Anguilla Holidays 2025 & 2026 | Caribbean

LUXURY ANGUILLA HOLIDAYS & TOURS

Tailor-Made Anguilla Holidays

The near year-round summer sun and the impeccable white sand.

LUXURY HOLIDAYS & TOURS ANGUILLA

IMPECCABLE WHITE SANDY BEACHES

Will you ever tire of the bliss of laying on the soft sand, the gentle waves of the warm sea washing over your feet, the sun slowly recharging your batteries with its solar power? Perhaps not. But…

Just in case you do manage to rouse yourself from the torpor induced by the turquoise sea, the rhythmic rustle of palm trees, the near year-round summer sun and the impeccable white sand – the island of Anguilla has some fascinating ‘other attractions’.

Ask our experts and they will mention Sandy Ground. It’s not another beach; it’s actually a charming, quiet village by day, transforming itself into the island’s entertainment capital by night. A Mecca of offbeat beach bars, light-hearted restaurants serving seriously good seafood and places for dancing, drinking and meeting up. The island has courts for tennis players or, if you’re a golfer, a challenging championship course.

And then there is the architecture. Wallblake House, across from the Old Cotton Gin, is the island’s last original plantation house. But Miss Marjorie’s, the Warden’s Place, Rose Cottage, the Old Salt Factory and Pumphouse are all living illustrations of Anguilla’s picturesque past.

There’s a picturesque present too. Island Harbour is astonishingly pretty – a delight for photographers – and if you’re a collector of breath-taking views you should climb Crocus Hill in time to witness the full glory of a fiery sunset spreading a golden cloak over the turquoise bay below.

WHERE TO STAY

ACCOMMODATION

With years of experience and first-hand knowledge, our dedicated team of Caribbean consultants will be able to find the perfect hotels and resorts for your Anguilla holiday.

VIEW ALL

WHY CHOOSE US

TRUSTED BY FELLOW TRAVELLERS

“IN SAFE HANDS, EVEN WHEN PLANS CHANGE”

Every detail of our Patagonia tour was expertly arranged – from transfers and flights to the choice of hotels. When our onward flight to the Falklands was delayed by two days, 91�� stepped in immediately and secured a hotel for us. It was an enormous relief, especially as we don’t speak Spanish and had no idea what to do next. That level of thoughtful, responsive service stayed with us – it turned a potential travel hiccup into a lasting positive memory.

“FLAWLESS, AGAIN”

This is the third time I’ve used TUTC. The service, as before, was flawless. Aside from putting in place all the major details of a complex trip to Japan, Dan at TUTC nailed every detail: train tickets were for seats with large luggage space (very important in Japan, as we discovered); a mobile internet wifi was included; together with a pre-charged use-pretty-much-anywhere travel card (again, important – Japan has multiple transport companies). For any kind of complex trip I won’t go anywhere else.

“EVERY TRIP EXCELLENT – AND MORE TO COME”

I’ve been on several small group holidays with 91�� and every one has been outstanding. My most recent trip in February was no exception – expertly organised, responsive to questions, and full of memorable experiences. The itineraries are well thought out, the hotels top-notch, and the group sizes just right. Their tour leaders are knowledgeable, supportive and great company. I haven’t looked elsewhere since discovering Ultimate – and I’m already planning my next.

DISCOVER MORE INDEPENDENT REVIEWS FROM FEEFO

5 OUT OF 5

WHEN TO VISIT

December – January

BEST TIME TO EXPERIENCE THE CULTURE AND FESTIVALS | 23°C – 29°C

January – April

BEST TIME TO VISIT FOR A QUIETER EXPERIENCE | 23°C – 30°C

April – August

CHEAPEST TIME TO VISIT | 24°C – 31°C

September – October

BEST TIME TO VISIT TO AVOID THE CROWD | 20°C

KEY FACTS

Anguilla

FLIGHT (FROM LDN)8 hrs (Indirect)
CURRENCYEast Caribbean dollar
POPULATION19.08K
BEST TIME TO GOMay – August
LANGUAGEEnglish
TIMEZONEGMT – 4
CAPITAL CITYThe Valley
GEOGRAPHIC SIZE91 km²

MEET THE EXPERTS

DESTINATION SPECIALISTS

Catherine

Catherine plans trips that leave you with stories to tell, whether driving California’s Pacific Coast Highway, snorkelling in the Maldives, exploring Lanzarote’s art and architecture, or island-hopping in the Seychelles.

Alison

Alison has been designing tailor-made trips for over 20 years, covering everything from European culture and Caribbean beaches to luxury cruises and skiing. She values the diversity of each trip and helping travellers find the right pace and style for them.

Sharon

Sharon designs trips that are about being there, feeling the reef below you in the Maldives, watching the sun set behind the Pitons of St Lucia, tasting your way through a souk. She brings a practical, global eye to planning across the Indian Ocean, Caribbean, Middle East and Europe.

ALL EXPERTS

FEATURED JOURNAL

INSPIRING STORIES

From the whispered secrets of centuries-old monuments to the vibrant accounts of our travel experts, let these tales ignite your imagination and inspire your travels.

VIEW ALL

Alison

Europe & Beyond Specialist