VINCENT VACATIONS
14 NIGHTS | WINDSTAR | STAR PRIDE

14-Night Star Collector: Lovely Leewards Cruise

Aboard Star Pride (Windstar) | Departing San Juan to San Juan | 2 Available Departures from $4,014

Live Cruise Search Engine →
14 NightsDuration
WindstarCruise LineStar PrideCruise ShipSan JuanEmbarkation PortCaribbean EasternRegion
$4,014Starting Fare
SELECT YOUR DEPARTURE DATE

Upcoming Sailings & Stateroom Fares (2)

Departure DateReturn DateInsideOceanviewBalconySuitePerks & Action
Nov 08, 2027
Sailing #1652557
Nov 22, 2027Call for Exclusive Rate$4,014$6,534$4,792
Mar 13, 2028
Sailing #1652661
Mar 27, 2028Call for Exclusive Rate$4,014$6,114$4,798
PORT-BY-PORT TIMELINE

Day-by-Day Cruise Itinerary

Day 1

SAN JUAN (PRSJU)

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

At Sea (SEAD)

Day 3

ST GEORGES, GRENADA (GDSTG)

Inhale the intoxicating aroma of the "Isle of Spice" as your eyes feast on what is widely claimed to be the most beautiful city in the Caribbean. Spend the day on 2-mile-long Grand Anse beach, and before you go, a taste of nutmeg ice cream is a must.

Day 4

BEQUIA (VCBQU)

The only ships in port are those small enough to anchor alongside the yachts and fishing boats in Admiralty Bay. Bequia's whaling heritage is on display in the museum in pretty Port Elizabeth, or watch the island's famed model boat builders at work on their miniature masterpieces.

Day 5

MAYREAU (VCMA6)

Mayreau is the smallest inhabited island of St. Vincent and the Grenadines, covering just about 1.5 square miles with a population of only a few hundred people. Tucked between Union Island and the Tobago Cays in the southern Grenadines, it's known for its laid-back, off-the-grid charm—there are no a

Day 6

LES SAINTES, GUADELOUPE (GPLSS)

This is the Caribbean as you've always imagined it, with yacht-filled harbors set against volcanic mountains and endless stretches of palm-fringed beach. The underwater world here attracted the likes of Jacques Cousteau, but even novice snorkelers will enjoy exploring these impossibly blue waters.

Day 7

MARIGOT BAY (MFMAR)

Established around 1689, Marigot is the attractive capital of French St. Martin, with its brightly colored houses, a lively open-air market, secluded beaches, and pretty waterfront promenade. Because of its tax-free status, Marigot is a popular center for duty-free shopping, where all of the world's

Day 8

SAN JUAN (PRSJU)

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 9

CRUZ BAY, ST JOHN (VICZB)

CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)

Day 10

BASSETERRE, ST KITTS (KNBAS)

With Georgian architecture situated against an irresistible backdrop of emerald green hills, Basseterre is one of the loveliest of the Caribbean's small capitals. Beyond town, more than a quarter of St. Kitts has been set aside as Brimstone Hill Fortress national Park, a UNESCO World Heritage Site.

Day 11

GUSTAVIA, ST BARTHELEMY (BLGUS)

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 12

PHILIPSBURG, ST MAARTEN (SXPHI)

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

Day 13

GREAT HARBOUR, JOST VAN DYKE (VGJVD)

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 r

Day 14

VIRGIN GORDA/PRICKLY PEAR, BVI (VGVIJ)

The beautiful Bank Barrier coral reef wavers just beneath you as your ship makes the break to the bird sanctuary of Prickly Pear Island, so named because it is dotted with prickly pear cacti. Althought uninhabited, it does have a beach bar and water sports facilities. Not far away lies the curious a

Day 15

SAN JUAN (PRSJU)

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.

COMPLIMENTARY EXTRAS

Available Promotions & Onboard Credits

Reduced Deposit

One or more fares on this sailing includes a reduced deposit promotion.