# Planning Tips For An Ultimate Cuba Getaway Boys Trip *By James Hills — Updated February 2025* Although it's only 90 miles from Florida, Cuba had severe travel restrictions for more than 60 years and despite moves almost a decade ago to open things back up so that Americans could fully enjoy the diverse music, food, and drinks that this island is known for, it remains off-limits to Americans with United States passports. Canadians, Europeans, and others though can enjoy this relatively unspoiled tropical destination. **Questions****Key Points****Article Index** ** No answer selected. Please try again. Please select either existing option or enter your own, however not both. Please select minimum {0} answer(s). Please select maximum {0} answer(s). /polls/travel-and-trip-ideas/what-do-you-prefer-to-call-your-guys-trips.html?task=poll.vote&format=json 1 Guys Trips (567 votes / 44.16%) 44.16% votes Guys Getaways (130 votes / 10.12%) 10.12% votes Mancations (118 votes / 9.19%) 9.19% votes Brocations (167 votes / 13.01%) 13.01% votes [{"id":5,"title":"Guys Weekends","votes":302,"type":"x","order":1,"pct":23.519999999999999573674358543939888477325439453125,"resources":[]},{"id":6,"title":"Guys Trips","votes":567,"type":"x","order":2,"pct":44.159999999999996589394868351519107818603515625,"resources":[]},{"id":7,"title":"Guys Getaways","votes":130,"type":"x","order":3,"pct":10.1199999999999992184029906638897955417633056640625,"resources":[]},{"id":8,"title":"Mancations","votes":118,"type":"x","order":4,"pct":9.1899999999999995026200849679298698902130126953125,"resources":[]},{"id":9,"title":"Brocations","votes":167,"type":"x","order":5,"pct":13.0099999999999997868371792719699442386627197265625,"resources":[]}] ["#ff5b00","#4ac0f2","#b80028","#eef66c","#60bb22","#b96a9a","#62c2cc"] ["rgba(255,91,0,0.7)","rgba(74,192,242,0.7)","rgba(184,0,40,0.7)","rgba(238,246,108,0.7)","rgba(96,187,34,0.7)","rgba(185,106,154,0.7)","rgba(98,194,204,0.7)"] 350 ** Vote Now** Vote Form** ResultVotes - **Cuba remains a unique Caribbean destination** with its rich cultural offerings in music, food, and drinks, and despite the travel restrictions for U.S. citizens, other nationalities can explore its relatively unspoiled landscapes and vibrant street life. - **Popular activities for a boys trip** include vintage car tours in Havana, attending a baseball game, and engaging in cigar and rum tours, showcasing Cuba's iconic contributions to automotive culture, sports, and its world-renowned cigars and rum. - **Exploration of Cuban cities** offers a rich historical and cultural experience, from the UNESCO World Heritage sites of Old Havana and Trinidad with their stunning architecture to the artistic and European influenced town of Cienfuegos. - **Accommodation options** vary from 4-star all-inclusive resorts to boutique hotels, catering to different tastes and ensuring a comfortable stay between explorations. - **Important travel tips for U.S. citizens** include carrying cash, understanding the dual currency system, and complying with specific travel restrictions and requirements like travel insurance and offline maps for better navigation. 1. [5 Things Guys Will Love to Do In Cuba:](https://www.mantripping.com/travel/ultimate-cuba-getaway-for-guys.html#5-things-guys-will-love-to-do-in-cuba:)[Vintage Car Tours In Havana -](https://www.mantripping.com/travel/ultimate-cuba-getaway-for-guys.html#vintage-car-tours-in-havana---) 2. [Attend a Baseball Game in Cuba -](https://www.mantripping.com/travel/ultimate-cuba-getaway-for-guys.html#attend-a-baseball-game-in-cuba---) 3. [Cigar Tours -](https://www.mantripping.com/travel/ultimate-cuba-getaway-for-guys.html#cigar-tours---) 4. [Rum and Cocktail Tours -](https://www.mantripping.com/travel/ultimate-cuba-getaway-for-guys.html#rum-and-cocktail-tours---) 5. [Explore Cuban History -](https://www.mantripping.com/travel/ultimate-cuba-getaway-for-guys.html#explore-cuban-history---) [Cuban Cities To Explore:](https://www.mantripping.com/travel/ultimate-cuba-getaway-for-guys.html#cuban-cities-to-explore:) 1. [Old Havana](https://www.mantripping.com/travel/ultimate-cuba-getaway-for-guys.html#old-havana) 2. [Trinidad](https://www.mantripping.com/travel/ultimate-cuba-getaway-for-guys.html#trinidad) 3. [Cienfuegos](https://www.mantripping.com/travel/ultimate-cuba-getaway-for-guys.html#cienfuegos) [Where To Stay When Visiting Cuba](https://www.mantripping.com/travel/ultimate-cuba-getaway-for-guys.html#where-to-stay-when-visiting-cuba)[What To Know Before Visiting Cuba](https://www.mantripping.com/travel/ultimate-cuba-getaway-for-guys.html#what-to-know-before-visiting-cuba)[6 Things US Citizens Need To Know Before Traveling to Cuba](https://www.mantripping.com/travel/ultimate-cuba-getaway-for-guys.html#6-things-us-citizens-need-to-know-before-traveling-to-cuba) 1. [Take Cash With You -](https://www.mantripping.com/travel/ultimate-cuba-getaway-for-guys.html#take-cash-with-you---) 2. [Tourist Travel to Cuba For United States Citizens Remains Prohibited -](https://www.mantripping.com/travel/ultimate-cuba-getaway-for-guys.html#tourist-travel-to-cuba-for-united-states-citizens-remains-prohibited---) 3. [Travel Insurance Is Required to Enter Cuba -](https://www.mantripping.com/travel/ultimate-cuba-getaway-for-guys.html#travel-insurance-is-required-to-enter-cuba---) 4. [Cuban Internet and Wireless Access Is Not Dependable -](https://www.mantripping.com/travel/ultimate-cuba-getaway-for-guys.html#cuban-internet-and-wireless-access-is-not-dependable---) 5. [Crime Statistics Are Not Available But Gun Crime is Nonexistent -](https://www.mantripping.com/travel/ultimate-cuba-getaway-for-guys.html#crime-statistics-are-not-available-but-gun-crime-is-nonexistent---)   ## 5 Things Guys Will Love to Do In Cuba: There are many things that are available on all Caribbean islands such as wandering around town enjoying the local culture, relaxing at your resort or hanging out on the beach. There's also great golf and fishing here too. However, there are some highlights that make Cuba a special place for guys to visit.  ### How To Get Free or Nearly Free Drinks During a Cruise Vacation Free drinks on a cruise ship might seem like an impossible dream but here's ways that you can achieve just that. ManTripping [Read More](https://ads.flowmediamarketing.com/go/n8ohDo_D_-pm1iCYy_W-kA.429) ### Things To Do In Ketchikan Alaska On A Cruise Ship Visit Ketchikan Alaska is the salmon capital of the state and has tons of great stuff to do on a cruise ship visit. 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While you can certainly walk around the city and explore on your own, various entrepreneurs are now offering car tours too. ### Attend a Baseball Game in Cuba - Cuba is home to some of the best baseball players in the Major Leagues so this is on the bucket list for a lot of you guys I'm sure. ### Cigar Tours - Especially in Havana you will find an amazing cigar culture. This includes small shops as well as large factory tours where you can see why the legendary Cuban cigar is so prized around the world. ## Man Gear Pick of the Month September's Pick Amazon (affiliate) ### Kenyon City Grill Portable Stainless Steel Electric Grill Why we picked it: a grill you can actually carry to the campsite, the tailgate or the cabin without borrowing a truck. Stainless, no propane tank to wrestle, and hot enough to cook for four guys rather than reheat for one. 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Like with cigars, you'll find local bars whipping up classic Cuban mojitos and daiquiris and you'll find tourist destinations like the Museo del Ron Havana Club in Havana. ### Explore Cuban History - Regardless of what type of history your group of guys is into, there's something here for you in Cuba. From architecture seemingly stuck in the 1950's to exploring Spanish forts like Morro Castle and Castro-era propaganda murals you are going to have a great time exploring Cuba. ## Cuban Cities To Explore: While Havana is certainly the first to come to mind for most Americans, it is far from the only vacation destination that guys will love to explore in Cuba. That's part of the fun of doing a [guys weekend](https://www.mantripping.com/guys-weekend.html) getaway in Cuba - you can do an urban guys getaway, a relaxing beach trip, or anything in between. ### Old Havana Old Havana, which the locals call "Habana Vieja", is a UNESCO World Heritage site that features gorgeous Neoclassical and Baroque buildings. Although renovated for modern times, the original architecture and cobblestone streets make visitors feel as if they are visiting the country 200 years ago. Many travelers visit Plaza Vieja. One of the most popular spots in the area, Plaza Vieja centers around Casa del Conde Jaruco, an 18th-century building best known for its exquisite stained glass windows. A nearby tower known as the camera obscura stands 35 meters tall and offers the perfect spot to get a bird's eye view of the surrounding scenery. Other attractions in Old Havana include Bodeguita del Medio, known as being a hangout for Ernest Hemingway, and the military fortress Castillo de la Real Fuerza. ### Trinidad Trinidad is a well-preserved colonial town and another UNESCO World Heritage site just a short drive from Havana. If you love old-school architecture, you'll enjoy bringing your camera and taking gorgeous photographs of your surroundings. Despite Trinidad's authentic beauty, some of the best things to do are in the surrounding areas. Nature lovers will enjoy the cool mist of the El Nicho waterfalls or riding horseback through the gorgeous trails of Topes de Collantes, not to mention relaxing on the gorgeous beaches of Playa Ancon. After a long day in the sun, be sure to stop by Disco Ayala, a cave that offers a late-night club scene, or Plaza Mayor, where you can get some of the best mojitos in the city. ### Cienfuegos Cienfuegos is a harbor town located on the west coast known for its art and culture. Additionally, a gorgeous bay has earned the town the nickname of Pearl of the South. Many tourists enjoy strolling the gorgeous streets of the town, and the European feel of Cienfuegos offers a unique stop during your tour of Cuba. When you're done people watching, be sure to visit one of the many art galleries located near Plaza de Armas. If you prefer historical monuments, the area also houses one for Jose Marti, a Cuban hero. Cienfuegos is home to the last Arch de Triumph in the country, located in Jose Marti Park. After spending the day taking in the beauty of the town, be sure to stop and have a meal at El Tranvia, one of the area's most popular restaurants. ## Where To Stay When Visiting Cuba There are a variety of 4-star [all-inclusive resorts](https://www.mantripping.com/resorts.html) in Cuba that allow you to relax in style between your day trips, but Iberostar is one of the most established brands. From gorgeous boutique-style hotels in the cities to lovely beachside resorts, Iberostar can help you find the perfect accommodations for your needs. Additionally, since things have thawed between the United States and the Cuban government, you can also use sites like Travelocity and Hotels.com just like you would to book any other trip ... or contact your travel advisor to make sure you pick the perfect spot for your boys weekend getaway. ## What To Know Before Visiting Cuba When visiting Cuba for a [boys trip](https://www.mantripping.com/boys-trip.html), it is important to note that it isn't as simple as getting on a plane and going. Remember that you'll need a passport and valid identification. You should also keep in mind that tourism to the area is limited to some specific reasons. Be sure to research thoroughly to ensure you follow travel guidelines, including understanding what you can and cannot bring back through customs. ## 6 Things US Citizens Need To Know Before Traveling to Cuba Before heading out to Cuba for a quick guys weekend getaway or a longer vacation, if you are a US Citizen it is essential that you understand what to expect. After all, while this might seem like any other tropical island ... this is far from ordinary. But realistically, the reason why you picked Cuba for your guys getaway is because of the exotic and somewhat forbidden nature of the country. However, this is something that shouldn't be done lightly ... you and the boys want to have fun, not end up stuck in a foreign country without being able to get home! ### Take Cash With You - Unlike most other Caribbean destinations where the US Dollar is king, here you are best to take Euros. In fact, with the US Dollar, you will actually have to pay an extra fee to use them. Visa and Mastercard will work in Cuba, but due to antiquated merchant systems at many vendors it shouldn't be the primary source of money during your trip. Also, American credit cards generally require foreign transaction fees. However, most resorts and major hotels will allow you to pay your bill there with a credit card. ***Cuba has Two Currencies. Luckily, tourists are only allowed to use CUC, the "Cuban Convertible Peso," aka the "Cuban Dollar." This currency is aligned to the US Dollar at $ 1 USD to 1 CUC. In tourist areas, this is the preferred*** currency and can generally be used for everything from tips to bar bills and taxi rides. ### Tourist Travel to Cuba For United States Citizens Remains Prohibited - According to the United States Department of State, [tourist travel to Cuba remains prohibited for anyone traveling from the United States to Cuba](https://travel.state.gov/content/travel/en/international-travel/International-Travel-Country-Information-Pages/Cuba.html). However, there are ways around that. There are 12 official reasons why US Citizens are allowed to travel to Cuba. For planning a guys weekend or [mancation](https://www.mantripping.com/mancation.html) in Cuba, the most important can include: "Educational Activities", "Public Performances", "Athletic and Other Competitions", "Support For the Cuban People", or "Humanitarian Projects". Depending on what you have planned, this might make taking in a baseball or soccer game as part of your plans, or perhaps working with an NGO to help build homes, a school or some other activity. ### Travel Insurance Is Required to Enter Cuba - While we're always a big supporter of making sure you invest in travel insurance, for visiting Cuba it is a requirement. In fact, they will often check at customs to ensure you have official paperwork available and if you don't they have coverage that you are required to buy before passing into the country. ### Cuban Internet and Wireless Access Is Not Dependable - Technology continues to improve in Cuba, but unlike the United States, where you can always depend on your phone for maps and reviews, you are best to download stuff before you leave. While major resorts will generally have good Wi-Fi, outside of the cities, you will need offline maps enabled to help you navigate. ### Crime Statistics Are Not Available But Gun Crime is Nonexistent - Various crimes, including theft, are very common in Cuba and police intervention is minimal here. However, gun crime and murders are much lower than in other Latin American countries. However, you should always protect yourself and be aware of your surroundings to avoid making yourself a target. 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