A 2-week itinerary from Anguilla to Antigua

White sands, fringed by palms and lapped by impossibly clear waters. You might think that one Caribbean island is much like another. But hop between two or three and you’ll soon notice plenty of fascinating differences. From exploring Anguilla’s ancient history, relaxing on the beaches of St. Barthélemy and sailing and diving in Antigua, let our itinerary inspire you to cast your net a little further. All from luxury Caribbean hotels you can book with one call to our Travel Advisors. 


  • 2-week independent itinerary in the Lesser Antilles, starting in Anguilla and ending in Antigua
  • Spend days unwinding on beaches, exploring historic towns and sailing the seas, and nights staying at specially selected SLH boutique hotels
  • Highlights include sailing and diving in Antigua, and experiencing modern beach culture and ancient sites in Anguilla 


Anguilla, Carribean

Out of reach of most direct flights, Anguilla feels a little more off-the-beaten-track than destinations such as Barbados or Aruba. This pocket-sized island is somewhere to immerse yourself in Caribbean culture, past and present. Communities here are close-knit and welcoming, with locals running down-to-earth restaurants and laid-back beach bars. Let the live reggae draw you in and sip a classic Caribbean rum punch. Though you might find that no two punches taste exactly the same, as many bars serve up their own closely-guarded recipes.

Beautiful bays such as Shoal and Merrywing may have you never wanting to leave your sun lounger. But there’s plenty of natural beauty and ancient history to discover, too. From St. Gerard’s church in the island capital, Valley, with its mosaic-like stone arches. To Fountain Cavern National Park, where you can explore caves that were sacred to the island’s first inhabitants, Amerindian tribes who lived here over 3,000 years ago.


Experience Anguilla in boutique hotel style at The Reef by Cuisinart, a luxury resort with a spa and golf course, on Merrywing Bay.  Suggested stay 4 nights.

The Reef by CuisinArt


With its dramatic volcanic landscapes, paradise beaches and sleek towns, St. Barthélemy is one of the Caribbean’s most exclusive destinations. And, following 2017’s hurricane, the island is getting back to business as usual, with many St. Barthélemy luxury hotels welcoming guests from autumn 2018.

With almost every Caribbean island boasting stunning beaches, what makes St. Barthélemy – or St. Barth, as it’s locally known – stand out? In two words: pristine beauty. Many of the bays on this elegant French isle are refreshingly free of bars and shops. It’s just sugar-fine sand, blue skies and clear water stretching to the horizon.


An exclusive escape right beside a peaceful lagoon, Le Barthélemy Hotel & Spa feels like your own piece of paradise. Suggested stay 4-5 nights.

Le Barthelemy Hotel and Spa


Next over the horizon is Antigua, where 18th-century Naval history has given way to a modern (and far more luxurious) sailing scene . A festival atmosphere settles over the island each spring, with crowds gathering for Antigua Sailing Week and the vintage style of the Classic Yacht Regatta.

Antigua isn’t just for keen yachters, though. Diving beneath the surface reveals hard lessons learnt over centuries of seafaring around its cliffs and rocky reefs. Novice SCUBA divers (and even snorkelers) can explore the Sea Terror wreck, with its enormous anchor and ship’s wheel surrounded by fish.

If you’d rather stay on dry land, you’ll have a beach for every day of the year to choose from. Highlights include peaceful Pigeon Point, where the sand seems to merge seamlessly with the mirror-flat waters. Or there’s Rendezvous Bay near English Harbour, which rewards those who hike down from Fig Tree Hill with space, serenity and sublime sunsets.


drift off

The Inn at English Harbour is a beachfront retreat wrapped in its own gardens, just a water-taxi away from yachting hotspot, Nelson’s Dockyard. Suggested stay 4-5 nights. 


Fly via Puerto Rico to reach Anguilla's, Clayton J. Lloyd International Airport - it's just a one-hour flight. Take a charter boat from Anguilla to St. Barts and onto the final stop, Antigua. Antigua is better served with international flights heading in most directions. As always, ask our Voice Reservation Team for details about transfers or transport provided by individual hotels. 


To book the hotels on this independent itinerary, get in touch with our Voice Reservation Team on 0800 0482 314 (UK) & 1-877-234-7033 (US). You can find a full list of our dedicated toll-free numbers here. We’re ready and waiting to plan luxury adventures 24 hours a day, seven days a week. So whenever inspiration strikes, just get in touch.