Quick Answer: A better vacation is usually about making better choices, not doing more. Where you stay, how fast you travel, and how you move between places all matter—and sometimes the best thing you can do for a trip is take something out of the itinerary.
I've traveled to all 50 states, visited roughly 27 countries across five continents, sailed on more than 40 different cruise ships, and crossed the Atlantic by ship twice.
And you know what all of that has taught me?
A better vacation usually isn't about doing more. It's about making better choices.
Where you stay matters. How fast you travel matters. How you get from place to place matters. And sometimes the best thing you can do for a trip is take something OUT of the itinerary.
It took me a lot of miles to figure some of that out.
And looking back now, I think my whole life was preparing me for the work I do today.
I've Been Everywhere, Man
Okay, not everywhere.
But every once in a while I start listing the places I've been and realize I sound a little like the Johnny Cash song.
I've been to all 50 states and roughly 27 countries across five continents. I've traveled all over Europe, through the Caribbean, Mexico and Central America, and to places like Egypt and Dubai. I've sailed on everything from huge Royal Caribbean ships to river ships in Europe, luxury ships, expedition-style ships, Disney ships, and even Queen Mary 2. I've crossed the Atlantic by ship twice.
When I started trying to count the actual ships recently, I got somewhere over 40 and realized I was forgetting some.
Apparently I've been on a lot of ships.
I'm still missing Australia and Antarctica, so clearly there is work to do.
But here's the thing. I don't think visiting a certain number of countries or sailing on a certain number of ships automatically makes somebody a great travel advisor. That's not why I'm telling you any of this.
It matters because being the traveler over and over again has completely changed the way I plan travel for other people.
I Don't Really Believe in "The Best" Anymore
People ask me what's best all the time.
What's the best cruise line? What's the best ship? What's the best itinerary? Where should I stay in Paris? What's the best way to see Alaska?
I get it. If you're spending $10,000, $15,000 or more on a vacation, you really don't want to screw it up.
The problem is that I don't think there is a universal "best."
I've been on ships I absolutely loved that I wouldn't recommend to certain clients. There are destinations I'd go back to tomorrow that might be completely wrong for the trip you're trying to plan.
And sometimes I'll recommend two completely different things to two people asking what sounds like the exact same question.
I want to know more about YOU first.
Who are you traveling with? What do you actually like to do? Are you someone who wants to be going from breakfast until dinner, or are you going to hate me by day three if I plan your trip that way?
Those things matter a whole lot more to me than somebody's list of the "10 Best Cruises."
Sometimes I'm Going to Tell You to Take Something Out
This is probably one of the biggest things travel has taught me.
You don't have to do everything.
Give me a week in Europe and I can probably figure out a way to get you into five cities.
But I probably won't.
Because at some point you're not experiencing Europe anymore. You're experiencing European transportation.
I've done versions of that trip myself. Get up early. Pack. Check out. Get to the train station. Get to the next city. Find the hotel. Check in. Hurry up because we only have today and tomorrow here.
There are absolutely trips where moving quickly makes sense. But there are also trips where I look at the itinerary and think, you're going to need a vacation after this vacation.
And some of my favorite travel memories weren't planned at all.
They happened because I had time.
So sometimes I'm going to find you an amazing experience and tell you we HAVE to put it in the itinerary.
And sometimes I'm going to look at everything you've asked me to fit into the trip and say, "Nope. We need to take two things out."
Both can be good travel planning.
I Love Cruising. That Doesn't Mean Every Trip Should Be a Cruise.
Forty-something ships. Obviously I love cruising.
I've sailed on giant ships and much smaller ones. I've done ocean cruises and river cruises. I've sailed luxury lines, family lines and everything in between. I've crossed the Atlantic on a ship twice.
But I also love being on land.
Sometimes a cruise is absolutely the best way to experience a trip. Unpack once, wake up somewhere new, and let the ship do the moving for you.
And sometimes I want you to get off that ship and stay awhile.
Maybe we add Rome before your Mediterranean cruise because flying all the way to Italy and giving Rome eight hours makes absolutely no sense for what you want to see. Maybe Alaska needs a land component. Maybe you don't need a cruise at all. Maybe an escorted tour is a better fit, or we piece it together with trains and private drivers.
I care about figuring out the best way for you to experience the place you're spending all that money and vacation time to see.
I've Learned to Ask Different Questions
This may be where all the traveling has helped me the most.
I want to know where the hotel actually IS.
What can you walk to? How much time are you going to spend getting back and forth every day? Are we saving $100 a night on the hotel and then making your entire trip more difficult?
Same thing with cruises.
That itinerary says Rome. Great. Where does the ship actually dock?
That European itinerary looks fantastic. Great. Now let's put it on a map.
How long are those train rides? How many times are you changing hotels? Are you going to spend more time moving than actually being anywhere?
And here's another one I think people forget:
Do you really need an excursion every single day?
Sometimes you do.
Sometimes I'd rather give you an afternoon to wander around, eat something, shop, sit at a cafe, get lost for a little while and actually remember what the place felt like.
I've learned some of that professionally.
But a whole lot of it I learned because I've been the person standing there with the suitcase.
So What Does Any of This Have to Do With Your Vacation?
Hopefully, quite a bit.
You don't need to win vacation.
You don't need to pick the cruise ship that somebody in a Facebook group says is the best ship in the world. You don't have to visit every city because you're worried this might be your only trip to Europe. And you don't have to come home with photographic evidence that you saw every major attraction listed on Google.
You need to figure out what you want this particular trip to feel like.
Maybe you DO want to go nonstop. Great. I have clients who love that.
Maybe you want a beautiful hotel, a few incredible experiences, long dinners and time to wander.
Also great.
Neither person is traveling incorrectly.
They're just two completely different travelers.
And they shouldn't have the same itinerary.
My Whole Life Prepared Me for This
When I look back now, becoming a travel advisor actually makes a lot more sense than it did when I first got into this business.
I've always loved learning. I research everything. I've always been a planner. And I've pretty much always wanted to know what's around the next corner.
So yes, the 50 states mattered. The countries mattered. The cruises mattered. So did the road trips, trains, wrong turns, places that surprised me, trips where I planned way too much and the trips where something I barely planned ended up being my favorite part.
My whole life really did prepare me for this.
All 50 states. Roughly 27 countries. Five continents. More than 40 cruise ships. Two transatlantic crossings.
And I'm nowhere near done traveling.
Australia and Antarctica, I'm looking at you ;-).
