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San Juan & the Virgin Islands

San Juan & the Virgin Islands

At a glance

Duration: 8 Days, 7 Nights

Coverage: Roundtrip San Juan, Puerto Rico

From: $1,999

Season: November - December, March

Activities: Adventure, Culture, History, Wildlife

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Wind Star Cruises

Begin and end your journey where Old World meets New, in historic San Juan, littered with more than 400 restored Spanish colonial buildings. As you continue on this bewitching Caribbean cruise through the Virgin Islands, no two days are alike. One day, you’re shopping chic French boutiques for the latest fashions from Paris. On another, snorkeling a secluded cove known only to lucky yachtsmen – like you.

Skip more common and commercial ports like St. Thomas in favor of less-visited destinations like Montserrat. Bypass the major cruise terminals in favor of exclusive marinas and anchorages on this Caribbean cruise. And as guests on larger cruise ships take an excursion from Tortola to reach tiny Jost Van Dyke, your elegant yacht is already there.

Popular Highlights

  • Admire the incredible views from El Morro’s 16th century ramparts, a UNESCO World Heritage Site, in San Juan
  • Learn all about the pirates’ favorite grog
  • Go for a hike in Puerto Rico’s El Yunque National Rainforest
  • Mingle with the glitterati in St. Barts
  • Discover a town swallowed by a volcano during a rare visit to Montserrat
  • Let the Bubbly Pool on Jost Van Dyke wash your cares away

Day-to-Day Itinerary

Day 1 - San Juan, Puerto Rico

The imposing façade of El Morro fortress is just one of the many UNESCO World Heritage Sites in San Juan. Admire the colorful colonial buildings from your casually elegant ship, docked right in the heart of Old San Juan.

Day 2 - Vieques, Puerto Rico

Just six miles east of mainland Puerto Rico lies the island of Vieques --Though it measures just 55 square miles, Vieques brims with natural flora, exotic animals, secluded beaches, and gracious people. It’s allure is that it is rustic and elegant at the same time. Vieques boasts more than 20 breathtaking and diverse beaches, each with its own character and appeal. Horses roam freely across the island, often flanked by elegant white egrets and brightly colored flamboyant trees dot the hillsides. There are no stoplights, fast-food chains, nightclubs, or shopping malls… the attractions are Mother Nature’s creations. You will find a delightful selection of restaurants with a variety of foods, a few stores and the interesting Vieques Conservation & Historical Trust Museum. It is also home to Hacienda Casa del Frances, a sugar plantation house built in 1910 and listed on the U.S. National Register of Historic Places.

Day 3 - Gustavia, St. Barthélemy

Affectionately known as St. Barts, the Caribbean’s most chic island adds a French flair to Riviera-like beaches and duty-free boutiques. Walk past gingerbread cottages in search of celebrities, shop for designer fashions, or sip the island’s signature ti punch as kite surfers fly by.

Day 4 - Little Bay, Montserrat, BWI

Today we visit “Pompeii of the Caribbean”—an island that is half lush and green, half gray and covered in ash by a volcano in 1995. And if a half-buried city isn’t intriguing enough, there are black-sand beaches and a perplexing Irish heritage to explore.

Day 5 - Philipsburg, St. Maarten

Pastel-colored buildings and shops filled with tempting souvenirs herald your arrival to bustling Philipsburg. Situated near the harbor on the Dutch side of St. Maarten, Philipsburg owes its discovery to Christopher Columbus in 1493. Today, celebrated Front Street is home to a number of local Creole restaurants as well as jewelry stores, stylish boutiques, and lively casinos for visitors seeking an upbeat island experience.

Day 6 - Jost Van Dyke, Great Harbour, B.V.I.

For an island comprised of a mere eight square miles, it’s amazing how much there is to do on Jost Van Dyke. Visit the national park on nearby Diamond Cay, snorkel among swaying sponges and angelfish at Sandy Spit, or pilot your own boat around Sir Francis Drake Waterway. After all that, you’ll be ready for an evening drink on the beach — where you can admire your Windstar ship aglow in the harbor.

Day 7 - Virgin Gorda, Prickly Pear Beach, B.V.I

A beautiful coral reef wavers just beneath you as your ship makes the break into exclusive North Sound. You can imagine the reaction of the locals watching from The Bitter End Yacht Club as your ship comes around the corner under full canvas. At the other end of the island lies the curious assembly of house-sized boulders called “The Baths,” which form huge underground pools and caverns that you’re free to explore.

Day 8 - San Juan, Puerto Rico

The imposing façade of El Morro fortress is just one of the many UNESCO World Heritage Sites in San Juan. Admire the colorful colonial buildings from your casually elegant ship, docked right in the heart of Old San Juan.

San Juan & the Virgin Islands itinerary map

Dates & Rates

Dates Ocean View Suite Ocean View Suite 1 Ocean View Suite 2 Ocean View Suite 3 Balcony Suite Balcony Suite 1 Classic Suite Owner's Suite
Nov 10, 2018 $1,999 $2,099 $2,299 $2,499 $3,099 $4,499
Nov 24, 2018 $1,999 $2,099 $2,299 $2,499 $2,899 $3,099 $4,499 $5,499
Dec 8, 2018 $1,999 $2,099 $2,299 $2,499 $2,899 $3,099 $4,499 $5,499
Dec 22, 2018 $3,199 $3,299 $3,399 $3,499 $4,299 $4,499 $5,699 $6,699
Mar 2, 2019 $2,199 $2,299 $2,499 $2,699 $3,099 $3,299 $4,699 $5,699

Ships

Star Pride

Star Pride The graceful, suite-only Star Pride is the first of Windstar's three new power yachts. With only 212 guests, you begin to feel like it's your own private yacht almost as soon as you step aboard. View ship details...

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