How to Plan a Trip: The TLGA Playbook

Looking at flight maps with an open mind often reveals incredible destinations that you might not have considered otherwise.

Start With Flexibility and a Clear Vision

A lot of times, the best travel hack is simply staying flexible. Knowing what kind of experience you want shapes your decisions, but keeping your destination and dates open can save you thousands of dollars.

I rely heavily on tools like Google Flights to see if there are any unexpectedly cheap destinations. For example, by keeping our departure open, we found a $400 round trip direct flight from Minneapolis to Dublin on Delta just by flying out on a Tuesday instead of a weekend. Once you have a cheap anchor flight, you can build out the rest of the vision.

Define the purpose of your trip

Before locking anything in, ask yourself what experience you actually want:

• Rest and downtime
• Adventure and outdoor activity
• Culture, history, and city exploration
• Food, nightlife, and social events

Researching neighborhood layouts and transit options is the key to spending your trip exploring rather than commuting.

Build a Smart Itinerary

Having the best of both worlds on one trip is entirely possible if you route it intelligently. You do not have to choose between a city break and a beach vacation if you use regional flights to your advantage.

We recently built a trip that linked the Old World history of Ireland, the big city energy of London, and a beach vacation in Tenerife. We booked the cheap flight to Dublin, then added low cost hops from Dublin to London, and London to the Canary Islands. We mapped out some great restaurants in London and Dublin, did a lot of walking tours, and still had plenty of time to relax on the beach.

Keep the balance right

Start with your must-see experiences, then group them geographically. Leave plenty of space for meals, rest, and wandering. Overplanning kills your ability to adapt when you find a neighborhood you want to spend more time in.

Knowing your daily spend limits ahead of time allows you to enjoy meals and activities without constantly checking your bank account.

Build a Realistic Travel Budget

Budgeting is not about being cheap. It is about spending intentionally so you can afford the things that matter most to your travel style.

Think through the major buckets first. Knowing your comfort range early helps you avoid stress and last-minute compromises.

Traveling with just a carry-on forces you to pack versatile clothing and skip the items you rarely end up wearing.

Pack Light and Pack Smart

When you link multiple countries and utilize low cost regional airlines, packing light stops being a preference and becomes essential. Checking bags on multiple short flights adds up quickly in fees and lost time.

We only do carry-ons for our international trips. We take one main overhead bag each, plus our smaller day bags that fit under the airport seats. A lighter bag makes every transit day easier, especially when navigating cobblestone streets or crowded train stations.

Focus on versatility

Choose versatile clothing and plan around layers. Use packing cubes to compress items and keep clean clothes separate from dirty ones.

Having your digital documents organized and offline maps downloaded reduces friction when you arrive in a new city.

Documents, Tools, and Travel Mindset

Technology should reduce friction, not add complexity. Take time before you leave to organize your digital life so you are not scrambling at the customs desk.

Create a dedicated folder on your phone with your passport photo page, insurance details, and key confirmations. Email yourself a copy too so it is easy to search later. Download offline maps for the cities you are visiting, and make sure your transportation comparison apps are updated.

Set the right expectations

Travel rarely goes exactly as planned. Delays, changes, and surprises are normal. Approaching travel with patience and flexibility makes the entire experience better. Some of the best travel moments are the ones you never planned for.