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How to Know Where to Go: Advice for the Boomer Traveler

How do Alan and I decide where to go? With an abundance of destinations, cruises, tour companies and road trip routes, planning a boomer trip can be daunting. Blame it on the Internet. I do. Daily, almost hourly, I’m tempted to start planning a trip because of an email, Facebook post or travel article. And if it’s not me lusting after a new boomer adventure, Alan’s calling from his office to show me his next want-to-travel idea.

But we’re not the only ones. Recently a reader sent this email:

“Hi Donna, Best wishes to both of you on the 9th anniversary of your blog! When I read about your ‘fear’ of heights, (like me) I felt a bit better. But it hasn’t stopped you from certain destinations (unlike me). You have Road Lag; I have Decision Lag. We’re looking at next year. Do we start with WHEN or WHERE to go? Land or sea? Travel alone or with a group? Have you ever written about pre-planning questions to answer? Regards, Judy, Toronto, Ontario.”

And, so Judy, and the rest of My Itchy Travel Feet readers who are having trouble making up their minds, these tips are for you.

Boomer travel tips. How do we decide which destinations to add to our boomer travel list? Read our tips for deciding where to go.

Antarctica was at the top of my bucket list. When I found a Seabourn itinerary that combined Christmas holidays with an adventure cruise, I knew exactly where to go. Alan agreed.

Keep a list of where to go

Call them bucket lists, want-to-do lists or travel goals. It really doesn’t matter. But knowing where to go is a big step forward in planning your next boomer travel adventure. Alan and I each keep lists of places we’d like to experience. Alan’s is a written one ordered by priority. Mine is all in my brain (maybe I should write it down). Our lists change depending on current interests or the latest destination news that inspires us.

Periodically, we sit down together over a glass of wine to review our separate lists. I explain why certain destinations are calling my name and then it’s Alan’s turn. From there, we choose two or three big trips that appeal the most to both of us to include in the next year’s adventures.

When deciding where to go on a boomer vacation, the wide open spaces in Montana are a good choice.

Alan loves the wide open spaces in Montana…and the horses at Grey Cliffs Ranch.

Know when to go

Current events, time of year, budget, health, family matters—many factors decide if the trip that’s at the top of our list becomes a reality. Alan and I are not fans of crowded destinations, which means that we rarely take big trips during the summer. If a destination is extremely popular, we’ll put off visiting for a year or so until the popularity calms down. Traveling during the off-season is our favorite way to avoid crowds.

Last year’s weekend stay in Iceland is a good example. After the Arctic cruise on Silver Explorer, we booked a land extension to briefly explore this extremely popular country. To be honest, Iceland is currently too popular, especially in August. While we would love to return for an in-depth visit, it won’t be during prime tourist season. Stunning waterfalls quickly lose their appeal when accompanied by huge crowds. But I’m thinking winter travel to Iceland would offer scenic, unique travel opportunities, so I’m adding it to my bucket list.

Is an Arctic cruise on your boomer bucket list? We offer tips on how to make it happen.

We didn’t know that our Arctic Cruise would include standing on ice above the Arctic Circle. What a thrill!

Stay informed

What’s going on in the world? When is the best weather for a destination? Are cruises or tour companies offering new routes and experiences? These are key questions to ask when deciding where to go on your boomer trip.

Travel inspiration comes in many forms. Perhaps your enthusiasm for a destination will be sparked by a magazine, book, movie or television show. And then there’s the Internet, which is filled with more travel ideas than you could accomplish in ten lifetimes. And hopefully our articles and photos at My Itchy Travel Feet are part of the mix that inspires your boomer travel adventures.

Once you’ve been inspired, it’s time for online research; and these days it’s more a matter of too much information rather than too little. I like researching destinations by taking a look at the official visitor’s website where I usually find an overview that also includes suggestions for activities, accommodations and dining.

Already know where to go? Start your hotel search with us.

When it’s time to get down to specifics for activities or accommodations, I read the reviews at Trip Advisor, usually throwing out the worst and best reviews. In my experience, the truth is always in the middle. Blogs about first-hand travel experiences are another way to learn more about a place. Of course you’ll need to understand the blogger’s travel philosophy, making sure that it’s the type of travel that you want to do. If it’s a cruise that you’re researching, the forums at Cruise Critic are excellent for asking questions about ships, ports and cruising in general.

How did we know where to go in Italy? We did our research. Read our boomer travel tips on deciding where to go.

Slowing it down on a visit to the Tremiti Islands in Italy.

Balance preferences with travel styles

A slow pace is important to Alan. I like a mix of luxury and adventure. Crowds or over-touristed destinations? Forget about it.

We both prefer small ship cruise itineraries that include lots of sea days. A port every day is not the cruise for us. And when it comes to international travel, bonus points if we depart or return on an ocean cruise. Avoiding long international flights is always at the top of our list.

What about group tours? If they’re small and offer unique experiences with excellent lodging, we’ll take a chance on them. There are some places in the world that are much easier to experience on a small group tour than figuring out on our own. We also look for itineraries that include a couple of nights at each destination. If the tour is a different city each night, it’s not for us.

Deciding where to go on a boomer vacation? Don't forget to include old favorites. That would be the South Pacific for us.

We don’t mind repeating favorite travel destinations like the South Pacific.

Budget wisely

If the top three travel ideas on our want-to-do-list require major money, they won’t be happening in the same year. And that’s why we also keep a list of short, more affordable trips to round out the travel year.

There are plenty of ways to save or economize on a trip but these are the strategies that we personally use as luxury travelers:

  • Contribute to a travel fund on a monthly basis.
  • Choose a cash-back credit card and dedicate the payout to the travel fund.
  • Sign up for newsletters from favorite travel providers to keep informed of any specials.
  • Join customer loyalty programs at airlines, hotels, cruise lines and other travel companies to receive money-saving offers and upgrades.
  • Look for 2 for 1 cruise specials, especially on repositioning cruises.
  • Follow companies and destinations on Facebook and Twitter. Did you know that many of them offer deals specifically for their social media audiences?
  • Choose a similar, but less expensive, destination.
  • Travel in the shoulder season or even off-season.
  • Book a vacation rental rather than a resort hotel

You may have noticed that I didn’t include airline frequent flyer programs in the list. In our opinion, airlines make it too hard to redeem miles. While Alan and I do belong to frequent flyer programs, we don’t depend on redeeming miles for international trips. But if that’s your strategy, be sure to factor in the amount of time you are spending on trying to redeem miles because your time is worth something, too.

If you aren’t a luxury traveler, other options that will save money include house sitting, swapping homes or traveling by RV. Choosing a more budget-friendly tour company that offers fewer amenities and a larger group size is another idea. Book a 4 or 3-star hotel instead a top-of-the-line property. And if luxury cruising on Silversea, Seabourn, Crystal or Regent doesn’t quite fit your pocketbook, check out boutique cruise lines like Oceania, Azamara or Viking. They offer a quality, small ship experience with interesting itineraries.

Know your limits when planning a boomer travel adventure.

Hiking in Dunedin, New Zealand

Set realistic expectations

For Alan and me, staying in touch with our priorities and abilities saves us from a disappointing trip. I’m afraid of heights, which can be a big problem on some—but not all—hiking trips. No matter how much I’d like to see Mt. Everest base camp, I’m not going to make it there. Heck, I’m not even sure that hiking the Highline Trail in Glacier National Park is doable for me. Skin-cancer-prone Alan has to be careful about too much sun exposure so we’re still working out how to accomplish a float down the Grand Canyon without baking his skin.

And we’re keenly aware that time is moving swiftly. Life changes in a heartbeat, which is one reason that active trips are a top priority for us right now. However, after living through a couple of years crammed with too many trips, Alan and I are balancing our love for travel with the enjoyment of home by spacing out trips. We want to venture off into the world, then return to Montana to process the experience plus appreciate the travel fun we can have right here at home.

Our current goal is to take one long cruise a year, at least one long road trip and fill in with shorter trips around our region of the U.S. Squeezing in an adventure cruise would be ideal, but that’s not always in the budget. And, lest you think that travel companies and destinations are paying for our trips, 90% of our travel is self-funded. And we prefer it that way.

Judy, I hope this answers your question. And, My Itchy Travel Feet readers, what about you? How do you decide when and where to go? Join the conversation at the My Itchy Travel Feet page on Facebook.

Do you have questions about boomer travel? send us an email. Your question just might inspire another travel tips article at My Itchy Travel Feet.

Disclosure: Affiliate links have been included for your convenience. However My Itchy Travel Feet receives a small percentage of the sale at no additional cost to you.

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