Anguilla, Caribbean
Le Toiny Beach Restaurant
Saint Barthelemy, a French-speaking Caribbean island commonly known as St. Barts
Belmond Cap Juluca, Anguilla

...Trip idea

Chic Caribbean Contrast

Enjoy a holiday in the Caribbean where you stay at two of its most exclusive islands – beautiful St Barths and exquisite Anguilla.


  • Enjoy a more immersive holiday in the Caribbean where you can soak up the cultural nuances of two different islands
  • Experience some of the best Caribbean accommodation at Le Toiny, St Barths and Belmond Cap Juluca on Anguilla
  • Explore breath-taking beaches and enjoy an excellent culinary scene in Anguilla
  • Lap up the exclusive social ambience and great French food on St Barths


A two-week trip that takes in two gorgeous Caribbean islands, staying in two world-class hotels.

When to go:

For sunny skies and warm weather we recommend heading to the Caribbean from November to April

How to get there:

Fly BA or Virgin Upper Class from London to Antigua and connect to Anguilla by charter flight. Onto St Barths, you’ll take another charter flight to the island.

Anguilla, Caribbean
Anguilla, Caribbean

Exceptional Anguilla

Without an international airport on its island, coming to Anguilla requires that bit more effort, connecting via Antigua. But it’s really worth the extra jump for a quieter more authentic atmosphere. On arrival you’ll be greeted by a warm, tropical breeze, exotic beaches framed by coconut trees, beach bars doling out rum punches accompanied by reggae music and all around the dazzling Caribbean Sea with its promise of swimming, sailing and snorkelling.

Only 16 miles long, Anguilla is a great island to enjoy beach life – with over 30 of them – from tiny, perfect coves or larger swathes of bone-white sand that come with excellent shoreside restaurants. Just offshore are the achingly beautiful Prickly Pear Cays, accessible by private yacht, revealing a chain of lush islands ringed by white sand that gives way to colourful coral reefs.

Belmond Cap Juluca

Scattered along a semi-circle of pristine beach, widely considered to be Anguilla’s finest, Belmond Cap Juluca is found on the white sands of Maundays Bay. Depending on your needs, take charge of a spacious villa with a private pool, garden, terrace and dining area. The villas open out onto the beach, where your private loungers await alongside an efficient beach service. Also along the shore is the Cap Shack for feet-in-the-sand dining at the food truck to the sound of reggae; for something more refined head to Cip’s by Cipriani. Finish your day the spa – with an irresistible mix of healing traditions and modern-day therapies.

Saint Barthelemy, a French-speaking Caribbean island commonly known as St. Barts
Saint Barthelemy, a French-speaking Caribbean island commonly known as St. Barts
Hotel Le Toiny, St Barths Caribbean
Saint Barthelemy, a French-speaking Caribbean island commonly known as St. Barts
Hotel Le Toiny, St Barths Caribbean

Buzzy St Barths

From Anguilla you will move to your next island paradise –Saint Barthelemy, known as St Barths, although some refer to it as the ‘St Tropez of the Caribbean’. By scheduled Tradewinds charter, you will reach French-speaking St Barths, your home for the next week. In between the lush interior, red-topped roofs and encircling, unspoiled beaches and glittering turquoise water, St Barths harbours a well-heeled community that like to holiday in low-key privacy on this exclusive island.

In-the-know spots include boutique shops in the town of Gustavia, beach club Shellona, whimsical cocktail bar Bonito and seafood fine dining at Maya’s – the fun part is finding the party at various restaurants and beach bars. By day, most people head to one of the island’s stunning beaches such as Colombier or Flammand, lulled by the waves and the scene of picturesque beauty. Out at sea, hire a yacht to drop anchor at idyllic spots accompanied by a gourmet picnic. As your holiday comes to an end you will board a charter back to Antigua before your international flight home.

Le Toiny two-bedroom villa

Le Toiny St Barths

Quiet and understated, perfect for those seeking a discreet, romantic glamour and the ideal respite from St Barth’s high society whirl, Le Toiny is located up and away on a verdant hill. The rooms are known for their refined elegance – each coming with a private plunge pool and views that stretch to the Caribbean Sea. Mornings are slow here – with a brimming breakfast tray delivered to your room so you can enjoy the tranquillity of the view from your terrace, before heading to the spa or one of St Barths glamourous restaurants. To get to the beach, grab a lift with a waiting jeep - once there you can enjoy one of the most peaceful beaches on the island.


Sophisticated but charming sums up both St Barths and Anguilla – two islands that will wow you with their exquisite natural beauty paired with an upmarket hospitality scene – and with two excellent hotels to retreat to, you can decide how active you’d like to be on holiday.

“This is the perfect combination holiday for our clients who don’t like to be stuck in a resort but prefer to get out and about and experience island life.”

Have questions? Our knowledgeable team of experts are on-hand to take your call or if you prefer by Zoom. Talk to us about your holiday dreams or challenge us with your travel conundrums.

Get in touch

Keep Browsing

Enjoy reading our colourful collection of travel blogs, insider journeys and first-person insights. Our articles are designed to fuel your wanderlust. Feeling inspired? Give us a call and our experts can start planning your next travel experience.

The collection
Caribbean Islands for Families

Gorgeous beaches are a given in the Caribbean, but each island varies hugely. Which resort should you choose for your family?

Sugar Beach, St Lucia, Caribbean
Booking with Bailey Robinson means access to the finest travel experiences. When planning your holiday we do all the hard work – in-depth research and meticulous organisation. You can be confident in the individual care for your holiday from your dedicated and experienced Personal Travel Designer and Concierge.
The Ultimate Caribbean
Mustique Private Island, Caribbean
The Other Caribbean – St Kitts & Nevis
Park Hyatt, St Kitts, Caribbean
Saint Kitts and Nevis
Travel Ideas