Find out what food your destination is know for and order it. It's always a good idea to taste the local specialty.

 

Add a Personal Touch to Your Trip

Create a Pre-Travel Ritual

Before you leave, do something fun to build anticipation:

• Watch a movie or read a book set in your destination.
• Make a playlist for the trip.
• Buy an outfit specifically for your trip. When you wear it back home, it will always remind you of your vacation!

Document the Journey

Bring along a journal or use an app to capture memories.

Not only will this create keepsakes, but it’ll also help you relive the magic when you’re back home.

 

FAQs About Vacation Planning

1. How far in advance should I plan my vacation? Ideally, start planning 6-12 months ahead for international trips, and 3-6 months for domestic travel.

2. What’s the most common travel planning mistake? Overpacking and trying to do too much in a single trip. Less is more!

3. Should I use a travel agent? If planning overwhelms you or you’re short on time, a travel agent can be a lifesaver.

4. What’s the best way to save money on flights? Book flights midweek, set alerts for price drops, and use comparison tools like Skyscanner or Hopper.

5. How can I avoid overpacking? Stick to a packing list and choose versatile clothing items that can be mixed and matched.

6. What’s the benefit of having a travel subscription box like Travel Well Box? Travel subscription boxes provide curated essentials, inspiration, and products that enhance your travel experience—so you’re always prepared and stylishly equipped.

 

Get Ready for Your Next Adventure!

Now that you’ve got the tools and tips, the only thing left to do is download our Travel Well Travel Planning Checklist, pack your bags and hit the road. And remember, the key to a successful vacation is equal parts preparation and flexibility. Happy travels!