Luxury holidays to the Caribbean

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Search for your luxury, bespoke holiday to the Caribbean by region, special interest, theme or feature

Holidays by region

Search here if you want a single-centre, hotel stay on one particular Caribbean island, for example, Barbados or Antigua.

Holidays by theme

Search here for a themed holiday such as an island-hopping holiday, a suggested two centre holiday, family holidays, honeymoons and special occasions.

Holidays by special interest

Search here if you are looking for, for example, a spa holiday, a golf holiday, a sailing holiday or a diving holiday. Many more special interest holidays in the Caribbean to be discovered here.

Holidays by feature

Search here for a special featured holiday that might be with a seasonal angle such as carnival, festivals, regattas, cricket and other sporting events. Combined early booking and special offer ideas will be found here too.

Then once you have had a look, speak to us and let us guide you using our knowledge and experience of the country.

Luxury holidays to the Caribbean: luxury hotel holidays tailor-made to Caribbean islands

Luxury Caribbean holidays from Caribbean Expressions. We provide a wide range of luxury, tailor-made hotel holidays to Caribbean islands featuring the most characterful and most exclusive luxury hotels and resorts in the Caribbean. With Caribbean Expressions you benefit from over thirty years’ experience in constructing luxury, tailor-made holidays. Our bespoke luxury Caribbean holidays are about relaxation, comfort and good service, idyllic surroundings coupled with the opportunity to glimpse the flavour and colour of local life. From the better-known and much-loved islands such as Barbados, Jamaica, Antigua and St Lucia to the less well-known such as Nevis, Anguilla and Grenada plus the French-speaking islands of Guadeloupe and St Martin, Caribbean Expressions offers you a choice of islands of amazingly varied scenery and charm. A Caribbean Expressions holiday is tailor-made according to your exact requirements. The basis of our truly bespoke holidays lies in the wide range and diversity of islands and hotel accommodation that we have selected to offer you. Reflecting the charm and character of the Caribbean islands, our hotels provide the very best quality of accommodation, service and facilities in the Caribbean. There is a choice to suit a range of budgets as well as special interests, from honeymooners to families, from sailing enthusiasts to spa treatment devotees. Multi-island combinations are our speciality. This is what we really enjoy and where our knowledge of the Caribbean and our skill as a tour operator come to the fore. Remember that we know the islands and have done a variety of island-hopping combinations ourselves. Popular combinations might be Grenada, Barbados and St Lucia or Barbados, the Grenadines and Grenada or Antigua, Anguilla and Nevis. Just let us your plans and we will execute them for you.

Our bespoke, luxury hotel holidays can be

● Single centre or multi-centre
● Long or short stays
● Combine a variety of different hotels in different regions
● Utilise a variety of transport arrangements including scheduled flights, private shared charter flights and local transfers

Included in all our holidays

● Concierge service
● Handcrafted helpful hints and local information provided with all our holidays
● Personal service by your sales consultant who looks after all aspects of your holiday
● Full financial protection with our ATOL (3076) for all holidays including a flight and our ABTOT for all non-air holidays

Call us on 01392 441245

Luxury holidays to the Caribbean: luxury hotel holidays tailor-made to Caribbean islands

Whilst it’s obvious to us at Caribbean Expressions and to our many regular clients, it’s worth explaining, if you are a newcomer to our site and our programme of luxury hotel holidays, what our holidays are all about and how they work. Expressions Holidays provides a framework for flexibility, personal requirements and individual arrangements. Everything we offer on this website and from our brochure can be booked as it is, or usually, customised at the request of clients. This might mean adding extra nights, reducing nights from suggestions, upgrading room types and including special arrangements. Ideally, once you have had a look at our holiday ideas, we speak to you about what you are looking for, so that we can then put together the ‘package’ for you, creating a tailor-made holiday and a price, along with upgrade and downgrade options. We find it most productive for us and our clients if we talk through the quotation, explain the day by day details and the pricing options. Then you have the full facts available in order to make your decision.

Our hotels

Our hotels are the very best on each island in the Caribbean. They have been chosen by us because they have something of intrinsic value for our clients. Our hotels include sophisticated Carlisle Bay on Antigua, genteel Coral Reef Club on Barbados, fragrant Round Hill on Jamaica and the luxury boutique Calabash on Grenada. Each description on our website is a personal description which conveys the character of each one whilst providing indispensable facts.

Choice of board basis

We offer you a range of meal choices from room only, where you pay extra either to us in advance or direct to the hotel for the meals you eat, to all-inclusive, where all meals and drinks by the glass are included. Some hotels opt for one or other arrangement, others offer you a choice. On Barbados many of the hotels offer a dine around option if you book half-board for your entire stay, which allows you to exchange your dinner at the hotel for a dinner at a local restaurant. Families often find the full board or all-inclusive arrangement excellent value for money, whilst people who want to dine out and about more might find a room only or a bed and breakfast arrangement more to their liking.

Travel

We have worked with British Airways for many years and include their scheduled flights in our basic holiday prices. Virgin Atlantic is also offered on applicable routes.

Premium cabins

We offer you advantageous prices for flying in the premium cabins with all our airlines. With British Airways there is a choice of Club on all routes, FIRST on Barbados and sometimes on St Lucia and World Traveller Plus is available on Barbados, St Lucia, Grenada, Tobago, and Nassau. Virgin Atlantic offer Upper Class and Premium Economy on all their routes to the Caribbean. The best possible supplement for these services can be provided by calling us.

Private charters

For many people, a private charter is the best way to island hop in the Caribbean. In a region of small islands, private aircraft are plentiful and have become the way to travel around. For certain destinations, we include private charters automatically in the holiday price, but on a shared basis, meaning that you may travel on the aircraft with the maximum number the plane holds, usually up to 5 or 8 passengers. However, if you want the privacy of your own plane, then Caribbean Expressions will arrange this for you in advance. The most frequently used routes for private charters are between Barbados and Mustique or between Antigua and Anguilla, Nevis and St Barts. Private charters are possible between most Caribbean islands - just ask us for a price.

Transfers

Caribbean Expressions has arranged for you to have private car transfers arranged by us or by the hotel. If the hotel makes the arrangements it is possible that you will share the car, which on many islands is a mini-bus or space wagon type vehicle seating up to 7 passengers, with other hotel guests arriving on the same flight. Sometimes these vehicles are air-conditioned.

Our bespoke, luxury hotel holidays can be

Included in all our holidays

Call us on 01392 441245

Luxury holidays to the Caribbean: luxury hotel holidays tailor-made to Caribbean islands

Luxury holidays to the Caribbean from Expressions Holidays aim to present you with the charm and allure of the Caribbean. The Caribbean is a familiar friend of a holiday destination that is most definitely a tropical paradise of translucent, turquoise waters, seemingly endless soft white-sand beaches and swaying groves of lush coconut palms. But it is also vibrant and fun, a zesty, spirited place where you are seduced by a warmth and the charm of its peoples. The fragrance and colours create a magical kaleidoscope that welcomes and relaxes.

Islands of the Caribbean

Think of the Caribbean, and you can’t help but picture palm-fringed beaches and gin-clear seas, rum punch cocktails and steel drum bands. The Caribbean is the perfect destination for a luxury holiday, offering sunshine, culture, activities and wonderful hotels. From Antigua to Grenada, the Caribbean is studded with some of the most indulgent and exclusive private-island hotels and beach resorts on earth. For most visitors, that’s more than enough: getting away from the beach means going out for a snorkel or hopping out on a windsurfer. Who can blame them? Sifted by the steady, gentle Tradewinds, with excellent coral reefs and an abundance of marine life, the Caribbean is a water sports Promised Land. However, dig a little deeper, and the Caribbean is a fascinating, diverse holiday destination, suffused in history, with each island boasting its own unique character and personality. From the forts of Jamaica and churches of Barbados to the sizzling carnivals of St Lucia, the Caribbean resounds with echoes of its colonial past, with an architecture and attitude to match. Hire a car and you’ll stumble across cricket games, church choirs and beach bars with spontaneous parties – whilst being a fabulous place just to fly and flop, the Caribbean is also wonderfully rewarding to explore. Geographically, the islands vary dramatically. The low-lying coral islands – the Bahamas, for example - have the best bone-white beaches and swimming but are less interesting inland. Volcanic islands by contrast – for example, the Windward Islands such as St Lucia, St Vincent and Grenada – are more dramatic, covered in steep, tangled forest plunging dramatically into the sea, with classic crescent bays and palm-tree beaches, brilliant for birdwatching and hiking, mountain-biking and nature-trails.

Country facts

Unmissable holiday experiences in the Caribbean

Hiking in St Lucia up the famous Piton mountains, as well as Jump Up parties every Friday; flying over the islands of the Bahamas; exploring the parishes of Barbados; trekking the forested slopes of Jamaica’s Blue Mountains; sailing in the Grenadines; watching cricket on the national cricket pitch of tiny Nevis; swimming in the clear turquoise seas off Anguilla; enjoying a lime squash or a rum punch at sundown; visiting Andromeda botanic gardens on Barbados; visiting a nutmeg plantation on Grenada.

Call us on 01392 441245

Beach in Saint Kitts, golden sand, turquoise sea, palm trees

CARIBBEAN FAVOURITE HOTEL HOLIDAYS

A selection of some of our favourite luxury hotel holidays in the Caribbean on islands such as Barbados and Nevis, Grenada and Antigua.

Morris Bay Beach in Antigua, sand, blue ocean , palm trees

CARIBBEAN ALL-INCLUSIVE HOLIDAYS

Luxury all-inclusive hotel and resort holidays in the Caribbean, tailor-made. Tailor-made, all-inclusive hotel holidays to islands such as Barbados, Antigua and Grenada.

CARIBBEAN LUXURY FAMILY HOLIDAYS

Luxury family holidays to hotels and resorts in the Caribbean including Antigua, Barbados, Grenada and St Lucia. Luxury tailor-made holidays for families with children of all ages. Kids’ clubs and activities.

Salt Whistle Bay beach in the Grenadines, white sand, palm tree, boat on the water

CARIBBEAN SMALL ISLAND HOTEL HOLIDAYS

Luxury hotel holidays to the smaller islands of the Caribbean providing a private-island experience or an authentic flavour of the Caribbean. Bespoke with travel included.

Paradise Beach in Saint Lucia, sand, sea, palm trees, Piton in background

CARIBBEAN TWO-CENTRE HOLIDAYS

A selection of suggested two-centre island holidays in the Caribbean, perhaps combining luxury hotel stays in two places such as St Lucia and Grenada or Nevis and Antigua.

Twin Pitons rock formation in St Lucia, sunset over rocks and ocean

BARBADOS AND ST LUCIA TWO-CENTRE HOLIDAY

10-night two-centre island combining Barbados and St Lucia in the Caribbean. Stay in two luxury boutique hotels, the Sandpiper and Anse Chastanet. From £4,520 per person.

Paradise Beach in Soufriere Bay in Saint Lucia, Piton in the background

GRENADA AND ST LUCIA TWO-CENTRE HOLIDAY

10-night two-centre island combining Grenada and St Lucia in the Caribbean. Stay in two luxury boutique hotels, the Calabash and East Winds Inn. From £4,680 per person.

Beach on the Grenadines, white sand, blue seas, palm tree

BARBADOS AND THE GRENADINES TWO-CENTRE HOLIDAY

10-night two-centre island combining Barbados and the Grenadines in the Caribbean. Stay in two luxury, charming hotels, Coral Reel Club and Petit St Vincent. From £5,990 per person.

Nevis beach, sand, sea, ST Kitts and the Narrows in the background

NEVIS AND ANTIGUA TWO-CENTRE HOLIDAY

10-night two-centre island combining Nevis and Antigua in the Caribbean. Stay in two luxury, charming hotels, Montpelier Plantation and Blue Waters. From £4,250 per person.

BLUE WATERS Antigua

A luxury resort with a wide choice of accommodation: rooms, suites and villas. Good for adults and families, with a wide range of activities and restaurants.

CARLISLE BAY Antigua

A luxurious beach resort with contemporary accommodation in suites, suitable for families and couples with an extensive offer of activities and facilities. Top quality.

ST JAMES'S CLUB Antigua

This is an all-inclusive resort with two superb beaches, numerous watersports, pools and restaurants and a large choice of rooms. Ideal for families. Excellent value.

COLONY CLUB Barbados

A luxury hotel with 96 rooms on an excellent beach on the west coast, offering elegant and traditional style with contemporary leisure facilities and a water taxi.

PORT FERDINAND Barbados

This is a sophisticated, self-catering resort on the north-west coast in a waterside location on a marina with choice of dining, watersports and water taxi service.

Aerial shot of St Peters Bay resort, pools, palm trees, hotel buildings, sea in background

ST PETERS BAY Barbados

A resort of self-catering villa suites, ideal for families, on the north-western coast of Barbados. Excellent water sports and kids' activities. Water taxi service.

Sandpiper Barbados pool and sun loungers ocean in the distance

THE SANDPIPER Barbados

This is a small, luxury hotel with 52 rooms and suites on a beach on the west coast. It offers a high-quality yet relaxing atmosphere. Charming attention to detail.

TURTLE BEACH Barbados

This is a south-coast beach resort of 101 suites, all-inclusive, and ideal for families. Kids' club, spa, tennis and water taxi to west coast included.

MOUNT CINNAMON Grenada

A luxury boutique resort on Grand Anse Beach with villa-suite accommodation ideal for couples and families. Good facilities and spa. Lots of acitvities.

HALF MOON Jamaica

This is an extensive resort with hotel rooms and villa accommodation in a beachfront location. Extensive choice of dining, land and watersports. Ideal for families.

Round Hill Jamaica lobby veranda gardens and trees

ROUND HILL Montego Bay

A luxurious beach resort with villas and hotel rooms, with spa and two beaches, about 10 miles from Montego Bay. Beautiful gardens.

FOUR SEASONS RESORT Nevis

A magnificent beachfront resort with hotel rooms and villas, golf course and tennis courts. Spa and activities for the children. A world-class resort.

Sugarbeach St Lucia outdoor seating area beside the beach

SUGAR BEACH, A VICEROY RESORT St Lucia

This elegant and luxurious resort nestling in tropical gardens in the south of St Lucia has 96 luxurious rooms, suites and residences. Extensive leisure activities and facilities. Top quality.

WINDJAMMER LANDING St Lucia

A superior, Mediterranean-inspired resort with 191 rooms, suites and villas on a lovely beach with extensive facilities and leisure activities, ideal for families.

Cuisinart Anguilla villas overlooking beach

CUISINART GOLF RESORT AND SPA Anguilla

A luxurious golf and spa resort with suites and villas in lush gardens overlooking white sand beaches in Anguilla.

Malliouhana birds eye view of beach showing sand and ocean with boats in the sea and buildings around the outskirts of the sand

MALLIOUHANA Anguilla

A luxury beach resort with a light and breezy feel with spacious rooms and suites on a bluff with long beaches and coves nearby.

Turquois sea and white sand beach with hills and palms beyond

CURTAIN BLUFF Antigua

An exclusive beach resort with excellent watersports and tennis, operating on a top quality all-inclusive basis. Rooms and suites on the beach and the bluff.

GALLEY BAY Antigua

A popular all-inclusive adults-only beach resort with 98 rooms with a range of accommodation on or very near the sandy beach. Wide range of sporting activities.

HERMITAGE BAY Antigua

An exclusive boutique luxury beach resort with just 30 spacious cottage suites near the beach or with outstanding views.Over 14s only. A calm and sophisticated ambience.

Aerial shot of Hodges Bay Resort, beach, white sand, hotel buildings

HODGES BAY RESORT AND SPA Antigua

A contemporary boutique beach hotel on a sandy cove with spa and wide choice of 79 rooms, suites, apartments and villas.

INN AT ENGLISH HARBOUR Antigua

A boutique luxury beach hotel with just 28 rooms and suites in an attractive bay near English Harbour. Some rooms beachfront. Half-board and all-inclusive offered.

JUMBY BAY Antigua

This superb island-resort offers world-class facilities and services in a stunning island setting about 10-minutes by boat from Antigua's mainland. Ultra-luxurious accommodation.

NONSUCH BAY Antigua

A resort on the east coast of Antigua offering all-inclusive for adults only and self-catering for families.

Exterior shot of South Point, hotel building, beach

SOUTH POINT ANTIGUA Antigua

Boutique, all-suite hotel on the seafront with marina views near English Harbour. One and two bedroom suites with kitchens.

THE VERANDAH Antigua

A superior 4-star adults-only, all-inclusive resort with a range of suites with a Caribbean feel.

FOUR SEASONS OCEAN CLUB Bahamas

An exclusive Four Seasons beach resort on Paradise Island posseses a fine white sand beach, excellent leisure and sports and beautiful gardens.

KAMALAME CAY Bahamas

This is an intimate and informal, all-inclusive, boutique hotel on a large, natural island offering long beaches, reef and bonefishing.

PINK SANDS Bahamas

This boutique hotel in the Bahamas offers laid-back, stylish informality on a long stretch of pink-sand beach.

Great House with pink exterior building, white shutters covering the windows and palm trees around

COBBLERS COVE Barbados

A boutique, beachfront hotel in a secluded west coast location, with 40 suites combining cosiness and style, with the ambience of a country house in a tropical climate.

CORAL REEF CLUB Barbados

A top quality traditional, charming hotel on a lovely West Coast beach, amidst beautiful tropical gardens offering excellent service.

CRYSTAL COVE Barbados

A modern-style, beach resort on the West Coast that exudes a cheerfulness with its light and airy decoration and lagoon-style swimming pools.

FAIRMONT ROYAL PAVILION Barbados

A luxury, beachfront hotel on the West Coast with the feel of a tropical plantation house with 72 rooms and suites, offering fine dining and numerous leisure activities.

Little Arches Barbados main building with pool and palm trees

LITTLE ARCHES BOUTIQUE HOTEL Barbados

This is a boutique resort with just 10 rooms and suites for over 16s only with a relaxed and charming atmosphere. Nightlife and restaurants at nearby Lawrence Gap.

TAMARIND Barbados

This is a contemporary resort in a prime location on the west coast with an excellent beach and wide range of facilities.

THE HOUSE Barbados

A refinded and calm boutique hotel on the west coast, for adults only with 32 elegant and spacious suites. All-inclusive.

TREASURE BEACH Barbados

With just 35 suites, this is a small, luxury hotel on all-inclusive for over 18s only on a west coast beach set in lovely gardens. Very good restaurant.

WAVES Barbados

A well-priced, all-inclusive beach resort with 70 rooms for couples and families on the west coast. Excellent spa and adult only rooms in one section.

CALABASH Grenada

This is an outstanding luxury, boutique hotel with just 30 spacious suites on a secluded, long bay. Outstanding service, cuisine and atmosphere.

LALUNA Grenada

This is a boutique hotel with just 16 cottage-style rooms with plunge-pools, decorated in sensual colours, on the hill-side descending to the beach.

SILVERSANDS Grenada

A new concept in luxury in the Caribbean with its 52 rooms, suites and residences on Grand Anse Beach. Sleek, modern but ultra-luxurious. A 100-metre long swimming pool.

SIX SENSES LA SAGESSE Grenada

A luxury boutique resort with 56 pool suites and 15 villas in natural surroundings on bluff and beach. Sustainability is a key feature. Six Senses Spa.

Spice Island Grenada entrance with trees and shrubbery

SPICE ISLAND BEACH RESORT Grenada

A popular, traditional, top quality beach resort on Grand Anse beach with 64 spacious suites, some beachfront, with outstanding restaurant, spa and watersports.

HERMITAGE INN Nevis

A charming, boutique, historic hotel with 14 rooms in the foothills of Mount Nevis about 15 minutes' drive from the beach.

MONTPELIER PLANTATION Nevis

An authentic, boutique, plantation-house hotel in the countryside of the island, adorned with local works of art. Intimate and cosy, ideal for a twin-centre.

ANSE CHASTANET St Lucia

This is a superior boutique hotel on its own beach with 49 rooms with amazing views of the Pitons in the south of St Lucia. Authentic creole ambience and great food. Good for diving.

Calabash Cove St Lucia resort exterior hotel main building pool

CALABASH COVE RESORT AND SPA HOTEL St Lucia

A boutique luxury hotel with 26 cottage-rooms and junior suites in the north-west of St Lucia. Over 18s only. Spa, restaurant, pool, swim-up bar, beach and lush gardens.

View of the pool at sunset with palm trees and chairs around and yellow sun setting in background

CAP MAISON St Lucia

This is a stylish boutique hotel with 49 rooms and suites overlooking a sandy cove about 20 minutes from Castries. Excellent restaurant, watersports, gym, spa and yoga.

EAST WINDS INN St Lucia

A traditional hotel, boutique with just 30 cottage rooms, is all-inclusive in its own lush gardens alongside a sandy beach. Excellent food and charming service.

JADE MOUNTAIN St Lucia

A luxury resort with just 24 suites, futuristic in archictural conception and eco-sensitive. Luxurious space, amazing views and excellent service. Unique in the Caribbean.

Serenity Coconut Bay St Lucia aerial shot of pool swimming pool plunge pool sun loungers umbrellas

SERENITY AT COCONUT BAY St Lucia

This is an all-inclusive, all-suite, adults only resort in the south of St Lucia. All suites have their own plunge pool and butler service. Oceanfront spa for relaxation.

THE BODYHOLIDAY St Lucia

A resort known for its all-inclusive arrangements with extensive sports facilities. One spa treatment per person a day included. Choice of dining. Excellent for single travellers.

La Samanna St Martin hotel exterior pool white building balconies gardens

BELMOND LA SAMANNA St Martin

The luxurious Belmond resort-hotel has 83 rooms and suites and combines American comfort and French flair. Location on an amazing beach. Good land and water sports.

Bequia Beach hotel exterior, buildings, gardens, lawn, palm trees

BEQUIA BEACH HOTEL Bequia

A cheerful, charming, beachfront hotel with 57 rooms on the island of Bequia. Low-key and relaxing with water sports and choice of dining.

COTTON HOUSE St Vincent and the Grenadines

This is a world-famous, luxury, boutique hotle with just 17 rooms and suites in luxuriant grounds on the exclusive island of Mustique.

PALM ISLAND St Vincent and the Grenadines

This is a relaxed but characterful, all-inclusive, island-resort reached by boat from Union Island with just 43 rooms and suites, all very close to the beachfront. Excellent for sailing, fishing, snorkelling. No chlidren under 12.

Petit St Vincent beach villa exterior decking out door seating sun loungers hammock

PETIT ST VINCENT St Vincent and the Grenadines

This is a luxurious boutique hotel with just 22 suites on a private island in the Grenadines, reached by boat from Union Island. Low-key luxury is the watchword here. Day charters to the Tobago Cays.

COCO REEF Tobago

Coco Reef offers excellent value on the laid-back island of Tobago. Worth upgrading to all-inclusive.

THE VILLAS AT STONEHAVEN Tobago

A country resort of just 14 spacious villas with private kitchen. Restaurant, pool and club house bar in the grounds. Beaches are five minutes away by car.