Dream Vacation: 5 Steps to the Trips You Didn’t Know You Could Afford

“The World is a book, and those who do not travel read only a page.”
– Saint Augustine

how to afford a dream tripThis week’s post is a guest post from Kate Phillips of Total Wealth. Kate is our marketing and communications manager and we’ve missed her while she’s been taking her dream trip!

How to Enjoy Awesome Vacations (without breaking your budget!)

I just returned from a FABULOUS 2-week vacation, enjoying Italy’s stunning southern coast on “The Ultimate Sorrento and Amalfi Coast Tour,” a small-group tour with Adventure On Italy. Truly my dream trip to Southern Italy, it was full of highlights I will never forget:

  • Exploring the medieval Arogonese Castle (Castello Arogonese) on the island of Ischia;
  • Spending a day at Pompeii and Herculaneum with our own guide;
  • Sitting in on a concert rehearsal at La Mortello Gardens;
  • Hiking “The Path of the Gods” (Sentiero Degli Dei) from Positano, with stunning views from the cliffs above Mediterranean Sea;
  • Touring the Cathedral and sampling Limoncello at Amalfi;
  • Viewing an amazing photography exhibit at the Villa Ruffalo at Ravello;
  • Exploring the island of Capri in a convertible and taking a chairlift to enjoy “top of the island” views;
  • Discovering my favorite shops and a fascinating museum in skinny back streets of Sorrento;
  • Enjoying a cooking class with a highly skilled and entertaining Italian chef.

Path-Positano-viewAs an added bonus, this trip was also the first time I enjoyed letting someone ELSE plan and arrange my accommodations and travel (except my flights and travel before and after the tour). This was especially a treat as travel planning can consume many hours (especially with my research-heavy tendencies!)

You might say I’ve been bitten by the travel bug, as I’ve also traveled to Hawaii, Grand Cayman, and Puerto Aventuras, Mexico recently. Looking at my travel itinerary, you might think that I’m in a different income bracket than I actually am! But travel doesn’t need to “break the bank.” I believe that almost anyone can make travel a part of their life experience. And why shouldn’t we? Travel enriches our lives, stimulates our minds as well as our senses, and nourishes our souls.

Many people wait to travel, perceiving they don’t have “enough” money or “enough” time. Sadly, some people put off traveling until retirement or worse, the mythical “someday” that never comes.

One of the recurring messages from Kim Butler of Partners for Prosperity is to stay productive and keep contributing through paid or volunteer work long past age 65. However, the concept of not retiring can sound like a whole lot of WORK, that is, until you see the big picture.

The question we should be asking is not, “When can I retire?” but rather, “How can I fill my entire life with a fulfilling balance of productivity, contribution, learning, recreation and travel?”

Door-in-sorrentoVacations and breaks are an absolute necessity. And according to a recent study quoted in Fortune.com, “Vacations are linked to decreased risks of heart attack and depression and even promote brain health.” Professors and pastors take sabbaticals. Serial entrepreneurs often take “breaks” between projects, such as after the sale of a company and before the next start-up. Even top performing artists in high demand such as Adele and Shania Twain have taken extended hiatuses from their work.

Who is to say that working 50 weeks a year and then quitting cold turkey at age 65 (more or less) and retiring to a golf course is the most satisfying model for life? Consider instead how you can construct your days, weeks, years, and life to balance productivity and relaxation, contribution and recreation.

Travel is not only soul-enriching and educational, it’s also one of the most important (and fun!) things I can do as a parent with my now college-age daughter. When my daughter was ten, we went to Paris with my mother/her grandmother. We ate onion soup and chocolate mousse at the Eiffel Tower and toured the Louvre, Musee D’Orsay, Notre Dame and other sights. She still remembers seeing the Mona Lisa, and I’ll never forget our “3 generations of women” trip to Paris.

New York CityTwo years ago, celebrating her 20th birthday, I took her on a whirlwind dream trip to New York City. Conceived of while watching the Tony Awards in June (stumbled upon while flipping channels to find something my father might both enjoy while I fixed dinner), I funded, planned, and paid for the trip in the time span of three short months.

In five action-packed days, we took a boat tour around Manhattan, saw a Broadway show from the second row, enjoyed the view from the Empire State Building and the “Top of the Rock” (Rockefeller Plaza), and attended a live taping of Late Night with Jimmy Fallon. (Special guests were Ben Affleck and Mindy Kaling and my daughter had a front row seat!) We also strolled through Little Italy, Times Square, the Upper West Side, and Central Park, visiting the beautiful Bethsada Fountain and John Lennon’s memorial, Strawberry Fields. And we paid our respects at the 9/11 Memorial at the World Trade Center.

So… how can you take the dream trips you didn’t know you could afford? It takes 5 steps:

Step #1: DREAM.

If you can’t imagine your dream trip, you can’t take it! Everything we accomplish begins as an idea first. Where are you longing to go? Start seeing yourself there. Post pictures on your wall and screensaver, and start reading about all there is to do on TripAdvisor.com.

Herculaneum2Not sure what your dream trip is? Ask friends for recommendations, read travel magazines, or browse the internet to see what strikes your fancy. Pay attention to your budget, and most importantly, listen to your heart.

If you’re single, you don’t need to wait until you have that “special someone” to go to Paris or Rome with. BE that special someone and treat yourself.

Step #2: COMMIT.

You don’t have to work out all the details, but you have to start somewhere. Pick your dates. Then take a bold step, such as purchasing airfare or saying “Yes” to joining a tour.

In a passage from The Scottish Himalayan Expedition, mountain climber William H. Murray writes:

We had definitely committed ourselves…. We had put down our passage money – booked a sailing to Bombay. This may sound too simple, but is great in consequence. Until one is committed, there is hesitancy, the chance to draw back, always ineffectiveness. Concerning all acts of initiative (and creation), there is one elementary truth, the ignorance of which kills countless ideas and splendid plans: that the moment one definitely commits oneself, then Providence moves too. All sorts of things occur to help one that would never otherwise have occurred. A whole stream of events issues from the decision, raising in one’s favour all manner of unforeseen incidents and meetings and material assistance, which no man could have dreamt would have come his way.

Step #3: SAVE.

It doesn’t matter if it’s $20 or $200, but it DOES matter if the fund exists in theory or in reality. Whether you’re saving in a whole life policy that you can borrow against for travel, or saving in a bank account or a jar, start putting away money for your trip! You can also purchase a hotel stay or book your airline tickets as you are able, thereby checking off your expenses as you go.

As you’re saving, you’ll also want to look for opportunities to save money on expenses by paying less than full price. Some ways to do that:

  • Use Hotwire or Priceline.com to book discounted hotels. Read specific tips on “bidding” on rooms with Priceline here.
  • Join the Starwood Preferred Guest program and let the special offers shape your travel plans. (Example: 5 nights on Maui in a room for 2 with ocean view room with rental car AND $100 resort credit: only $750.)
  • Compare different travel days and seasons. Travel off-season, for instance, early December instead of Christmas break time, or spring and fall instead of summer break or mid-winter high season in the tropics. And in general, flying on Tuesdays and Wednesdays proves to be less expensive than flying Friday – Monday.
  • Compare vacation package prices on Expedia.com and similar sites to save on airfare-plus-hotel-plus-car “bundle” deals.
  • Consider hotel alternates such as AirBnB.com (rentals in someone’s home), or even a home exchange.
  • Use our own P4P Rewards website to save big on travel plans with your Travel Savings Passport. (We’ll have further details on this program soon.)


Italy-Capri-viewFew people have unlimited budgets. What’s important to you? Decide what’s negotiable and what’s not.

As I looked at traveling in Italy, I weighed the hassle of planning my own trip vs. the convenience of having it done for me, plus the considerations of traveling alone or finding a travel companion. When I decided a tour was the best fit, I found a small group tour (10 people) where I wouldn’t feel like a number in a big crowd. And instead of studying about the accommodations, activities, and transportation options of each town, I let my tour guide do that, which let me focus on work projects prior to my trip. The work projects paid for the trip, and my vacation felt effortless!

When approaching New York City on a budget, I wanted to stay in Manhattan, but was willing to get an inexpensive hotel. (In Manhattan, under $200/night is a bargain, and I found just such a bargain, in a safe neighborhood right by a subway station.) I wanted great seats for the Broadway show, but was willing to take public transportation around Manhattan, which was really part of our NYC experience. And we dined out for two nice dinners, while also eating a lot of pizza, street vendor meals and other “quick” food.

I also found myself prioritizing my expenses leading up to the trip. (Did I need to go to Starbucks or a movie, or should I just put the money in my New York fund instead?) Dreams are a powerful motivator! You’ll find many ways to save once your goal is in sight.


Enjoy yourself! Try new things (except the water in Mexico). Meet new people. Bring earplugs, comfortable shoes, and an open mind. Remember your phone charger, but unplug from the internet. Be present. Pack light. Stay safe. And leave earlier than you think you need to for the airport.

NYC-Kate-at-ESBTravel may be an expense on your spreadsheet, but it is a truly valuable experience worthy of investment!

Kate Phillips coaches advisors and entrepreneurs on mindset, marketing and money. Learn more at Total Wealth. Kate also co-authored Financial Planning Has Failed with Kim Butler, which is part of our complimentary Prosperity Accelerator Pack.

Where’s YOUR Favorite Dream Trip?

Whether it’s your favorite destination or the one you’re still dreaming about, please share below!

2 thoughts on “Dream Vacation: 5 Steps to the Trips You Didn’t Know You Could Afford”

  1. Disicplined budgeting and saving, along with a “travel rewards” credit card has enabled my family to take annual trips to New York City during February school vacation, a 25th anniversary trip to Hawaii in 2014 where we used our credit card points to cover our hotel expense, and a wonderful family trip to Colorado this past summer where we went whitewater rafting, took a cog railroad ride to Pike’s Peak, visited Rocky Mountain National Park, and visited the Boulder area. Hmmm, where to next?

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