CUBA: 1st Friday Weekend in Havana
Cuba: Havana Weekend Getaway
Travel Portal Directory
MEMORABLE MOMENTS
- Trip Itinerary & Overview
- Flight Information
- Accommodations, Meals & Services
- Visa & Travel Documents
- Vaccinations & Shots
- Travel & Medical Insurance
- Weather & Packing List
- Currency, Tipping, Souvenir & Gifting Guidelines
- FAQ – Frequently Asked Questions
- Cuba Weekend Getaway : Videos
- Important Contact Information
- Final Pre-Departure Checklist
Enjoy an In-Depth
Exploration of Havana On
this Weekend Getaway
HIGHLIGHTS
FINCA VIGIA
One of the most famous expatriates to have settled in Cuba is Ernest Hemingway, who lived here, on and off, between 1939 and 1960. The Havana neighborhood of San Francisco de Paula Ward is where Hemingway settled, and his house, Finca Vigía, is open to the public as a museum. The house has been left more or less as it was when the author vacated it, lending visitors a fascinating insight into his life.
OLD HAVANA
The cobblestone streets and attractive plazas of the Cuban capital’s historic district, Old Havana, are a UNESCO World Heritage Site. Spot vintage cars rumbling down the Malecón, the city’s seaside esplanade, and visit the impressive fortresses Castillo del Morro and La Cabaña. If Finca Vigía has piqued your interest in all things Hemingway, be sure to check out El Floridita, one of his favorite spots for a daiquiri
SLOPPY JOE’S
This Havana institution, re-opened in 2013 after almost half a century away, was once a favorite haunt of American visitors in the Prohibition era. It’s since become an icon of the city – Alec Guinness even dropped by in “Our Man in Havana” – and is particularly famous for its cocktails. You’ll meet the bar staff and even get the chance to learn how to mix some drinks yourself, including Cuban classics like the mojito and daiquiri.
MUSEUM OF FINE ARTS HAVANA
Amid all of Havana’s historic delights, you’ll also explore the city’s thriving modern art scene with a visit to the Museum of Fine Arts of Havana. The museum houses the finest collection of Cuban art you’ll find anywhere, with works by the likes of René Portocarrero, Wilfredo
Lam and Rita Lonja. It’s not just modern Cuban art, though: international artists are also represented, going back centuries – there’s a particularly fine collection of 19th-Century Spanish art on display.
ITINERARY
DAY 1: Arrive and Get to Know Havana
Arrive in Havana and meet your Cool Havana Nights group before we embark on a panoramic tour of the city’s main sites, including the Malecón, Revolution Square, and Vedado. Havana pulses with life, with its vintage cars and murals of Che Guevara and Fidel Castro making it feel like you’ve stepped back in time. After dinner tonight, we visit an old factory that has been transformed into a center for Cuban arts and music. (L,D)
DAY 2: Visit Hemingway’s House in San
Francisco de Paula
After fresh Cuban coffee and breakfast we’ll head to San Francisco dePaula, the neighborhood that Ernest Hemingway once called home. Tour Hemingway’s house and see fir thand where he wrote some of his most famous novels. Afterwards, dive into Havana’s vibrant music scene with a presentation from a local Afro-Cuban dance troupe, and learn some basic salsa moves. In the afternoon, we take a guided tour of the imposing churches, cobbled streets and colonial architecture of Old Havana. In theevening, enjoy a traditional jazz café. (B,L,D)
DAY 3: Explore the Old Town and
Havana’s Art Scene
On our last full day in Havana, we’ll continue our exploration of the old town before ending up at legendary bar Sloppy Joe’s, a favorite of Prohibition-era Americans – here, you can learn how to whip up classic cocktails including the mojito. After lunch, we’ll explore Cuba’s contemporary art scene at the Museum of Fine Arts, shop for handicrafts and souvenirs, and enjoy a farewell dinner overlooking Old Havana and the Caribbean at the famous Hotel Nacional. (B,L,D)
DAY 3: Return Home
Today sadly sees our Havana adventure come to an end. After enjoying breakfast together, we’ll say our goodbyes then head back to the airport for our return flights back home. (B)
Standard Lodging
You will have the unique opportunity to stay in casas particulares, or private homes, while in Cuba. Casas are similar to family-run bed & breakfasts (think AirBnB with breakfast in the morning) and all include private bathrooms, air condition, and security. On this trip, stay in the colorful center of Havana walking distance to all the action. Listen to music fill the streets just outside your window each day.
Understanding Legal Travel to Cuba
Everything You Need To Know
Cool Havana Nights has always remained a legal way to travel to Cuba because we operate under the support for the Cuban people license. On June 4, 2019 the Treasury Department released their updated policy (read it here), which caused many companies to panic. In short, the new regulations stopped the use of the People to People license as a way to legally travel to Cuba, which was one of the top two most popular licenses utilized in the travel industry. This meant:
- Many cruise lines and companies who were operating under the people to people license will no longer be able to visit Cuba.
- Cruise ships can no longer dock in Cuba.
- ommercial flights will continue as always to the island, you just need to make sure you are traveling with a company who operate under a legal license.
The people to people license allowed these companies to hire government agencies to help plan activities, hire guides, and stay in
government-run hotels. Because of Cool Havana Nights’ unique focus, this was never the way we approached travel to Cuba
Support for the Cuban People – How Does it Work?
This license truly ensures that you are traveling with the intention and itinerary planned that will help support Cuban micro-entrepreneurs. Cool Havana Nighs has always operated under the belief that travel should be an exchange, where we leave the destination a little bit better than we left it. For this reason, our five Cuba itineraries have always been operated responsibly with the intention to make the world a better place – in Cuba, for us that means supporting individual Cuban individuals and businesses, and help grow the private sector in the country.
- Stay at casas particulares, or privately owned bed and breakfasts.
- Eat at local paladars, or privately owned restaurants.
- Spend 8 hours per day engaging in activities that support the people of Cuba. For Cool Havana Nights, this includes
hands-on learning at a local music and arts center, visiting local artist studios, volunteering at a center for special
needs children, connecting with local farmers in Viñales Valley, supporting local dance troupes, and more. - Hire guides and drivers who do not work for a government agency.
You still need to travel with a tour company in order to travel to Cuba legally, and it is important that you have your paperwork organized. Cool Havana Nights will be able to keep the proper paperwork (receipts and your itinerary) on file for you and help you obtain the correct Cuban visa so you can travel to Cuba stress-free.
If you ever have any questions, don’t hesitate to let us know! Also check out our Cuba FAQs webpage for more
information.
CUBA: HAVANA
WEEKEND GETAWAY
3 DAYS / 2 NIGHTS
| Date | PRICE |
 |
|---|---|---|
| February 7-9, 2025 | $1,495 |
 |
| March 7-9, 2025 | $1,495 |
|
| April 4-6, 2025 | $1,495 |
|
| May 2-4, 2025 | $1,495 |
|
| June 6-8, 2025 | $1,495 |
|
| July 4-6, 2025 | $1,495 |
|
| August 1-3, 2025 | $1,495 |
|
| September 5-7, 2025 | $1,495 |
|
| October 3-5, 2025 | $1,495 |
|
| November 7-9, 2025 | $1,495 |
|
| December 5-7, 2025 | $1,495 |
|
| January 2-4, 2026 | $1,495 |
|
The above prices reflect the price of double occupancy. Single Room Supplements are $250 per person. Due to the nightlife we experience on this trip, it is recommended for those at least 18 years old and older
WHAT’S INCLUDED
International airfare. (Flight from (FFL) Fort Lauderdale to Havana, Cuba)
- Cuban Visa
2 nights lodging in casas particulares
- All meals throughout the trip (6 total)
- Pure bottled water while touring.
- Bilingual Cuban guides that are there to support, guide, and inform you throughout the trip
- Reliable in-country transportation with experienced drivers.
- Admissions and entrance fees to national parks, historic sitesand other scheduled events throughout the trip
- $50,000 emergency medical evacuation insurance.
- Turnkey customer support from preparing for your trip to arrival back home.
WHAT’S NOT INCLUDED
- Domestic airfare. (Flight from where you live in the US to (FFL) Fort Lauderdale
- Tips for Discover Corps guide and driver
- Laundry services, room-service, or phone calls
RESERVE YOUR TRIP TODAY
Trips are limited to 12 travelers and do fill. Reserving a trip with Cool Havana Nights is easy. Simply visit our website and fill out the online registration form and pay a $365 deposit and $30 non-refundable booking fee per person. If you have any questions or would like to speak to a Travel Specialist, call/text us at (443)571-3230 or e-mail us at info@coolhavananights.com
RETURNING ALUMNI?
We like to reward those who travel with us again and again.
Enjoy a $250 discount off our trip if you are a returning
Cool Havana Nights traveler
CUSTOM GROUPS?
Have a group of 6 or more? We can operate a trip for your
group. Whether it’s a family reunion, corporate group, alumni
association or a professional or student organization, we’ll
make it easy and turnkey for your group to have an
incredible experience.
MONTHLY PAYMENT PLANS AVAILABLE
Discover Corps offers monthly payment plan options for all of our
trips. Contact us anytime, before or after booking, to sign up for a
monthly payment plan or with any questions:
Call/Text: 443-571-3230 Email: info@coolhavananights.com
THE FINE PRINT
Child prices apply to those 16 years younger sharing a room with
an adult.
Although unlikely, prices, dates, and accommodations subject to
change with a 60 day notice from Discover Corps.
(B, L, D): Breakfast, Lunch Dinner
Dates don’t work? Contact us about adding a new date for the trip.
FAMILY FRIENDLY • SMALL GROUPS • POSITIVE LOCAL IMPACT • DISTINCTIVE LODGING • HANDPICKED GUIDES
Visit coolhavananights.com/register to place a $395 deposit down to hold your space, or reach out to us at the contact information below with questions.