San Juan to San Juan

The San Juan to San Juan is a 11-night Caribbean cruise aboard Star Pride, operated by Windstar Cruises. Departing San Juan, Puerto Rico on October 28, 2026, the voyage visits 10 ports. Fares start from $4,290 per person.

Length: 11 nights
Departs: Oct 28, 2026
Returns: Nov 8, 2026
Ports of call: 10
Days at sea: 1

from $4,290

$390 / night per person, incl. taxes & fees

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Itinerary

Day 1 Oct 28, 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. San Juan, Puerto Rico port guide Search cruises visiting San Juan, Puerto Rico

San Juan, Puerto Rico photo — Day 1 Oct 28, 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. San Juan, Puerto Rico port guide Search cruises visiting San Juan, Puerto Rico

Day 3 Oct 30, 2026 Gustavia, Saint Barthelemy 08:00 – 22:00 14.0 hrs ashore Cherry red roofs, yacht-sprinkled bays and a sophisticated French flavour all add to the gorgeous Caribbean allure of Gustavia. The island's capital rolls around a horseshoe-shaped harbour, where gleaming yachts hover and fancy boutiques, bars and restaurants fizz with life and clinking cutlery. Head up to red and white Gustavia Lighthouse to look down over the revered waters, which attract many a celebrity guest and diving enthusiast to these shores. View less Christopher Columbus was the first European to discover this volcanic island in 1493, giving it the name St Barthelemy in honour of his younger brother. The island has a unique history as a Swedish colony, following a deal with the French King Louis XVI to exchange the island with Sweden for better trading rights. It was returned to French control in 1878 and is now a French Overseas Collectivity. Learn more of the Swedish legacy at Fort Karl - which sits on a 29-metre-high hill above Shell Beach. The fort now lies in ruins, but you'll meet wandering iguanas, and the views down of sweeping sea and emerald coastline are some of the island's finest. Down below, a delightful spread of tiny pebbles and shell fragments are scattered like confetti and lapped by crystal-clear water. A little exploration uncovers countless other glorious beaches and natural wonders. Colombier Beach is a little out of the way but cradles silky-smooth sands and typically turquoise waters. If you have chance, find somewhere to settle and sip fruity rum cocktails as the sunset flares across the waves.

Day 4 Oct 31, 2026 Basseterre, St. Kitts 08:00 – 18:00 10.0 hrs ashore Columbus discovered St. Kitts (short for St. Christopher) and Nevis on his second voyage in 1493. Arawak and Carib Indians who had moved up through the islands from South America already inhabited both islands. While European immigrants massacred many of them, the Caribs continued to stage fierce battles, which became legendary. In 1632, the West Indies' first British settlement was established on the island, which soon developed into an important colony thanks to its sugar industry. France and England shared St. Kitts for some time, but the partition ended with the Peace of Utrecht in 1713. After being declared a British colony in 1783, St. Kitts and Nevis, along with Anguilla and the British Virgin Islands, were administered as a single colony until 1871 when the Leeward Islands Federation was formed. This continued up to 1957 when St. Kitts and Nevis were granted self-government, with Britain remaining responsible for external affairs and defense. Both islands became an independent state within the Commonwealth in 1983. Basseterre, St. Kitts' capital, still shows signs of colonial architecture. However, its setting against the emerald green hills ensures a distinct Caribbean ambiance. Many travelers agree that Basseterre is one of the prettiest of the Caribbean's small capitals. Basseterre, St. Kitts port guide Search cruises visiting Basseterre, St. Kitts

Basseterre, St. Kitts photo — Day 4 Oct 31, 2026 Basseterre, St. Kitts 08:00 – 18:00 10.0 hrs ashore Columbus discovered St. Kitts (short for St. Christopher) and Nevis on his second voyage in 1493. Arawak and Carib Indians who had moved up through the islands from South America already inhabited both islands. While European immigrants massacred many of them, the Caribs continued to stage fierce battles, which became legendary. In 1632, the West Indies' first British settlement was established on the island, which soon developed into an important colony thanks to its sugar industry. France and England shared St. Kitts for some time, but the partition ended with the Peace of Utrecht in 1713. After being declared a British colony in 1783, St. Kitts and Nevis, along with Anguilla and the British Virgin Islands, were administered as a single colony until 1871 when the Leeward Islands Federation was formed. This continued up to 1957 when St. Kitts and Nevis were granted self-government, with Britain remaining responsible for external affairs and defense. Both islands became an independent state within the Commonwealth in 1983. Basseterre, St. Kitts' capital, still shows signs of colonial architecture. However, its setting against the emerald green hills ensures a distinct Caribbean ambiance. Many travelers agree that Basseterre is one of the prettiest of the Caribbean's small capitals. Basseterre, St. Kitts port guide Search cruises visiting Basseterre, St. Kitts

Day 5 Nov 1, 2026 Falmouth Harbour,Antigua 08:00 – 18:00 10.0 hrs ashore With 365 beaches to choose from, it's said that Antigua has a sandy escape for every day of the year. The sheltered twin bays of English Harbour hold an ever-alluring appeal and draw a beauty-seeking flotilla of yachts to drop anchor in their calm waters. Strap on scuba gear, crunch through paths of dense jungle, or soar up above to volcanic peaks in a helicopter - the choice is yours. Whether you seek adventure, or simply want to take it easy with a paperback and the song of the waves – a beautiful island of sun, sea, and sand lies before you. As the name implies, there's an unrestrained British Colonial influence here, and Horatio Nelson's name is imprinted deep into Falmouth's story. Walk in his footsteps at Nelson's Dockyards - the gorgeously restored, working Georgian dockyard. The colonial spirit is an evocative throwback to this important 17th-century Royal Navy base. Museums tell the story of the British exploits in the West Indies, and the life of Nelson - who lived here for three years. Clarence House is also close by, and the 200-year-old residence continues to draw visits from British royals to this day. This being Antigua, there's no shortage of jaw-dropping beaches and bathing opportunities. Take to pearly-white sands or explore the Pillars of Hercules – a set of smooth, rounded columns of rock that plunge dramatically into the waters below. Pigeon Point Beach is a ravishing amalgam of blues and pristine white sands, where turtles and stingrays glide through patches of coral reefs. Enjoy the best views of the naturally coddled bays of English Harbour by rising to Shirley Heights. Sunset is thrilling from this elevated vantage point, as reds and pinks spill across the skies.

Day 6 Nov 2, 2026 Les Saints 08:00 – 18:00 10.0 hrs ashore During the feast of All Saints in 1493, Christopher Columbus discovered this archipelago of nine islands that he named "The Saints". Today, only two of them are inhabited. Terre de Haut, in the east, is dominated by the Morne Mire hill; at the summit stands Fort Napoleon, paying homage to the islands' history. In the heart of the botanical garden, shared by iguanas and cacti, there is an exceptional view of the Baie des Saintes, one of the most beautiful in the world. The long shady beach of Pompierre, where it is forbidden to drop anchor, is a peaceful place for a swim, while Pain de Sucre Beach offers wonderful opportunities for snorkelling. On the island, don’t forget to taste the local speciality, the “tourment d’amour”, a cake made with coconut.

Day 8 Nov 4, 2026 St Georges, Grenada 10:00 – 18:00 8.0 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 10 Nov 6, 2026 Jost Van Dyke 08:00 – 22:00 14.0 hrs ashore Glowing turquoise waters, lazily bowing palm trees, and pristine white sand beaches – it's all waiting for you in Jost Van Dyke's picturesque Caribbean splendour. Slip off your shoes, you won't be needing them too much in these parts, as you wander soft, heavenly sands, and paddle out into impossibly clear waters. The island escape of choice for dallying yachts, which visit to soak up the off-the-beaten-path good life. Join them around the pristine beaches of this tiny celebrity magnet of an island. View less If this is your first experience of the Caribbean's splendour, you may be a little sceptical about the reality of those famed, shockingly bright colours that you see in photographs. If so, Jost Van Dyke will be love at first sight. Splash into water that glows with a bright teal hue and is blotched with occasional swells of deeper royal blue. Snorkellers will adore the explosions of colourful fish beneath the waves. White Bay is a slice of island perfection, with a neat hill of trees framing a sandy sweep of shaded beach bars. There's nothing for it but to indulge on a bed of soft pearly-white sand, and soak in the staggering beauty of it all. The wander up to Majohnny Hill is the most exertion needed to explore this four-square-mile island, and it's worth it to see the heavenly beaches emerging from tranquil waters below. Even the natural sea formations here encourage you to unwind, with waves gurgling and frothing over the rocks to create Bubbly Pool, a natural jacuzzi. Jost Van Dyke has a reputation as the off-the-radar island getaway of choice for celebrities like Keith Richards. A lot of that comes down to the calypso charm of its rustic beach bars - especially the legendary Foxy's Bar, which is run by island legend Foxy Callwood. Rum-drenched cocktails and icy buckets of beach beers await - sure to get you into the island’s party spirit in no time.

Day 11 Nov 7, 2026 Virgin Gorda (BVI) 08:00 – 17:00 9.0 hrs ashore Local lore has it that the unusual shape of this little bit of paradise reminded Christopher Columbus of a reclining, voluptuous woman, so he named it Virgin Gorda, the "Fat Virgin." She is suitably adorned with dramatic heights that plunge down from Gorda Peak to the sparkling turquoise waters far below. This is a good place to explore in a jeep, swim with dolphins, or hike the rugged trails throughout the island. Virgin Gorda is most famous for The Baths, where giant granite boulders are strewn across the beach and in the water, creating pools, caves, and grottos – a sort of natural water park. Virgin Gorda (BVI) port guide Search cruises visiting Virgin Gorda (BVI)

Virgin Gorda (BVI) photo — Day 11 Nov 7, 2026 Virgin Gorda (BVI) 08:00 – 17:00 9.0 hrs ashore Local lore has it that the unusual shape of this little bit of paradise reminded Christopher Columbus of a reclining, voluptuous woman, so he named it Virgin Gorda, the "Fat Virgin." She is suitably adorned with dramatic heights that plunge down from Gorda Peak to the sparkling turquoise waters far below. This is a good place to explore in a jeep, swim with dolphins, or hike the rugged trails throughout the island. Virgin Gorda is most famous for The Baths, where giant granite boulders are strewn across the beach and in the water, creating pools, caves, and grottos – a sort of natural water park. Virgin Gorda (BVI) port guide Search cruises visiting Virgin Gorda (BVI)

Pricing

Lowest fare we've tracked over the observed 85-day span: $4,199 · range $4,199–$4,510

Lower than 67% of peers This longer-duration sailing's from-price per night is lower than 67% of comparable sailings.

same cruise line and duration · from-price per night · as of Jun 24, 2026 · Broader cohort: same cruise line and duration, compared by from-price per night.

Current prices

Per person · 2 guests · incl. taxes & fees

Inside

Not available

Oceanview

from $4,290

$390 / night

Fare rows

Star Porthole Suite

Cabin grade

Available

from $4,290

$390 / night

per person · incl. taxes

Ocean View Suite

Cabin grade

Available

from $4,785

$435 / night

per person · incl. taxes

Star Ocean View Suite

Cabin grade

Available

from $4,950

$450 / night

per person · incl. taxes

Ocean View Suite

Cabin grade

Available

from $5,115

$465 / night

per person · incl. taxes

Ocean View Suite

Cabin grade

Available

from $5,280

$480 / night

per person · incl. taxes

Balcony

from $7,040

$640 / night

Fare rows

Balcony Suite

Cabin grade

Available

from $7,040

$640 / night

per person · incl. taxes

Star Balcony Suite

Cabin grade

Available

from $7,150

$650 / night

per person · incl. taxes

Balcony Suite

Cabin grade

Available

from $7,370

$670 / night

per person · incl. taxes

Star Balcony Suite

Cabin grade

Available

from $7,590

$690 / night

per person · incl. taxes

Suite

from $10,285

$935 / night

Fare rows

Deluxe Suite

Cabin grade

Available

from $10,285

$935 / night

per person · incl. taxes

Classic Suite

Cabin grade

Available

from $11,990

$1,090 / night

per person · incl. taxes

Owner's Suite

Cabin grade

Available

from $14,190

$1,290 / night

per person · incl. taxes

Prices verified Jun 22, 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

Show all 13 cabin grades

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