Spirit of Ponant

La Désirade

Araok II

Smiley

Seychelles

Polynesia

Mediterranean

Caribbean

SMILEY

SMILEY

Lagoon 55

Lagoon 55 Smiley – A Journey into the Heart of the Caribbean

Step aboard Smiley, a Lagoon 55 catamaran with plenty of space and light. 
This boat offers comfort and the real experience of sailing.
Enjoy open-air living areas, simple design, and quality materials.

1 Premium Destination

Caribbean

Explore the Caribbean Aboard Smiley

Your journey follows the trade winds.
Sail from Guadeloupe to the wild shores of Dominica, then explore quiet anchorages in Antigua and the blue lagoons of Saint Barthélemy.
Enjoy a rare escape, guided by the wind and the ocean’s call.

1 Yacht with crew

Smiley

Smiley is a spacious and comfortable Lagoon 55 catamaran, perfect for exploring the Caribbean in complete serenity.
With 5 double cabins, each with its own private bathroom, it can accommodate up to 10 guests in a warm and modern setting.

GUEST CABINS
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GUESTS
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BUILT
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The Layout

Smiley has four elegant cabins and a large owner’s suite.
It is designed for comfort and privacy. There are many outdoor spaces to relax and enjoy beautiful sea views. The bright main salon is perfect for spending time together.

Onboard Comfort & Amenities

SUP Boards

SUP Boards

Snorkeling

Snorkeling

Dinghy

Dinghy

Wakeboard

Wakeboard

Waterskis

Waterskis

Wingfoil

Wingfoil

Air Conditioning

Air Conditioning

Wi-Fi

Wi-Fi

Tiwal Dinghy

Tiwal Dinghy

Watermaker

Bluetooth Sound

Smart TV

Deck Shower

Hydraulic Platform

Linens

Caribbean Map

7-Days Suggested Itinerary in the Caribbean

From chic Gustavia to Anguilla’s serene bays and back, this route blends short sails, powder-white sands, calm anchorages and starlit evenings — perfect for effortless island-hopping.

Day 1 · Gustavia, Saint-Barthélemy

Your voyage begins in the heart of Gustavia, Saint-Barthélemy’s chic and sun-drenched capital. The yacht sails toward Maundays Bay, one of Anguilla’s most iconic beaches, where powder-white sands meet the sleek design of Cap Juluca.

Highlights: Sunset cocktails on deck, a first swim in crystal-clear waters, and dinner under the stars.

Day 2 · Maundays Bay, Anguilla

A serene bay lined with white sands and aquamarine waters. Maundays Bay is a sanctuary of calm elegance, embraced by the curved architecture of Cap Juluca and the scent of frangipani in the breeze.

Moments to savor: Swimming in translucent waters, sunset aperitif on deck, dinner with refined island cuisine.

Day 3 · Road Bay, Anguilla

An anchorage rich in local character. Road Bay is Anguilla’s gateway to authenticity — colorful, musical, and quietly vibrant.

Suggested experiences: Strolls along Sandy Ground beach, local rum tasting, or a peaceful evening under the stars.

Day 4 · Scrub Island, Anguilla

Untouched and uninhabited, Scrub Island offers a return to nature in its purest form. An exclusive escape for those who seek silence, clarity, and connection with the sea.

Signature moments: Morning meditation, snorkeling in coral gardens, barefoot walks on windswept shores.

Day 5 · Grande Case – Marigot, Saint Martin

An elegant port of call on the French side of Saint Martin. Grande Case is celebrated for its fine gastronomy and relaxed, artistic atmosphere.

Unmissable experiences: Lunch at a French bistro, visit to local art galleries, or a curated dinner under soft island lanterns.

Day 6 – 7 · Gustavia, Saint-Barthélemy (Return)

As the cruise comes full circle, Gustavia welcomes you back with its timeless allure. Red rooftops, designer boutiques, and gentle trade winds signal the end of an unforgettable passage.

Caribbean Bay
Turquoise Waters & Granite
Island Anchorage
Sunset Anchorage

Charter Rates by Season

LOW - SEASON

STARTING AT

€14,000

PER WEEK

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MID - SEASON

STARTING AT

€30,000

PER WEEK

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HIGH - SEASON

STARTING AT

€38,000

PER WEEK

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