Windward & Leeward Islands

Caribbean & Florida · Land & cruise

Windward & Leeward Islands

St. Augustine · Zuiderdam cruise · Saint Lucia

Apr 4, 2027 – Apr 17, 2027

14 days

From, per personUS$4,995

See departure for fare details

About this journey

Begin in St. Augustine before sailing aboard Zuiderdam to the eastern Caribbean. The voyage includes Sint Maarten, Antigua, Saint Lucia, St. Kitts, St. Thomas and Half Moon Cay.

St. Augustine

Zuiderdam cruise

Saint Lucia

St. Kitts

St. Thomas

Views along Windward & Leeward Islands

Your itinerary

St. Augustine · Zuiderdam cruise · Saint Lucia

Day by day
Day 1

St. Augustine FL

We depart Jacksonville airport and our optional pre-tour hotel at 11am for the short drive to St Augustine with lunch at the Columbia Restaurant with its award winning Spanish and Cuban cuisine. Later, 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

St. Augustine FL

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

St. Augustine FL

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 San Sebastian Winery to name just a few options.

Day 4

Ms Zuiderdam

After breakfast, a short drive to Orlando to board Brightline, the newest and most exciting idea in train travel in the USA in decades.

Day 5–6

At sea

Time at sea.

Day 7

Philipsburg, Sint Maarten

Philipsburg, the bustling capital of the Dutch side of Sint Maarten, offers visitors a mix of cultures, 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 journey away, the French side of the island offers its own distinct charm and culinary delights.

Day 8

St. Johns, Antigua & Barburda

St. Johns, Antigua, a treasure trove of 365 pristine beaches, offers an unmatched Caribbean adventure.

Day 9

Castries, Saint Lucia

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

Day 10

Basseterre, St. Kitts & Nevis

The dual-island nation of St. Kitts and Nevis beckons travelers with a past, evident in the British architecture of Basseterre and sprawling colonial plantations.

Day 11

St. Thomas USVI

St. Thomas offers an array of exciting shore excursions that showcase the island's natural beauty and cultural vibrancy.

Day 12

At Sea

Time at sea.

Day 13

Half Moon Cay, Bahamas

Call at Half Moon Cay in the Bahamas.

Day 14

Miami, Florida

Time in Miami, Florida.

Dates & fares

Apr 4, 2027 – Apr 17, 2027

14 days · Land & cruise

From US$4,995 per person

Published WeTravel starting fare · confirm the selected package.

Entry-package deposit: US$1,750

On WeTravel, choose your accommodation, review current availability and payment and cancellation terms, then reserve.

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Accommodation & published fares
PackagePer personDeposit
Inside Standard | double occupancyUS$4,995US$1,750
Inside Superior | double occupancyUS$5,295US$1,850
Inside Standard | single occupancyUS$7,095US$2,475
Inside Superior | single occupancyUS$7,295US$2,550
Oceanview Standard | double occupancyUS$5,995US$2,100
Oceanview Superior | double occupancyUS$6,195US$2,175
Oceanview Standard | single occupancyUS$8,995US$3,150
Oceanview Superior | single occupancyUS$9,395US$3,275
Balcony Standard | double occupancyUS$6,395US$2,325
Balc Superior | double occupancyUS$6,695US$2,350
Balcony Standard | single occupancyUS$9,495US$3,325
Balcony Superior | single occupanyUS$9,595US$3,375
Signature Suite | double occupancyUS$7,895US$2,775
Signature Suite | single occupancyUS$12,745US$4,475
Neptune Suite | double occupancyUS$8,995US$3,150
Neptune Suite | single occupancyUS$14,895US$5,225

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