Two Hearts, One Island — A Cuban Honeymoon
Slow romantic days in Old Havana and leafy Vedado, three barefoot days on the white sand of Cayo Santa María, and a colonial finish in candlelit Trinidad.
For: Honeymooners and couples celebrating
1 · Budget first
A transparent, itemised estimate for 2 travellers · 9 nights · premium tier. Every line is a planner range in USD — an estimate to budget with, not a quote.
| International airfare | $1,200 – $2,800 |
| Entry documents (tourist card) | $60 – $150 |
| Travel insurance | $80 – $300 |
| Accommodation | $1,170 – $2,430 |
| Local transportation | $770 – $1,505 |
| Food | $1,260 – $2,430 |
| Guides & activities | $90 – $240 |
| Connectivity | $30 – $110 |
| Tips | $45 – $180 |
| Water, laundry & sundries | $27 – $108 |
| Emergency reserve | $353 – $1,118 |
| Total (2 travellers) | $5,085 – $11,371 |
- Per traveller
- $2,543 – $5,686
- Per day
- $565 – $1,263
- Ground only (no airfare)
- $3,532 – $7,453
- Airfare est. / traveller
- $600 – $1,400
Basis: premium hotel · premium food · private driver · 3 guided days.
Adjust every number in the planner →Estimates in USD to help you budget — not observed prices, quotes or guaranteed availability. Most US cards don’t work in Cuba; carry cash and keep the reserve.
2 · Fly in
Milan (MXP) → Havana (HAV) — José Martí International
Cuba's principal international gateway — the only truly diversified one, with links across the Americas, Europe, Asia and Africa.
Example dates 2026-09-15 → 2026-09-24 (adjust on the live search). CubaAtlas books nothing — these open live results:
3 · Day by day
Where to sleep and dine each day is a real listing from the CubaAtlas provider dataset, nearest your base.
Morning
Land at José Martí and settle into a restored colonial suite in Habana Vieja.Afternoon
A private vintage-convertible spin along the Malecón at golden hour.Evening
Rooftop dinner over the old city with a bottle of something cold.
StayHotel Blau Arenal Habana Beach4★ · Grupo Cubanacán · La Habana(53 7) 77991200/ 77991274Website ↗Map →Source: Cuba Travel (MINTUR official portal)DinnerCantabria, Restaurante Hotel Armadores de SantanderCimex · Internacional · La Habana(537)8628000Map →Source: Cuba Travel (MINTUR official portal)Open Havana on the map →Nearby: Viñales, Varadero, MatanzasMorning
Coffee on Plaza de la Catedral, then a slow wander through Vieja and San Francisco.Afternoon
Hemingway's haunts and a rum tasting for two.Evening
Jazz in an intimate cellar club, then a nightcap on the seawall.StayHotel Blau Arenal Habana Beach4★ · Grupo Cubanacán · La Habana(53 7) 77991200/ 77991274Website ↗Map →Source: Cuba Travel (MINTUR official portal)DinnerCantabria, Restaurante Hotel Armadores de SantanderCimex · Internacional · La Habana(537)8628000Map →Source: Cuba Travel (MINTUR official portal)Open Havana on the map →Nearby: Viñales, Varadero, MatanzasMorning
Breakfast in leafy Vedado, then the sweeping staircase of the university and the necropolis art.Afternoon
Spa afternoon and a stroll through the Callejón de Hamel murals.Evening
Candlelit dinner in a garden paladar, live bolero.Morning
Drive the long causeway across the flats to Cayo Santa María.Afternoon
Check into a beachfront room; first swim in impossibly clear water.Evening
Toes-in-the-sand dinner and a champagne sunset.Morning
A private catamaran sail to a sandbar for snorkelling.Afternoon
Nothing but a hammock, a book, and the sea.Evening
Lobster on the beach, a bonfire, and stars.Morning
Kayak the mangrove channels and watch flamingos on the flats.Afternoon
Couples massage and a long lazy swim.Evening
Seven-course tasting menu and a slow dance.Morning
Drive south through Santa Clara to cobblestoned Trinidad.Afternoon
Wander Plaza Mayor and the pastel streets; climb a bell tower for the view.Evening
Dinner in a courtyard, then the open-air steps of the Casa de la Música.Morning
The Valley of the Sugar Mills and the Manaca Iznaga tower.Afternoon
Beach hours at Playa Ancón, snorkelling off the reef.Evening
Fresh fish by the harbour, and a horse-cart ride back under the stars.Morning
Slow breakfast and last photographs on the cobbles.Afternoon
Drive back toward Havana with a lunch stop en route.Evening
Farewell dinner and toast before the late flight home.
4 · Visa, entry & customs
Every visitor needs a Cuban tourist card (tarjeta del turista) plus a passport valid for the stay and proof of onward travel and medical insurance. Buy the tourist card before you fly — the price and colour depend on your departure country and airline.
Nationals of Italy travel on the ordinary tourist card — no consular visa for a standard holiday stay.
5 · Book direct, or compare an agency
This plan is costed to book direct — the $7,444 (expected) above is what the trip actually costs, itemised, with no package margin. A travel agency bundles flights, hotel and transfers into one price and adds a service fee for the convenience. We don’t quote agencies (we’d never invent a price) — so take a package quote and compare it line-for-line against the breakdown above.
Operating Italy agencies serving Cuba, if you prefer a package:
- Alpitour ↗
Bravo Club resorts + tours (Varadero, Cayo Largo, Cayo Coco, Havana).
Sells: packages, tours
- Turisanda ↗
Operating since 1924 (Alpitour group); Havana–Varadero, self-drive.
Sells: packages, tours · +39 011 0171111
- Veratour ↗
Veraclub resorts (Cayo Largo, Varadero) + Avana & Varadero tours.
Sells: packages, tours · 06 500 66 777
- Havanatur Italia ↗
Italian Cuba specialist since 1992; incl. casa particular.
Sells: flights, packages, hotels, cars, excursions · 02 6760691
- Eden Viaggi ↗
Ciao Club resorts (Varadero, Cayo Largo, Holguín).
Sells: packages
CubaAtlas is non-commercial and takes no commission. Agency links go straight to the operator; we don’t book, broker or earn from them.
Every Cuba agency, compiled — with the free equivalent for each →Questions
- How much does the "Two Hearts, One Island — A Cuban Honeymoon" trip cost?
- An estimated $5,085–$11,371 all-in for 2 traveller(s) over 9 nights ($3,722 per traveller expected), including airfare, lodging, food, transport and a reserve. It is a planner estimate, not a quote — you book each part direct, with no agency margin.
- Do I need a visa to travel to Cuba?
- Every visitor needs a Cuban tourist card plus a valid passport, onward travel and medical insurance — no consular visa for a standard holiday stay. See the CubaAtlas visa & entry guide.
- When is the best time for this trip?
- Best months: November–April (dry, warm evenings).
- Can I book this trip on CubaAtlas?
- No — CubaAtlas is a free, non-commercial planner. It gives you the itinerary, the budget, live flight-search links and real hotel and restaurant listings, and you arrange each part directly at the source. We book nothing and take no commission.