8 Days  •  7 Nights

Luxury Cuba: Havana, Trinidad & Private Cays

Havana (3N) - Trinidad (2N) - Cayo Santa Maria (2N)

Tour Includes

Accommodation
Meals
Sightseeing
Transfers
Local Guide
Activities
Overview

About the Trip

Cuba's rough-edged romance takes on a new glamour with this eight-day luxury journey, which pairs the island's cultural riches with its most characterful boutique hotels and seamless private touring. You stay in a beautifully restored mansion in Old Havana, sweep through the city in your own vintage convertible with a private guide and historian, and dine at the finest paladares. You continue to colonial Trinidad for its cobbled beauty and rooftop music, then unwind at an exclusive beach retreat on one of the northern cays, with private catamaran sails and toes-in-the-sand dining. Every transfer, guide and hard-to-get reservation is handled with care, and Cuba's inimitable atmosphere is delivered without a single logistical worry. It is the most refined way to experience one of the world's most captivating countries.
Highlights

Trip Highlights

  • A restored mansion hotel in Old Havana
  • Private vintage-convertible touring with a historian
  • The finest paladares and rooftop cocktails
  • Colonial Trinidad and its rooftop music
  • An exclusive beach retreat on the cays
  • Private catamaran sails and seamless service
Itinerary

Day by Day

A detailed day-by-day plan for this 8-day journey.

Day 1

Met at Havana airport and transferred in comfort to a beautifully restored boutique mansion in Old Havana. Settle into your suite and enjoy a gourmet welcome dinner at one of the city's finest paladares.

Your Journey This Day
Havana Airport
Arrival · Private luxury
Havana
Meals Included
Breakfast|Dinner
Day 2

A private walking tour of Old Havana with a historian, followed by your own vintage convertible sweeping along the Malecon at golden hour, ending with a rooftop cocktail and live music.

Meals Included
Breakfast
Day 3

A day to indulge at your own pace, a private cigar-and-rum tasting, exclusive art studios, a spa, or simply the pool and terrace of your mansion hotel.

Meals Included
Breakfast
Day 4

A private transfer south to colonial Trinidad, with a stop in elegant Cienfuegos on the way. Check into a boutique hotel and enjoy an evening of rooftop music.

Your Journey This Day
Havana
Road · Private luxury
Trinidad
Meals Included
Breakfast
Day 5

A private tour of Trinidad's plazas and mansions and the Valley of the Sugar Mills, with free time for craft markets and a final evening of live son.

Meals Included
Breakfast
Day 6

A private transfer along the causeway to an exclusive beach retreat on Cayo Santa Maria. Slip into barefoot luxury with a sunset cocktail on the powder-white sand.

Your Journey This Day
Trinidad
Road · Private luxury causeway
Cayo Santa Maria
Meals Included
Breakfast
Day 7

A private catamaran sail with snorkelling and drinks, and an afternoon on your beautiful stretch of beach, ending with a private dinner under the stars.

Meals Included
Breakfast|Dinner
Day 8

A final barefoot-luxury morning before your private transfer to the airport for your onward international departure.

Your Journey This Day
Cayo Santa Maria
Departure · Private luxury
Airport
Meals Included
Breakfast
Route Map

Where You Will Travel

Package

What's inside the package?

Inclusions

  • 7 nights accommodation in hotels or casas particulares
  • Daily breakfast, gourmet dining as specified, a welcome dinner and a private classic-car tour
  • Airport transfers
  • Touring and activities as per itinerary with English-speaking guides
  • Ground transfers between cities
  • Entrance fees as per itinerary
  • private Havana and Trinidad touring and a private catamaran sail

Exclusions

  • International airfare
  • Visa or tourist card fees where applicable
  • Travel insurance (strongly recommended)
  • Premium wines, spirits and cigars beyond those included
  • Optional private charters and experiences
  • Meals not mentioned in the itinerary or inclusions
  • Drinks unless specifically stated
  • Optional excursions and experiences
  • Personal expenses and gratuities
  • Anything not specifically mentioned under Package Inclusions
Best Time to Travel

Know when to go.

Place
Cuba
Conditions
Warm, dry
Daily max temperature
26°C
Monthly rainfall
60mm
Weather data is based on monthly averages. Popularity rating
Good to Know
  • Tourist card: Almost all visitors need a Cuban Tourist Card (visa) to enter, which we help you arrange before travel, along with a passport valid for at least six months. Requirements vary by nationality and by the country you fly from
  • US travellers: US citizens and residents face specific restrictions and must travel under one of the authorised categories rather than general tourism, and US-issued bank and credit cards do not work in Cuba; we will advise you carefully if this applies to you
  • Cash is king: Cuba is largely a cash economy and many foreign cards, especially those linked to US banks, do not work; bring enough cash (euros, pounds, Canadian dollars or US dollars) to exchange for local currency and cover your trip
  • Currency: The local currency is the Cuban Peso. Exchange rates and rules change frequently, so we brief you on the current situation before you travel and recommend carrying cash in good condition
  • Medical insurance: Proof of travel medical insurance is required to enter Cuba and is strongly recommended in any case; we can advise on suitable cover
  • Internet: Internet access is limited and can be slow, typically via wifi in hotels and public squares using prepaid cards; embrace the chance to disconnect and enjoy Cuba's music and street life
  • Best time to visit: The dry season from November to April offers the most pleasant weather and is ideal for sightseeing and beaches; the summer is hotter and wetter and falls within the Atlantic hurricane season
  • Casas particulares: Staying in a casa particular, a licensed private guesthouse, is a wonderful way to meet Cubans and enjoy home cooking; we can mix these with hotels to suit your comfort and style. Tipping in cash is customary and appreciated
FAQs

Frequently Asked Questions

What sort of hotels will we stay in?

You stay in Cuba's most characterful luxury properties, a restored colonial mansion in Old Havana, a boutique hotel in Trinidad and an exclusive beach retreat on the cays. Cuba's luxury tier is boutique rather than ultra-modern, which is part of its charm; exact properties are confirmed on booking.

Is everything private?

Yes — this is a fully private, tailor-made journey with private guides, a dedicated vintage car, transfers and a private catamaran, and hard-to-get restaurant reservations arranged for you throughout.

What meals are included?

Daily breakfast is included throughout, along with any meals named in the itinerary such as a welcome dinner. Cuba's paladares (private restaurants) and casa home-cooking are a highlight, so most lunches and dinners are left free, and we are happy to recommend the best.

Do I need a visa for Cuba?

Almost all visitors need a Cuban Tourist Card, which we help arrange before you travel. US citizens and residents face additional rules and must travel under an authorised category; we advise you fully based on your nationality.

Can I use my credit card and ATMs in Cuba?

Cuba is largely a cash economy, and many foreign cards, especially US-linked ones, do not work. Bring enough cash in euros, pounds or Canadian dollars to exchange; we brief you on the current money situation before departure.

When is the best time to visit Cuba?

The dry season from November to April is the most comfortable and popular, ideal for Havana, the colonial towns and the beaches. Summer is hotter, wetter and within the hurricane season.

Is Cuba safe for travellers?

Cuba is generally very safe for visitors, with low levels of violent crime and warm, welcoming people. As anywhere, take normal precautions with valuables, and your guides are on hand throughout to help.

Can the itinerary be customised?

Absolutely. We can adjust the balance of city, colonial towns and beach, mix hotels and casas particulares, add regions like Santiago or the cays, and tailor the pace to your interests.