Leeward Islands

From English Harbour to
English Harbour.

  • 7 Nights
  • English Harbour
  • Shirley Heights
  • Green Island
  • Deep Bay
  • Great Bird Island
  • Carlisle Bay
  • English Harbour

DAY ONE

English Harbour

  • Duration: 0m
Overview

In the south of Antigua, English Harbour is the island’s yachting heart and home to the UNESCO-listed Nelson’s Dockyard. Once a strategic base for the Royal Navy in the 18th century, it now blends maritime history with a lively modern marina scene. Restored stone buildings house boutiques, museums, and waterfront restaurants, all set against a backdrop of gently swaying masts. Wander the dockyard, explore ruined forts, or take a short trip to nearby Pigeon Point and Galleon Beach. Visit during Antigua Sailing Week and you’ll find the harbor alive with energy, music, and world-class racing.

DAY TWO

English Harbour to Shirley Heights

  • Distance: 3 nm
  • Duration: 30m
Overview

Perched high above English Harbour, Shirley Heights offers one of the most famous views in the Caribbean. The restored military lookout commands sweeping panoramas of the coastline, where emerald hills give way to turquoise bays. Visit in the late afternoon to watch the sky turn gold, pink, and violet, or time your stop for the legendary Sunday night party with live music, local cuisine, and a vibrant crowd. It’s a perfect blend of history, culture, and pure island atmosphere.

DAY THREE

Shirley Heights to Green Island

  • Distance: 8 nm
  • Duration: 1h 5m
Overview

Just off Antigua’s east coast, privately owned Green Island is a quiet, unspoiled escape. Once home to a sugar mill, its ruins still whispering of the island’s colonial past, it’s now a haven for snorkelers and beach lovers. Coral reefs fringe its shores, sheltering warm, clear waters alive with tropical fish and sea turtles. On land, lizards and rabbits roam the soft sands. While tour boats visit occasionally, moments when you have Green Island to yourself are nothing short of magical.

DAY FOUR

Green Island to Deep Bay

  • Distance: 19 nm
  • Duration: 2h 25m
Overview

Deep Bay is a calm, protected anchorage embraced by lush green hills and overlooked by the ruins of Fort Barrington. The bay’s glassy turquoise water is perfect for swimming, paddleboarding, or snorkeling over the famous Andes shipwreck resting in its shallows. A short hike to the fort rewards you with sweeping coastal views, while the crescent of white sand below invites a languid afternoon under the sun.

DAY FIVE

Deep Bay to Great Bird Island

  • Distance: 12 nm
  • Duration: 1h 35m
Overview

Tiny and uninhabited, Great Bird Island is a gem for those seeking nature and solitude. Its surrounding coral reefs make for exceptional snorkeling and diving, with waters so clear you can watch eagle rays glide by from your tender. The island’s beaches are shaded by palms and sea grape trees, and its rocky interior is home to rare Antillean iguanas and nesting seabirds. Spend the day swimming, kayaking, and soaking in the untouched beauty, or head to nearby St. John’s for an evening of vibrant nightlife and dining.

DAY SIX

Great Bird Island to Carlisle Bay

  • Distance: 20 nm
  • Duration: 2h 30m
Overview

Carlisle Bay is an exclusive hideaway on Antigua’s south coast, where a sweeping arc of silver sand meets calm, aquamarine waters. Here, refined luxury blends effortlessly with natural beauty. Spend your day lounging under graceful palms, indulging in spa treatments, playing tennis, or enjoying the full menu of watersports. Hike into the nearby Mt. Obama National Park for panoramic island views, or tee off at two renowned golf courses within easy reach.

DAY SEVEN

Carlisle Bay to English Harbour

  • Distance: 5 nm
  • Duration: 40m
Overview

Returning to English Harbour offers another chance to enjoy its rich maritime heritage and easy access to Antigua’s south coast highlights. Whether revisiting Nelson’s Dockyard, exploring nearby beaches, or enjoying a final dinner at one of its acclaimed restaurants, the harbor is an ideal place to reflect on your journey.

DAY EIGHT

English Harbour

  • Duration: 0m
Overview

Savor your final moments in English Harbour. Stroll through the dockyard one last time, shop for local crafts, or take in the harbor views over a leisurely brunch. For those with time before departure, a last visit to Shirley Heights or a swim at Pigeon Point provides the perfect closing chapter to an unforgettable Antigua charter.

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