Caribbean Elegance by Rail & Sea: A journey from historic Florida to the enchanting islands of the West Indies

Rediscover the romance of travel on a sojourn through the Caribbean's beguiling Windward & Leeward Islands and historic St. Augustine via premium rail and a classic ocean cruise.

Sunset over the ocean viewed from a sandy beach with tall grass and dunes in the foreground.

There is a Caribbean beyond the familiar—a place where emerald mountains tumble into sapphire seas, trade winds drift through colorful harbors, and the pleasures of unhurried travel remain wonderfully intact. This uncommon journey begins with three enchanting nights in historic St. Augustine, America's oldest city, where timeless streets, exceptional cuisine, and rich history provide an elegant introduction to the days ahead.

A scenic journey aboard Brightline's Premium Class service carries you effortlessly to Miami, where Holland America Line's gracious ms Zuiderdam welcomes you aboard. From there, sail among the captivating islands of the Windward and Leeward chain, discovering the soaring Pitons of Saint Lucia, the sunlit shores of Antigua, the tranquil beauty of St. Kitts & Nevis, vibrant Sint Maarten, charming St. Thomas, and the pristine paradise of Half Moon Cay. Combining classic ocean travel, modern rail, and thoughtfully paced exploration, this is a journey that celebrates not only extraordinary destinations, but the enduring pleasure of traveling beautifully.

Tropical landscape with mountains, lush greenery, calm blue water, a tall palm tree, and pink flowers in the foreground.

The UNCOMMON CARIBBEAN ELEGANCE JOURNEY

  • Historic Florida Before You Sail: Enjoy three relaxing nights in charming St. Augustine with included sightseeing, exceptional dining, and plenty of time to explore at your own pace.

  • Brightline Premium Rail Experience: Travel from Orlando to Miami aboard America's newest high-speed passenger train, enjoying spacious seating, attentive service, and a comfortable start to your voyage.

  • The Caribbean Beyond the Ordinary: Discover beautiful islands including Saint Lucia, Antigua, St. Kitts & Nevis, Sint Maarten, St. Thomas, and Half Moon Cay aboard Holland America's elegant ms Zuiderdam.

TOUR HIGHLIGHTS

  • Fully escorted throughout by an experienced Uncommon Journeys Tour Manager for personal attention

  • Three nights in historic St. Augustine, Florida

  • Deluxe accommodations in the heart of the Historic District

  • Guided sightseeing including Castillo de San Marcos and the Lightner Museum

  • Sunset cruise on scenic Matanzas Bay

  • Welcome luncheon at the legendary Columbia Restaurant

  • Brightline Premium Class rail journey from Orlando to Miami

  • Ten-night Holland America Line cruise aboard ms Zuiderdam

  • Visit the beautiful islands of Antigua, Saint Lucia, St. Kitts & Nevis, Sint Maarten and St. Thomas

  • Relax at Holland America's exclusive Half Moon Cay

  • Spacious accommodations, acclaimed cuisine and classic Holland America service

  • Leisurely itinerary with generous free time ashore

Aerial view of a small town at sunset with historical buildings, parking lots, trees, and a river with boats in the background.
Sunset view from the deck of a cruise ship showing the ocean and a colorful sky with clouds.
Lighthouse shining its light through trees at dusk or dawn.

2027 JOURNEY Dates & PRICING

April 4 - 17
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