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San Juan, Puerto Rico

14 nights · Caribbean

14-night Caribbean cruise from San Juan, Puerto Rico on Star Pride

The San Juan to San Juan is a 14-night Caribbean cruise aboard Star Pride, operated by Windstar Cruises. Departing San Juan, Puerto Rico on December 6, 2026, the voyage visits 11 ports including St Georges, Grenada, Bequia, Mayreau. Fares start from $6,272 per person.

Length
14 nights
Departs
Dec 6, 2026
Returns
Dec 20, 2026
Ports of call
11
Days at sea
2

Voyage code PR20261206-14D

from $6,272 pp

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Why this route stands out

A closer look at the journey

Fixed editorial images from the places on this itinerary. They stay stable each time you return to this sailing.

San Juan, Puerto Rico

Blessed with some of the oldest buildings in the Western Hemisphere, San Juan, Puerto Rico’s cap-ital, is romantically charming with its bright pastel Spanish colonial facades, wrought-iron balconies abloom with flowers, narrow cobblestone streets and beloved park squares. Once you arrive on an MSC Caribbean and Antilles cruise at the port, explore Old San Juan (Viejo San Juan), a UNESCO World Heritage district, widely renowned for the fortresses of Castillo San Felipe del Morro and the Castillo San Cristóbal. The old town occupies the headland of a 2.5-mile-long island (connected by bridge to the mainland) that shelters San Juan Bay, for centuries a key port in the New World. It was originally known as Puerto Rico, or “rich port,” because its location made it the perfect stop for shipping. Several MSC excursions offer walking tours that let you soak up amazing views of San Juan, while making cultural discoveries of a lifetime. Wander through the old town along the Paseo de la Princesa, San Juan’s oldest tree-lined avenue; head up its southern city wall, La Muralla, which until the late 19th century encircled all of Old San Juan with sandstone; and tour the 16th-century fortress of El Morro, with its six different lines of defence. Take a coffee-tasting walking tour to explore Puerto Rico’s rich coffee culture, and learn how the island’s rich volcanic soil and climate have contributed to the rise of coffee as one of its main crops. Taste a delicious cup of freshly brewed Puerto Rican café con leche, learn about the island's historical ties with the caffeine-rich beverage, and explore how coffee and the church are connected on this MSC excursion through the streets of Old San Juan. Or savour San Juan’s culinary delights, in a Martha Stewart excursion curated exclusively for MSC that will have you tasting local cuisine and drinks at five destinations along the route through the fortified colonial city. From Puerto Rican fritters at historic El Convento Hotel, to chocolate tasting at a fourth-generation chocolatier, you won’t want to miss this tour, which ends at La Casita de Rones for a rum lesson and a piña colada, the national drink of Puerto Rico. With more than 80% of the world's rum coming from Puerto Rico, delve deeper into the spirit on an MSC excursion to Casa Bacardí in the town of Cataño. Discover the story behind Bacardí’s legendary cocktails, sniff the products on display and learn about the rum-making process including wood barrelling, ageing and finishing. For the grand finale, enjoy a fascinating mixology show. Nature lovers will not want to miss a visit to El Yunque, the only tropical rainforest in the U.S. territory and one of Puerto Rico's finest spots of natural beauty. Marvel at its small horsetail waterfalls, giant ferns and tropical hardwoods. For an enchanting experience, kayak into the enchanting bioluminescent bay at Laguna Grande of Fajardo on another MSC excursion. Under the blanket of the night sky and the lighthouse of Fajardo, paddle through the water and watch it glow with the bioluminescence of millions and millions of tiny organisms.

Bequia

An almost mythical utopia of virgin beaches, rustic rum shacks and bays so scenic you feel like you’re intruding - Bequia Island is an island mirage of Caribbean perfection. This is the real, unspoiled experience - and with just 6,000 locals living here, you quickly start to recognise the same smiling faces, welcoming you with outstretched arms. Offering glorious - often deserted - beaches of pure golden sand, and hillside sweeps of forest and almond trees, Bequia Island is an extraordinary feast for the senses. Unlike some of the flashier Caribbean islands, Bequia - a part of the Grenadines - is a rustic, unassuming and off-the-beaten-path choice. The staggeringly picturesque natural harbour, Admiralty Bay, greets you on arrival, and is peppered with day-tripping yachts bobbing on the gentle waves. The island’s tiny capital, Port Elizabeth, sits behind, with its bustling fruit and vegetable market, turtle sanctuary, and stalls selling hand-crafted model ships. This tiny, pretty island is ridged along the centre, and you can earn your beachside bliss with a gentle hike to the top of Mount Peggy, looking out over views of Grenada and St Vincent. At just seven miles long, you can discover the whole island in a few hours – but that would be to miss the point somewhat. Bequia Island coaxes you in to slow the pace and soothe your soul on blissful beaches, where you can revel in the uncomplicated joys of sitting, reading and swimming in heavenly shallow waters. The royally approved Princess Margaret Beach is one of the finest - an arching band of soft sand and cobalt-blue waters. As evening sets in, you may find you’re beckoned to share with communal barbecues of the day’s fresh catch with the locals, or to indulge in rum-heavy cocktails at beachside bars, lashed together from sea-blanched wooden limbs.

Deshaies

The port of Deshaies has a magnificent setting on the north-west coast of Basse-Terre Island, the western half of Guadeloupe. Nestling in the crook of a pretty bay on the Caribbean Sea, the village of wooden Creole-style houses extends along the foot of hillsides covered in tropical rainforest. Beyond the bay, the former property of famous French comedian Coluche is now a magnificent botanical garden where you can wander among West Indian trees and flowering plants and spot exotic birds. A little farther to the north is Grande Anse beach, one of most beautiful on the island.

Price tracking

Today’s fare, in context

Price history

Cheaper than 73%
30 days
Fare details

Fare details

Per person · taxes & fees included
Current fares
Verified 23 hours ago
Oceanview
$6,272
Balcony
$7,364
Suite
$8,904
Tracked range
156 days
Price history by cabin type
CabinCurrentLowestHighest
Oceanview $6,272 $4,480 on Jun 3 $6,636 on Jul 26
Balcony $7,364 $6,048 on Jun 3 $8,148 on Jul 24
Suite $8,904 $7,168 on Jun 3 $10,299 on Mar 26
Cabin grades
13 total
Balcony SuiteBalcony · BS
Balcony SuiteBalcony · BS1
Star Balcony SuiteBalcony · SBS
Star Balcony SuiteBalcony · SBS1
Ocean View SuiteOceanview · S
Ocean View SuiteOceanview · S1
Ocean View SuiteOceanview · S2
Ocean View SuiteOceanview · S3
Star Porthole SuiteOceanview · SP
Star Ocean View SuiteOceanview · SS1
Classic SuiteSuite · CS
Deluxe SuiteSuite · DS
Owner's SuiteSuite · OW

○ = last seen (sold out or delisted). · Verified 23 hours ago.

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Current prices

Per person · 2 guests · incl. taxes & fees

Inside

Not available

Oceanview

from $6,272

$448 / night

Fare rows

Ocean View Suite

Cabin grade

Available

from $6,272

$448 / night

per person · incl. taxes & fees

Ocean View Suite

Cabin grade

Available

from $6,608

$472 / night

per person · incl. taxes & fees

Balcony

from $7,364

$526 / night

Fare rows

Balcony Suite

Cabin grade

Available

from $7,364

$526 / night

per person · incl. taxes & fees

Star Balcony Suite

Cabin grade

Available

from $7,476

$534 / night

per person · incl. taxes & fees

Balcony Suite

Cabin grade

Available

from $7,700

$550 / night

per person · incl. taxes & fees

Star Balcony Suite

Cabin grade

Available

from $7,896

$564 / night

per person · incl. taxes & fees

Suite

from $8,904

$636 / night

Fare rows

Deluxe Suite

Cabin grade

Available

from $8,904

$636 / night

per person · incl. taxes & fees

Owner's Suite

Cabin grade

Available

from $14,392

$1,028 / night

per person · incl. taxes & fees

Prices verified Aug 27, 2026

Prices come from third-party data feeds via Windstar Cruises and may differ from the cruise line's current fare. Confirm the final price before booking. How our pricing works

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The journey

14 nights, in order

Follow the entire sailing from its first day to its last, with the route and schedule in one view.

San Juan, Puerto Rico

Day 1 Dec 6, 2026

San Juan, Puerto Rico

Blessed with some of the oldest buildings in the Western Hemisphere, San Juan, Puerto Rico’s cap-ital, is romantically charming with its bright pastel Spanish colonial facades,…

Explore San Juan, Puerto Rico

Day by day

The full itinerary

15 scheduled calls
Star Pride

Your ship

Star Pride

With only 212 guests, a Star Pride cruise will make you feel like you're on board your own private small ship almost as soon as you step aboard. The sitting area of your spacious, newly refurbished suite gives you an expansive ocean view — making it a welcome retreat. When you're ready to make an appearance, the lounges, club, screening room, and library are waiting to be explored. Take some "you" time in the tranquil WindSpa . . . enjoy a dip in the pool . . . work off that decadent dessert in the Fitness Center . . . and, of course, you are always welcome to visit the Bridge to examine navigation charts with the Captain. Star Pride is large enough to pamper and entertain you, yet small enough to tuck into delightful tiny harbors and hidden coves that others can’t reach.

4★ 9,975 GT 212 Passengers Built 1988
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from $6,272 pp

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