Luxury Private Sailing Tours in St Thomas

Our Signature Experiences

Champagne Sunset Sail

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Maho Bay Turtle Snorkel Sail

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Lime Out Snorkel

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The Lady Lynsey

Departing from the Beach at the Ritz-Carlton, St. Thomas

Set sail aboard our luxury sailing catamaran, The Lady Lynsey. Christened alongside the grand re-opening of The Ritz-Carlton, St. Thomas, The Lady Lynsey is among the finest catamarans anywhere in the world. Her style and service are built on the legacy and service of the original Lady Lynsey, which served guests from the hotel for over 20 years.

Experience the Lady Lynsey

The Lady Lynsey

Departing from the Beach at the Ritz-Carlton, St. Thomas

Set sail aboard our luxury sailing catamaran, The Lady Lynsey. Christened alongside the grand re-opening of The Ritz-Carlton, St. Thomas, The Lady Lynsey is among the finest catamarans anywhere in the world. Her style and service are built on the legacy and service of the original Lady Lynsey, which served guests from the hotel for over 20 years.

Experience the Lady Lynsey

Our Onboard Experience

Legendary Staff & Service

Each excursion includes a selection of gourmet food and beverage offerings prepared by The Ritz-Carlton, St. Thomas culinary team. Our captains and crew members pride themselves on upholding the legendary service standards at the core of the Ritz-Carlton brand at all times.

Experience The Lady Lynsey

Our Onboard Experience

Legendary Staff & Service

Each excursion includes a selection of gourmet food and beverage offerings prepared by The Ritz-Carlton, St. Thomas culinary team. Our captains and crew members pride themselves on upholding the legendary service standards at the core of the Ritz-Carlton brand at all times.

Experience The Lady Lynsey

The Story of Lady Lynsey

Many years ago, when the Golden Age of sail and piracy came to the Caribbean, a young girl was born to a poor family that lived in the Virgin Islands. She was named “Lynsey”, and she would become one of the fiercest pirates to ever sail the seas.

But women couldn’t become captains in those days, let alone become part of the crew. So when she came of age, she dressed up as a lad, kidnapped her best friend Jack, and signed up as part of a ship’s crew.

Jack eventually became the ship’s cook and was nicknamed “Dusty” for constantly covering the ship’s mess with flour as he hastily prepared the crew’s meals. But headstrong Lynsey was never promoted to anything higher than a swab, relegated to cleaning the bilges and tidying up after the rest of the crew. Still, she never lost sight of her dream.

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The Story of Lady Lynsey

Many years ago, when the Golden Age of sail and piracy came to the Caribbean, a young girl was born to a poor family that lived in the Virgin Islands. She was named “Lynsey”, and she would become one of the fiercest pirates to ever sail the seas.

But women couldn’t become captains in those days, let alone become part of the crew. So when she came of age, she dressed up as a lad, kidnapped her best friend Jack, and signed up as part of a ship’s crew.

Jack eventually became the ship’s cook and was nicknamed “Dusty” for constantly covering the ship’s mess with flour as he hastily prepared the crew’s meals. But headstrong Lynsey was never promoted to anything higher than a swab, relegated to cleaning the bilges and tidying up after the rest of the crew. Still, she never lost sight of her dream.

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5-Star Experiences

⭐⭐⭐⭐⭐

Joshua Neisinger | October 2020

This trip was very special for us and the overall experience exceeded every expectation. The Lady Lindsey ll crew are extremely polished, very hard working and are sure to deliver an unforgettable memory through their silent anticipation of your every need and extremely well thought out preparation to ensure sailing perfection.

Jason S | October 2020

My family and I had a fantastic time. The boat was great and the crew is phenomenal. We have 3 boys and Bret, Erin and Heather treated them like gold. Thanks for the wonderful time.

Cameron Crenwelge | July 2020

The highlight and best kind of conclusion to an amazing stay. Here’s what’s up: friendly/informative staff, great views, and OPEN BAR. What more can you ask for?

MelBrown62 | October 2020

We did the snorkel/Lime Out tour and it was fabulous! The guides were amazing, as were the tacos at Lime Out!

Steve Z | October 2020

We boarded the brand new and beautiful Lady Lynsey II sailing catamaran at the Ritz Carlton St Thomas for a sunset champagne cruise and loved it! Plenty of room to find seating and move around, extremely friendly crew and a great open bar with hors d’oeuvres. Highly recommend!

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