San Juan to San Juan

7 nights Dec 20, 2026

The San Juan to San Juan is a 7-night Caribbean cruise aboard Star Pride, operated by Windstar Cruises. Departing San Juan, Puerto Rico on December 20, 2026, the voyage visits 5 ports. Fares start from $2,485 per person.

from $2,485

$355 / night per person, incl. taxes & fees

See prices

You'll continue on Windstar Cruises's official site. Affiliate disclosure

from $2,485 pp

Continues on Windstar Cruises's site

See prices

Itinerary

Day 1 Dec 20, 2026 San Juan, Puerto Rico Departs 19:00 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. Go to San Juan, Puerto Rico Cruises visiting San Juan, Puerto Rico

San Juan, Puerto Rico photo — Day 1 Dec 20, 2026 San Juan, Puerto Rico Departs 19:00 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. Go to San Juan, Puerto Rico Cruises visiting San Juan, Puerto Rico

Day 3 Dec 22, 2026 St Georges, Grenada 09:00 – 22:00 13.0 hrs ashore Scents of spices such as cloves, cinnamon and nutmeg waft through the air as you arrive on MSC Caribbean and Antilles cruise to St. George’s, the capital of the island of Grenada. Nicknamed the “Spice Island” for its agriculture, Grenada’s symbol is the nutmeg, the island’s most famous product, which also appears on the nation’s flag. Originally colonized by the French in the 1600s, who wiped out the native Carib peoples during conflicts, Grenada was captured by the British in 1762 and remained under British rule until its independence in 1974. St. George’s offers many attractions starting with its beautiful views, botanical gardens, parks and heavenly beaches, most notably the Grand Anse Beach nearby. Start your journey with a guided walk on an MSC excursion through the capital’s winding maze of streets from the Carenage, the horseshoe-shaped harbour, with its lively waterfront promenade. Gaze at picturesque 19th-century pastel-coloured Creole houses made of brick and stone with red-tile roofs made from ship ballasts. Get a first-hand look at the wonderful palette of spices and scents of the island on an MSC excursion that stops at Dougaldston Estate. At this rustic, 300-year-old cocoa plantation in Gouyave, discover what drying trays for spices and cacao look like and learn how these spices are processed from seed pods, or how cinnamon is harvested from the bark of a tree. From there, proceed to an old-fashioned nutmeg cooperative plant where the work is done by hand. Grenada features a host of beautiful waterfalls, the most spectacular of which are Annandale Falls, about 7 miles from St. George’s. Hidden by a grotto of dense vegetation in the mountains, the waterfall cascades 30 feet down into the midst of leaves and branches, creating a natural pool where you can swim. For a throw-back to Grenada’s past, hop on a Creole bus on a guided MSC excursion along a labyrinth of steep roads to higher elevations. Enjoy sumptuous panoramas from the 18th-century forts of Fort George and Fort Frederick, nicknamed “The Backward Facing Fort,” for the cannons facing the land and not the sea.

Day 4 Dec 23, 2026 Bequia 08:00 – 22:00 14.0 hrs ashore 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. Go to Bequia Cruises visiting Bequia

Bequia photo — Day 4 Dec 23, 2026 Bequia 08:00 – 22:00 14.0 hrs ashore 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. Go to Bequia Cruises visiting Bequia

Day 5 Dec 24, 2026 Mayreau 08:00 – 17:00 9.0 hrs ashore Sip a tangy rum cocktail and leave your phone behind, as you sink into unbridled, undeveloped Caribbean bliss. An island gem of the Grenadines, Mayreau is the smallest island to house permanent residents, and a tiny gathering of just 200 are lucky enough to call it home. With limited infrastructure, and less than two square miles to explore, this is a place to enjoy the simple beauty of the here and now, as waves gently splash and the sun bronzes your skin. View less Dive spots invite you below the surface to a world of coral and tropical fish. Or you can stay put on Mayreau, to sprawl out across beautiful beaches like Saline Bay's - perhaps the island’s most enticing wedge of sand and tranquil blue waters. If that sounds too indulgent, earn your beachside bliss with a short hike up the small, densely-forested hill. You'll be rewarded with a great lookout across the other emerald islands, emerging from the azure seas. Jump aboard and hold on tight as your speedboat rips across the waves, or take a leisurely sailing tour of the surrounding islands of paradise. The glorious Tobago Cays are close by, and these uninhabited lands sparkle with a world of colour and sensory indulgence, immersing you in vistas lifted straight from the pages of a travel guide. Swim, snorkel, and let it all go.

Day 6 Dec 25, 2026 Deshaies 11:00 – 18:00 7.0 hrs ashore 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. Go to Deshaies Cruises visiting Deshaies

Deshaies photo — Day 6 Dec 25, 2026 Deshaies 11:00 – 18:00 7.0 hrs ashore 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. Go to Deshaies Cruises visiting Deshaies

Pricing

Lowest fare we've tracked over the observed 88-day span: $1,987 · range $1,987–$3,299

Lower than 62% of peers This week-long sailing's from-price per night is lower than 62% of comparable sailings.

same cruise line, destination, duration, and departure window · from-price per night · as of Jun 21, 2026

Current prices

Per person · 2 guests · incl. taxes & fees

Inside

Not available

Oceanview

from $2,485

$355 / night

Fare rows

Star Porthole Suite

Cabin grade

Available

from $2,485

$355 / night

per person · incl. taxes

Ocean View Suite

Cabin grade

Available

from $2,590

$370 / night

per person · incl. taxes

Ocean View Suite

Cabin grade

Available

from $2,660

$380 / night

per person · incl. taxes

Star Ocean View Suite

Cabin grade

Available

from $2,800

$400 / night

per person · incl. taxes

Ocean View Suite

Cabin grade

Available

from $2,870

$410 / night

per person · incl. taxes

Ocean View Suite

Cabin grade

Available

from $3,010

$430 / night

per person · incl. taxes

Balcony

from $3,185

$455 / night

Fare rows

Balcony Suite

Cabin grade

Available

from $3,185

$455 / night

per person · incl. taxes

Star Balcony Suite

Cabin grade

Available

from $3,220

$460 / night

per person · incl. taxes

Balcony Suite

Cabin grade

Available

from $3,395

$485 / night

per person · incl. taxes

Star Balcony Suite

Cabin grade

Available

from $3,500

$500 / night

per person · incl. taxes

Suite

from $4,480

$640 / night

Fare rows

Deluxe Suite

Cabin grade

Available

from $4,480

$640 / night

per person · incl. taxes

Owner's Suite

Cabin grade

Available

from $6,020

$860 / night

per person · incl. taxes

Prices verified Jun 15, 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

All cabin grades (13) Detailed cabin specs available at booking.

Name	Supplier code	Type
Balcony Suite	BS	Balcony
Balcony Suite	BS1	Balcony
Star Balcony Suite	SBS	Balcony
Star Balcony Suite	SBS1	Balcony
Ocean View Suite	S	Oceanview
Ocean View Suite	S1	Oceanview
Ocean View Suite	S2	Oceanview
Ocean View Suite	S3	Oceanview
Star Porthole Suite	SP	Oceanview
Star Ocean View Suite	SS1	Oceanview
Classic Suite	CS	Suite
Deluxe Suite	DS	Suite
Owner's Suite	OW	Suite