How to Plan a Caribbean Vacation

Brought to you, with love, by Camille. 

I like to plan. Lists, spreadsheets, and calendars are dearer to me than I’d care to admit.


I arrange my outfit for the next day, right down to the jewelry.

The books on my coffee table never stray from a perfectly aligned stack.

If I am missing one ingredient from my recipe I will drive across town to get it.

I schedule my day down to the minute, armed with checklists. I don’t like when reality deviates from my plan.

You might call me controlling.

But the magic of travel is that it forces you to relinquish all control and just let life happen.

When the heat rash on my legs grew to epic proportions (think solidified cottage cheese) due to the “beauty treatment” I gave myself with coarse sand on the beach on none other than the day of my birth, all I could do was slip on a maxi dress and throw back a shot of tequila. That night the boy I liked told me I was irresistible at least five times. He never touched my legs.

The day that Andie and I walked five miles along the beach, broke open our artfully composed salads, and found ourselves in the middle of a torrential downpour, we ran under a hut covered in palm leaves and ate our sandy lunch, water flooding through the roof. We stayed on the beach for at least an hour, having a grand time on the rainy shore.

young coconut

After Andie made the grave decision of drinking an entire glass of tap water and consequently was confined to the bed and the toilet, I couldn’t simply skip over to Bartell’s. I made the two mile trek to Duende Gourmet, our nearest water source, then persistently opened two young coconuts with a serrated knife. And I didn’t mind. At all.

But this story begins with control, not flexibility. Ferocious planning. My attempt to create a perfect paradise in two and a half months of travel with my best friend.

Costa Rica is a country that has always appealed to me on many levels. It combines relaxation, beauty, and adventure in a compact package, and is a short plane ride away. Growing up with parents who are products of the 1960s, they met at an organic farm that housed displaced hippies, I deeply value environmentalism and sustainability. Costa Rica has a strong reputation for environmental conservation and wildlife protection.

Once Costa Rica was on the table I began asking friends for recommendations. I drafted multiple itineraries that ranged from three months in one locale to twelve different towns spread between four countries. Created google docs indicating the price and travel time for each destination. Scoured craigslist and VRBO for vacation rentals. Responded to dozens of ads. And admittedly spent hours every day on Lonely Planet. That was before I picked up their guidebooks.

Finally I settled on three locations: Puerto Viejo, Bocas del Toro, and Manuel Antonio. Why three? Practically speaking Andie needed peace and time to write a book. Taking ten hour long bus rides to Nicaragua then chartering a tiny plane to take us to an island with no electricity hardly seemed feasible. With two and a half months at our disposal, a few weeks in each location offered adequate time to acclimate and relax but still be stimulated.

Lonely Planet is the source that directed me to Puerto Viejo. Still, it presented a risk. And control freaks like to minimize risk as much as possible.

I spoke with several people who spent time all over Costa Rica, none had ever set foot on the Caribbean Coast. Monteverde, La Fortuna, Manuel Antonio, and Mal Pais all sounded like approachable options that others enjoyed on their vacations. For me, finding a place where I could live was key. Lonely Planet painted Puerto Viejo as a place where I could spend months, certainly weeks. It promised stunning beaches, flavorful cuisine, laid back Caribbean vibes, abundant wildlife, world class surfing, and access to nightlife whenever my feet felt the itch to dance. All this and it came with a lower price tag than the Pacific. I was sold.

Countless hours on VRBO led me to very few unreserved cabins. The most desirable rentals were well equipped and cheap for large groups, but too pricey for just the two of us. We ended up renting through Habitat PM Services, a vacation rental company run by expats. Our home, Villa Shiva, in the housing community of Cabinas Ita Ita, was affordable and just fifty meters from Punta Uva, the most beautiful beach in the area.

After placing a deposit on the cabin I began hearing stories about Puerto Viejo. Scary stories. Stories that would make Andie’s mother single-handedly bankrupt the airline industry just to keep her from going. Young girls on study abroad programs being raped or worse… in Punta Uva. Where we were to live. This was a moment to give up control and accept the risks that coincide with travel. The plans had been made. However, rather than just give in, I gave in to control. My excitement became anxiety. I actually sent Andie an email with a bulleted list of the things we would not do for safety’s sake. The list included: “We will never enter an unmarked taxi,” “We will never have more than three drinks in public,” “We will never walk at night.”

As I stated earlier, travel forces you to let go of any and all control.

Our first night we arrived in the dark jungle, suddenly aware of how rustic our accommodations were. Our kitchen was outside on our deck. Geckos crawled all over our walls. Complete darkness surrounded us for miles. When our taxi arrived we realized it was a rusty 1994 black Nissan with mismatched white doors. I held my breath and got in, already breaking the first rule on my list. “We will never enter an unmarked taxi.” Esteban, our taxi driver that first night, is one of my favorite people in Puerto Viejo. Andie loves him even more. He calls us “mi reina,” “mi amor,” and “mami,” as often as possible.

“We will never have more than three drinks in public.”

I can proudly say that town never saw two more enthusiastic dancers. And yes, it took more than three drinks.

Walking at night is something that I, and the locals, will tell you is a bad idea. It just is. Even at 6pm. The sad truth is that when you live an hour and a half outside of town and you lose track of time, darkness may fall faster than your feet can carry you. I will admit this happened to Andie and I a few times.

The point of all this is to say that as much as I tried to anticipate my future, you are never truly prepared. That is what makes it an adventure. Puerto Viejo was much more than I could have planned. It was perfect and flawed and in it I found contentment.

But as they say, all good things must come to an end.

The next chapter of our journey is a short one, in Bocas del Toro, Panama.

Andie liked how exotic Panama sounded. I liked that it had rave reviews and only took three hours to reach from Puerto Viejo. With calm turquoise waters and cabins built over the ocean on stilts, I fell in love before I even arrived.

Paradise was the plan, but not the reality.

I found us a cabin on VRBO while we were still in the states, in a community called Monkey Tree Casitas on Isla Colon, the main island in Bocas. The cabin was far outside of town, and Isla Colon lacks the small communities of Puerto Viejo. In fact anything you would ever need is in Bocas town and nothing lies outside of it.

The nearby beaches offered no sand for my sarong. The small strip lining the ocean was covered in coral and cars drove across it freely. It took at least half an hour to walk to a beach that did not double as a road. Bluff Beach. Fondly called “the backbreaker” with waves so large a body dare not enter without a board. It was beautiful and jungle backed, but unimpressive compared to the picturesque shores we left behind.

That was the only day we made it to the beach.

It rained every day we spent in Bocas del Toro. We never saw the starfish covered sand in Bocas del Drago. Never swam next to poison dart frogs on Isla Bastimentos. Never hiked through the jungle to the best Thai restaurant the Caribbean had to offer.

We did, however, make lifelong friends and drink ten too many shots of tequila at Aqua Lounge, a party hostel on Isla Carenero directly across the water from Bocas town on Isla Colon.

(My quick endorsement: Aqua Lounge is loud at all hours and the dorm beds are hard, but I fell in love with every single person I met who was staying there during our time in Bocas. That’s at least fifteen people for the record.)

We also learned an important fact about Isla Colon: taxis stop running around midnight.

The plan was three weeks. We lasted five days. Puerto Viejo had won our hearts and we felt it pull us back. Andie said, “why waste any time being somewhere we don’t want to be?”

I wish I had seen more in Bocas to share with you. What I can say is that both for proximity to beaches and access to town conveniences, staying in Bocas town is key. The town itself is rather quaint with hotels and restaurants hanging over the water. The most beautiful wilderness beaches on Bastimentos are best accessed from water taxis in town. Also, did I mention land taxis stop running past midnight?? Trust me on this one. Stay in town.

We returned to Puerto Viejo with only plans of where we would dance that night. We contacted Evi, who managed our cabin in Punta Uva through Habitat PM Services. However, most accommodations were booked. The control freak inside me felt frantic to instantly rebuild the life we had left behind.

Long and lazy days on the beach.

Fifteen mile hikes to and from town.

Meals brimming with fruit and vegetables.

Deep sleep to the sounds of cicadas.

Wild nights dancing at our favorite Puerto Viejo haunts.

I waited long enough those five days in Bocas del Toro.

I hadn’t planned on running a fever. Nor staying in an eco-lodge overrun by travelers playing loud music during my siesta, their drunken banter outside my door until 5am. I could not have predicted that on the night of our arrival most of the bars would be closed because of police raids. There is no way I could have known that Tasty Tuesday would be postponed. How could I guess that the rain would follow us from Panama? Perhaps I should have assumed that the guy I left behind for Bocas left me behind in mind.

We spent our last few days at Cabinas Gabriel y Bianca per Evi’s recommendation. The cabins are run by a gracious German/Italian couple who offer full use of their dream kitchen (an oven, sharp knives, a whisk?!) with the rental of a small detached room with private bathroom. They lie right outside of town on the main road; far enough for peace, close enough for night walking to town. While I longed for the pure jungle immersion in Punta Uva, I would recommend Cabinas Gabriel y Bianca to budget travelers looking for proximity to town but more privacy than a hostel.

We never made it to Manuel Antonio.

I spent the last week of my trip on the famed Nicoya Peninsula, up the Pacific coast from Manuel Antonio. This leg of the trip involved no plan. I piggybacked on the plans made by my British friends Charlotte and Louise (whom I met where else but at Aqua Lounge in Bocas del Toro). I made the reactionary decision in ten minutes, packed my bags, returned my bike, and hopped on the bus headed to San Jose, Puerto Viejo disappearing behind me in the distance.

While I cannot tell you how or why I planned the last leg of this trip, I can tell you why Charlotte and Louise chose our destinations. Charlotte’s sister spent time in Montezuma and recommended it. It is known for being a tiny town with beautiful beaches and a strong hippie/yogi presence. The streets are lined with vendors selling their handcrafted jewelry.

santa teresa beach

The beach that stretches from Mal Pais to Santa Teresa is a famous surf destination and only a thirty minute bus ride from Montezuma. I considered Santa Teresa as part of my itinerary in the early planning stages, as it is less touristy than other Pacific coast destinations, but still has a strong surf presence (ahem, cute boys). Lonely Planet called it a place for morning yoga, afternoon surf, and all night partying. Yes please.

Did I mention it does not rain on the Pacific this time of year? That was the real motivation.

The bus from Puerto Viejo to San Jose runs about four hours, and the bus to our first stop, Montezuma, was six hours from San Jose. Roads are few and indirect, so venturing from one coast to another almost always necessitates a night’s stay in San Jose. We stayed at creepy accommodations in a dangerous neighborhood on the outskirts of town. This sometimes happens when you don’t plan. That night Charlotte had nightmares that the manager Pierre knocked her out with chloroform while he abducted Louise in the bed next to her. It wasn’t outside the realm of possibility.

The bus to Montezuma leaves the Coca Cola station in San Jose at 6am. The journey is six hours, however two of those hours are spent on a lovely ferry with stunning views of the surrounding country.

The hostel Charlotte booked in Montezuma had no record of her reservation. Montezuma is a small town so we hoisted our bags on our shoulders, and went door to door asking about prices. We found a nice, clean, reasonably priced place in town. Unfortunately, I do not remember the name.

The beaches in Montezuma are beautiful in a strange way. Like an overexposed Massimo Vitali photograph. Like being on the moon.

Ylang Ylang beach resort has an upstairs yoga studio with stunning views. The downstairs restaurant is the perfect place for sunset cocktails on the beach.

The next day we set out for Santa Teresa.

It is safe to say that the road between Santa Teresa and Mal Pais is the driest terrain I’ve ever encountered. Clouds of dust billow from the ground as cars drive by. Wearing white is out of the question.

We stayed at Cuesta Arriba Hostel per Lonely Planet’s recommendation. It had clean dorms, a hot shower, a large kitchen, and a very nice pool. As far as hostels go, it is prime.

The beaches in Santa Teresa are reminiscent of Southern California. Flat expansive beach that stretches for miles, deep blue ocean, and a hazy pale blue sky.

The sunsets are absolutely breathtaking.

We never found yoga in Santa Teresa. Nor did we find any nightlife worth noting. The one “happening” bar (Coco Loco) was similar to, as Louise described, “When your friend invites you to his co-worker’s wedding, but he never shows up and there you are: stuck at a stranger’s wedding.”

What I did find was worth more than any guide book could promise: genuine friendship. I learned intimate details of these amazing women’s struggles and achievements. I found support when I felt completely lost. The lessons I learned throughout my travels came together as we discussed our journeys through life. It was nothing short of therapeutic.

Oh, and did I mention we conducted a book club on The Alchemist? On the beach. After midnight. Surrounded by candles. Don’t worry, there was rum.

Our final night was spent in San Jose, where all flights come and go. This time we stayed in the city center at Hostel Pangea. With a rooftop bar and restaurant, pool, and shuttle service to and from the airport, it is the perfect place for travelers simply stopping through.

My general comparison between the Pacific and Caribbean of Costa Rica is this. The weather and surf are more predictable on the Pacific and it is easier to beach hop to different coastal towns.

The ocean and jungle on the Caribbean are much more beautiful, food is more delicious and diverse, and the nightlife is livelier.

This assessment is based on what little I saw of the country as a whole.

Puerto Viejo is the one place throughout my travels that I will certainly return to.

Would I call my planning a success in the end? I did not learn to surf. I never went kayaking. I only did yoga twice. I took more shots than my liver would like to remember. I broke every rule I laid out before my departure. My biggest deviation from the plan? I fell for a guy. I gave in and let life happen. He, the practical one, would not. And I left more hurt than my king size ego or my marshmallow heart would choose to believe.

But I also learned to be flexible. To adapt in uncomfortable situations. To accept where I am and what I have rather than chase an the ideal. To be in the moment when life pulls me in many directions. To appreciate the process that life presents, for better or for worse. To completely give in to my surroundings and find pure joy in them, regardless of the accomplishment. And thanks to my dear Andie, to laugh more than I ever thought imaginable.


Vacation Rentals
Habitat PM Services

Caribe Shuttle
Easy Ride Costa Rica

Puerto Viejo Guides
Puerto Viejo Satellite
Lonely Planet

Cabinas Gabriel y Bianca: tel. 27500720
Evi at Habitat PM Services:
Ylang Ylang Beach Resort:
Cuesta Arriba Hostel:
Hostel Pangea:
Aqua Lounge:



23 thoughts on “How to Plan a Caribbean Vacation

  1. Mildly Entertained

    I am a control freak. Andie’s mother might be having a melt-down right now! :)Are you a writer as well Camille or did you take a leave of absence to travel? Funny how living on the beaches sounds incredible but the realities are often quite different.

  2. Morgan

    Loved the recap. Beautifully written, but I have a question…did you and Andie split up at the end? It sounds as though you left her to travel with your new friends you met along the way? Sorry about the guy, but I’m sure the memories will live on forever.

  3. Michelle in N. Cal

    Beautiful writing about your adventures! Loved every word and it almost felt as though I was transported there through your words ….

  4. Erin E

    Fabulous post! I, too, am a control freak and traveling the way you did stresses me out to think about, haha. Thanks for sharing!

  5. Alison

    Thank you for the recap!

    I am a planner too but it’s funny how I tend to plan more for the little things and just go-with-the-flow on larger things. For example, I’ll fixate on scheduling weekend plans that no one but myself seems to care about, but then just pick a random car off the lot and decide it will do.

    Glad you had such a wonderful time. I wish life would have a way for me to pack up and take a long stint away from work without having to worry about employment on the return. Maybe one day. :)

  6. Corinne

    Hi! I am going for a month and a half to Central America and I was wondering what kind of clothing would be best. Of course, I am sure sun dresses are fun at the beach but when you walk around the cities/take the bus, what did you wear?

    Thank you, Corinne

  7. Bethany

    Camille, your description of Puerto Viejo sounds absolutely imperfectly beautiful. I envy you and Andie for spending time in such a beautiful place. As far as heartbreak goes, I’m so sorry your feelings weren’t returned. But the thing about paradise crushes is that they will always be left behind in a specific time and place, and you don’t have to see them in your everyday life.

  8. francine

    thank you so much for sharing your stories and your tips!! i was trying to think of a great honeymoon spot and this sounds like a winner indeed! xoxo

  9. Amanda

    Hmm. You know that moment when you realise that having icing for breakfast is not okay? I just hit that. Unfortunately AFTER I already ate it, but whatever. Your blog has inspired me like nobody’s business! I’m starting my journey for weightloss. I want to be happy like you obviously are. Fingers crossed I don’t fall off too often.. Thank you for being an inspiration!

  10. Powelly

    The point of all this is to say that as much as I tried to anticipate my future, you are never truly prepared. That is what makes it an adventure

    Greatest life sentiment I’ve heard in a long time.

  11. Rose

    As Andie’s unadopted (as yet) Aussie Mum, I say, sensible girls, good times without crazy foolishness. So glad you went and did it.

  12. I.n

    Hello once again,

    I love your website, it’s very well written and your pictures from Costa Rica are amazing. :)
    I hope you don’t mind me asking but did you ever have excess skin after your weight loss? I already lost 50lbs and no matter what I do, I can see that my skin doesn’t get better. I am really terrified how it will look after I lost all my weight. :(
    It would be great if you have some advice!

  13. ricardo

    I strongly recommend to avoid going in unsecure cabins in punta uva. recently I had the worst experience in cabinas ITAITA where we got all our things stolen, and you do not know whether to trust the same guardian of the hotel, do not bring any valuable things, the place is full of rats thieves.

  14. Pingback: A Perfect Saturday in Puerto Viejo | This American Girl

  15. Cait

    I fell upon your blog, and my world has been turned upside down by a crashing wave of memories. I am just about to turn 21, a third year university student in central Canada and everything from your height to your begining weight to your travel stories we’ve had in common. I am just begining my weight loss journey and your blog has done nothing but continuously energize me and give me the courage to get on that saddle.
    Speaking of Puerto Viejo, I spent my 4 month summer break last year working in Costa Rica and I am about to spend my next 4 in Vietnam.
    But I know already that country, and that town have holds on my heart and my memories. next time you go for a wild night, an eclectic group of travellers, and an amazing young cook from california check out Rocking Jay’s! and makesure you get back to see Manuel Antonio as well as Hermosa in Puntarenas!
    Thanks again for the encouragement!

  16. Pingback: A Perfect Saturday in Puerto Viejo

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