Inspiration
Caribbean Contrast: Antigua to Anguilla
This twin-island escape invites you to experience two distinct sides of the Caribbean.
Sunkissed shores and slow rhythms
From the sun-drenched beaches and lively charm of Antigua to the serene elegance of Anguilla, you’ll soak up the rhythm, colour and character of island life at its most refined.
Snorkel in turquoise coves, explore colonial harbours and unwind in barefoot luxury with space to move at your own pace. Whether you’re sipping rum to the sound of steel drums or kayaking under a canopy of stars, this is a journey to savour, slow down and reconnect with the beauty of the present moment.
- Antigua
- Anguilla
Nici Davies
With over 30 years of expertise at Travelwise, Nici specialises in family adventures, luxury ski holidays and indulgent beach escapes. Her extensive knowledge of diverse destinations allows her to offer the perfect suggestion, even when you're not exactly sure what you're looking for.
Antigua
Your Caribbean journey begins on Antigua, an island with a beach for practically every day of the year. Base yourself on the island’s unspoilt southwest coast, where lush hills give way to soft white sands and calm, clear waters. The pace is relaxed and the atmosphere joyful, with plenty of ways to explore both land and sea.
You could choose to snorkel over coral reefs at Prickly Pear Island, wade through stingrays at Stingray City or walk to the lookout at Shirley Heights for panoramic sunset views backed by the sound of steel drums.
Take time to visit the UNESCO-listed Nelson’s Dockyard and stroll the historic harbour at English Harbour, or just spend your days unwinding by the water with a good book and the sea breeze.
This is island life at its most effortless: rich in history, colour and natural beauty, with every moment designed to help you disconnect and slow down.
While in Antigua:
Snorkelling at Cades Reef
Head out by boat to this vibrant marine reserve, just off the island’s southwest coast. Swim among coral gardens, tropical fish and the occasional sea turtle in crystal-clear waters.
Sunset at Shirley Heights
Join locals and visitors for a Sunday evening tradition: steel drum music, Caribbean barbecue and panoramic views over English Harbour as the sun dips below the horizon.
Private heritage tour
Dive into the island’s past with a guided tour of Nelson’s Dockyard, Clarence House and the island’s historic sugar mills, ideal for culture lovers and curious minds.
Helicopter flight to Montserrat
For something truly unique, take to the skies on a short helicopter tour over neighbouring Montserrat. See the dramatic lava fields and volcanic peaks from above.
Anguilla
A short flight brings you to Anguilla, renowned for its understated charm. With powder-soft beaches, turquoise waters and a slower rhythm, this is the perfect place to truly unwind.
Explore the island at your own pace – maybe by hiring a colourful moke and driving between hidden coves and laid-back beach bars. Spend a day at Sandy Island, a tiny islet surrounded by crystal-clear sea or take in sweeping views of the Atlantic from the Anguilla arch viewpoint. As the sun sets, swap sandy shores for a glow-in-the-dark kayak on a night paddle beneath the stars.
This final stretch of your journey is all about stillness, space and simplicity: the kind of calm that stays with you long after you’ve left.
Glow-in-the-Dark Kayaking in Anguilla
As the sun sets over Anguilla, the ocean takes on a new kind of magic. Slip into a transparent kayak lit from beneath, and glide across the glowing water under a canopy of stars. This otherworldly night-time paddle reveals the bioluminescent shimmer of the sea, with each movement leaving a trail of light behind. Silent, surreal and deeply soothing, it’s a chance to see the Caribbean in an entirely new light – literally.
While in Anguilla:
Sailing to Prickly Pear Cays
Set off on a catamaran for a peaceful day at sea, stopping to snorkel, swim and enjoy lunch on this tiny, uninhabited island surrounded by reef.
Gallery hopping in the Valley
Spend a morning exploring local art at small galleries and creative studios in the island’s cultural heart. Meet local artists and browse unique works inspired by island life.
Rum tasting at a beach bar
Sample the Caribbean’s finest at one of Anguilla’s relaxed beach bars. Learn about local blends and distilling traditions with your toes in the sand and a sunset in view.
Scenic coastal drive to Shoal Bay
Hire a moke and head east to discover one of the island’s most beautiful beaches. Stop along the way for photos, beach walks and a fresh seafood lunch.
Talk to our specialists to start planning your trip
