Travel Tale: How I Missed My Trip to the Dominican Republic

sailboat – Caribbean

Travel Tale: How I Missed My Trip to the Dominican Republic

I’ve never been to the Dominican Republic. Yet.

But I came this close to visiting just one year ago. I did all the research. I made my whole plan. In fact, I made two whole plans.

In the end, I had to give them all up and return to my beloved SE Asia instead.

However, my research and excited planning taught me a lot about this mountainous Caribbean island. Such as:

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The Dominican Republic occupies the eastern half of the island of Dominica. Poor, bedraggled Haiti occupies the western half. Domica lies just a stone’s throw west of Puerto Rico, across a channel in the Caribbean Sea. Regular ferries run between the two islands, taking about twelve hours one way.

On the other end of Dominica, just west of Haiti, lies the long narrow island of Cuba. And Cuba lies just a stone’s throw south of Miami, Florida.

sunset on the beach in Dominican Republic.

Dominican Republic is famous for stunning beaches backed by swaying coconut palms. The quintessential tropical island paradise. Certain areas have hefty wind, creating perfect conditions for kite boarding. Cliffs line other parts of the coast. Inland the country is mainly mountainous. Coffee plantations blanket many mountainsides. Rivers with pretty waterfalls and hiking trails wind through the mountains as well. All in all, the country is a great place for outdoor enthusiasts.

Domican Republic is a fairly poor country. But not nearly as poor as impoverished Haiti or of Cuba. The main city, Santo Domingo, lies on the south coast. Like many old Caribbean towns, Santo Domingo is full of historic colonial-era buildings, plazas and churches. The city is blessed with a good harbor with a marina that welcomes many passing sailboats. Another harbor and sailing marina lies on the country’s north coast, though conditions are usually much rougher there.

Cascadas de Limon – Dominican Republic.

I created my first exciting plan for traveling through Dominican Republic while staying with my brother in St Petersburg, Florida 1 ½ years ago. I discovered that flights between Florida and Puerto Rico were astoundingly inexpensive. I could get there for under $100 US.

On top of that, since Puerto Rico is considered part of the USA, there are no borders to cross, no immigration checks, no visas required. It’s exceedingly easy for Americans to make their holidays in Puerto Rico, as well as Dominican Republic.

So I would fly to Puerto Rico. How could I miss such a great opportunity?

One drawback, though. Puerto Rico, and all the Caribbean islands are expensive for budget travelers, especially in terms of accommodation. But I could resolve that.

I would stay with some couch surfing hosts in San Juan and around the island. I would also do one or two WWOOFing gigs. Those arrangements would allow me to explore historic San Juan and several regions of the island.

San Juan – Puerto Rico

From Puerto Rico I would catch the ferry over to the Dominican Republic. There I would do more couch surfing around the island, stay at a couple local home stays and WWOOF at a coffee plantation in the mountains. I’d enjoy the island’s gorgeous beaches and explore inland. Then I’d head overland to Haiti. And on to Cuba.

Ah, what a great plan! Island hopping through the Caribbean.

Quite unfortunately, my first promised WWOOF gig in Puerto Rico fell through unexpectedly, just before I booked my flight. Other WWOOF hosts never returned my emails. The coffee WWOOF farm in Dominican Republic suddenly disappeared from the WWOOF registry. My plans started to fall apart.

Just then, out of the clear blue, a German traveler I’d met years earlier in Laos suddenly contacted me. He informed me that he was in the Virgin Islands with his own sail boat, preparing to sail around the Caribbean for several months. Did I want to join him?

Well of course I did!

I wasn’t able to dash off instantly to meet him in the Virgin Islands, where his boat was undergoing repairs. So we agreed to meet in early January on the north coast of the Dominican Republic. I immediately delved into my second Caribbean island hopping scheme.

historic church in Santo Domingo – Domiican Republic.

I researched more thoroughly about the Dominican Republic. I discovered that flights between Florida and Santo Domingo are also quite inexpensive. I located guest houses and home-stays. I learned all of Santo Domingo’s famous historic sights. I found a cool home stay in the center of the island. I researched the costs and travel times for buses between Santo Domingo and the north coast. I discovered Dominican Republic’s main beach haunts. I was ready to book my flight.

Then my friend’s boat repairs were delayed. And delayed some more. I quickly learned the reality of hooking up with sailing boats. Simply put, it requires exceedingly flexible meeting dates and locations. Sailors cannot predict with any accuracy when they will reach any particular harbor. There are too many potential delays. Storms, poor wind conditions or boat problems could all delay a sailing vessel for indefinite time periods.

inland of Domiican Republic

Besides those issues, the captain and crew may find an amazing spot en route they love so much that they stay an extra day or week or month. Sailors don’t like to be set to a time table or itinerary. Even if it’s to meet up with new crew or friends.

Unfortunately, that posed a huge problem for me. Although the Dominican Republic is quite cheap compared to the USA, it is still entirely too expensive for me, a budget traveler, to hang out at guest houses indefinitely, waiting to meet a promised boat. And I had a deadline for leaving Florida.

Since my friend could not set any particular meeting time, even within a one-month window, I had to very regrettably decline his offer.

coconut plantation – Domiican Republic

In any event, I’ve already made the research and plans for visiting Puerto Rico, Dominican Republic, Haiti and even Cuba. Next time the opportunity arises, I’m all set to go. One day I’ll be lounging on the Dominican Republic’s breeze-swept beaches, climbing its pristine mountains and exploring its historic districts.

QUESTIONS:

 Have you ever been to the Dominican Republic? If so, how did you like it? 

Have you ever made extensive travel plans that later fell through? 

If so, were you able to carry out the plans later, or are you still waiting? 

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(* Flickr CC photo credits: @NOO /  Liz Salda  /  Barbara Walsh  /  Ricardo_Mangual  /  rapidtravelchai  *)

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