Havana
DreamsPrivate Tour · 5 days / 4 nights
Five days centered on Havana with one countryside escape to Viñales—ideal for travelers who want depth in the capital without a longer loop.
Havana
Cuba’s vibrant capital is a living museum where vintage cars roll past pastel-colored colonial buildings. Travelers are drawn to its electric energy, legendary nightlife, and the historic charm of Old Havana.
Viñales
Famous for its dramatic limestone hills called mogotes and lush tobacco fields, this valley offers some of Cuba's most iconic landscapes. Travelers come here to horseback ride through the countryside and learn the secrets of rolling authentic Cuban cigars.
Activities on the Havana Dreams tour
- Old Havana walks & cultural time
Layered city days with private artists, restaurateurs, and drivers.
- Classic mobility & photo moments
Curated vehicle time where your route includes it.
- Countryside & nature windows
Biosphere and valley pacing matched to your PDF or departure.
- Colonial towns & live music
Evenings and town time in places like Cienfuegos and Trinidad when on route.
What's included in Havana Dreams
Cuban visa & paperwork
We'll assist you with the Cuban visa (about five minutes), filling out the D'Viajeros form, and any other paperwork you might need for the trip.
Airport transfers
Door-to-door arrivals and departures when included on your quote.
Private ground transport
Ground transport is private to your party. On small-group departures, vehicles carry only travelers booked on that same tour—we never mix unrelated guests into your route transfers.
Expert local guiding
Bilingual storytellers and specialists aligned with Support for the Cuban People.
Boutique casas particulares
Hand-picked casas particulares or quoted hotel upgrades—rooming on your confirmation. Every room has its own private en-suite bathroom, air conditioning, and hot water.
Scheduled entries & cadence
Museums, parks, and timed visits as listed for your tour style.
Meals
Daily breakfast at the casa and one lunch included in Viñales. Dinners are not included.
Not included in the tour price
International flights
Travelers join us from across the United States and from other countries, so we leave flights to Cuba to you—you choose the routing that works from home.
Most lunches & dinners
We leave these meals off the package so you have more flexibility to choose where to eat each day. We're more than happy to recommend places and make reservations whenever you need.
Tips & gratuities
Tipping is customary in Cuba, but it isn't compulsory. In other words, it's optional.
Cuba, with the people who live there
Many trips to Cuba are a resort week, a state-hotel circuit, or an open stay with nothing on the calendar. A traveler from the United States is then left to guess whether the week qualifies. This trip is a full-time program, with private homes, a private vehicle, and help through the paperwork.
- 01
Legal for US travelers
The itinerary is a full-time Support for the Cuban People program. We assist you through the process of getting what you need to travel to Cuba from the United States.
- 02
A private home, not a state hotel
You stay in hand-picked casas particulares. Every room has a private bathroom, air conditioning, and hot water. The cost of the night stays with a Cuban family. A hotel upgrade is quoted when you want one.
- 03
Time with independent Cubans
The days are built around private homes, paladares, and local guides. The program is not a state tourism package, and it is not a resort with an empty calendar.
- 04
A vehicle for your party
Ground transport is private to your group. On a small-group departure, the vehicle carries only travelers booked on that same trip.
- 05
Guides who own the company
Cuba 360 is run by the Cuban guides who travel with you. The people who design the route are the ones who meet you. A distant office does not hand the week to a stranger in each city.
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The paperwork is part of the trip
We help with the Cuban tourist card, D’Viajeros, and the papers a US traveler needs before the flight.
“As a US citizen, I was worried about the rules. Cuba 360 handled everything—the trip from the States was easy.”
Legal Travel for US Citizens
We've brought thousands of US families to Cuba. Since 2017, more than 5,000 US travelers have joined our OFAC-compliant itineraries.
100% OFAC Compliant
Our itineraries are designed to fulfill the "Support for the Cuban People" general license (31 CFR § 515.574). Each day includes a full-time schedule of meaningful interactions that support independent Cuban civil society.
Worry-Free Documentation
- Certified full-time schedule for your trip length
- Professional record-keeping and traveler-facing certificates
- Direct support to private entrepreneurs and casas
Havana Dreams prices per person
Rates depend on season, party size, and hotel category. Share your travel dates and we’ll send a quote that matches this itinerary.
Pricing & availability
From $500 / person (double occ.) — larger parties save; see table for all tiers.
| Party Size | Rate PP | Room Allocation |
|---|---|---|
| 2 guests | $700 | 1 double/twin |
| 3–4 guests | $610 | 2 double/twin rooms |
| 5–6 guests | $560 | 3 rooms |
| 7+ guests | $500 | Custom allocation |
Room counts in the table pair travelers in shared double or twin rooms when possible. Anyone who occupies a room alone pays the single-room supplement once for the entire trip—for example, five guests in three rooms usually means two shared rooms plus one single, so one supplement applies for that guest for the whole tour, not nightly.
What’s next
Send your dates and party size (private tours start at two guests)—we’ll confirm inclusions and rooming.
Single supplement
Prefer your own room instead of sharing? A $125 supplement applies for a private room for the full tour—one total charge per traveler in a single room (not per night).
Support Local
Your trip channels spending toward private casa hosts, paladar owners, drivers, and guides.
Talk to Cuba 360Traveling on your own?
Private itineraries start at two guests. Solo travelers usually get more from our scheduled small-group departures—great pacing and a shared table.
View small group toursThe Casa Particular
Experience
We host you in curated Casas Particulares—boutique, family-run B&Bs that offer the warmth of a Cuban home with the amenities of a well-appointed guest suite.
Authentic Soul
Stay in restored homes with character, art, and conversation at the breakfast table.
Local Flavor
Hand-prepared breakfasts with farm-fresh tropical fruits and Cuban coffee.
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Havana Dreams itinerary: day by day
Expand each step for activities and pacing.
Download PDF itineraryVoices of the Journey
Real stories from travelers who have explored the rhythmic heart of Cuba with us.
Tieu
Bella Cuba
Unforgettable trip and people
...The whole trip has been one of the best I've had. I miss the people I met and the friends I made there!
William R
Bespoke itinerary (based on Bella Cuba tour)
Excellent time in Cuba
We had a great experience with our Cuba 360 Bella Cuba tour. Daynel, our guide, was top-notch. For our week-long stay, we were drawn toward all the positive reviews, and they do not exaggerate...
Norm
Taste of Cuba
Far More Than Expected!
My wife and I went on a ... Taste of Cuba Tour, covering the west half of the country... We covered all the natural, historic, cultural, and gastronomic attractions in the area. We had a great guide in Beberli ... I highly recommend this tour, especially if Beberli is the tour guide!
Anne A
Bella Cuba
Amazing tour! Amazing tour guide!
I loved everything about this tour. From the customized planning, the places we stayed and the tour guide Claudia!! I highly recommend this company!!
Positive Feedback
Our travelers consistently rate their Cuba 360 experience as the highlight of their year.
165 reviews on TripAdvisor
Havana Dreams photos
Moments from the road — the textures, light, and rhythm of Cuba as our travelers experience it.
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Book
Havana Dreams
Rates depend on season, party size, and hotel category. Share your travel dates and we’ll send a quote that matches this itinerary. Our team aligns flights, visas, and licenses with your itinerary.
Boutique Itineraries • US-Rule Aligned • Local Partners
Havana Dreams FAQs
Practical answers for traveling to Cuba with us—especially if you are coming from the United States.
Before you fly
Passport, eVisa, insurance, D’Viajeros, and cash in one printable page.
Open the travel checklistWant more tips for the trip?
Our guidebook has a lot more advice on traveling to Cuba—practical tips, what to expect on the ground, and stories from the road.
Explore the guidebook