Cuba Sailing Adventure

 

For a 7-day sailing holiday in Cuba, I would suggest the south coast from Cienfuegos, rather than trying to circumnavigate the island. You get a lovely combination of sailing, deserted beaches, snorkelling, wildlife and—most importantly—time ashore in Trinidad.

There are established sailing itineraries from Cienfuegos through the southern cays, and the area is well suited to catamarans because many of the cays have very shallow water.

Day 1 — Cienfuegos

Cienfuegos → Punta Gorda / overnight aboard

Fly into Havana and transfer to Cienfuegos, or arrange your trip around Cienfuegos if flights work.

Spend the afternoon exploring the wonderfully preserved French-influenced city before boarding your catamaran.

Highlights

Cienfuegos historic centre

Palacio de Valle

Punta Gorda

Welcome dinner aboard

Short evening sail if conditions allow

Cienfuegos is a particularly good starting point because it gives access to both the southern coastline and the offshore cays.

Day 2 — Cienfuegos → Guajimico → Casilda

A beautiful coastal sailing day.

Stop at Guajimico, where you can:

snorkel

swim

explore caves

have lunch ashore

Then continue towards Casilda, the port serving Trinidad.

Overnight: at anchor near Casilda.

This is broadly the route used by established Cuba sailing itineraries.

Day 3 — Trinidad

This would be my big cultural day.

take a taxi or organised excursion into Trinidad, one of Cuba's great colonial towns.

spend the morning and afternoon:

wandering the cobbled streets

visiting Plaza Mayor

exploring the old churches and mansions

having lunch in a local paladar

visiting the Valle de los Ingenios if you want an excursion

Then return to the boat for a swim and sunset.

Evening: I'd definitely arrange a night in Trinidad for Cuban music and dancing.

Day 4 — Casilda → Cayo Blanco de Zaza

Now the holiday changes character completely.

Leave civilisation behind and sail towards the small offshore cays.

Cayo Blanco de Zaza is ideal for:

deserted beaches

snorkelling

kayaking

swimming

paddleboarding

a barbecue or seafood dinner aboard

Spend the night at anchor beneath the stars.

This section of the south coast is particularly attractive because it receives relatively little cruising traffic. One experienced Cuba sailing account describes sailing roughly 250 nautical miles around the southern coast in a week and encountering remarkably few other sailboats.

Day 5 — Cayo Blanco → Cayos Machos de Fuera

A relaxed sailing day between the cays.

I'd deliberately keep the schedule flexible rather than trying to cover huge distances.

Spend the afternoon:

snorkelling over reef

exploring the beach

kayaking through mangroves

looking for iguanas and other wildlife

fishing from the boat

Then enjoy a sunset dinner on deck.

Day 6 — Cayo Machos → Cayo Blanco de Casilda

Another relatively short sailing day.

This is your "Caribbean paradise" day—no sightseeing agenda whatsoever.

I'd spend the morning sailing, then anchor somewhere beautiful for:

swimming

snorkelling

paddleboarding

lunch aboard

beach walk

afternoon nap!

The Cuban government tourism site highlights the excellent snorkelling, coral reefs, beaches and private-charter possibilities around its northern cays; similar shallow-water conditions are found throughout Cuba's island cruising grounds.

Day 7 — Cayo Blanco → Cienfuegos

Set sail early for the return to Cienfuegos.

Make the most of the final morning with one last swim or snorkel before heading back.

Arrive in Cienfuegos in the afternoon, allowing time for:

a final wander around the city

dinner overlooking the bay

Cuban music

final night aboard or in a hotel

Then transfer back to Havana the following morning.

The real attraction is the combination: you get one fantastic Cuban town (Trinidad), one interesting colonial city (Cienfuegos), and five days of increasingly wild islands and beaches.

⛵ Catamaran or monohull?

I'd choose a 40–45 ft catamaran for this trip. The shallow water around the Cuban cays makes a shallow-draught catamaran particularly practical, while giving you much more space for swimming, eating and relaxing.

One caveat: Cuba requires a little more logistical planning than Greece, Croatia or the Seychelles. Provisioning can be unpredictable, and customs/coastguard formalities are part of sailing there.

For weather, the traditional cruising window is roughly November–April, with December–April generally regarded as the strongest period for chartering.

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