Fly fishing travel has evolved significantly over the last decade, with several key changes shaping the way fly anglers experience and approach their adventures.  Anglers have more accessibility to hard-to-reach destinations than ever before.  With the rise of global connectivity, fly anglers have more choices and a wider variety of unique fishing destinations worldwide.  Social media platforms have made it easier for anglers to discover new places as well as share their experiences.  Travelers often are seeking a more immersive experience when traveling for fly fishing.  This can include learning the local cultures, engaging with local communities and seeking to unplug and enjoy nature.

When Stillwater Travel hosted its first trip to Cuba back in February 2020, we were introduced to a world that time forgot.  Cuba is a special and beautiful country with generous and spirited people and incredibly vibrant ecosystems.   The pristine coral reefs and the shallow water flats within them were a sight to behold.   Being just 90 miles from Key West, it was jaw dropping to see how Cuba’s archipelagos compared to others around the Caribbean…undisturbed by man.  Needless to say, we fell in love with Cuba.

Five years later, our love for Cuba hasn’t wavered.   The Cuban people are some of the kindest, most upbeat people you will ever encounter, which is an amazing statement due to the oppression they are subjected to daily.  Despite that, they are overcomers, and we have the utmost respect for their resilience.  We are proud to be able to help the guides, liveaboard crew, and their families on every hosted trip as we deliver medicines, clothing, and everyday household items that they cannot access.   Through this process, Stillwater and our returning clients have developed deep friendships with the Cubans, relationships that will last a lifetime, not just 6 guided days of fishing.

Stillwater Travel is proud to host the largest number of weeks and fly anglers to Cuba each year.  Spending 8-12 weeks a year hosting clients on trips to Cuba may seem like a lot to most, but it still doesn’t seem like enough for us. Although it would be wonderful to be able to share the Cuban liveaboard experience with everyone, the limited numbers of visitors is what keeps this place so special.   The remote (but luxurious) liveaboard trips to the Cuban angling destinations allow one to truly disconnect from our everyday lives and truly take in some of the most beautiful island habitats on earth. Clients will often take part of a day off from fishing to snorkel, visit an isolated beach, or just relax on the boat.

Spending weeks upon weeks fishing with the same Cuban guides and staff members has allowed us to develop deep relationships that can only be created through the shared experience of time on the water.  The relationships that Stillwater has developed with the Captains, Staff and Guides have changed from clients to family and it shows.

Stillwater trips are not normal weeks for our Cuban Family. They are special times. They are times to share, times to laugh and times to encourage the best from one another. Our hosted trips are about fishing with our family members in Cuba, not just guides.  They are our brothers.  The guides and staff treat and care for us like family as we do for them.  We encourage you to ask them about their opinions on Stillwater weeks on your next trip with us.  See what our Cuban family has to say.

We want to thank all of you who have shared this Cuban experience with us on so many of our hosted trips, and it directly betters the lives of not only the Cuban crew and their families, but spreads throughout their entire communities.  Your generosity is overwhelming and has been felt by our Cuban family.  We truly appreciate you being part of our family as well as our Cuban family.   For those who haven’t yet experienced Cuba with us on one of our hosted trips, we encourage you to take a closer look at this incredible adventure.  You are missing out on an experience on multiple levels, not just the insane fishing.  We would love to have you join our family as well as theirs.

Brett Dennis
Owner/Operator
Stillwater Fly Shop and Stillwater Travel

Don't forget to check out our comprehensive Travel Guide for Cuba 2025 here!