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Leewards: A Barefoot November Catamaran Escape

Leewards: A Barefoot November Catamaran Escape

Winter 14 days Caribbean Sea

Round trip from Pointe-à-Pitre

from 8,500 zł per person

Overview

Set sail for two golden weeks of warm trade winds, coral-blue anchorages and island-hopping bliss across Antigua, Barbuda, Montserrat and Nevis. This catamaran escape is made for easy swimming, lazy lunches and unforgettable sunsets in the heart of the Caribbean.

Route

21 November 2026 – 5 December 2026

Slip away from November gloom and into a sunlit Caribbean rhythm: relaxed morning sails, snorkel stops in clear water, and evenings at anchor under a sky packed with stars. This 14-day catamaran journey is built for easygoing island-hopping — perfect for those who want the magic of the Leeward Islands without the rush.

From Antigua’s sheltered harbours to the powdery beaches of Barbuda, the volcanic drama of Montserrat, and the green hills of Nevis and Saint Kitts, every day brings a new shoreline, a new swim spot, and a new excuse to linger just a little longer. Expect a comfortable boat, confident local-style passages, and plenty of time to swim, snorkel, explore ashore and simply enjoy the ride.

Why this cruise feels special

  • Catamaran sailing with short, comfortable legs and plenty of protected anchorages
  • A true Caribbean “greatest hits” route blending wild nature, elegant harbours and hidden beaches
  • November timing for warm weather, steady breezes and that fresh-start feeling before the holiday rush
  • Round-trip convenience from Guadeloupe, making the whole adventure feel seamless and easy

This is not just a holiday — it’s the kind of voyage that resets your pace, fills your camera roll, and leaves you already dreaming of the next departure.

Day-by-day itinerary

  1. 1

    Welcome to Guadeloupe

    Arrive in Pointe-à-Pitre, the gateway to the French Caribbean. After settling aboard, you'll stock up on fresh local produce before enjoying your first Caribbean sunset from the marina.

  2. 2

    Guadeloupe → Antigua

    50 nm

    Set sail north across crystal-clear Caribbean waters toward Antigua, famous for its 365 beaches and rich maritime history. Anchor in one of the island's picturesque bays and enjoy your first evening under the stars.

  3. 3

    Discover Antigua

    Spend the day exploring Antigua. Visit the historic Nelson's Dockyard, relax on white-sand beaches, snorkel vibrant reefs, or enjoy lunch at a beachfront restaurant before another peaceful night at anchor.

  4. 4

    Antigua → Barbuda

    30 nm

    A short morning sail brings you to the untouched paradise of Barbuda. With its pink-sand beaches, turquoise lagoons and almost deserted coastline, this island offers one of the Caribbean's most exclusive natural experiences.

  5. 5

    Barbuda

    Enjoy a full day in Barbuda. Swim with rays, visit the famous Frigate Bird Sanctuary, paddleboard through calm lagoons or simply relax on miles of pristine beach where you may not see another soul.

  6. 6

    Barbuda → Saint Kitts

    60 nm

    Cross south to Saint Kitts, one of the Caribbean's most charming volcanic islands. The lush green mountains provide a dramatic backdrop as you arrive in a welcoming harbor.

  7. 7

    Explore Saint Kitts

    Discover colorful Basseterre, hike through tropical rainforest, visit Brimstone Hill Fortress or simply unwind on golden beaches. The island perfectly combines history, culture and nature.

  8. 8

    Saint Kitts → Nevis

    10 nm

    A short sail across the channel brings you to elegant Nevis. The relaxed atmosphere, colonial charm and spectacular views of Nevis Peak make this one of the most peaceful stops of the journey.

  9. 9

    Discover Nevis

    Spend the day exploring boutique plantations, soaking in natural hot springs, snorkeling over coral reefs or enjoying one of the island's renowned beach bars.

  10. 10

    Nevis → Montserrat

    35 nm

    Sail to the remarkable island of Montserrat, often called the "Pompeii of the Caribbean." Dominated by the Soufrière Hills volcano, the island offers dramatic scenery unlike anywhere else in the region.

  11. 11

    Explore Montserrat

    Visit the abandoned capital of Plymouth, buried by volcanic eruptions, hike volcanic landscapes and experience one of the Caribbean's least-visited yet most fascinating islands.

  12. 12

    Montserrat → Guadeloupe

    45 nm

    Enjoy a scenic sail back toward Guadeloupe. Depending on weather and timing, you may stop in the idyllic archipelago of Les Saintes for swimming, snorkeling and a relaxed evening.

  13. 13

    Southern Guadeloupe / Les Saintes

    Spend your final full day exploring the beautiful bays of Guadeloupe or Les Saintes. Enjoy one last swim in crystal-clear waters and celebrate the journey with a farewell dinner on board.

  14. 14

    Return to Pointe-à-Pitre

    After breakfast, sail back to Pointe-à-Pitre Marina for check-out, bringing home unforgettable memories of six unique Caribbean islands.

Destinations

Pointe-à-Pitre

The vibrant gateway to the French Caribbean. A lively marina, colorful markets, Creole cuisine and easy access to Guadeloupe's lush landscapes make it the perfect place to begin and end your sailing adventure.

St. John's Harbour, Antigua

Bustling yet sheltered starting point for a relaxed Leeward Islands catamaran loop.

Barbuda

Low-lying coral island known for broad beaches, lagoons and a wonderfully untamed feel.

Basseterre, Saint Kitts

Gateway to the twin-island charm of Saint Kitts with scenic coastline and easy access ashore.

Charlestown, Nevis

Historic harbour area on a lush island famed for calm water, beaches and elegant island atmosphere.

Montserrat

A volcanic island of black-sand shores, steep green slopes and dramatic seascapes.

What's included

  • Catamaran charter with skipper
  • Fuel, marina and mooring fees
  • Bedding, towels and onboard essentials
  • Food and drinks
  • Final cleaning and turnaround service
  • Cruising permits and local port charges
  • Internet
  • Insurance
Estimated cost per person 8,500 zł

Highlights

  • Round-trip catamaran adventure from Guadeloupe with easy island-hopping logistics
  • Barbuda’s legendary pink-sand beaches and wild, uncrowded shoreline
  • Montserrat’s dramatic volcanic landscapes and unforgettable sea views
  • Nevis and Saint Kitts for green hills, calm anchorages and relaxed island charm
  • A chic stop in Saint Barth for French-Caribbean flair, boutiques and waterfront dining
  • Snorkelling, beach time, island walks and sunset cocktails all in one trip

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