# 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** - **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.  ### Viking Expeditions vs Victory: Which Great Lakes Cruise Is Right for You? Viking vs Victory Great Lakes cruises: Compare expedition features, port access, and guest experiences. First-hand insights on tender operations vs direct docking. Perfect for choosing your ideal crui CruiseWestCoast [Read More](https://ads.flowmediamarketing.com/go/L5Hn1_oBOROeubnk01Y6eA.446) ### Guys Weekend Guide To Visiting Santa Maria California Here's what you should do on a guys wine weekend getaway in Santa Maria, California. ManTripping [Read More](https://ads.flowmediamarketing.com/go/L5Hn1_oBOROeubnk01Y6eA.1481) ### Thailand Experiences and Adventures (9 days) Enjoy your 9 day trip around Thailand. Visit the top highlights in Bangkok, Chiang Mai, Koh Samui and Koh Tao Viator (affiliate) $3,149.41[See Current Price](https://ads.flowmediamarketing.com/go/L5Hn1_oBOROeubnk01Y6eA.551) ### 400 Years of Drinking in One Night: Boston's Most Historic Bars Boston historic bars guys weekend: pub crawl through America's oldest taverns, from the Revolutionary War to JFK's booth. Warren Tavern, Union Oyster House, and bars older than the country itself. ManTripping [Read More](https://ads.flowmediamarketing.com/go/L5Hn1_oBOROeubnk01Y6eA.1037) Promoted by FlowAds ### Vintage Car Tours In Havana - Havana is a step back in time to the 1950s as far as the car culture goes. You'll find classic automobiles on every corner here and they are all running. 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 November's Pick Amazon (affiliate) ### COROS Pace 4 Pro GPS Sport Watch Why we picked it: a screen big and bright enough to double as a photo frame, a titanium and sapphire build that came through a month of daily wear without a scratch, and battery life that still runs weeks between charges. [Check The Price](https://ads.flowmediamarketing.com/go/VtOIqTAJHKO8VvhR_AtUGw.2471) [October's Pick Made In Cookware - Cleaver - Full Tang With Olive Wood Handle - Crafted in France $199.00](https://ads.flowmediamarketing.com/go/VtOIqTAJHKO8VvhR_AtUGw.2472) [August's Pick LiberNovo Maxis Electric Big and Tall Ergonomic Office Chair, Graphite 52cm $1,393.00](https://ads.flowmediamarketing.com/go/VtOIqTAJHKO8VvhR_AtUGw.2350) [July's Pick Powerful Propane Torch Gun, Adjustable Flame Thrower Gun, Kitchen Torch with Detachable Design, Flamethrower Blow Torch for BBQ, Searing Steak, Welding, Camping Charcoal Lighter(Tank Not Included) $39.99](https://ads.flowmediamarketing.com/go/VtOIqTAJHKO8VvhR_AtUGw.2397) Promoted by FlowAds ### Rum and Cocktail Tours - If there's something more iconic than the Cuban cigar, it's got to be Cuban rum. 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. Top Picks Flow Voyages ### Book your next cruise with Heather at Flow Voyages Flow Voyages is a travel advisor specializing in cruises and resorts. [Contact Flow Voyages](https://ads.flowmediamarketing.com/go/R9_KZNHdESoFUE-MgmU7wg.617) Promoted by FlowAds Details Written by: James Hills Last Updated: 27 February 2025 ### 🚢Ready To Book A Vacation? Let us help you plan a cruise, all-inclusive resort, or tour for your next guys trip, family vacation, or romantic getaway. Click here to [**Book Your Next Vacation**](https://www.mantripping.com/vacation-planning.html). #### Is Your Money Better Spent on Lobsters and Beer Than a Week Glued to Cruise Ship WiFi? Oct 26, 2026 [Is Your Money Better Spent on Lobsters and Beer Than a Week Glued to Cruise Ship WiFi?](https://www.mantripping.com/travel/is-your-money-better-spent-on-lobsters-and-beer-than-cruise-ship-wifi.html) [Plan Your Next Vacation Today!](https://www.mantripping.com/vacation-planning.html) ### Products & Gift Ideas #### Made In Olive Wood Cleaver Makes Quick Work Of Chopping Chicken, Ribs and Carne Asada Nov 04, 2026 [Made In Olive Wood Cleaver Makes Quick Work Of Chopping Chicken, Ribs and Carne Asada](https://www.mantripping.com/stuff/made-in-olive-wood-cleaver-review.html) #### The Victorinox Connex Reminded Me How Nice A Good Suitcase Looks and Feels When Traveling Nov 04, 2026 [The Victorinox Connex Reminded Me How Nice A Good Suitcase Looks and Feels When Traveling](https://www.mantripping.com/stuff/victorinox-connex-review.html) #### Monument Grills Denali 605 Is The Perfect Grill For Cooking Outdoors This Fall Nov 04, 2026 [Monument Grills Denali 605 Is The Perfect Grill For Cooking Outdoors This Fall](https://www.mantripping.com/stuff/monument-grills-denali-605-review.html) ### Top Guys Trip Ideas: #### What Most Guys Miss When Planning a Cruise Ship Casino Trip Jan 27, 2026 [What Most Guys Miss When Planning a Cruise Ship Casino Trip](https://www.mantripping.com/travel/how-to-plan-a-cruise-ship-casino-trip-with-the-guys.html) #### Five Ways We Used Cellular at Sea Cruise+ on Our Canada and New England Cruise Nov 16, 2025 [Five Ways We Used Cellular at Sea Cruise+ on Our Canada and New England Cruise](https://www.mantripping.com/travel/cellular-at-sea-on-norwegian-getaway-canada-and-new-england-cruise.html) #### Gozo Over Valletta: Malta's Quieter Island for a Mediterranean Guys Trip Jun 02, 2026 [Gozo Over Valletta: Malta's Quieter Island for a Mediterranean Guys Trip](https://www.mantripping.com/travel/gozo-quieter-malta-mancation.html) ### Related Articles #### Not All All-Inclusive Resorts Truly Include Everything! Here's How To Manage Expectations So Nobody Gets Surprised [Not All All-Inclusive Resorts Truly Include Everything! Here's How To Manage Expectations So Nobody Gets Surprised](https://www.mantripping.com/travel/all-inclusive-resort-extras-for-guys.html) #### How to Plan a Caribbean Golf Trip That Will Make The Guys That Didn't Join You Jealous [How to Plan a Caribbean Golf Trip That Will Make The Guys That Didn't Join You Jealous](https://www.mantripping.com/travel/caribbean-guys-golf-trip-planning-guide.html) #### Raymond Bowen of EXPLR.SX on How To Plan a Private Boat Charter for a Guys Trip to St Maarten [Raymond Bowen of EXPLR.SX on How To Plan a Private Boat Charter for a Guys Trip to St Maarten](https://www.mantripping.com/travel/st-maarten-private-boat-charter-guys-trip-interview.html) #### A. Erazo From Las Verandas Shares Why Men Love Roatán for a Caribbean Guys Trip [A. Erazo From Las Verandas Shares Why Men Love Roatán for a Caribbean Guys Trip](https://www.mantripping.com/travel/las-verandas-roatan-guys-trip-interview.html) #### Planning the Ultimate Guys Getaway? Ocean’s Adults-Only Resorts Have Everything You Need [Planning the Ultimate Guys Getaway? Ocean’s Adults-Only Resorts Have Everything You Need](https://www.mantripping.com/travel/ocean-adults-only-resorts-caribbean-guys-getaway.html) - [**](https://www.mantripping.com/search.html) - [**](https://www.mantripping.com/sitemap.html) - [** Polls](https://www.mantripping.com/polls.html) - [Community Login](https://www.mantripping.com/registration/login.html) - [Brand Engagement Newsletter](https://www.mantripping.com/pr-ops-newsletter.html) - [Links](https://www.mantripping.com/links.html) - [Pitch Portal](https://www.mantripping.com/pitch.html) - [Men's Travel Survey](https://www.mantripping.com/the-mantripping-guys-trip-report-spring-2026.html) --- *Source: [Planning Tips For An Ultimate Cuba Getaway Boys Trip](https://www.mantripping.com/travel/ultimate-cuba-getaway-for-guys.html)* **Tags:** Caribbean Guys Trip Ideas, Travel Ideas, Boys Trip