Caribbean island-hopping in the Lesser Antilles: Anguilla, Antigua and Barbuda

There’s no rule that says your Caribbean escape has to be a one-island affair. Anguilla, Antigua and Barbuda are close enough to link in a single trip — and different enough to keep every day feeling new. This Lesser Antilles itinerary links three Leeward Islands; Anguilla’s laid-back, barefoot glamour with Antigua’s lively harbours and Barbuda’s blush-pink beaches, with all the best beachfront villas and sea-facing suites to book along the way.

At a glance

  • 10-day independent island-hopping escape through the Caribbean’s Lesser Antilles, based on flying into and out of Antigua’s V.C. Bird International Airport, and chartering a private yacht to sail to Barbuda and onwards to Anguilla.
  • Start with Antigua’s lively harbours and hidden coves before casting off for Barbuda’s off-the-map seclusion, then drift north to Anguilla for laid-back, barefoot luxury and world-class dining.
  • Highlights include sunrise swims in Antigua’s aquamarine bays, anchoring off Barbuda to picnic on deserted beaches, and stepping ashore in Anguilla to sip sundowners at some of the Caribbean’s most stylish beach clubs.

START WTH A SPLASH: ANTIGUA

With 365 beaches — one for every day of the year — Antigua makes it hard to sit still. Spend mornings swimming in the crescent-curved Half Moon Bay’s waters, then wander the cobbled paths of Nelson’s Dockyard before sailing into English Harbour for sunset. Equally, you could pick one or two of those glorious beaches, and spend a sun-drenched day stretched out on the golden sands.

DROP ANCHOR IN BARBUDA

Sailing north from Antigua, Barbuda feels like the world just falls away — fewer crowds, more horizon. This is an island of wild beauty: pink-sand beaches that stretch for miles, mangroves made for kayaking, and a lagoon that’s home to one of the largest frigatebird colonies anywhere. Days here are less about ticking off sights and more about embracing the stillness, whether that’s paddling through glassy waters or just being contently cast away.

Travel Tips

The best way to link these islands is by sea — chartering a yacht lets you set your own pace (and drop anchor wherever the water looks irresistible). Antigua is the natural launchpad, with plenty of marinas and charter companies offering everything from sleek catamarans to classic sailing yachts. As for timing, the sweet spot is December through April, when the trade winds are steady, the seas calm, and the sunshine endless — a perfect excuse to swap winter blues for Caribbean hues.

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