How You Can Run Away to the Caribbean With Kids in Tow

By Kirk Horsted

Brainstorming Your Breakaway

No doubt there are times you dream of running away from your family…but perhaps you should consider running away WITH them instead. Sound radical? Perhaps. But I’m here to assure you that you can (and perhaps should) take a break and get away—leaving your stuff and responsibilities behind.

For the next five minutes, shift your attention from your PDA to focus on your Breakaway. Start visualizing a prolonged and faraway escape. Yes, a sabbatical. The fact is, few experiences can be so eye-opening, exhilarating, and cathartic.

Intrigued? Here are some suggestions:

Go away, far away. Chances are, there’s some place on the globe you harbor a strong urge to visit. For more than one frazzled week. So leave the predictable confines of the USA behind and expand your worldview. You’ll never see things the same way again.

Accept your mission. That’s the difference between your Breakaway and an extended vacation: Mission. There’s something you’ve been longing to do, and this is your once-in-a-lifetime opportunity. Go deep into yoga, help your kids learn Spanish, or find your roots in the homeland. Elevate your sabbatical with a quest for a coveted desire you’ve been neglecting.

Stretch it out. Strive for a minimum of three months. Whether alone or with a family, travel is hard work; it can take weeks to overcome time changes, exhaustion, and confusion. Plus, what you’re doing—and what you’re seeking—is complex. Give it time. If you rush your extended getaway, it won’t feel like one.

Put your job on hold. Oh sure, you could plug in and talk shop all along the way. And if your mission is to test your professional portability—or there is no other way out of town—go for it. Otherwise, know that you’ll have a better experience if you focus on the experience. For a change, work will wait.

Balance structure with spontaneity. Is that not one of life’s more cosmic challenges? In this case, it means giving yourself a few months in one special place—but also room to roam. Map out a path to advance your Mission, but welcome worthy detours. Set up the stability and comfort you need to relax. Then seek the adventures that you crave.

Travel light. Most of us swear we will, but then schlep an apothecary and spare wardrobe. Fuggedaboutit! Carry your life on your back—literally. Remember: You’re leaving behind your burdens, responsibilities, and baggage. (You probably won’t miss a thing.)

Consider service. Want your legacy to include making the world a better place? Just do it. Help feed hungry families. Teach English to third-world students. Dig into sustainable agriculture. Show your children another way of life. Chances are great you’ll gain more than you give.

Record your own history. Although this flies in the face of “travel light,” please do cart along your camera, camcorder, PowerBook, sketchpad, diary, or other recording device of choice. There’s no better way to capture precious daily details and—more important—to remember them later.

Useful websites

We didn't use that many general websites for this trip...

Mostly a lot of Googling to research destinations and find relevant local blogs and links. That said, here are a few:

tripadvisor.com: especially the reviews & forums—invaluable.
perpetualtravel.com: a treasure trove of information—not pretty, but thorough.
lonelyplanet.com: info & tips off the beaten track.
homeexchange.com good source for long-term exchanges and vacation rentals.
sabbaticalhomes.com: geared for academics, but works for the rest of us.
travelwithyourkids.com: what to do to amuse the littles when you get there.
familysabbatical.com: a good book (and site) with helpful resource links.
escapeartist.com: lots of content—with an expat spin.
cdc.gov: serious health risks or outbreaks? know before you go.
mobal.com: if your cell or plan doesn't work abroad.
ebags.com: if your luggage doesn't comply with new airline requirements.

“It’s not a financial decision”

Sounds good, right? So what’s stopping you? For most people, the stumbling block is money. Powerful stuff, those numbers on paper. That’s why we need to fight back with this omnipotent mantra: “It’s not a financial decision.”

Really now, did you make your biggest life decisions based on some spreadsheet? No. Consider: choosing a college, then a career; getting married, or unmarried; having children; quitting a crappy job; moving. Sure, “costs” received attention. But following your passion and values mattered most. Moreover, regardless of your net worth, you likely already enjoy among the cushiest lifestyles on the planet. How will you spend your lifetime of good fortune?

Also ask yourself: Whatever your “work” may be, isn’t the point to earn the pursuit of life, liberty and happiness? Are your discretionary dollars better spent on bigger vehicles, homes, and stuff—or bigger vistas? Would you work three years longer at your career’s end to free up three years along the way? Can you maintain a fresh, productive point of view without refreshing experiences? On your deathbed, will you reminisce about meeting deadlines—or meeting mates in Australia?

Now for some little leaps

If you’re still reading without cynicism, you’re probably ready to take a few small leaps. Like, talk to other families who’ve done it. Start a journal. Propose it to your life-partner. Run it by your employer. Watch for windows (of time and place) and windfalls (of cash). Take a test-run vacation, and take pride in using up ALL your vacation days! In time, create a schedule and budget that accommodates this priority.

As if three months away were not their own reward, expect generous, ongoing dividends. You’ll overflow with new ideas from novel places. You’ll gain the wisdom of the well-rounded person who knows that balance is essential to both work and life. You’ll have initiated a new life plan driven by heartfelt convictions, worldly relationships, and real independence. And if you take your journey as a family, you’ll come home with deep bonds and beloved memories.

But take your time—because you’ll need ample patience and persistence. And be willing to adopt the mantra, “Everything is right on schedule.” It can work wonders when you’re getting frustrated and losing hope.

After all, believing in Breakaways is not just about lusting for leisure. It’s also about finding faith. So feel free to disregard all these ideas and follow your own bliss. Above all, feel free.

Photograph of Elsa Horsted courtesy of the Horsted family.

Tags: breaking away, families, Minnesota, trips

How the Horsted Family Got Used to "Island Time"

Read Part 1 of the Horsteds' adventure here. To launch a slideshow of Horsted family photos, click here.

How does a person—make that a family—get to take almost three months off in the winter?

Kirk: It helps to save some money, of course, which we do (in part) by preferring big-time experiences over big-ticket items. Planning IS key—and takes discipline—but once you have a vision, keep your eyes on the prize.

How long did it take to plan, and what was that process like?

Jesper: The day before we left I threw some swimsuits and clothes into a suitcase, zipped it up and went off to play. At the time 69 days seemed like a week.

Kyia: I think we floated the idea around for a few years and began saving the money. We didn’t kick into serious planning and actualization mode until pretty late in the game—about September of 2008, approximately three months before we left. Which made the process very condensed and intense—not exactly the best approach to something that is supposed to be fun and inspiring to plan. Putting together a journey like this is a LOT easier since the internet has happened.

What were some of the hardest parts about making it happen?

Jesper: It seemed more stressful around the house. I think my parents had more arguments about little stuff. Maybe it was a little hard to leave my basketball team and friends, but not very.

Kyia: I was so busy with work that I could hardly spare the mental energy to envision—let alone plan—the trip. I felt too overwhelmed with daily life to get in the “space” of dreaming and scheming. Doing the destination research and coordinating all the reservations and arrangements and logistics (typically my role in the process) felt like too much to add to my already-full plate.

Kirk: Some of my roles seemed endless and thankless: Procuring the right stuff (including medical, watersports, and technology); dealing with the home schooling details; arranging care of the cat, house, security, cars, insurance, bills, end-of-year bookwork for our business, and on and on

What were some of your fears and concerns about going somewhere new for so long?

Jesper: I was a little nervous about being away from my friends for so long. And I was also a little bit worried about there being poverty or crime in some of the places we were going, and being the only white people.

Kirk: The biggest worry beforehand, really, is just that you won’t get everything done and make the plane! I fret more about the uncontrollables: lost luggage or theft , stranded; serious illness or injury (it has happened on these trips). And frankly, I was concerned for the kids’ contentment and basic needs—food, good water, sleep, entertainment, social life, and equanimity. But one of the many cosmic benefits of a Breakaway is that it makes you face down your fears—and tap into your trust.

Did the trip have a particular purpose; did it mean different things to each of you?

Jesper: I knew the trip would change me, but I wasn’t sure how. I wanted to deep-sea fish, snorkel, and try new foods. But I was mostly just looking forward to missing a few months of winter and school.

Kyia: I had been working REALLY hard all year so I was looking forward to some serious downtime—and the opportunity to really reconnect as a family. I also wanted to simplify life and escape all the responsibilities and “stuff” of our life at home.

How did you pack; what was useful and what was useless? Did you ship anything?

Jesper: We brought a basketball and it turned out to be pretty useless. There were hardly any hoops or courts on the islands we were on. We brought baseballs and gloves and didn’t use them much. It wasn’t baseball season and there were always other things to do on the beach.

Kyia: Our packing was limited by the stringent restrictions of the island puddle jumper airlines we were flying. So we really needed to streamline. We were deliberately visiting a diverse range of accommodations—from local guesthouses to luxury boutique resorts—which came with different wardrobe expectations and requirements. That said, I still had more clothes than I needed—and so did the kids. Beyond clothes and my computer, I really didn’t bring much. I figured I’d find books and diversions and stuff along the way. I let Jesper make his own decisions about what gear and “toys” he wanted to bring but I took a pretty controlling role with our daughter to make sure she brought the right (condensed) combination of paperback books, art supplies, PollyPockets, cards and games.

Kirk: The clothes part comes pretty easily, since you don’t need much warm attire! But from there, I’m in charge of some complex gear. Sports: beach stuff, snorkel equipment, baseball gear, toys. Music: guitar and accessories, iPod, dock. School stuff: many books and papers. Medical: a bit of everything anyone might need. Food: With kids and travel uncertainties, one must always have at least water, snacks, and fruit handy. Technology: two computers, three cameras, one camcorder, countless cords and chargers. All of this had to fit into strict requirements. I vividly remember repacking and weighing and measuring bags for days. What was useless? Probably 10 percent of it—but you don’t know what’s unnecessary till afterward.

How did life on the islands compare to life back home; was it easy to find a groove and feel comfortable?

Jesper: It took a while to get in the groove. Getting used to the slow island lifestyle. Some places we walked into and instantly I could tell it would be a cool place and I would like it. Other places we arrived and I thought, “Oh boy, this is going to be an adventure…”

Kyia: I had a hard time decompressing at first. The weeks before departure were so intense, and I was really running in overdrive. It took a few weeks for my heartbeat to slow and my mind to quiet. To realize that this wasn’t just a vacation but our “new life” for the next few months

Kirk: Moving from island to island—and place to place—was often tedious, with some adjustments necessary each time. But it was worth it. Caribbean life really doesn’t compare to life in Minneapolis/St. Paul, especially as we went further south and to relatively non-touristed locales.

What were some of the challenges you faced in your new life amid new cultures?

Jesper: Sometimes it was really hard to understand people who talked fast and pronounced words differently. There were times, especially on the more remote islands, when the local people would just stare at us. We were driving around and people would look at us like they had never seen anything like us before. Sometimes they would point, or glare, or even laugh.

Kyia: Everywhere we went we had to figure out how to take care of the basics: find groceries, get around on public transportation, do laundry—just day to day stuff like that. Or good local restaurants, nice quiet beaches. I also had a hunger to meet new people—both locals and other travelers—that wasn’t always easy to satisfy. And finding playmates for the kids wasn’t as effortless as we had hoped it would be. Aside from the Christmas break, there were very few families traveling, except for a few European families who were on extended sailing trips.

Kirk: Internet access and technology problems were nonstop, which wasted my time and drove me nuts. “Island time” and waiting for everything can test the best, though it rarely bothers the natives! Negotiating with macho people wasn’t always fun; that’s so NOT Minnesotan. And sleep can be a challenge—keeping the kids rested and adapting to new beds and environments.

What about communication?

Jesper: I brought my iPod touch and was able to get wireless at some places we stayed. I got some new games and apps before the trip and added more along the way. Sometimes I’d chat with my friends and try to describe what I was seeing and doing but they couldn’t really get it.

Kyia: Every place we stayed had internet service—or at least it was advertised that way. I usually had pretty good luck getting online with my laptop, and kept in touch with family and friends via e-mail. Skype came in handy for a few client conference calls.

Kirk: Staying in touch enough was easy enough. But let’s just say the information super-highway is still under construction down there, and was a major, unexpected annoyance for me. I especially got perturbed when a resort or hotel would say they have wireless everywhere, but didn’t—and then have a “don’t worry be happy” attitude about it.

Did you try homeschooling? How did you prepare for that, and was it successful?

Jesper: Before we left I set up a plan with my teacher to read several novels, write some papers, and get through about 130 pages of math. I also agreed to create a blog to share my experiences—that counted for my social studies and science requirements.

At the beginning of the trip we weren’t very disciplined about the school part so we fell behind, and needed to work extra hard at the end to catch up. I’ll admit that there were many times that I would have much rather been building sandcastles or snorkeling but after coming back I really wish I would have written in my blog more often.

Kyia: I must confess that I played quite a bit of hooky when it came to the homeschooling piece of the trip, as I’m rather more of an “unschooler” at heart. I couldn’t take the kindergarten “syllabus” very seriously, and I didn’t feel qualified to assist Jesper with math, which was his biggest responsibility and challenge. I did help him create and maintain a blog and encouraged (nagged?) him to post on it.

Kirk: To be honest, there were some lackadaisical attitudes and family conflicts. So while this experiment was successful, my memories of having to play Bad Cop and Math Master are not all pleasant.

After 69 days of fun in the sun, what was the comeback to reality in Minnesota like?

Jesper: It was kind of like starting over because all my friends had kind of lost respect for me while I was gone. They kind of forgot about me, I think. Plus they thought I was getting home four days later, so they didn’t expect me. I play center on a traveling basketball team. We had a big tournament right away, and it was hard playing so much without even learning the new plays and stuff. But within about a week, I felt at home again. It all turned out well in the end, and now people barely remember that I even went on a trip.

Kyia: Honestly, it was pretty ugly. We arrived home late in the evening on February 24 (in the thick of winter) after a long day of travel. The kids were ecstatic to be home, but I felt a sense of heaviness—facing 2-plus-months-worth of mail on the counter and a very loud and unhappy cat. Outside, the world was stark and grey and completely devoid of all the vibrant colors, smells and sounds that I’d been basking in for so long. And everyone seemed so depressed. The harsh winter—and even more brutal economic meltdown—had really beaten people down. The next few weeks were a combination of culture shock and re-entry challenges—reluctantly jumping back into the work/life jungle.

Kirk: It was hard to have to live indoors again—and wear umpteen oppressive layers to stay warm. The “high” of the trip did carry on for quite a while, though. Whenever I return, I’m always awash with gratitude for our blessed life at home. And there’s a lingering sense accomplishment and appreciation for completing a safe and successful trip. But the comeback may be the most taxing part of a Breakaway.

How did you pay for such a journey, and—long-term—what does it mean to you financially?

Kyia: We live beneath our means and made lifestyle choices that allowed us to save for this goal. We set a budget in advance, and used credit cards (paid off in full every month) to fund most aspects of the trip—before, during and after.

Kirk: We’ve had decent luck. But we also work hard, are good savers. The trip depleted our savings—which could have long-term implications if our investments and business don’t turn around. But we’re still sitting on a fairly comfortable cash cushion (as I advise everyone to do). I’m happy to say that I don’t worry much about money any more. It doesn’t help.

Photograph of Jesper Horsted courtesy of the Horsted Family.

Tags: breakaway, Caribbean, kids, Minnesota, sabbatical, St Paul, travel

One Family's Caribbean Sabbatical

The Horsted family, from St. Paul, Minn., believes in taking mini-sabbaticals every few years. On their latest adventure, parents Kirk and Kyia took their eleven-year-old son, Jesper, and five-year-old daughter, Elsa, through the islands of the Caribbean for over three months this winter. Kirk created a website to chronicle their trip. Make Your Breakaway. The family is sharing their experience with Your Comeback today. We begin with a timeline that Kirk put together.

On December 17, 2008, our family of four set off on a 69-day Breakaway to the West Indies to escape Minnesota winter—and continue a tradition of radical sabbaticals. We ventured to five islands. Stayed in eight different places. Traveled by air, land and sea. It was the best of times, mostly—with the occasional meltdown and snafu.

September 28, 2007. I present the sabbatical vision—a “someday” dream—to the kids’ elementary school principal. She not only approves, she wants to come along!

May 5, 2008. Mom and Dad sit down Jesper and Elsa to seek their (symbolic) buy-in; no problem, mon.

September 16, 2008. I launch makeyourbreakaway.com and begin blogging about sabbaticals by asking, “What’s the Big Idea?”

September 17, 2008. Planning is impossible, big "buts" are everywhere, and blogging feels embarrassing. But I toil away anyway.

October 9, 2008. This journey is simply NOT coming together. Doom and gloom loom while the odds-of-going meter plummets to 33 percent.

October 20, 2008. No turning back now: We’ve bought tix to St. John, and will fly home from San Juan. But where to go in between—who knows!?!

October 21, 2008. A HUGE day! Serendipity strikes when an old travel article falls in my lap: Grenada, we must invade!

October 28, 2008. 50 days before takeoff, the the costs and worries are piling up.

November 9, 2008. Another Breakaway breakthrough day: An itinerary of five alluring islands gets loosely set, and the odds-of-going meter hits a new high (90 percent).

November 29, 2008. The anxiety is getting relentless and I find myself seriously doubting this idea, not to mention my own sanity.

December 13, 2009. With only four days till takeoff, emotions and panic run high—but so does the odds-of-going meter: 95 percent.

December 15, 2008. 29 hours before takeoff, everything hits the fan: two are very sick; sewer backs up; sleeplessness and a storm rage on.

December 18, 2008. Yes! It’s day one of our 69-day sabbatical, on familiar St. John. We hunker down into a state of liberation and bliss.

December 19, 2008. We are not alone! We befriend a couple who throws a dart to determine the destination of their annual Breakaway.

December 21, 2008. This solstice brings less winter and more warmth—so it’s easy to find 11 reasons to love this pagan holiday.

December 27, 2008. Breakaway bummer: Requisite medical emergency occurs when our daughter, Elsa smashes her finger in a heavy door.

January 3, 2009. 18 sweet days have flown by. Now we must fly away too, on a 14-plus hour journey to the isle of St. Vincent.

January 5, 2009. St. Vincent surprises with unspoiled beauty and lost-in-time authenticity.

January 8, 2009. We ferry to beautiful Bequia, an unheard-of island that will be our home for 17 days; it’s love at first sight!

January 17, 2009. Paradise lost: Gnarly neighbors, nasty insects, and more problems conspire to inspire a rant about a Breakaway’s dark side.

January 19, 2009. Home schooling is well underway, and we parents receive a solid “B” for effort.

January 21, 2009. “Obama” is the word as we join ex-pats, Bequians, and the world in watching the inauguration of a new era.

January 26, 2009. The most challenging travel day features three boats, seasickness and storms, and (eventually) a dramatic landing on Grenada.

January 31, 2009. Dreams come true: Grenada is like Harry Belafonte’s gentle Caribbean, and it’s our “home” for a month.

January 31, 2009. Home schooling is great, but the kids are learning more from locals, okra, and conch.

February 17, 2009. With only ten days left, it’s time to focus on the important stuff: The First-Ever Great Caribbean Beer-off!

February 20, 2009. Isle of Grenada, I’ll miss you and your passion most of all.

February 21, 2009. This hellish travel day includes Grenada’s revenge, a customs nightmare, and LOTS of islander stinkeye.

February 25, 2009. Help! We’re “home!” To “reality!” Where cultures, climates, and agendas quickly clash! And yet…the kids are giddy, and life is good.

April 7, 2009. I end the travelog with a heartfelt letter to my children, whom I now realize made this Breakaway perfect—just like they are.

Kyia Downing is a creative strategist, copywriter and branding consultant—and one-half of 2 Heads Communications, a miniscule Minneapolis marketing consultancy.

Kirk Horsted is a sabbatical advocate, avid dad and part-time hedonist—and the other half of 2 Heads Communications.

Photograph of Jesper and Elsa Horsted courtsey of the Horsted family.

Tags: Bequia, Caribbean, family travel, Grenada, Puerto Rico, sabbatical, St John, St Vincent, vacation