Havana

Airport transfer to Old Havana casa particular(40 minutes)

Arrange through your casa host (15-25 USD) or grab a classic car taxi outside arrivals — negotiate before getting in

Check-in and orientation with your casa host(1 hour)

Casa hosts are invaluable — ask about restaurant recommendations, taxi contacts, and current CADECA exchange rates

Evening walk along Calle Obispo(1.5 hours)

Havana's busiest pedestrian street stretching from Parque Central to Plaza de Armas. Live musicians on every corner, art galleries, and souvenir shops. End at El Floridita for a frozen daiquiri (6 USD) at Hemingway's old spot

Dinner at Dona Eutimia(1.5 hours)

Tucked behind the Cathedral on Plaza de la Catedral — arguably the best ropa vieja in Havana. Mains 8-12 USD. Arrive before 7PM or expect a wait

Plaza de la Catedral and Havana Cathedral(1 hour)

Arrive by 8:30AM — the baroque cathedral facade glows golden in morning light. Entry is free. The square fills with art vendors by 10AM

Plaza de Armas and secondhand book market(1 hour)

Browse stalls selling vintage Cuban posters, old coins, and Che memorabilia. Haggling is expected — start at 50% of asking price

Plaza Vieja(45 minutes)

The most architecturally diverse square with restored 17th-century buildings. Climb the Camera Oscura tower (2 CUP) for a live 360-degree projection of the city

Lunch at La Bodeguita del Medio(1.5 hours)

Hemingway's mojito bar on Calle Empedrado — walls covered in signatures. Mojito: 6 USD. The food is decent (lamb shank 10 USD) but you're here for the atmosphere and the drink

Museo de la Revolucion(1.5 hours)

Housed in the former Presidential Palace. Entry: 8 CUP. See the Granma yacht in the glass memorial behind the building — the boat that brought Castro and Che from Mexico in 1956

Sunset at the Malecon(1.5 hours)

Walk the 2 km from Old Havana along the seawall as the sun drops. Locals gather with guitars and rum. Grab a can of Cristal beer from a street vendor (1 USD)

Classic car tour of Havana(2 hours)

Negotiate a 1950s convertible from Parque Central — 30-40 USD for a 2-hour loop covering the Malecon, Vedado mansions, Plaza de la Revolucion, and the Colon Cemetery. Fits 3-4 people per car

Plaza de la Revolucion(45 minutes)

Photo stop at the massive square with the Che Guevara steel mural on the Interior Ministry and the Jose Marti Memorial tower (109m). Climb the tower for 5 CUP

Lunch at San Cristobal Paladar(1.5 hours)

The paladar that hosted Obama in 2016. Walls crammed with religious icons and vintage memorabilia. Creole dishes 8-15 USD. Located on Calle San Rafael in Centro. Reserve through your casa host

Callejon de Hamel(1.5 hours)

Afro-Cuban art alley in Centro covered in murals, sculptures, and bathtub shrines. Free to visit. If it's Sunday, arrive by 11:30AM for the free rumba performance — drums, dancing, and spiritual energy that's electrifying

Drinks at Hotel Nacional terrace(1.5 hours)

Art deco landmark on the Vedado waterfront where Winston Churchill and Frank Sinatra once stayed. Cuba libre on the garden terrace with cannon battery views: 8 USD. Live music most evenings

Drive to Vinales Valley(2.5 hours)

Depart by 7AM. The drive passes through Pinar del Rio province — Cuba's tobacco country. Classic car taxis charge 80-100 USD round trip for up to 4 people

Visit a tobacco farm (vega)(1.5 hours)

Watch a guajiro (farmer) roll cigars by hand and learn the difference between wrapper, filler, and binder leaves. You'll get to smoke a fresh-rolled cigar and buy directly — 1-2 USD per cigar vs 15+ USD in official shops

Cueva del Indio cave boat ride(45 minutes)

Underground river trip through a limestone cave. Entry: 5 CUP. Motor boat ride through illuminated caverns. Short but memorable. Can get crowded — arrive before 11AM

Lunch at a Vinales paladar(1.5 hours)

Try El Olivo or Finca Agroecologica — farm-to-table meals with roast pork, black beans, rice, and fried plantains. Full meal: 8-12 USD including a mojito

Mirador de los Jasmines viewpoint(30 minutes)

The iconic vista over the valley with mogotes rising from the tobacco fields. Free to access. The Mural de la Prehistoria (a 120m-tall painting on a mogote face) is visible from here

Return to Havana(2.5 hours)

Arrive back by early evening. Grab dinner at your casa — hosts prepare incredible lobster dinners for 8-12 USD

Late breakfast at your casa particular(1 hour)

Most casas include breakfast — fresh tropical fruit, eggs, toast, coffee, and fresh juice. Ask for a cafe cubano

Necropolis Cristobal Colon(1.5 hours)

One of the Americas' most important cemeteries with elaborate marble tombs, angels, and mausoleums. Entry: 5 CUP. Map available at entrance. 57 hectares of funerary art dating to 1876. Look for La Milagrosa — the most visited tomb

Walk through Vedado neighborhood(1.5 hours)

Stroll along Linea and Calle 23 past art deco apartment buildings and the University of Havana campus. The ice cream at Coppelia (the famous ice cream parlor on Calle 23, 1-2 CUP for locals' line) is worth the wait

Dinner in Vedado(1.5 hours)

Try Cafe Laurent on the penthouse floor of a faded mansion on Calle M — French-Cuban fusion, mains 10-18 USD, stunning rooftop terrace. Reserve ahead

Fabrica de Arte Cubano (FAC)(3 hours)

Havana's converted cooking oil factory turned multi-floor cultural venue. Open Thu-Sun 8PM-3AM. Entry: 2 USD. Art galleries, live bands, dance performances, film screenings, and bars on every floor. Dress smart casual. This is the best night out in Havana

Finca Vigia (Hemingway's house)(1.5 hours)

Hemingway lived here from 1939-1960. Entry: 10 CUP. You can't enter the house but peer through open windows at his writing desk, typewriter, and 9,000-book library exactly as he left them. The swimming pool and his fishing boat Pilar are in the garden. 15 km southeast of Old Havana

Cojimar fishing village(1 hour)

The small coastal village where Hemingway moored his boat and befriended fisherman Gregorio Fuentes — the inspiration for Santiago in 'The Old Man and the Sea.' See the Hemingway bust on the waterfront. Quiet and authentic

Lunch at La Terraza de Cojimar(1.5 hours)

Hemingway's favorite seafood restaurant in Cojimar, open since 1925. His corner table is preserved. Fresh fish and lobster 10-18 USD. The grilled red snapper is excellent

Fusterlandia(1.5 hours)

In the Jaimanitas neighborhood, artist Jose Fuster has transformed an entire district into a mosaic wonderland — houses, bus stops, park benches, and gates covered in Gaudi-like tilework. Free to wander. Fuster's studio is open for visits. 20 minutes west of Old Havana

Farewell dinner and live music in Old Havana(2 hours)

Dinner at Paladar Los Mercaderes on Calle Mercaderes — elegant colonial setting, Cuban-fusion cuisine, mains 10-15 USD. Then walk to Plaza Vieja for live son cubano music at Cafe Taberna — no cover, drinks 4-6 USD

Cigar shopping at La Casa del Habano(1 hour)

The official Habanos shop at the Hotel Conde de Villanueva on Calle Mercaderes. Authentic cigars only — a box of Cohiba Robustos: 250-350 USD. Staff can advise on varieties. Never buy cigars on the street (almost always fake)

Last walk through Old Havana(1 hour)

One final loop through the plazas. Pick up rum at a shop — Havana Club Anejo 7 Anos (5-8 USD/bottle). Check US customs rules for cigar and rum limits before buying

Transfer to Jose Marti Airport(40 minutes)

Allow extra time — check-in at HAV can be slow. Keep your tourist card handy for exit immigration. Taxi or pre-arranged classic car: 20-30 USD

Airport transfer to Old Havana casa particular(40 minutes)

Arrange through your casa host (15-25 USD) or grab a classic car taxi outside arrivals — negotiate before getting in

Check-in and orientation with your casa host(1 hour)

Casa hosts are invaluable — ask about restaurant recommendations, taxi contacts, and current CADECA exchange rates

Evening walk along Calle Obispo(1.5 hours)

Havana's busiest pedestrian street stretching from Parque Central to Plaza de Armas. Live musicians on every corner, art galleries, and souvenir shops. End at El Floridita for a frozen daiquiri (6 USD) at Hemingway's old spot

Dinner at Dona Eutimia(1.5 hours)

Tucked behind the Cathedral on Plaza de la Catedral — arguably the best ropa vieja in Havana. Mains 8-12 USD. Arrive before 7PM or expect a wait

Plaza de la Catedral and Havana Cathedral(1 hour)

Arrive by 8:30AM — the baroque cathedral facade glows golden in morning light. Entry is free. The square fills with art vendors by 10AM

Plaza de Armas and secondhand book market(1 hour)

Browse stalls selling vintage Cuban posters, old coins, and Che memorabilia. Haggling is expected — start at 50% of asking price

Plaza Vieja and Camera Oscura(45 minutes)

Climb the Camera Oscura tower (2 CUP) for a live 360-degree projection of the city from the rooftop

Lunch at La Bodeguita del Medio(1.5 hours)

Hemingway's mojito bar on Calle Empedrado — walls covered in signatures. Mojito: 6 USD. The lamb shank (10 USD) is surprisingly good

Museo de la Revolucion(1.5 hours)

Housed in the former Presidential Palace. Entry: 8 CUP. See the Granma yacht in the glass memorial behind the building

Sunset at the Malecon(1.5 hours)

Walk the 2 km from Old Havana along the seawall. Locals gather with guitars and rum. Grab a Cristal beer from a street vendor (1 USD)

Classic car tour of Havana(2 hours)

Negotiate a 1950s convertible from Parque Central — 30-40 USD for a 2-hour loop covering the Malecon, Vedado mansions, Plaza de la Revolucion, and Colon Cemetery. Fits 3-4 people

Plaza de la Revolucion photo stop(45 minutes)

The Che Guevara steel mural on the Interior Ministry and the Jose Marti Memorial tower (109m, climb for 5 CUP)

Lunch at San Cristobal Paladar(1.5 hours)

The paladar that hosted Obama. Walls crammed with religious icons. Creole dishes 8-15 USD. Reserve through your casa host

Callejon de Hamel(1.5 hours)

Afro-Cuban art alley covered in murals and bathtub shrines. Free. Sunday rumba performances at noon are electrifying

Drinks at Hotel Nacional terrace(1.5 hours)

Art deco landmark where Churchill and Sinatra stayed. Cuba libre on the garden terrace: 8 USD. Live music most evenings

Drive to Vinales Valley(2.5 hours)

Depart by 7AM. Classic car taxis charge 80-100 USD round trip for up to 4 people

Visit a tobacco farm (vega)(1.5 hours)

Watch a guajiro roll cigars by hand. Smoke a fresh-rolled cigar and buy directly — 1-2 USD per cigar vs 15+ in official shops

Cueva del Indio cave boat ride(45 minutes)

Underground river trip through a limestone cave. Entry: 5 CUP. Arrive before 11AM to beat crowds

Lunch at a Vinales paladar(1.5 hours)

El Olivo or Finca Agroecologica — farm-to-table roast pork, black beans, rice. Full meal: 8-12 USD

Mirador de los Jasmines viewpoint(30 minutes)

Iconic valley vista with mogotes rising from tobacco fields. The Mural de la Prehistoria is visible from here

Late breakfast at your casa particular(1 hour)

Fresh tropical fruit, eggs, toast, and cafe cubano — most casas include breakfast

Necropolis Cristobal Colon(1.5 hours)

One of the Americas' most important cemeteries. Entry: 5 CUP. 57 hectares of funerary art. Look for La Milagrosa tomb

Coppelia ice cream parlor(1 hour)

Join the locals' line at the famous ice cream cathedral on Calle 23 in Vedado. 1-2 CUP for a bowl. The tourist line is faster but less fun

Dinner at Cafe Laurent(1.5 hours)

Penthouse of a faded mansion on Calle M — French-Cuban fusion, mains 10-18 USD, stunning rooftop terrace. Reserve ahead

Fabrica de Arte Cubano (FAC)(3 hours)

Converted cooking oil factory. Open Thu-Sun 8PM-3AM. Entry: 2 USD. Art galleries, live bands, film screenings. The best night out in Havana

Finca Vigia (Hemingway's house)(1.5 hours)

Hemingway lived here 1939-1960. Entry: 10 CUP. Peer through windows at his writing desk, typewriter, and 9,000-book library. The swimming pool and boat Pilar are in the garden. 15 km southeast

Cojimar fishing village(1 hour)

Small coastal village where Hemingway moored his boat. See the Hemingway bust on the waterfront. Quiet and authentic

Lunch at La Terraza de Cojimar(1.5 hours)

Hemingway's seafood restaurant, open since 1925. His corner table preserved. Grilled red snapper: 12 USD

Afternoon at Playas del Este(3 hours)

Havana's beach strip 20 minutes east — white sand, warm Caribbean water. Santa Maria del Mar is the best stretch. Beer vendors on the sand, 1-2 USD. Locals play dominoes under palm trees

Fusterlandia(1.5 hours)

In Jaimanitas, artist Jose Fuster has transformed an entire district into a mosaic wonderland — houses, bus stops, benches covered in Gaudi-like tilework. Free. Fuster's studio is open for visits. 20 minutes west of Old Havana

Cuban cooking class(3 hours)

Learn to make ropa vieja, black beans, mojo sauce, and mojitos. Several paladares offer classes — try Casa Miglis or book through AirBnb Experiences (25-40 USD). You'll eat everything you cook

Afternoon at Malecon(2 hours)

Grab a bottle of rum (Havana Club 3 Anos, 3 USD) and sit on the seawall with locals. This is Havana's living room — fishermen, lovers, musicians, and kids swimming off the rocks

Dinner at El del Frente(1.5 hours)

Rooftop paladar on Calle O'Reilly with craft cocktails and ceviche. The rooftop has the best sunset views in Old Havana. Mains 8-14 USD

Transfer to Vinales(2.5 hours)

Viazul bus from Havana (12 USD) or shared taxi (15-20 USD per person). Arrive by mid-morning

Check into a Vinales casa particular(30 minutes)

Casas in Vinales are excellent — 20-30 USD/night with breakfast. Many have rocking chair porches overlooking the valley

Horseback ride through tobacco valley(3 hours)

Ride through mogote-lined trails past tobacco fields, coffee plantations, and a waterfall swimming hole. 25-35 USD per person through your casa host. No experience needed — the horses know the route

Lunch at a valley farm(1 hour)

Your horseback guide will stop at a farm for fresh-cooked rice, beans, roasted pork, and fresh juice. Included in the tour or 5-8 USD

Gran Caverna de Santo Tomas(2 hours)

Cuba's largest cave system — 46 km of galleries. Guided tours only: 10 CUP. Stalactites, underground rivers, and bat colonies. Headlamps provided. 20 minutes west of Vinales town

Sunset from the valley lookout(1 hour)

Your casa host will know the best spot. The light hitting the mogotes at golden hour is extraordinary. Bring rum

Rock climbing on the mogotes(3 hours)

Cuba Climbing organizes guided climbs on the limestone cliffs — routes for beginners to advanced. 25-40 USD including gear. The views from the top of a mogote are unmatched. Book through your casa host or find them in town

Lunch in Vinales town(1 hour)

Try El Olivo for Mediterranean-Cuban fusion or Tres Jotas for traditional comida criolla. Mains 6-10 USD

Return to Havana(2.5 hours)

Afternoon transfer back. Arrive in time for evening plans

Evening at Plaza Vieja(2 hours)

Craft beer at Factoria Plaza Vieja — Cuba's first microbrewery, right on the square. Pints 2-3 USD. Live son cubano at Cafe Taberna next door — no cover

Drive to Trinidad(4 hours)

Depart by 6AM. Viazul bus (25 USD) or shared taxi (25-30 USD per person). The drive passes through sugar cane country and the Escambray Mountains

Plaza Mayor and colonial churches(1.5 hours)

Trinidad's main square surrounded by pastel-colored mansions and the Iglesia Parroquial. Climb the bell tower of the Museo de la Lucha Contra Bandidos (2 CUP) for the best town views

Lunch at Sol Ananda(1 hour)

Rooftop paladar overlooking the terracotta rooftops. Cuban-fusion cuisine, mains 8-12 USD

Explore cobblestone streets(1.5 hours)

Trinidad's streets are original cobblestone — cars can barely fit. Browse pottery workshops, lace-making demonstrations, and the local honey market

Canchanchara cocktail(45 minutes)

Trinidad's signature drink at the bar of the same name on Plaza Mayor — honey, lime, aguardiente, and ice served in a clay cup. 2-3 USD. The bar has live music all afternoon

Sleep in and late breakfast(1.5 hours)

Ask your casa host for a full Cuban breakfast — scrambled eggs, fresh mango, toast with guava jam, and strong cafe cubano

Morning at Playas del Este(3 hours)

Take a taxi (15-20 USD) to Santa Maria del Mar beach. Rent a beach umbrella (5 USD). Crystal-clear water, white sand, and far fewer tourists than Varadero. Beach restaurants serve lobster for 8-10 USD

Afternoon siesta(2 hours)

Return to your casa and rest during the hottest part of the day — this is what Cubans do

Evening Malecon stroll(2 hours)

Walk the seawall at golden hour. This is the night to simply sit, share rum with locals, and soak in the atmosphere that makes Havana unlike any other city on Earth

Museo Nacional de Bellas Artes (Cuban Art Building)(2 hours)

Two buildings — focus on the Cuban art collection on Calle Trocadero. Entry: 8 CUP. Five centuries of Cuban art from colonial to contemporary. The Wifredo Lam collection is outstanding

San Jose Artisan Market (Almacenes de San Jose)(1.5 hours)

Massive waterfront warehouse market with paintings, woodwork, leather goods, and crafts. Prices are negotiable. A great spot for unique souvenirs. Open daily 10AM-6PM

Lunch at O'Reilly 304(1 hour)

Trendy tapas bar on Calle O'Reilly in Old Havana. Cuban-fusion small plates 3-6 USD each. The octopus and the yuca fritters are standouts

Afternoon photography walk through Havana Vieja(2 hours)

The light in Havana between 3-5PM creates deep shadows and golden facades. Walk Calle Mercaderes, Calle Cuba, and the back streets behind Plaza del Cristo where tourist cameras rarely venture

Salsa dancing at 1830 Club(3 hours)

Live salsa band and open-air dance floor on the Malecon at the mouth of the Almendares River. Entry: 5-10 USD. Cubans will teach you to dance — just say yes. Drinks 3-5 USD. Goes until midnight

Ferry to Regla(20 minutes)

Catch the ferry from the Old Havana terminal (1 CUP, runs every 15 minutes). The 10-minute crossing offers stunning views of the Havana skyline. Regla is a working-class town deeply rooted in Santeria

Iglesia de la Virgen de Regla(45 minutes)

This church houses the Black Madonna — a Catholic/Santeria syncretic figure (associated with Yemaya, goddess of the sea). Locals come to make offerings. Respectful visitors welcome. Free entry

Guanabacoa Afro-Cuban museum(1 hour)

Small museum dedicated to Afro-Cuban religious traditions. Entry: 2 CUP. Displays on Santeria, Abakua secret societies, and Palo Monte. Located 10 minutes from Regla by taxi

Lunch in Guanabacoa(1 hour)

Eat at a local peso restaurant — comida criolla at prices Cubans pay. Rice, beans, pork, and salad for 50-100 CUP. No English menus, point and smile

Return to Old Havana and farewell walk(2 hours)

Final evening in the streets you've come to know. Pick up last souvenirs, say goodbye to your favorite bar, and sit on the Malecon one last time

Farewell dinner at Paladar Los Mercaderes(1.5 hours)

Elegant colonial setting on Calle Mercaderes. Cuban-fusion cuisine, mains 10-15 USD. A fitting goodbye to Havana

Cigar shopping at La Casa del Habano(1 hour)

Official Habanos shop at Hotel Conde de Villanueva. Box of Cohiba Robustos: 250-350 USD. Staff can advise on varieties. Never buy street cigars

Rum shopping and last walk(1 hour)

Havana Club Anejo 7 Anos: 5-8 USD/bottle. One final loop through the plazas of Old Havana

Transfer to Jose Marti Airport(40 minutes)

Keep your tourist card for exit immigration. Taxi: 20-30 USD. Check-in at HAV can be slow — arrive early

Airport transfer to Old Havana casa particular(40 minutes)

Arrange through your casa host (15-25 USD) or grab a classic car taxi — negotiate before getting in

Check-in and orientation with your casa host(1 hour)

Ask about restaurants, taxi contacts, and current CADECA exchange rates

Evening walk along Calle Obispo(1.5 hours)

Havana's busiest pedestrian street. End at El Floridita for a frozen daiquiri (6 USD) at Hemingway's old spot

Dinner at Dona Eutimia(1.5 hours)

Behind the Cathedral — best ropa vieja in Havana. Mains 8-12 USD. Arrive before 7PM

Plaza de la Catedral and Havana Cathedral(1 hour)

Baroque cathedral glows golden in morning light. Free entry

Plaza de Armas and secondhand book market(1 hour)

Vintage posters, coins, and Che memorabilia. Haggle at 50% of asking

Plaza Vieja and Camera Oscura(45 minutes)

Climb the Camera Oscura tower (2 CUP) for a live 360-degree rooftop projection

Lunch at La Bodeguita del Medio(1.5 hours)

Hemingway's mojito bar. Mojito: 6 USD. Lamb shank: 10 USD

Museo de la Revolucion(1.5 hours)

Former Presidential Palace. Entry: 8 CUP. See the Granma yacht memorial

Sunset at the Malecon(1.5 hours)

Walk along the seawall. Cristal beer from a vendor: 1 USD

Classic car tour of Havana(2 hours)

1950s convertible from Parque Central — 30-40 USD for a 2-hour loop

Plaza de la Revolucion(45 minutes)

Che Guevara mural and Jose Marti tower (climb for 5 CUP)

Lunch at San Cristobal Paladar(1.5 hours)

Obama's paladar. Creole dishes 8-15 USD. Reserve through your casa

Callejon de Hamel(1.5 hours)

Afro-Cuban art alley. Free. Sunday rumba at noon is electrifying

Hotel Nacional terrace drinks(1.5 hours)

Art deco landmark. Cuba libre: 8 USD on the garden terrace

Finca Vigia (Hemingway's house)(1.5 hours)

Entry: 10 CUP. Peer through windows at his writing desk and 9,000-book library. 15 km southeast

Cojimar fishing village(1 hour)

Inspiration for 'The Old Man and the Sea.' Hemingway bust on the waterfront

Lunch at La Terraza de Cojimar(1.5 hours)

Hemingway's seafood spot since 1925. Grilled red snapper: 12 USD

Fusterlandia(1.5 hours)

Jose Fuster's mosaic wonderland in Jaimanitas — Gaudi-like tilework covering an entire neighborhood. Free

Evening son cubano at Cafe Taberna(2 hours)

Live traditional Cuban music on Plaza Vieja. No cover, drinks 4-6 USD

Sleep in and late breakfast(1.5 hours)

Full Cuban breakfast at your casa — eggs, mango, guava jam, cafe cubano

Morning at Playas del Este(3 hours)

Taxi (15-20 USD) to Santa Maria del Mar. White sand, clear water. Beach lobster: 8-10 USD

Evening Malecon stroll(2 hours)

Sit on the seawall, share rum with locals, and soak in the atmosphere

Transfer to Vinales(2.5 hours)

Viazul bus (12 USD) or shared taxi (15-20 USD per person). Arrive mid-morning

Check into a Vinales casa particular(30 minutes)

20-30 USD/night with breakfast. Rocking chair porches overlooking the valley

Visit a tobacco farm(1.5 hours)

Watch a guajiro roll cigars. Buy direct: 1-2 USD per cigar vs 15+ in shops

Cueva del Indio cave boat ride(45 minutes)

Underground river in a limestone cave. Entry: 5 CUP

Lunch at El Olivo(1.5 hours)

Mediterranean-Cuban fusion in Vinales town. Mains 8-12 USD

Sunset from Mirador de los Jasmines(1 hour)

The iconic valley vista with mogotes. Bring rum

Horseback ride through tobacco valley(3 hours)

Ride past tobacco fields, coffee plantations, and a waterfall swimming hole. 25-35 USD. No experience needed

Farm lunch on the trail(1 hour)

Fresh-cooked rice, beans, roasted pork. Included or 5-8 USD

Gran Caverna de Santo Tomas(2 hours)

Cuba's largest cave system — 46 km of galleries. Guided tours: 10 CUP. Stalactites and bat colonies

Evening in Vinales town(2 hours)

Live music at the town square. Rum and cigars on your casa porch as the valley darkens

Rock climbing on the mogotes(3 hours)

Cuba Climbing organizes routes for all levels. 25-40 USD including gear. Views from the top are unmatched

Lunch in Vinales(1 hour)

Tres Jotas for comida criolla. Mains 6-10 USD

Dinner at El del Frente(1.5 hours)

Rooftop paladar on Calle O'Reilly. Craft cocktails and ceviche. Mains 8-14 USD

Museo Nacional de Bellas Artes (Cuban Art)(2 hours)

Five centuries of Cuban art on Calle Trocadero. Entry: 8 CUP. The Wifredo Lam collection is outstanding

San Jose Artisan Market(1.5 hours)

Waterfront warehouse with paintings, woodwork, leather goods. Prices negotiable. Open 10AM-6PM

Lunch at O'Reilly 304(1 hour)

Tapas bar — Cuban-fusion small plates 3-6 USD. The octopus and yuca fritters are standouts

Photography walk through back streets(2 hours)

Calle Mercaderes, Calle Cuba, and behind Plaza del Cristo. The 3-5PM light creates deep shadows on golden facades

Visit independent artist studios(1.5 hours)

Several artists in Old Havana open their homes as studios. Ask your casa host for recommendations. Prints start at 20-50 USD

Morning transfer to Trinidad(4 hours)

Viazul bus (25 USD) or shared taxi (25-30 USD per person). Depart by 7AM

Check into Trinidad casa particular(30 minutes)

Stay in the colonial center — casas here are gorgeous: high ceilings, interior courtyards, rocking chairs. 20-35 USD/night

Plaza Mayor exploration(1.5 hours)

Pastel mansions, the Iglesia Parroquial, and the Museo de la Lucha bell tower (2 CUP) for the best views

Canchanchara cocktail(45 minutes)

Trinidad's signature: honey, lime, aguardiente in a clay cup. 2-3 USD at the bar on Plaza Mayor. Live music all afternoon

Sunset from the Casa de la Musica steps(1.5 hours)

The grand outdoor staircase becomes Trinidad's social hub every evening. Mojitos from vendors (2 USD), live salsa bands, and the whole town shows up to dance

Valley de los Ingenios(3 hours)

Taxi or tour to the historic sugar valley. Climb the 44m Manaca Iznaga tower (1 CUP) — a watchtower used to monitor enslaved workers on the plantations. Haunting history, stunning views. 12 km from Trinidad

Lunch at Finca Ma Dolores(1.5 hours)

Farm restaurant in the valley serving wood-fired roast pork and traditional sides. Full meal: 8-10 USD

Afternoon at Playa Ancon(3 hours)

Trinidad's beach 12 km south — white sand and warm Caribbean water. Taxi: 5-8 USD each way. Beach bar with lobster for 8 USD. Less crowded than Varadero and more beautiful

Evening salsa at Casa de la Musica(2 hours)

Live bands play on the outdoor stage from 9PM. Entry: 1-2 CUP. The dancing spills down the steps. Locals are eager to teach

Transfer to Topes de Collantes(45 minutes)

Shared 4x4 truck from Trinidad (10-15 USD round trip). The road up is rough but scenic. Depart by 8AM

Hike to Salto del Caburni waterfall(3 hours)

Moderate trail (4 km round trip) through coffee plantations and cloud forest to a 62m waterfall with a natural swimming pool. Entry: 10 CUP. Bring swimwear and water shoes

Lunch at the park restaurant(1 hour)

Basic but decent food at the Topes visitor center. Rice, beans, chicken: 5-8 USD

Farewell dinner in Trinidad(1.5 hours)

Sol Ananda rooftop restaurant overlooking terracotta rooftops. Cuban-fusion, mains 8-12 USD. One last canchanchara for the road

Transfer to Cienfuegos(1.5 hours)

Shared taxi: 10-15 USD per person. Scenic coastal road

Check into Cienfuegos casa particular(30 minutes)

Stay near Parque Jose Marti in the centro historico. 20-30 USD/night

Parque Jose Marti and Tomas Terry Theatre(1.5 hours)

Cienfuegos' UNESCO-listed main square with neoclassical buildings. Tour the 1890 Tomas Terry Theatre (2 CUP) with its hand-painted ceiling and Caruso-graced stage

Lunch at Villa Lagarto(1.5 hours)

Waterfront paladar on the bay — fresh seafood, the grilled lobster (12 USD) is outstanding. Ask for a bayside table

Palacio de Valle(1 hour)

Spectacular Moorish-Gothic-Venetian palace on the Punta Gorda peninsula. Entry: 3 CUP. The rooftop bar has sunset cocktails (5 USD) with views across the bay

Evening walk along the Malecon de Cienfuegos(1 hour)

Quieter and more intimate than Havana's. Locals fish and socialize. Buy a peso pizza from a window vendor (5-10 CUP)

El Nicho waterfall(2.5 hours)

Stop en route at this series of cascades and natural pools in the mountains. Entry: 10 CUP. Swim in the turquoise pool below the main falls. 1 hour detour from the main highway

Lunch at a roadside paladar(1 hour)

Stop in a small town for comida criolla — rice, beans, pork. 5-8 USD

Continue to Havana(3.5 hours)

Arrive in Havana by late afternoon. Shared taxi total Cienfuegos-Havana: 25-30 USD per person

Quiet evening in Old Havana(2 hours)

Return to your original casa. Casual dinner at a familiar spot and early night after the long travel day

Sleep in(2 hours)

You've earned it after 14 days. Let the sounds of Old Havana wake you naturally

Wander with no plan(3 hours)

Walk streets you haven't walked. Duck into doorways, follow music, sit in a plaza. The best moments in Havana are unplanned

Long lunch at a neighborhood paladar(2 hours)

Ask your casa host where they eat — not where tourists eat. Budget 5-8 USD for an enormous meal

Malecon sunset ritual(2 hours)

By now you have your spot on the wall. Bring rum and sit. This is Havana at its purest

Ferry to Regla(20 minutes)

From Old Havana terminal (1 CUP, every 15 minutes). Stunning skyline views from the water

Iglesia de la Virgen de Regla(45 minutes)

Houses the Black Madonna — syncretic Catholic/Santeria figure. Free. Locals make offerings

Guanabacoa Afro-Cuban museum(1 hour)

Displays on Santeria, Abakua, and Palo Monte traditions. Entry: 2 CUP

Lunch in Guanabacoa(1 hour)

Local peso restaurant — comida criolla at Cuban prices. 50-100 CUP for a full plate

Afternoon Cuban percussion lesson(2 hours)

Arrange through your casa host — several musicians in Havana teach congas, bongos, and claves. 15-25 USD per hour. Learn the rhythms behind son, rumba, and salsa

Cuban cooking class(3 hours)

Learn ropa vieja, moros y cristianos, tostones, and mojitos. Book through AirBnb Experiences (25-40 USD). You eat everything you cook

Jardin Botanico Nacional(3 hours)

600-hectare botanical garden 25 km south of Havana. Entry: 2 CUP. Tractor-train tour included. The Japanese garden and Cuban palm collection are highlights. Few tourists visit. Taxi: 20 USD each way

Lunch at El Bambu in the garden(1 hour)

The garden's vegetarian restaurant — rare in Cuba. All-you-can-eat buffet of creative vegetable dishes: 12 USD. One of the best meals in Havana

Evening salsa at 1830 Club(2.5 hours)

Open-air dance floor on the Malecon. Entry: 5-10 USD. Live salsa band. Cubans will teach you

Drive to Las Terrazas(1.5 hours)

70 km west of Havana. Taxi: 50-60 USD round trip for up to 4. Entry to the biosphere: 6 CUP

Walk through the eco-village(1.5 hours)

Cuba's first eco-community, built in 1971. Artists' studios, a radio station, school, and homes integrated into reforested hillsides. Population: 1,000

San Juan River and waterfall swim(1.5 hours)

Hike along the river to natural swimming pools and a small waterfall. Bring swimwear. The water is refreshingly cool after the hike

Lunch at Casa del Campesino(1.5 hours)

Farm restaurant overlooking the lake. Wood-fired roast pork, root vegetables. 8-12 USD

Birdwatching walk(1.5 hours)

Sierra del Rosario is a birdwatcher's paradise — the Cuban Trogon (national bird), tocororo, and 73 other species. Guided birdwatching: 10-15 USD

Morning at Playas del Este(3 hours)

One last beach morning at Santa Maria del Mar. By now you know the best spot and the best lobster vendor

Lunch at your casa particular(1.5 hours)

Ask your host to cook their specialty. The meal you share with your host family is often the most memorable of the trip

Afternoon in a Havana plaza(2 hours)

Bring a book and sit in Plaza del Cristo or Parque Central. Watch the chess players, the school kids, the classic cars rolling by. No agenda

Evening rum tasting(1.5 hours)

Museo del Ron (Havana Club Rum Museum) on Avenida del Puerto. Entry with tasting: 7 CUP. Learn the distillation process and sample aged rums

Morning at Museo de la Ciudad(1.5 hours)

In the Palacio de los Capitanes Generales on Plaza de Armas. Entry: 3 CUP. Traces Havana's history from indigenous Taino to the Revolution. Beautiful courtyard with a Ceiba tree

Lunch at Ivan Chef Justo(1.5 hours)

One of Havana's best paladares on Calle Aguacate. French-Cuban fine dining in a colonial mansion. Tasting menu: 25 USD. Worth the splurge for your last full day

Afternoon shopping for last souvenirs(2 hours)

San Jose market for art, Calle Obispo shops for rum and coffee. Official Habanos shops for cigars

Jazz at La Zorra y El Cuervo(2 hours)

Havana's legendary jazz club in Vedado — enter through a red British phone box. Shows at 10PM. Entry: 10 USD. Cuban jazz musicians are world-class

Final Malecon goodbye(1 hour)

Walk the seawall one last time. Let Havana say goodbye in its own way — with music drifting from somewhere, the smell of salt and old stone, and the sound of waves against the wall

Breakfast at your casa(45 minutes)

Say goodbye to your hosts. Exchange contact info — you'll want to come back

Final morning walk(1 hour)

One more loop through your favorite plaza. The morning light in Old Havana is the gentlest

Transfer to Jose Marti Airport(40 minutes)

Keep your tourist card for exit immigration. Taxi: 20-30 USD. Allow 3 hours before your flight — HAV check-in is slow