8 Days in Cuba

Cuba is the most complex and challenging place we have traveled yet. It was also fascinating, deeply rewarding and, most importantly, possible. For detailed information on how we did it, check out our Cuba travel guide.

Travel time: 5 PTO days + 2 weekends in April of 2017

During this time, we wandered our way through museums, narrow city streets, Viñales Valley, Tobacco farms, an eco-community called Las Terrazas, rainforest ruins, and more. For more on our adventures and misadventures, see our posts below.

How to pack for any adventure in under an hour and never forget anything
We are notorious last-minute packers. Fortunately, I made up a system for that, and it works brilliantly. (I'm not even
Gone Fishin’ … with Cormorants
Cormorants are heavier and more intelligent-seeming than you would expect, with neck feathers that are as soft as high-end cupcake
14 days in Israel and Palestine
Israel and Palestine were complex places with a lot to unpack. We really look forward to doing so here!
10 Days in Panama
Let’s just start at the beginning, shall we?
4 days in Baja
A road trip with friends plus camping on the beach,…
Packing for Cuba
We tried to keep our packs super light this trip (about 10 lbs in half-full 40L packs). Here's how.
We’re famous!
This happened to us at both museums we visited.
Photo Post: Life in Jerusalem
People actually live in the old city of Jerusalem, surrounded…
Packing for Panama
This is all the clothing I brought with me to…
Cuba Travel Guide
Cuba was the most difficult place to travel I've visited yet. It was also fascinating, deeply rewarding and, most importantly,
Sample Itinerary for a Trip to Cuba
This is a sample itinerary for a person-to-person educational visa circa April 2017.
More Than 50% Lost
“I think we are more than 50% lost right now.”…
Metro Envy
  The Mexico City Metro is the best public transit…
Staying Warm
When we were there, temperatures hit record lows. Fortunately our…
Welcome to Havana
We arrived in Cuba around 10pm at night, exhausted from…
Crespo Street Mid-Morning
Everyone says Cuba is a time capsule. But is it really true?
Museo de la Revolución (Museum of the Revolution)
The Museum of the Revolution: As Americans, we didn't feel much love here.
Give us this day our daily bread
The vertical, low-tech lifestyle of street-vending in Havana.
(Photo) Out and About in Cuba
Trans culture was surprisingly visible out and about in Cuba! Especially in Central Park.
How (Not) To Buy Things In Cuba
Buying goods in Cuba can be tough, especially if you get outside of the tourist areas.
Graffiti in Havana
A person could spend an entire vacation exploring graffiti in Havana.
Traveling to and Staying in Viñales
This may give you some sense of what it's like to travel in Cuba.
Hiking Deep Into Cuban Cigar Country With Edrey
The tobacco farms in Viñales Valley produce some of the best cigars in the world.
Ephemeral Peso Ice Cream (This is important)
In what appears to be a closed down storefront in Viñales, there is an ephemeral ice cream shop.
The things that parked outside our casa in Viñales
These magnificent beasts were parked outside our casa when we arrived back from the valley.
Caught in the rain in Viñales, Cuba
With no internet connection or any way to get a forecast, the best we could do was look up at
Reduce, Reuse, and Recycle like a Cuban
Cubans are master recyclers, perhaps to a fault.
That Time A Wheel Flew Off Our Taxi
We were driving down the highway when...
Las Terrazas: Vacation like a Cuban
Video: "This is easily my favorite place we've been so far."
Raising Chickens in Cuba
Abuelo digs out some eggs from the nest of a free-roosting chicken. This man was probably my favorite person we
Traipsing Through the Jungle in Río San Juan
We flagged down an off-duty driver, who had a friend, who had a family member, who was able to give
Regla: A Well-Kept Secret
Just across the bay from Havana sits Regla, a fascinating town with a rich cultural history.
(Video) Old Cars in Cuba
For the grandparents and gear heads.
8 Days in Cuba
Cuba is the most complex and challenging place we have traveled yet. It was also fascinating, deeply rewarding and, most
4 days in Mexico City
This trip is the one that made us realize that quick, cheap, international long weekends are an amazing strategy to
3 Days in England
The highlights of the trip were tours of Stonehenge and a nearly 1,700 year old Roman bath house.
Welcome to London! Walking Tour – Part I
A self-guided walking tour through the heart of London, from Victoria Station to Parliament Square.
London Walking Tour – Part II
This is part 2/3 of our walking tour of London, heading from Parliament Square to Trafalgar Square.
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Michelangelo, Raphael & Leonardo at the National Gallery
We decided to pop in to the National Gallery while we were in Trafalgar Square.
The British Museum
The British Museum: "It's just a bunch of stuff that's been nicked from other countries."
London Walking Tour – Part III
The London Wall, The London Tower, Tower Bridge, London Bridge, and All Hallows By The Tower
How to eat cheaply in England
England is not a cheap vacation destination by any stretch of the imagination. We did figure out one good trick
Hampton Court Palace is a really spooky place
Most everything about the former home of King Henry VIII was creepy, unwelcoming, and a little bit off.
How to build a clothing system for fast and light travel
  Our clothing system for fast and light travel was…
Beautiful Bath, England
Walk centuries old stone streets, enjoy beautiful 18th century golden limestone architecture, and explore a 2000-year-old Roman bath house.
Stonehenge
I was probably pretty annoying the entire day because of my barely contained excitement.
How to find the cheapest flights to anywhere for a given date range
Let's say you have a week off work. Where would you go? This article lists step-by-step instructions for finding the cheapest
Cardboard Craigslist
Near el Prado, a main boulevard in Havana, exists the closest thing that Cuba has to Craigslist.
4 Days in Colombia
We took 1 day of PTO on Memorial Day Weekend…
The Only Subterranean Cathedral in the World is OK We Guess ​
"Zipa! Zipa!" An overpriced and underwhelming unofficial church in an old salt mine... but I guess the pictures came out
Gastronostalgia ​
We went to Colombia with a list of foods that we wanted to eat that was 2 pages long.
That Time We Tried Coca ​
Andeans across Peru, Ecuador, Colombia and Bolivia have been chewing coca leaves or drinking coca tea for thousands of years
Faking Calm in Bogotá ​
A strategy for surviving densely packed experiences in densely packed cities.
Just A Cool Elevator in Edificio Sucre
The purpose of this post is just so we don't forget this excellent elevator in Edificio Sucre, Bogota.
3 days in Jamaica
Total Trip Time: 4 days (2 weekend days + 2 days PTO)
The Best Layover: The Everglades
The plan was this: Get in at 5am, rent a car, drive to the Everglades for a sunrise hike, take
How Bogota Feels
This post is just a set of pictures from around the city that capture the feeling of Bogota.
Monseratte
The monastery-topped mountain Monseratte looms over the East horizon of Bogota.
Paloquemao Market
Paloquemao, a gigantic, pungent, colorful, bountiful market in the middle of Bogota, did not disappoint.
The Gold Museum: A Very Shiny Place
The gold museum in Bogota was one of the shinier places we've ever been.
Trip Highlight: The Bogota Graffiti Tour
Growing up, we were taught that graffiti is bad. The Bogota Graffiti Tour turned that worldview upside down.
A Trip to the Museum of Anthropology
We have been to museums on 5 continents and all across the United States and The Museum of Anthropology in
Evidence of the 2017 Earthquake
We visited CDMX a few short months after a 7.1 earthquake that rocked the city and killed hundreds. Amazingly, there
How Mexico City Defied Our Expectations
Mexico City has a reputation for being dirty, poor, crowded, uncultured, and unsafe. Don't believe the hype.
Fantastic Food. (#priorities).
We would take a trip back to Mexico City for the food alone.
Teotihuacan
Josh thinks visiting Teotihuacan was cooler than visiting the Pyramids of Giza. I'm on the fence.
Mexico City Walking Tour
Our Airbnb host helped us plan an amazing walking tour of the heart of Mexico City.
Templo Mayor
In the heart of Historic Mexico City, on Zocalo Square and partially buried under the Cathedral of Mexico City, is
What Old Jerusalem Feels Like
Old Jerusalem is an ancient, fragrant, complex, dusty, emotionally-, politically-, and religiously-charged space.
The Western (Wailing) Wall
We were fortunate to be able to visit 2 major religious sites in Old Jerusalem: The Western Wall and the
The Israel Museum
It was a Dead Sea Scroll kinda day. Here are…
Kosher Mcdonalds
Want cheese on that? Too bad.
Sleeping Out on the Sea of Galilee
One of my most cherished memories of Israel.
Swimming in the Jordan River
We always had the vision of the Jordan River as a wide, formidable, ageless, and important-looking. It's not.
Dunes on the #5 Highway
If you are ever driving down the #5 Highway from MexiCali down the coast of the Sea of Cortez, keep
Palapa Camping on the Sea of Cortez
San Felipe is a beautiful place to hang out on the beach, explore the nearby rocks and pools, catch a
Valle de los Gigantes (Valley of the Giants)
This nature reserve is home to 1,000 year old, absolutely gigantic cacti.
Seaside Bathing in Puertecitos Hot Springs
Puertecitos Mexico, Population 41, is located a few hours south of San Felipe and is home to excellent natural hot
Baja Salt Flats
We spent a little while here in the pretty landscape, just enjoying the views.
Montego Bay Has a Curfew (But it’s largely ignored)
There’s a city-wide 8pm curfew and state of emergency called in response to a high number of gang-related homicides.
The Mobay Kotch is a Hidden Gem
Built in the 1760s, this beautiful building has had many lives. Most recently, it was our temporary home (and inspiration
It glows! Swimming in a Bioluminescent Bay in Jamaica
It was one of the coolest things we've seen in this world.
The Greenwood Great House
The Greenwood Great House was one of the only plantation homes to survive the Christmas Rebellion of 1831.
Observations on Schools in Jamaica
“Parents will go without, but Jamaicans take great pride in getting their children to school every day in a crisp,
Snorkeling Doctor’s Cave
Climate change and overfishing have decimated the Jamaican reef and turned it into a bleached, algae-covered mess. Still, we managed
Bogota on Election Day
We were both nervous and excited to be in the Colombian capital on the presidential Election Day. Let me break
Iglesia Nuestra Senora del Carmen
Josh flexed his photography muscles on this devastatingly beautiful candy cane cathedral.
14 Days in China
Our 1 week trip in China turned into 2, due to Super Typhoon Mangkhut.
Financially speaking, how do we do it?
Many people think that international vacations need to cost thousands of dollars. I'd like to dispel that myth right now.
The Holy Sepulcher/ Things I Didn’t Quite Understand
We walked out of the hot, bright Israeli sun and were immediately surrounded by darkness
Welcome to Jericho
We negotiated our way into the heart of Palestine by taxi using sign language, nods, smiles, cash, and the help
Floating in the Dead Sea
The Dead Sea is simultaneously harsh, desolate, and devastatingly beautiful.
Yes, as in the one from the Bible
One of the craziest things about Israel is recognizing names and places from the bible ALL THE TIME.
It Begins
4 days ago, I decided to take a last-minute trip to anywhere south of Mexico and found an absurdly cheap
Panama City
Panama City. It was just a city, really. With an ocean. And a canal. And more brown people than I'm
Filthy Bus Selfie and a Small Victory!
Latin American Buses hold such a special place in my heart.
A Very Unpleasant Bus Ride and a Lesson Learned
After less than 24 hours in Panama City I knew I had to escape.
Boquete, land of forests, quetzals and waterfalls
9 hours and 4 busses later, I found a region of the country in the mountains near Costa Rica where
Bastimentos: Care-free and Car-free
Bastimentos is magical. It's a tiny Panamanian island in the Caribbean that can only be reached by boat and is