Wondering How to Plan an Overseas Trip? Start Here!

Dreaming of cobblestone streets, sunset dinners by the sea, and checking off your European bucket list? 🌍 Before you dive into booking flights overseas and packing your bags, there are three key things to decide first:

1. Your destination
2. Your budget
3. Your travel dates

But here’s the exciting part…

Why stop at one country?

One of the best parts of traveling overseas, especially in Europe, is how easy it is to hop between countries.
Visiting Portugal? It’s a breeze to pop over to Spain. Headed to France? Why not add on Belgium or Germany?

On our 2023 trip, Greg and I spent just over two weeks exploring Portugal, Spain, and Italy. A quick train ride got us from Lisbon to Madrid, and flights within Europe (especially on budget airlines) were far cheaper than flying from the U.S.

Budgeting: Think Bigger Than Flights and Hotels

Once you know where you’re going then it’s time to get real about your budget.

Ask yourself:

  • How many paid days off do I have?
  • Will I need to take any unpaid vacation time?
  • Am I traveling during peak tourist season (i.e., $$$) or in the quieter shoulder months?

Pro Tip: Check the national holidays of your destination. Local holidays can mean higher prices, fewer available services, and more crowds.

Season matters.
Summer hotspots like the Amalfi Coast or Mykonos are stunning—but packed and pricey. We love traveling in September or October: fewer crowds, better weather, and more value for your money.

Here’s what to actually include in your travel budget (don’t skip the small stuff):

  • ✈️ Flights (round trip and in-country hops)
  • 🚆 Transportation (trains, metros, buses, Ubers, rental cars)
  • 🏨 Accommodations (hotels, hostels, service fees)
  • 🍝 Food & Drinks (restaurants, groceries, wine tastings, coffee breaks)
  • 🎟 Experiences & Tours (museum entries, guided walks, day trips)
  • 🐶 Pet Care (boarding, house sitter, or daily check-ins)
  • 📱 Phone/Internet Coverage (international SIM cards or eSIMs)
  • 🏥 Travel Insurance (medical, cancellations, baggage)
  • 💳 Bank & Card Fees (ATM charges, currency exchange, foreign transaction fees)
  • 🧴 Toiletries & Meds (sunscreen, cold meds, travel-size must-haves)
  • 🎁 Souvenirs & Gifts (for yourself or others!)
  • 🧳 Luggage Fees (checked bag charges, extra weight)
  • 🖼 Museum or Gallery Passes (often cheaper when booked ahead)
  • 🎧 Entertainment (audiobooks, Spotify for flights, local concerts)
  • 📸 Photo Storage or Cloud Backup (if you’re taking tons of travel pics)
  • 🛍 Last-Minute Travel Gear (adapters, power banks, walking shoes)
  • 💁‍♀️ Tipping/Service Charges (especially in countries where it’s expected)

💡 Reality check: Things usually cost more than you think. Always add a 15–20% buffer so you’re not stressed mid-trip.

Choose the Travel Style That Fits You

Everyone travels differently. Some love the social vibe and savings of hostels. Us? We learned early on that having our own space and a quiet place to recharge is worth the extra spend. No wrong answer—just know what matters most to you.

Also keep in mind:
Your employer’s vacation calendar may work in your favor. Travel during off-peak times like early spring or late fall, and you might get more flexibility and better deals.

Now for the Fun Part: Your Wish List

Once the basics are set, start dreaming. This is the time to list out the must-see spots and can’t-miss experiences.

On our first trip to Rome, we splurged on:

An evening tour of the Vatican, complete with wine in the Pinecone Courtyard (yes, that’s a thing—and it was amazing)

An underground Colosseum tour

In Portugal and Spain, we made sure to:

  • Take a scenic tour of the Douro Valley, home of Port wine 🍷
  • Marvel at the art nouveau architecture in Barcelona 🤩

🧭 Planning tip: Don’t overload every day with “once-in-a-lifetime” tours. It’s exhausting and can crowd out the spontaneous moments that make travel magical.

Our approach?

  • A few big-ticket experiences
  • Plenty of time for casual strolls, outdoor cafés, and unplanned “ohh, what’s that?” discoveries

Final Thought

Traveling abroad isn’t just about seeing the sights—it’s about giving yourself space to experience them.
With thoughtful planning upfront, you can focus more on sipping that espresso in a quiet plaza—and less on logistics.

Where will your adventure take you?

Taking a long trip overseas?

Make sure you know about the Schengen Zone restrictions for European travel