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Anniversary Getaway in Havana
Planning a anniversary getaway in Havana? Compare hotels and vacation rentals on Expedia — a boutique hotel for two or a private home with a view, whatever makes the trip. Celebrate the years with a trip that feels like a gift.
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Planning a anniversary getaway in Havana
1950s cars, sea-spray on the Malecón, live son music spilling out of every doorway in Old Havana. For two, decide between a hotel with service and a private rental with space — Expedia lists both in Havana, so you can weigh price, location and reviews in one search.
What to eat in Havana
Eat in paladares, the private restaurants legalised in the nineties, not state ones. Ropa vieja, shredded beef in tomato, and cerdo asado come with rice, black beans, fried plantain and yuca in mojo almost regardless of what you ordered. Dona Eutimia off Callejon del Chorro makes its ropa vieja with lamb. Shortages are real: menus are aspirational and the kitchen tells you what actually exists.
Havana after dark
Fabrica de Arte Cubano, the converted oil factory in Vedado that defined the city's night for a decade, announced an indefinite pause and now opens only for announced events, so check before planning around it. What remains is live: son and trova at La Zorra y el Cuervo and the Casa de la Musica, rumba in Callejon de Hamel on Sunday around midday, and blackouts that end evenings without warning.
What's actually worth your time in Havana
Habana Vieja's four squares, Catedral, Vieja, San Francisco and Armas, are a restored core surrounded by an unrestored city, and the contrast is the point. The Malecon costs nothing and is best at dusk when it fills with people and fishing lines. El Capitolio's dome was regilded and reopened for guided tours only. Skip the Plaza de la Revolucion beyond a photograph of the Che outline.
When the weather turns in Havana
Hurricane season runs June to November and a Malecon storm sends waves over the seawall and floods the Vedado streets behind it. Indoors means the two Bellas Artes buildings, the Museo de la Ciudad in the Palacio de los Capitanes Generales on Plaza de Armas, and the Museo del Ron on Avenida del Puerto. Power cuts affect museums too, so carry a torch and cash.
What first-timers get wrong in Havana
Bring every peso of your budget in cash: foreign cards issued by American banks do not work, ATMs are unreliable, and notes must be unmarked and untorn to be accepted. The official bank rate and the street rate differ by a wide margin, and the street rate moves monthly, so check before changing anything. Buy the tourist card before flying. Wifi needs an Etecsa card and works in patches.
When to go to Havana
| Best months for anniversary getaway | Avg daily high | Rain days |
|---|---|---|
| January | 27°C / 81°F | 8 days |
| February | 28°C / 82°F | 8 days |
| December | 27°C / 81°F | 8 days |
The month to avoid is July — around 33°C (91°F) with roughly 20 rain days. Prices and crowds track the weather here: January is the sweet spot, July the month most people skip.
Pack for peak season: Summer clothes, plus one light layer for air-con and evenings, High-SPF sunscreen, sunglasses, and a refillable water bottle, A packable rain shell or compact umbrella earns its space, Comfortable walking shoes — every guide on this site assumes you'll use them.
Where to base yourself in Havana
- Habana Vieja (Old Havana) — The UNESCO-listed colonial core — plazas, colonnades, live salsa, restored casas.
- Centro Habana — A crumbling, lived-in barrio between the Old Town and Vedado — real Havana at street level.
- Vedado — Mid-century Havana — the Malecón waterfront, hotel Nacional, ice-cream at Coppelia.
- Miramar — Leafy embassy district west of the harbor — quieter, upscale paladares, good sunset drives.
Common questions
What's the best stay for an anniversary?
For two, a romantic boutique hotel or a private whole-home rental with a view, a hot tub, or a great terrace makes the trip. Choose somewhere central so you can walk to dinner without a car.
How do we make it special?
Book a place with a standout feature — a plunge pool, a sea or skyline view, a fireplace — and pick a walkable neighbourhood near the restaurants and sights you want. Mention the occasion; many hosts and hotels add a small touch.
When should we book?
Two to three months ahead for weekends; sooner for peak season or a specific view. Free-cancellation listings let you hold the date and adjust if plans change.
Where should we stay for a anniversary getaway in Havana?
In Havana the areas worth basing yourself in are Habana Vieja (Old Havana) (the unesco-listed colonial core — plazas, colonnades, live salsa, restored casas); Centro Habana (a crumbling, lived-in barrio between the old town and vedado — real havana at street level); Vedado (mid-century havana — the malecón waterfront, hotel nacional, ice-cream at coppelia). 1950s cars, sea-spray on the Malecón, live son music spilling out of every doorway in Old Havana. On Expedia, compare hotels and whole-home rentals side by side, sort by guest rating, and check free-cancellation terms before booking.
When is the best time for a anniversary getaway in Havana?
January (around 27°C, ~8 rain days), February (around 28°C, ~8 rain days), December (around 27°C, ~8 rain days) rate best on Havana's 5-year climate normals. July is the month most groups skip.