Living Big Travel

Living Big Travel Blog

Travel tips, guides, and real life stories to inspire your next adventure. Go explore! 

TRAVEL TIP: the conversation that will make your vacation 1000X better!


If you’re planning to travel with a group of friends, your family, a group of couples, or a new partner —- do yourself a favor and spend some (valuable!) time up front talking about your trip, and not just a “should we do Cabo or Cancun…” kind of conversation. I’m talking about a conversation that will help ensure everyone in your traveling group has a chance to make their opinions, preferences, wishes and any limitations known. Not only will this help the planning process for you (or your Travel Designer) it will also set everyone up for a better trip.

See below for a few questions and topics to get the conversation started — and if you’re planning on working with Living Big to have your vacation designed, please make sure you talk through these topics with your traveling group before your initial scope call:


  • What time of year do you want to travel? And how long do you want to be away?

  • Are there any fixed dates for traveling? —- i.e. you can’t leave until X date, or you need to be in a certain city on a specific day for an event, etc.)

  • What type of experience are you looking for? The sun, culture, amazing food, a big city, outdoor adventure, festivals, etc.

  • What budget do you have in mind for the trip?

  • Do you have any air miles or points you’re hoping to redeem? And are you willing to be flexible with your travel plans in order to use your air miles or points?


  • Is there a goal, purpose or theme of the trip?

  • What is each person interested in doing on the trip?

  • Do you prefer activities that you can do solo or with a guide or group?

  • What experiences are worth paying extra for?

  • When it comes to eating out, do you like to go out for every meal? What kind of eating establishments do you like? Do you like to have dinner reservations booked?


  • What are your flight preferences? —- do you prefer to take a route with multiple stops (if it means saving money) or do you prefer direct flights (sometimes at a higher price.) Are you open to red-eye flights? What cabin do you want to travel in?

  • Comfort level with various modes of transportation —- i.e. hiring a driver, taking public transportation, renting a car, etc.

  • Accommodation preferences (both level, quality and budget) — i.e. hostels, home stays, apartment rentals, hotels, etc.

  • How do you like to structure days when you’re on vacation? Do you like to go-go-go all day? Do you like to explore in the morning and then rest in the afternoon? Do you like to have your days planned? Do you like to just go with the flow and make plans along the way?

  • What is the ONE THING each traveler wants to do? In other words, if you only did this one thing, your trip would be amazing.

  • How much ‘alone time’ do you want or need each day?

  • Ask everyone to share their favorite travel memory from a past trip, and why it was a favorite memory (and be sure to share this information with your Travel Designer!)

Happy traveling + cheers to ‘living big’ (and enjoying all parts of the vacation — planning included!)

Mary and the Living Big team!