Looking back at the previous year is always enjoyable. Seeing a full year laid out helps me remember what I did, what I missed, and how things changed. With that in mind, here’s my 2019 year in review.
I almost skipped this recap, but I’m glad I didn’t. Writing an annual summary gives me a concrete record to look back on.
2019 was an eventful year. We sailed to the Bahamas, bought a van for hurricane season and overland exploration, then returned to the Bahamas, which is where we are now. Along the way we saw mountains, oceans, beaches, deserts, and everything in between.
Overall, 2019 was full of travel and meaningful memories. Like any year, it had highs and lows, but I’m grateful for the life we lead. We enjoy having both our sailboat and our van: the sailboat is an exciting way to travel, and the van allows us to pursue land-based adventures like hiking, biking, and rock climbing.
You can read more about living on our sailboat in my post “Welcome To Paradise – We’re Living On A Sailboat!”
Recent life updates from the past year include:
- Why I took a year-long blog and social media semi-sabbatical
- The honest truth about van dwelling: answers to the most common van life questions
- Living on a boat – the good, the bad, and the beautiful
- Is full-time traveling as good as it sounds?
If you’re not following me on Instagram yet, I recommend it. I share many photos and stories from the places we visit.
Here’s what we did in 2019:

January – The Florida Keys and Bahamas
We kicked off 2019 by sailing from the Florida Keys to the Bahamas—the first time we’d left the U.S. with our sailboat. It was a new experience for us, especially traveling with our dogs across international waters. Thankfully, the Bahamas made that relatively straightforward, so the trip went smoothly.
A strong storm hit after we reached Bimini, so we ended up staying there longer than planned. Bimini was beautiful and a pleasant place to wait things out.

February – Grand Bahama and Berry Islands
In February we sailed from Bimini to Grand Bahama and then to the Berry Islands. Our time at Great Harbour Cay in the Berries was a highlight: the boating community was friendly, local vendors delivered homemade bread and pizza right to the boat, there were marina BBQ nights, and we enjoyed a memorable wahoo soup at someone’s home.
After Great Harbour Cay we headed to Chub Cay, where we stayed a while because a friend visited. We made many friends there, and it was heartwarming to be remembered when we returned in December.

March – New Providence Island, the Exumas, and Eleuthera
We set sail for Nassau on New Providence Island, where one of my favorite spots was the Queen’s Staircase—its carved limestone walls are striking and photos don’t fully capture the place. After provisioning and waiting for a weather window, we sailed into the Exumas. We explored the northern Exumas, swam near reef sharks, snorkeled, kayaked, and visited the island of iguanas.
From there we sailed to Eleuthera, a place we’d loved on a family trip in 2018 and were excited to revisit by boat.

April – Florida
In early April we sailed back to Florida. After buying the boat the year before, we had several repairs and upgrades to complete. We also lost our prop while navigating the New River—an unpleasant event, but it didn’t lead to disaster.
Because dogs aren’t allowed in the Lauderdale Marine Center boatyard and our slip had no nearby green space, we rented a house for the month while work was completed.

May – Florida and Memphis
Repairs and warranty work took longer than expected, altering our plans for heading up the East Coast. Much of the warranty work involved third-party systems like our electronics and navigation. With time running short before hurricane season, we needed a secure place for the boat and called several marinas. A spot opened at the St. Pete marina where we’d previously left the boat, so we moved there in early June.
In May we also bought a 4×4 van. We’d discussed van life long before buying the boat, and having a van alongside the sailboat gives us flexibility: we can cruise by sea most of the year and use the van to explore inland destinations, hike, bike, and climb during hurricane season.
While waiting for boat repairs to start, we took a short road shakedown trip to visit Wes’s parents in Memphis. It was a busy month overall.

June – Sail to St. Pete
After sailing to St. Pete, I flew to New Hampshire for a weekend of yoga, rock climbing, hiking, and good food—a welcome break where I didn’t work and simply relaxed. When I returned, we tucked the boat away for hurricane season and lived in the van for a few months. Hurricane season is a natural time for cruisers to step away from the boat and explore on land, and that’s exactly what we did.

July and August – Colorado and Utah
We spent the summer exploring Utah and Colorado in the van, focusing on hiking as many 14ers as we could and mountain biking whenever possible. Our 4×4 van allowed us to reach remote backcountry spots. We climbed Mount Elbert and several other 14ers—Missouri Mountain, Quandary, Lincoln, Cameron, Democrat, Sherman, Bross Trail, and more. We also spent a lot of time visiting my sister in Fruita, Colorado, which helped keep this adventure social and far from lonely.

September – Utah and Colorado
We waited for cooler weather to head into Utah, but it stayed hot, so we went anyway. Temperatures hovered around 100°F during much of our time there, but we enjoyed favorite routes like the Burr Trail, Robbers Roost, Moab, Montezuma Canyon, Goblin Valley, Zion, Bryce, Capitol Reef, Canyonlands, and more. We also spent several restorative days in Estes Park, Colorado, where Wes was a groomsman at a friend’s wedding.

October – Annapolis and back to SV Paradise
In October we drove across the country to Annapolis for the sailboat show, stopping to visit friends and family in Fruita, Longmont, Columbia, St. Louis, Bentonville, and other stops along the way. We planned to continue north into Maine and Canada, but missing the boat pulled us back early. Returning to Florida, we found several things had broken while we were away—typical #boatlife—and spent the next month preparing the boat to leave Florida again.

November – St. Pete
In November I made a last-minute trip to Chicago for a family emergency. It was a difficult visit, so I’ll keep details private. Back in Florida we ran errands in the van and put it in storage mid-month. We then sailed overnight to the Dry Tortugas, spent a few nights exploring, and sailed on to Key West.

December – Bahamas
From Key West we waited for a weather window and then sailed to Bimini with the goal of reaching the southern Exumas by Christmas for visiting family. We moved quickly through the Bahamas—Bimini to the Berries to the Exumas—mostly revisiting areas we’d explored earlier in the year. In the southern Exumas we hosted Wes’s brother and his family aboard SV Paradise for an eight-day Christmas stay—seven people and two dogs aboard—an unforgettable holiday full of visiting and reconnecting.
That wraps up 2019. Writing this recap helps me remember small moments I might otherwise forget.
What’s the plan for 2020?
For 2020 we have loose plans. Each year tends to unfold differently than expected, so we’ll remain flexible—heading south, north, or somewhere in between. I don’t want to spoil specific plans yet, but stay tuned.
The best part of full-time travel is that plans can shift and it still feels like an adventure.
Here are my 2020 goals:
- Get at least three months ahead on Making Sense of Cents posts. I fell behind in 2019 after an unexpected break. Being ahead on posts makes life easier and allows me to focus on travel and family without work deadlines looming.
- Work less than 40 hours per week. Most weeks I already work less, but some weeks stretch into long days and late nights. I want to maintain a better work/life balance.
- Be more present. My top goal is to be more present with life outside the business. I love running Making Sense of Cents, but I want 2020 to emphasize being truly present during our travels and time with family and friends.
- Read five books. Over the last few years I’ve mostly read work- or sailing-related books. I’d like to enjoy reading for pleasure again and complete five books that aren’t directly related to business or boat life.
What are your life, business, and travel plans for 2020? What was your favorite part of 2019?