Our Cruising Quinquennial

August 9, 2015 was a regular Sunday in New Orleans. It was expectedly hot, humid, cloudy, and the summertime sluggishness had settled over the city like a smothering blanket. It did not feel like a special day for us, yet it was arguably one of the most momentous days of our lives. After our morning coffee and a final weather check, we fired up Pura Vida’s engine, unceremoniously untied all our dock lines, and left our land life behind knowing we would never return.

We had held our bon voyage party the week before, so there were no onlookers waving goodbye as we glided silently out of the marina and into Lake Pontchartrain. Despite the lack of fanfare, we felt energized. Ten years of planning had just come to fruition. The lightness of our mood belied the weight of our decision. We left no possessions behind except for our French Quarter home for sale. We had no cars, storage units, jobs, or anything else pulling us back. We left loved ones behind, but we knew we would see them again, somewhere.

During the first three days of sailing, we were still plowing our familiar sailing grounds in the Mississippi Sound, so it did not seem any different to us than a normal summer vacation. When we passed Pensacola, Florida, however, it truly hit us. We had never sailed this far from home on our boat and we were not going back. From now on, everyplace we would arrive was going to be new. Nothing but unfamiliar waters and ports awaited us. After dropping anchor that night, we toasted with nervous excitement to new destinations.

When we look back to those early days, we hardly recognize the neophyte sailors we were then. Full of enthusiasm, motivation, and apprehension, yet woefully lacking in experience and sailing wisdom. Fortunately, the sea is a boundless teacher, albeit sometimes harsh and unforgiving. We laugh now at the dumb mistakes we made then with the levity afforded by having survived those mistakes unharmed.

Our early days

The mistakes we made and the challenging situations we faced during the past five years have taught us volumes about sailing and our boat, but mostly about ourselves. When life-threatening adversity strikes, you understand how you behave in ways you never did before. When you are a team of two, alone against the elements at sea, the veneer of pleasantries vanishes, but in a good way. We barked instructions at each other, we yelled over howling winds, we saw each other at our worst and our best. After the dangers passed, we always tried to honestly evaluate our behavior and what we could have done differently. This is something we seldom, if ever, did when living on land. It made us a better team and deepened our closeness. We say this with humility, knowing that there is so much more for us to learn. Fortunately, the sea patiently awaits, ready to continue her instruction.

Sometimes you have to…
…slow down

One of the most significant lessons we learned is to take our time. Most sailing cruisers joke that our travel plans are written in the sand, at low tide. They are quickly erased by myriad forces beyond our control. Don’t fight it, go with the tide and enjoy the ride. Our plan upon departure from New Orleans was to spend a couple of months in the Bahamas, a few more cruising the northern and eastern Caribbean, and arrive in Grenada by hurricane season 2016. Well, it took us two years to get there.

We realized right away in the Bahamas that there was simply too much beauty to go as fast as we planned. Our open-ended journey was about discovery and experience, not about checking off locations on a list. We were both elated at our realization, but knew it came with added dangers. A slow journey implied spending one or two more hurricane seasons in “the zone.” We would need to be ready to bolt on short notice or prepare Pura Vida to ride out any potential storms. It was not a decision we made lightly, but it was the right choice for us.

The Bahamian blues will take your breath away
Staniel Cay’s most famous residents

The resolution to slow down opened up new destinations for us. Thanks to the detailed blog by an online (now in-person) friend, Tammy on sv Dos Libras, we added Haiti to our itinerary. Because Haiti is off the traditional cruising path and there are no services for visiting boats, it added a level of risk and excitement to our plan. We are so grateful we chose this route and got to spend a few days among the welcoming people of Île-à-Vache.

Anchored in Île-à-Vache, Haiti
A young girl in Île-à-Vache loved playing with Kimberly’s locks while her parents prepared dinner for us
Every sailboat arriving in Île-à-Vache is greeted by friendly boys is kayaks and dugouts asking for work
Sailing an authentic, hand-made Haitian fishing boat

I cannot fully describe the beauty and diversity of the Greater Antilles and the smaller islands of the northern Caribbean. Rushing through them would have been cheating ourselves, and contrary to our traveling style. After two years, however, we felt we had used up all our luck in dodging hurricanes and longed for a summer where we did not have to fret about major storms on a regular basis. We also heard the siren song of the eastern Caribbean beckoning us to move on and explore new islands.

Cabo Rojo Lighthouse, Puerto Rico
Isla Culebra, Puerto Rico
Old San Juan, Puerto Rico
Looking west from Jost Van Dyke, BVI
A Caribbean landmark
Cayo de Luis Pena

We would sail to Saint Martin and work our way down the archipelago to arrive in Grenada by July 2017. We would spend the summer there, and sail west to the fabled diving mecca of Bonaire. Well, once again we slowed down. We loved Grenada so much that we stayed into October and this was limiting the time we could spend in Bonaire, Curaçao, and Aruba before the howling trade winds off the coast of Colombia made it unsafe to continue our westward track.

Carnival in Grenada is spectacular
The J’ouvert street party goes on until the next morning
Learning to harvest urchins from Sperry, a Granadian fisherman
Chasing waterfalls in Grenada

That’s when we made another fundamental assessment, one that we still refer to as the “Bonaire Decision.” We asked ourselves “Why are we feeling pressured to go west?” We did not have a good answer. It was a self-imposed, and arbitrary deadline. We resolved then to spend almost another year going back up and down the eastern Caribbean we liked so much and head west when conditions were right in 2018. The “Bonaire Decision” taught us to get rid of self-imposed restrictions, to avoid fixating on a deadline just because we had talked about it for a long time. It seems obvious now, but it was a fundamental change for us. Giving ourselves more time lifted our spirits and eased our minds. That night, we toasted to slowing down even more.

The most beautiful place that almost nobody knows, Terre-de-Haut, Îles des Saintes, Guadeloupe
Nelson’s Dockyard, English Harbor, Antigua
Sarong sales on the beach, Saint Martin
Living it up in St. Barths

With the luxury of time on our side, we spent a glorious month in Bonaire in August 2018. We went diving almost every day in some of the most spectacular reefs in the entire Caribbean. We celebrated my 50th birthday underwater, just how I wanted it. We now could continue westward unhurried and in favorable weather conditions.

Reached our 300th dives in Bonaire
All the diving helped us improve our underwater photography skills
Bonaire donkey sanctuary
Sunken airplane, Aruba

In October, 2018 we arrived in Colombia, our first port of call in South America, and the first non-island since leaving the U.S. Here, another “a-ha!” moment occurred. Colombia is so large, that we had to take trips by bus or plane to explore beyond our immediate vicinity. I have no idea why this did not occur to us sooner, but we both finally started seeing our travels as going far beyond the shoreline for the first time. We took a flight to Bogota to visit friends and explore the sprawling capital and all the big city life it has to offer. But why stop there? Cusco, Peru was just a short flight away and Machu Picchu just a train ride from there. Just like that, we booked our first “inland” trip.

Santa Marta Marina, our home base in Colombia
The gold museum in Bogota is stunning
Mercado de Paloquemao in Bogota is overwhelming with colors, aromas, and flavors
Land and air travel

A few months later, upon arriving in Panama we realized that a fabulous international hub existed just a couple of hours away at the Panama airport. It has daily flights to almost anywhere in the Americas. This facilitated our travel to Rio de Janeiro in 2019 to attend the wedding of a young cruising couple we met in the eastern Caribbean.

Luiza and Stephen, the beautiful wedding couple

As crazy as it would have seemed on land, it seems perfectly normal among cruisers to attend the wedding of someone you recently met, and spent just a few days total in their company.

Rio at sunset from atop Sugarloaf Mountain
Rio de Janeiro Botanical Garden
Caipirinha stands all over the streets in Rio, YES PLEASE!!!

Cruising friendships are different than land friendships or those you make on short vacations. When you click, everything is on fast-forward. You can become quick friends with people from all over the world. The sailboats at most of the anchorages we have visited are adorned with flags from far-away places.

Kimberly made courtesy flags in preparation for the ABCs, Colombia, and Panama

The common bond of sailing the seas in small boats seems to reduce cultural and language differences and facilitate friendships. You can be inseparable for days, weeks, then part for different countries, not knowing when, if ever, you will meet again. Luckily, social networks make it easier to stay close, as our hulls go further away from each other. Letting go of people and places we love has become routine. It’s never easy, but it is a requisite part of being a maritime nomad. One day, perhaps, we will find a patch of land that tugs at us more powerfully than our wanderlust. Who knows? We may have already been there and just don’t know it yet.

Quepos, Costa Rica
Downtown Panama City
Getsemani neighborhood, Cartagena, Colombia

We have been asked several times, “What’s your favorite place? and “What’s your favorite part of cruising?” The first question is impossible to answer. We have visited too many idyllic and diverse spots to have a favorite. The second question is easier. The best part about cruising is that you get to see incredible, rare sights because you just happen to be “out there” a lot. These events are special because they don’t happen often, or only happen in remote places. You can’t buy your way to see them because you never know for sure when they will occur. By being at sea almost constantly for five years, we expose ourselves to a lot more opportunities for jaw-dropping sights and events. The best example I can recall is the confluence of being in a bioluminescent bay (there are only five in the world) at three in the morning during a moonless night while a meteor shower streaked the sky. That is definitely the best part of cruising.

Something humbling happened just this morning before I sat down to write this blog. It is a good way to punctuate my thoughts about the last five years of cruising. A military colleague from long ago reached out to me out of the blue. He said he is retiring in eighteen months and is not happy considering a life in just one location. He has been following our travels and wants to join the community of aquatic wanderers. He did not know this was a thing until he read our posts. Just like we were inspired by so many that went before us, he was inspired by us to take a leap. He is ready to jump into a life of adventure, and pursue his dreams. He has already begun to look at boats, the poor guy. He’s done for. Once you get the bug, it doesn’t go away, it only gets worse.

Flags of countries and territories we visited

It has been five years. In that time we have visited over twenty-five countries and territories, hundreds of islands, and too many anchorages to count. We have logged 9,240 nautical miles at sea. We have friends all over the globe. We were amazingly lucky to be in one of the most remote, yet friendly places in the world when the pandemic started, and are still here, enjoying the hospitality of the Guna people and the generosity of all Panamanians. Our journey has been remarkably different than we imagined…but so much better!

Mito, an extremely friendly Guna fisherman, and our provider of crab and lobster
Celebrating Panamanian independence, Bocas del Toro
The reefs of the Guna Yala, Panama


  1. John-Michael,

    Good see your post hit my email. Stacey and I have relocated to Pensacola as part of my retirement plan. We sold our Hunter 410 last January in Annapolis and are currently looking for the next boat. We (she) has decided that full time cruising just won’t quite fit into the life she wants. We have 5 grand kids and their parents in Louisiana and she just cannot detach herself from them. So we are currently living on NAS Pensacola in base housing while we learn the area and decide where to buy a small house. She still loves sailing and we have already rented a boat and sailed the Pensacola Bay. It was so nice to be able to exit the marine and immediately raise the sails. In DC we had to motor a day and a half to get to the Chesapeake and hope for wind. There is always wind here. We are currently looking to buy a boat OCT 21. We have our eye on a super clean 2014 Catalina 445 but I’m sure she will be gone by then. There will be others. Our plan is for me to find a job and work full time for 3 more years while I rack up seas days and get my USCG 6-Pack License. Once I fully retire we will cruise the Gulf Coast and Caribbean for 1-2 months at a time and spend our on land time with the grand kids. We may even let their parents visit too. I’m hoping to teach the ASA cruising and navigational courses on the side as a hobby job. I’m already an ASA Instructor for their basic courses just need to pick up the advanced stuff and the USCG License. Keep the blogs coming I enjoy a glimpse into at least a part of our future travels.

    LTC Tom Porter (ARNG Retired almost)

    1. Tom, that’s great news. We know many couples that cruise part time. Some have their boat at a single home base like Panama, Grenada, Puerto Rico, or the USVI. Others move from year to year and are doing the Caribbean loop in stages over several years. The nice thing about it is you get to pick your pace. Good luck with finishing it up to retirement, it goes by fast!

    1. Hi. We have met a few sailors from NOLA out here. Glad to know you are representing in Grenada. That’s one of our all-time favorite destinations. We felt so at home there during carnival.

  2. 5 years already? Wow.

    “The “Bonaire Decision” taught us to get rid of self-imposed restrictions, to avoid fixating on a deadline just because we had talked about it for a long time”… that’s wisdom!

  3. I can’t believe it’s been 5 years! Such beautiful freedom, adventure and connection – I long for that more than I can ever say. This may be my most favorite post so far! I love the summary of great lessons and a-ha moments – I hope you’re saving all this for a future book 🙂
    I love and miss you guys so much!

    1. We miss y’all tons. Our time together in Antigua seems so long ago. We must figure out where to link up when things open back up.

  4. I always love reading your posts. I am not a carefree spirit like the two of you however, I am fascinated by your cruising life. Hats off to you for all of your accomplishments! Fail forward is a truth in life and you two are succeeding mightily! I love that you are documenting all of your adventures so that we can live vicariously through you! Safe travels and please keep writing!

    1. Thanks, Jennifer. Glad you enjoy our posts and the pictures. We try to balance the good with the bad to provide a realistic view of what it’s like out here. Most places are so beautiful, we feel like we can’t do them justice sometimes.

    1. Hi Kathy. How’s our neighborhood doing? Serena is getting quite used to boat life and is spoiled rotten.

  5. Wow-just wow! Great recap and photos- Here’s to your future adventures! Happy 5 year celebration. I just raised a glass for you two!

  6. Seeing y’all twice in 5 years does not a happy mom make. Knowing you are living the life you dreamed makes it more bearable. I just miss you is all!

  7. Congratulations on the 5 years! You’ve had the adventure of a lifetime and a life of stories to tell your friends and family.

    We can’t wait to have drinks one night with you both!

    1. Thanks! We look forward to toasting together in person again. Congrats on your new job and look forward to hearing details about the adventure.

  8. I am not a carefree spirit like the four of you however, I am fascinated by your cruising life. you had the adventure of a life time and life of stories to tell us and us, friends and family. I love that you are documenting all of your adventures so much that we can live vicariously through you.

  9. Congratulations! Five years – wow! I don’t follow y’all enough. All this needs to be a book. One of my dreams is to figure out a way to meet up with y’all in some exotic port!

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