The Rome of the Caribbean - Experience classic Havana style the best way possible

Detached from the modern capitalist development of the last 7 decades, Cuba tantalizes the intrigue of travelers abound, calling them to experience a different world. Left behind in their socialist time capsule, you can taste what life was like in 1950's America cruising around in classic convertibles past the arco deco architecture lining the streets. Regardless of its political leanings, Cuba has become a hotspot destination for international travellers catering to this crowd. Tourism has become such a large part of the economy, that Cuba has instituted a secondary currency, the CUC, or tourism dollars. 

Whatever your preconceptions are, throw them to wind, because Cuba is open for you whether you're American, Canadian, or other country, there are a number of daily direct flights into Havana. Come experience the rum, cigars, and culture of this classy caribbean paradise. 

With something for everyone, you can fill your days with culture, music, beach, or stay out all night where the nightclub scene is lively 7 days a week. Hit the seas and go after that prize marlin in one of our deep sea fishing vessels or head to the interior to explore the cigar plantations and surrounding caves. 

Travelling with Highlife means that you'll experience the only best that Havana has to offer from your private mansion rental to your private fleet of classic convertibles to the private excursions and VIP nightilfe. 

Highlife Havana is about providing you the ultimate experience in this tropical metropolis. We are your personal concierge to get you anything you want while in Havana. 

With so many options

select from:


  • Accommodations 

    • Mansion

  • VIP Nightlife 

    • top Miami-style clubs

    • Secret bar

    • Cabaret Show

  • Private Yacht Charter

    • Deep Sea Fishing 

  • Full Day Excursion

    • Cigar Plantation/ Cave Tour/ Hike

  • Daytime Activities - Around Havana

    • Fort El Morro

    • Beach - Playas del Este

    • Rum Museum

    • Cigar Factory

    • Armory

    • Revolutionary Museum

    • Ernest Hemingway Bar Crawl

  • Extras

    • Cuban phone provided

    • Welcome gift upon arrival

    • Bilingual Cuban host

    • Only the best classic convertibles


When you're on a bachelor party, you need a party mansion that matches the group - we got you covered. 

We've teamed up with Point2Cuba to lock down only the best bachelor-friendly mansions and penthouses in Havana. Our go to option is the 7 bedroom luxury castle pictured here to the right that has all the modern amenities of home with an anything goes attitude. Hit the bar by the pool and nurse that hangover in the pool of your own castle. 

You're a smaller group? No problem! We have water front penthouses with 360 views of Havana so you can live it up in style regardless of the size of your group. 

We set you up with a Cuban phone as well so you're only a call away from your Highlife Host and your drivers on stand by.




Day 1 | Arrival

Welcome to Havana! 

No better way to start off the trip than a beautiful female host to greet you as you exit customs and escorted out to your private caravan of classic convertibles; 1950's chevy, ford, dodge, and buicks - only the best, most well kept. With energies high, we cruise into Havana with the tops down and cigars in hand. Upon arrival to the Highlife Luxury Castle, get comfortable and have a cocktail by the pool.  

Either chill at the mansion or join us for happy hour mojito at the emblematic Hotel Nacional before we head out to one of the best restaurants in town, near the mansion. We'll seemlessly blend dinner into the night as we invite you to the VIP of the largest club in Cuba that is going off every night. We'll keep the night going based on the vibe of the group and cater the next location to your style. 

Day 2 | Pick & Choose

Wake up at your leisure. We build our packages to cater to your group's schedule so flexibility is king. Once the group is ready to go, our team will be on stand by. Pick and choose your activities for the day. With tons of options, just let us know what you'd like to do: pick either 2 options if you want to stick around Havana, or upgrade to go deep sea fishing. 

At night, we recommend starting it off with a cabaret show to get the juices flowing.  With a bottle of rum and cigar in hand the skantly clad dancers should get you ready and riled up to hit the town. Leaving the show around midnight, you'll be ready to keep the party going. We'll follow it up with one of the best clubs in Havana and potentially the secret bar of Old Havana. 


Cigar Factory
Rum Museum
Beach - Playas del Este
Fort El Morro
Revolutionary Museum
Ernest Hemingway Pub Crawl










Day 3 | Pinnacle Event

For Day 3 we like to mix it up a bit and we say either hit the beach, go deep sea fishing, or head out to the interior to explore the cigar plantations and surrounding caves. Based on what your group is into, we can set up the fishing boat for the afternoon - usually about 5 hours of fishing and you'll be going after the prize marlins, dorados, and yellowfin tuna. Not into boats - we keep it light and go hit the beach about 20-30 min outside downtown Havana. We'll load the cooler with ice and beer so no worries. Want a little more adventure? Then we head inland about 2.5 hours to Viñales where they grow the tabacco for their world famous cigars. Here, you'll get a more rural Cuban experience with traditional mixed lunch and check out the breathtaking landscape. 

At night, we go big for your last night either returning to your favorite spots or showing you something new - either way, we won't let you down. 

cave tour in Viñales
deep sea fishing
Cuba deep sea fishing
deep sea fishing Havana

Day 4+ | Departure

Didn't get enough and want to stay more days? No problem, we can arrange your trip for as long as you want. If you did make the most of your 4 days and 3 nights then you'll be ready for a vacation from this vacation at the end.  

For your final day, chill by the pool or head down to Old Havana one last time - we'll be there to drive you guys to the aiport. If you're staying longer, then let's talk to see what you want to do. In reality, just around Havana with our listed options we have enough activities to keep you busy for a straight 7 days - 6 nights. Whatever your plan, talk to one of our Highlife Representatives to plan your unforgettable bachelor trip to Cuba! 

USD$850 - $1350

Frequently asked questions

Can Americans go to Cuba?

Yes! Tensions between the United States and Cuba have been pretty icey for decades, but with the Obama administrations steps towards loosening restrictions and sanctions, the doors for Americans have been opened. Even though Trump has discussed closing those doors again, this has all been nothing but bark with no bite. The travel restrictions lifted under the Obama administration are still in effect. You can travel direct from the US to Cuba without problem, but you will need to say (or mark on the form) the appropriate response to avoid any questions. You’re going to Cuba for Cultural and Educational Exchange – done.

Do you need a travel visa to visit Cuba?

Yes! Regardless if you are Canadian or American, you will need a tourist Visa. Most of the time this can be purchased at the check-in desk of the airline if they don’t include it in the price of the flight ticket. You will want to check specifically with your airline on this one. The price of this visa varies depending on where you are flying in from, not your citizenship. If you are an American flying to Cuba from Panama then you’ll only need to pay $20 for your tourist visa. If you’re flying to Cuba from the United States you may need to pay upwards of $200 for your tourist visa, so factor this into your budget. It may be cheaper to layover in Mexico or Costa Rica and get a tourist visa there.

Will my credit cards work in Cuba?

Cuba has lessened restrictions on the use of Visa and Mastercard, but don’t let this fool you. Just because the Cuban government says it is ok to use these credit cards, doesn’t mean that the local stores or restaurants have the capability of accepting these or any credit card for that matter. Cuba is still stuck in the 60’s as it slowly enters the new 21st century, so cash rules king.

Oh and if you’re American, forget about using any of your credit cards or debit cards that are linked to an American financial institution. If you even attempt to access your bank accounts online, your accounts will be frozen (only Americans) so just don’t mess around – bring cash.

Can I use my debit card at the ATMs in Cuba?

Yes and no! Are you American, then no. Are you Canadian or European, then yes. Make sure you tell your bank that you’ll be travelling to Cuba so that any transaction is flagged and denied. It’s a good idea to also use non USD accounts to pull from, because the exchange fees are higher on USD than other currencies.

Can I use USD to pay for things?

USD is not commonly accepted. Some individuals might take it, but this is few and far between. The exchange rate is regulated by the Cuban government so it will be the same rate at any and all money exchange dealers, so just take care of this at the airport when you land to get it out of the way. There are a few “casas de cambio” in Havana central so don’t worry about exchanging all of your money, but then again do you really want to take time out of your trip to go wait in lines without AC.

Can I book direct flights from the USA to Cuba?

Yes! There are a number of direct flights from all over the south and east coast directly into Havana. It couldn’t be more easy to fly into Cuba.

Is my checked luggage safe travelling in to Cuba?

Relatively safe. We don’t recommend packing anything of value in your checked luggage or it could be stolen by the baggage handlers. It is a good idea to pack light and only come with a carry-on if possible. For a debaucherously long weekend in Havana, you don’t need to bring the whole wardrobe.

What can you take out of Cuba?

Most guys want to take cigars and rum – the main staples of Cuba. That’s no problem if you’re Canadian. You can take up to 20 loose cigars without import duty or up to 50 if they are sealed. For Americans, if you’re flying direct it’ll be hard to get away smuggling cigars or anything into the US since the trade embargo is still in effect. If you do attempt to take the cigars back direct, then at least remove the bands on the cigars and don’t pack them in a Cuba box of any kind.

Will I have access to roaming or wifi on my phone or devices?

You will not have roaming on your phone. Canadians do have the option to pre-purchase, but it's overpriced and not even worth it. Internet connectivity is not as prevalent as your home country and is much harder to come by. You will have wifi at the house, but don’t expect to have internet access anywhere else. If you really need to get connected then you’ll need to purchase internet cards on the street and then find a government public hotspot usually located around parks or international hotels.

As a Highlife client, we do provide you with a Cuban cellphone so you’ll at least always be able to contact your host, house, transport, etc.

How much stuff should you pre-book before arrival?

Given the lack of internet access and non-built up service economy it will be difficult to arrange activities last minute once in-country. You will be able to pay top dollar for the main tourist attractions or overpriced taxis, but preparation is key in Cuba or else you risk losing time, patience and money.

How prevalent is English in Cuba?

It isn’t, so feel free to stumble your way around and immerse yourself. In case you don’t feel like doing this, no problem, your Highlife Hostess speaks English and can take care of anything you need.

Should you dress to impress when going out at night?

You should always be looking your best when hitting the town at night, but leave the bling at home. You don’t need to be flexing in Cuba for people to know you’re the shit. You’re an international tourist – they already assume you have stacks. So, dress to impress, but be mindful because you don’t want to draw unwanted attention your way.

Is prostitution legal in Cuba?

It is definitely not legal and if caught carries some jail time with it. It is not to say, there are working girls out and about and even chilling on the street trying to get your attention. Your safer bet is to find a regular girl and take her home at night, or else risk some shady hooker situation. If your group is looking more for hookers and harder party then we don’t recommend Cuba – we recommend Panama. Check out the Panama option here.

When is the best time of year to travel to Cuba?

Anytime of the year is good to travel to Cuba, it just depends on what you want to do more. If you really want to go deep sea fishing then anytime between May – September is the time to go, but know that May – July is the rainy season. This rain also makes the tobacco fields come to life so a good time to visit the cigar plantations. If you’re looking for more beach then July – Oct is perfect water temp. If you’re focused on nightlife then any day any time of the year it will be going off. Havana’s nightlife is a 7 day a week scene.

© 2018 by Highlife Havana

Design Support: South by North Designs

35A Terramar,  Via Israel

Panama City, Panama

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