Windward & Leeward Islands by Train & Holland America Line

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Windward & Leeward Islands by Train & Holland America Line
Charlotte Amalie, St Thomas 00802, USVI
Apr 4 - 17, 2027
Uncommon Journeys image
Uncommon Journeys
$4,995
Deposit: $1,750

About this trip

Most people have cruised to Caribbean ports of call like Nassau, Grand Cayman, and Cozumel so many times that it is rare to come across a West Indies cruise of great appeal and distinction, but we have done so. With a ship of immense appeal and distinction, Holland America’s ms Zuiderdam combines this exceptional itinerary, which includes seldom-visited ports like St Lucia, Antigua, St Kitts & Nevis, and the US Virgin Islands, with a great pre-cruise visit to charming St Augustine, Florida, with the luxury of a three-night hotel stay. And a trip on America's newest and best high-speed train, Brightline.

Our holiday begins in Jacksonville, a city with excellent airline and train service, and after a one-hour drive, we arrive in historic St Augustine, where we enjoy a three-night stay. More and more, we offer these longer hotel stays and this program, with three nights in the Historic District of St Augustine, along with comprehensive sightseeing, some exceptional dining, including the legendary Columbia Restaurant. As always, all sightseeing and admission fees are included, and we have left plenty of free time for you to enjoy things at your own pace.

After our three-night stay in historic St Augustine, a short drive takes us to Orlando, where we board Brightline, the most exciting train development in the USA in decades. We enjoy a high-speed ride south to Miami in Premium Class with roomy leather seats, big windows, a friendly staff, and complimentary snack and beverage service. This privately operated passenger service already gets rave reviews from travelers, and we are sure you will agree. Upon arrival in Miami, a short drive takes us to the ms Zuiderdam.

Our uncommon West Indies itinerary visits San Juan, Puerto Rico, lovely Antigua, stunningly beautiful St Lucia with the towering Pitons, British-flavored St Kitts & Nevis, Dutch St. Maarten, and always popular St Thomas in the US Virgin Islands. Saving the best for last, our final day is spent on a pristine Half Moon Cay, Holland America’s private out island in the Bahamas, a relaxing way to end your voyage.

Aboard ship, travelers enjoy a century and a half of superb Dutch seafaring tradition aboard the quietly elegant Zuiderdam with all of the amenities of a modern resort in a relaxed, refined, and civilized setting far removed from the frenetic pace of ordinary Caribbean cruise ships, one of grace and elegance without crowds.

With the charm of St. Augustine, the thrill of a scenic train ride, a carefully curated itinerary, and the expertise of a professional tour manager, this journey offers the perfect blend of relaxation, exploration, and luxury. Our programs with Holland America Line always sell out, so prompt reservations are a wise idea.

All Aboard!

A tradition of excellence at sea.

While dozens of ships offer Caribbean cruises, there is a special feeling and style on a voyage with Holland America Line that reminds one of why during the heyday of transatlantic liners. So many fabled Holland America ships like the ss Rotterdam, the ss Nieuw Amsterdam and the postwar ss Statendam were considered among the finest ships afloat. The tradition continues today with acclaimed cuisine, superb art collections, roomy and spacious staterooms and a sense of grace simply not found on modern cruise ships. This holiday is masterful in that in combines a leisurely and indolent itinerary with a fine ship and nicer still, the fun and exploration of historic St Augustine, Florida before we board the ship. We look forward to welcoming you aboard.

What's included

Personalized attention

Fully escorted by a professional tour manager.

Historic St Augustine

Three-night hotel stay in wonderful St Augustine at the Doubletree by Hilton Hotel St Augustine Historic District, a superb location with spacious rooms, a nice pool, excellent restaurant and right by

A celebrated restaurant

Special welcome luncheon at the fabled Columbia Restaurant, a Florida institution and a beautiful restaurant with hundreds of hand-painted tiles, art works and a Spanish-style fountain, surroundings t

In-depth sightseeing

St Augustine historic tour along with visits to the acclaimed Lightner Museum, the historic Fort as well as a sunset cruise on Matanzas Bay.

A splendid train ride

Express ride from Orlando to Miami on sailing day aboard Brightline, America's newest and privately operated passenger train in speed, comfort & style in Premium Class with roomy seating and snacks an

A leisurely cruise

Ten-night West Indies cruise round trip from Miami aboard Holland America’s ms Zuiderdam with exceptional ports of call in quaint St John's, Antigua, stunningly beautiful St Lucia, charming St Kitts

Day 1

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St. Augustine Florida

We depart Jacksonville airport and our optional pre-tour hotel at 11 am for the short drive to St Augustine with lunch at the famed Columbia Restaurant with its award-winning Spanish and Cuban cuisine. Later, we enjoy a historic district tour with many buildings dating to the 1700's and filled with dining and shopping choices with the balance of the evening at leisure.

Day 2

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St. Augustine Florida

Today we explore St Augustine with visits to the ancient fort, Castillo de San Marcos, and the Lightner Museum, renowned for its collection, including lamps by Louis Comfort Tiffany, American and European paintings, geological specimens, sea shells, and mechanical musical instruments of the Victorian Era. And later today, a sunset cruise with great views of St Augustine.

Day 3

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St. Augustine Florida

The phrase all savvy travelers enjoy applies today, "all day at leisure” for you to enjoy at your own pace, interrupted only by an included lunch. There is time to explore the historic district, visit the nearby Lighthouse, golf, take a dip in the ocean, or visit the acclaimed San Sebastian Winery to name just a few options. Our final night in historic St. Augustine.

Day 4

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ms Zuiderdam

All Aboard! After breakfast, a short drive to Orlando to board Brightline, the newest and most exciting idea in train travel in the USA in decades. This impressive privately owned and operated railroad offers a smooth and speedy trip to Miami and we enjoy Premium seating on this 3.5 hour trip. For anyone wondering how nice train travel could be, this train provides the answer. At Miami, a short transfer to the pier and we set sail.

Day 5

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At sea

Day 6

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At sea

Day 7

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DAY 7 Philipsburg, Sint Marten

Philipsburg, the bustling capital of the Dutch side of Sint Maarten, offers visitors a mix of cultures, scenic beaches, and excellent shopping opportunities. From the historic Fort Amsterdam to the vibrant Boardwalk, Philipsburg invites travelers to immerse in its lively atmosphere and Dutch heritage, while just a short trip away, the French side of the island offers its own distinct charm and culinary delights.

Day 8

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St. Johns, Antigua & Barburda

St. Johns, Antigua, a treasure trove of 365 pristine beaches, offers an unmatched Caribbean adventure. With Holland America, explore the intriguing Nelson's Dockyard, relax on sun-swept shores, and take in panoramic views from Shirley Heights Lookout for a memorable escape.

Day 9

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Castries & Saint Lucia

In Castries, Saint Lucia comes alive with its bustling markets, historical sites, and scenic views. It’s a gateway to adventure, from hiking to the Pitons to immersive cultural experiences like learning about banana farming.

Day 10

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Basseterre, St. Kitts & Nevis

The dual-island nation of St. Kitts and Nevis beckons travelers with a storied past, evident in the British architecture of Basseterre and sprawling colonial plantations. The islands offer sandy retreats for relaxation, jungle adventures for thrill-seekers, and a taste of local life through bars and restaurants with sunset views and local cuisine.

Day 11

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St. Thomas USVI

St. Thomas offers an array of exciting shore excursions that showcase the island's natural beauty and cultural vibrancy. From the pristine sands of Magens Bay Beach to the majestic underwater sites that await via scuba diving explorations, each experience in St. Thomas promises unforgettable memories. Seek thrills in zip-lining adventures or unwind amid the charm of Charlotte Amalie — there's an activity for every traveler's taste.

Day 12

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At sea

Day 13

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Half Moon Cay Bahamas

RelaxAway, Half Moon Cay™ is Holland America Line’s award-winning private island, a Bahamian paradise reserved for our guests. Designed to inspire effortless relaxation, this idyllic retreat includes a Beach Club, serene lounging spaces, island-only menu items, and much more.

Day 14

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Miami Florida

Disembarkation, and then travel home.

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1. Charlotte Amalie, St Thomas 00802, USVI

Charlotte Amalie, St Thomas 00802, USVI

About your organizer

Since 1990, Uncommon Journeys has offered distinctive and unique trips through North America by riverboat combined with brilliant programs on land, almost all with two-, three- or four hotel stays and exceptional dining. Examples include French & Atlantic Canada with Cunard's RMS Queen Mary 2, the great National Parks of the West with the Rocky Mountaineer train and Mexico's stunning Copper Canyon with the famed Chihuahua al Pacifico Railroad. Some of our trips even include vintage private train travel.

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Windward & Leeward Islands by Train & Holland America Line