Holidays in Anguilla

Tailor-Made Holidays to Anguilla – Your Bespoke Caribbean Escape

When you imagine the perfect Caribbean holiday, chances are you picture flawless white-sand beaches, warm turquoise waters, and days that unfold at a pace set entirely by you. Welcome to Anguilla – a small, refined island in the British West Indies that offers all of that and more. Unspoilt yet sophisticated, Anguilla is the kind of place that makes seasoned travellers fall in love instantly. For UK visitors, it’s an exclusive hideaway where luxury comes with a smile and the atmosphere is unhurried.

With our tailor-made Anguilla holidays, you’re not booking a package – you’re designing a personal journey. Whether you dream of beachfront villas, romantic boutique hotels, private yacht charters, or a week hopping between the island’s thirty-three beaches, every element can fit your style. From the moment you leave the UK to the last sunset cocktail, we create a seamless escape where the only surprises are the pleasant kind.

Why Choose Anguilla?

Anguilla is a place where luxury blends with authenticity. Anguilla is not the Caribbean of crowded cruise stops or souvenir stalls. Instead, it’s a haven of low-rise architecture, pristine bays, and a warm local culture that’s as genuine as it is welcoming. The island is only 16 miles long and 3 miles wide, yet it’s home to some of the finest beaches in the world, often fringed by nothing more than coconut palms and a scattering of beach bars.

It’s small size means you can truly make it your own. Explore hidden coves, discover secret snorkelling spots, or enjoy a private picnic delivered to an empty stretch of sand. And when you’re ready for fine dining, Anguilla punches well above its weight, boasting award-winning restaurants and some of the Caribbean’s most innovative chefs.

Tailor-Made Travel from the UK

Getting to Anguilla from the UK is part of the adventure. There are no direct flights from London, which is precisely why the island feels so exclusive. Most visitors arrive via Antigua or St Maarten, where we arrange smooth, stress-free transfers, usually a quick inter-island flight to a scenic boat ride across crystal-clear waters.

As part of your tailor-made holiday, we’ll design an itinerary that suits your preferences:

  • Overnight city stopovers in Antigua or Miami for those who like to break up the journey.
  • Private transfers that whisk you from plane to beach without queues.
  • Flexible dates and durations, so you can stay as long as you like.

Whether you’re a couple seeking barefoot romance, a family craving quality time, or a group of friends celebrating something special, we’ll handle all the logistics so you can focus entirely on enjoying Anguilla.

When to Visit

Anguilla enjoys a warm, sunny climate year-round, with temperatures typically ranging from 26°C to 30°C. The high season runs from December to April, when the island is at its most vibrant and the UK’s winter blues feel a million miles away. May to August is slightly quieter, offering better value without compromising on sunshine. September and October are the hurricane season’s peak, and many hotels close, so we’ll help you choose your dates to get the best of the island.

Accommodation Options

Your choice of accommodation will define the tone of your Anguilla holiday. Here are just a few favourites we recommend for UK travellers looking for that perfect mix of comfort, style, and service:

1. Belmond Cap Juluca

A legendary name in Caribbean luxury, Cap Juluca sits directly on the crescent of Maundays Bay, one of the most photogenic beaches you’ll ever see. The white Moorish-style villas are spaced along the shoreline, each with direct beach access and views across turquoise waters.

Perfect for: Couples and honeymooners who want pure romance, impeccable service, and an elegant yet relaxed atmosphere.

2. Zemi Beach House

On the powdery sands of Shoal Bay East, Zemi Beach House combines contemporary design with authentic Caribbean touches. The spa, set in a 300-year-old Thai house, is a standout, while the rum bar offers a taste of the island’s spirited culture.

Perfect for: Travellers who appreciate modern luxury with a strong sense of place.

3. Frangipani Beach Resort

A family-owned boutique hotel on Meads Bay, Frangipani offers a personal touch that larger resorts can’t match. Think beachfront rooms, water sports, and friendly staff who remember your name and favourite drink.

Perfect for: Families and small groups seeking a balance of activity and relaxation.

4. Private Villas

For the ultimate tailor-made holiday, consider a private villa. We can arrange everything from ocean-view hideaways for two to sprawling estates with infinity pools, private chefs, and direct beach access. Villas give you complete flexibility, privacy, and the chance to live like a local – albeit one with a very enviable address.

Perfect for: Multi-generational holidays, celebrations, or travellers who want total privacy.

Things to do Beyond the Beach

While Anguilla’s beaches are the headline act, there’s more to the island than sunbathing:

  • Sailing & Boat Trips – Charter a yacht to explore offshore cays such as Sandy Island or Prickly Pear, where powdery sands meet world-class snorkelling.
  • Gourmet Dining – From toes-in-the-sand BBQ shacks to Michelin-level tasting menus, Anguilla’s food scene is superb.
  • Music and Culture – The island has a vibrant live music scene, especially in beach bars and during festivals like Moonsplash.
  • Wellness – Yoga on the beach, luxury spa treatments, and sunrise meditations all fit seamlessly into island life.
  • Watersports – Kayaking, paddleboarding, and kite surfing for the adventurous.

Why a Tailor-Made Holiday Works in Anguilla

Unlike “off-the-shelf” packages, our Anguilla holidays are built entirely around your vision. That might mean:

  • Combining a luxury villa stay with a few nights in a beachfront hotel for variety.
  • Planning a multi-island itinerary, perhaps pairing Anguilla with Antigua or St Barths.
  • Including exclusive dining experiences, such as a private beach barbecue under the stars.

Our UK-based travel specialists work directly with trusted contacts in Anguilla, ensuring you get the very best rates, the finest rooms, and those little extras that make a holiday memorable.

Your Anguilla Story Starts Here

When you book with us, you’re not just visiting Anguilla, you’re curating your own Caribbean story. From the first conversation to the moment you land back in the UK with sand still in your shoes, every detail is tailored for you.