fbpx
Hosted Villas
Search
Start Planning1-800-374-6637
Contact Information: 1-800-374-6637

A Perfect Week in Anguilla

Category: Destination Guides | 11.5.2025

Would you like to have a festive dinner cooked and served to your group at your villa? On Anguilla, the island has more than 70 restaurants pushing the boundaries of Caribbean gastronomy — and in 2025, the food scene is stronger than ever, with new chef-led concepts and culinary festivals adding extra flavour.


Relax on nearly thirty-three pristine beaches with tranquil turquoise water and no crowds of high-rise hotels; explore dive sites and coral gardens where sea life plays among vibrant reefs. Or how about mixing with the locals at live-music beach bars, under a star-filled sky? Welcome to Anguilla — your perfect week awaits.

Why Anguilla?

This British Overseas Territory in the Caribbean remains wonderfully boutique and lightly travelled, located east of Puerto Rico and the Virgin Islands, and north of St. Martin. In 2025, the island is set to accelerate its luxury offering, with new resorts, improved connectivity, and a full calendar of festivals all in motion.

Here you’ll find white-sand shores untouched by mass tourism, set against an island of character, culture and elegance.

2025 Highlights & Trends

  • The Anguilla Summer Festival (July-August) returns with a full parade line-up, boat races, and music events.

  • New ultra-luxury resorts and wellness experiences are set to arrive in 2025, making Anguilla even more appealing to high-net-worth travellers.

  • Improved connectivity and boutique-scale development mean you can reach Anguilla more smoothly while retaining its off-the-beaten-path character.

  • Sustainability and conservation are top of mind: marine parks, heritage sites & low-impact tourism remain priorities.

Must-Do, Can’t Miss (2025 Edition)

  1. Bike or stroll along the island’s legendary boat-racing shores

  2. Visit at least one of the 33 beaches — Shoal Bay, Little Bay, Captain’s Bay all standout

  3. Attend Anguilla’s Summer Festival or Culinary Experience (April & July/August)

  4. Dine at a villa-chef and explore the elevated food scene

  5. Book a private yacht or sailing excursion among the cays

Beach Day One – Arrival at the Villa

You’ll be greeted at your villa by dedicated staff, settle into your private sanctuary, grab a slow swim in a calm bay and ease into Caribbean time.

Day Two – Beach Hopping & Snorkelling

With 33 beaches to explore, you might start with Shoal Bay East — often ranked among the world’s top beaches — or choose the secluded Little Bay, accessible only by boat, for a feel-like-your-own-private-cove luxury.
Snorkelling gear in hand, you’ll explore coral gardens and hidden dive wrecks — part of Anguilla’s five marine parks and nine dive sites.


Add a spa treatment or a private chef dinner at sunset for the perfect blend of activity and indulgence.

Day Three – Culture & Heritage

Take a deeper look at the island’s history. The Heritage Trail leads you through 10 historic sites — from colonial architecture to plantation-era landmarks, such as Wallblake House.


You’ll gain insight into the island’s past and present through engaging, walkable exploration.

Day Four – Water Adventures

Whether you’re into kite-surfing, paddle-boarding, fishing or diving, Anguilla delivers. From the calm waters of Shoal Bay East to the more active sport conditions at Savannah Bay, choose the pace that fits your mood.


Chartered trips, full-day fishing excursions, and private boat tours add a luxury travel edge.

Day Five – A Day at Your Villa

Sometimes the best day is the quiet one — relax by the pool, enjoy a private yoga session on the terrace, or book an in-villa masseuse for a bespoke spa experience.

Your villa team is on call; they’ll ensure you stay completely in the moment without worrying about logistics.

Day Six – Explore Inland

Beyond beaches, Anguilla offers nature and activity: bird-watching at salt-ponds like Cauls Paul Pond, cycling scenic routes, or even arranging a round of golf or horseback ride on the sand.


Dinner at the iconic eatery Straw Hat Restaurant on Meads Bay rounds out the experience with island-inspired cuisine and ocean-front ambiance.

Day Seven – Choose Your Adventure

The last full day? You pick the tempo. Want more beach loungin’ and villa time? Done. Want a thrilling boat ride to offshore cays like Scrub Island and Dog Island? We’ll arrange it.


Boat racing remains the national sport, and you might find yourself watching or even participating in a local sailing event.

Day Eight – Departure

It’s time to pack, breathe one more salty breeze, and whisper “see you soon” to Anguilla. Something tells us you’ll be back.

Your perfect week in Anguilla starts here — explore our curated Anguilla villas and connect with an Experience Manager to start crafting your bespoke island getaway today.

If you liked “A perfect week in Anguilla” you might also like articles about other Caribbean destinations:

Close Close the modal