Deciding to go is one thing; deciding where to go is immediately overwhelming. Folks come to me and say, “Hey, I want to go on a trip.” I’m genuinely excited every time someone thinks of me (it’s a pinch-me moment), but we have to get into the grit of it.

• How long do you want to be gone?
• Who’s traveling with you, and how old are they?
• What’s your budget?
• What kind of things do you want to experience?

From there, I either get, “OMG, you have too many questions,” or, “Oh, I didn’t really think about it.” Realistically, friend, this is how we can decide whether your “ideal where” is going to work, or I can suggest options based on what you want to do.  So let’s walk through some of those schematics, shall we?

How long do you want to be gone?

Are we trying to be gone for a whole week? So, a full calendar week, seven days?

or

Are you really trying to keep this short in a three-night, four-day trip? Wham bam! Thank you, ma’am. I’m back home to go to the grocery store.

That depends a lot on where you’re going. If we’re talking about crossing an ocean (or seeing one), and you live in the north, you can expect one day on either side to be a travel day. On travel days, you want no real commitments besides getting through the airport and eating something. With that in mind, where you go can vary a lot.

• Rule of thumb: One person should decide for the group. The person who ultimately calls the shots; too many cooks in the kitchen, so to speak, will ultimately make someone feel bad, and we don’t want any negative juju affecting a happy time.  I would focus on the location and vibe of the stay first, then tailor the activities to each person’s needs.

What is your budget?

I’ve even made the mistake of not being clear about what a budget actually looks like. Look, I want to exist in rainbows, sunshine, and quality pistachio gelato ok, but we have to adult here and make wise choices. Suppose your budget is three thousand dollars total with flights, food, and excursions included. That’s a totally different story than if my budget is three thousand dollars for just excursions and the hotel, resort, or base cruise fare. So being clear up front about how much you are willing to spend today, and how much you are willing to spend overall for that trip, matters.

A good rule of thumb for an average 4-night/5-day vacation before flights for a family of 4:

• $3K on a short 3-night sailing  on a Mainstream cruise line (Think Carnival, Royal, Norwegian), or a US-based trip with a simple hotel stay and some fun excursions
• $5K is a good base-level all-inclusive stay with private transportation to and from the hotel and the airport
• $7K is a great starting point for let’s go across an ocean!

Of course, these numbers can swing GREATLY depending on where you’re headed and the specifics, but it gives you a solid starting point. Keep in mind, the average trip deposit is around 10-15% of the total cost to hold your space and rate at the time of booking. Financial preparedness matters.

Are you an “I just want to go see, I want to learn, I want to explore, or I want to flip off of things” person?

“I want to go on a ten-mile bike ride on vacation,” sounds lovely for some, or “I want to sit by a pool and read a book from cover to cover,” sounds like the ticket for others. I need to know. My focus is balancing relaxation with arts, history, and culture in your vacation planning. If those are things you definitely DO NOT want to do, that’s a different activity level or ability than for those who want to do more adventurous things, like a 20-mile pre-marathon hike.

Do you have a passport?

When you book your trip, is your passport valid for six months beyond your return date? Why? A country can deny you entry if your passport expires a certain number of days after you’re set to return. It sounds wild, but it’s a thing. Is there a name difference? Does it need renewing? If so, head to the closest US Post Office; the form is pretty straightforward and so worth it. All of those items affect where you can go safely and successfully, or whether it’ll be a hassle.

How much actual downtime feels ideal?

Everybody travels differently. Some people think that downtime makes the vacation. People think downtime is for wussies. It depends on who you are.  My exact question is: What do you do in the evening after work every day? For most of us, that’s our downtime: sitting down to read a book, deciding to work out, cooking dinner, or playing a game with our family. It’s what we do when we’re not doing the have-tos. On vacation, that downtime is still necessary to feel like you’re creating memories instead of rushing through them.

There you have it. That’s the start. The beginning questions so that I can then look and say, “Maybe you should go here,” with confidence.

At the end of the day, this all comes down to me actually getting to know you as a person. Yes, there are more questions than these, friend, plenty more, but every single one is there so we can get you going on the trip that feels right for you, right now. No one cares what looks good online. That one-way window has no investment in the outcome. I do. Truthfully, I didn’t get here overnight. This process is the product of a few growing pains and a lot of paying attention, and I’m still sharpening it.

Ready to get started? Click here to choose the service suite that works for you, and let’s get you going today.