Ocean Crossings

The Ocean Crossings is a 16-night Caribbean cruise aboard Star Pride, operated by Windstar Cruises. Departing San Juan, Puerto Rico on April 3, 2028, the voyage visits 4 ports. Fares start from $2,720 per person.

Length: 16 nights
Departs: Apr 3, 2028
Returns: Apr 19, 2028
Ports of call: 4
Days at sea: 13

from $2,720

$170 / night per person, incl. taxes & fees

Book with CruiseDirect Book direct with Windstar Cruises

We may earn a commission

from $2,720 pp

via CruiseDirect

Book

Book direct with Windstar Cruises we may earn a commission

Itinerary

Day 1 Apr 3, 2028 San Juan, Puerto Rico Departs 16:00 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 Apr 3, 2028 San Juan, Puerto Rico Departs 16:00 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 12 Apr 14, 2028 Lisbon 12:00 – 22:00 10.0 hrs ashore Lisbon, the capital of Portugal, is a city open to the sea and carefully planned with 18th-century elegance. Its founder is said to be the legendary Ulysses, but the theory of an original Phoenician settlement is probably more realistic. Known in Portugal as Lisboa, the city was inhabited by the Romans, Visigoths and, beginning in the 8th century, the Moors. Much of the 16th century was a period of great prosperity and overseas expansion for Portugal. Tragedy struck on All Saints' Day in 1755 with a devastating earthquake that killed about 40,000 people. The destruction of Lisbon shocked the continent. As a result, the Baixa (lower city) emerged in a single phase of building, carried out in less than a decade by the royal minister, the Marques de Pombal. His carefully planned layout of a perfect neo-classical grid survived to this day and remains the heart of the city. Evidence of pre-quake Lisbon can still be seen in the Belém suburb and the old Moorish section of the Alfama that sprawls below the Castle of St. George. Lisbon is a compact city on the banks of the Tagus River. Visitors find it easy to get around as many places of interest are in the vicinity of the central downtown area. There is a convenient bus and tram system and taxis are plentiful. Rossio Square, the heart of Lisbon since medieval times, is an ideal place to start exploring. After a fire destroyed parts of the historic neighborhood behind Rossio in 1988, many of the restored buildings emerged with modern interiors behind the original façades. The city boasts a good many monuments and museums, such as the Jeronimos Monastery, Tower of Belém, the Royal Coach Museum and the Gulbenkian Museum. High above the Baixa is the Bairro Alto (upper city) with its teeming nightlife. The easiest way to connect between the two areas is via the public elevator designed by Gustave Eiffel. Cruising up the Tagus River to the ship's berth, you can already spot three of Lisbon's famous landmarks: the Monument to the Discoveries, the Tower of Belém and the Statue of Christ, which welcomes visitors from its hilltop location high above Europe's longest suspension bridge. Lisbon port guide Search cruises visiting Lisbon

Lisbon photo — Day 12 Apr 14, 2028 Lisbon 12:00 – 22:00 10.0 hrs ashore Lisbon, the capital of Portugal, is a city open to the sea and carefully planned with 18th-century elegance. Its founder is said to be the legendary Ulysses, but the theory of an original Phoenician settlement is probably more realistic. Known in Portugal as Lisboa, the city was inhabited by the Romans, Visigoths and, beginning in the 8th century, the Moors. Much of the 16th century was a period of great prosperity and overseas expansion for Portugal. Tragedy struck on All Saints' Day in 1755 with a devastating earthquake that killed about 40,000 people. The destruction of Lisbon shocked the continent. As a result, the Baixa (lower city) emerged in a single phase of building, carried out in less than a decade by the royal minister, the Marques de Pombal. His carefully planned layout of a perfect neo-classical grid survived to this day and remains the heart of the city. Evidence of pre-quake Lisbon can still be seen in the Belém suburb and the old Moorish section of the Alfama that sprawls below the Castle of St. George. Lisbon is a compact city on the banks of the Tagus River. Visitors find it easy to get around as many places of interest are in the vicinity of the central downtown area. There is a convenient bus and tram system and taxis are plentiful. Rossio Square, the heart of Lisbon since medieval times, is an ideal place to start exploring. After a fire destroyed parts of the historic neighborhood behind Rossio in 1988, many of the restored buildings emerged with modern interiors behind the original façades. The city boasts a good many monuments and museums, such as the Jeronimos Monastery, Tower of Belém, the Royal Coach Museum and the Gulbenkian Museum. High above the Baixa is the Bairro Alto (upper city) with its teeming nightlife. The easiest way to connect between the two areas is via the public elevator designed by Gustave Eiffel. Cruising up the Tagus River to the ship's berth, you can already spot three of Lisbon's famous landmarks: the Monument to the Discoveries, the Tower of Belém and the Statue of Christ, which welcomes visitors from its hilltop location high above Europe's longest suspension bridge. Lisbon port guide Search cruises visiting Lisbon

Day 15 Apr 17, 2028 Brest 07:00 – 16:00 9.0 hrs ashore Brest is a port town in the Brittany region on the west coast of France. Your MSC cruise will take you on the discovery of a place full of charm, history and culture, set in a natural inlet whose beauty will leave you breathless. There are many things to be seen in Brest, including the Tanguy Tower which houses historical findings from the city dating from ancient times to the period of World Wars. Another institution worth visiting is the National Maritime Museum located inside Château de Brest containing a real submarine. To start your tour of Brest, you can walk along Rue de Siam, a lively commercial district. The look of the road is severe, in full 1950s style. Both here and the entire district found between Pont deRecouvrance and the Town Hall is filled with large multi-story residential buildings, symmetrically arranged on a perfectly straight axis. Pont de Recouvrance, which dominates the docks and military port, was built in 1954 with a vertical lifting device. For a long time, it was the largest lifting bridge in Europe and is undoubtedly a stop not to be missed on your visit to Brest during an MSC cruise. Another really interesting place found at the docks is Les Ateliers des Capucins, a series of buildings that face the sea, built during the 19th century. In 2009, they were converted into a cultural and commercial center. In the bay of Brest, you can also see the delightful Phare du Petit Minou, a lighthouse built in 1848 that stands in front of the fort with the same name and is connected to the mainland by a stone bridge in the commune of Plouzané. Aligned with the Portziclighthouse, the Petit Minou had guided ships for over one hundred and fifty years along the safest route to make their way through the natural channel that unites Brest to the Atlantic Ocean. Brest port guide Search cruises visiting Brest

Brest photo — Day 15 Apr 17, 2028 Brest 07:00 – 16:00 9.0 hrs ashore Brest is a port town in the Brittany region on the west coast of France. Your MSC cruise will take you on the discovery of a place full of charm, history and culture, set in a natural inlet whose beauty will leave you breathless. There are many things to be seen in Brest, including the Tanguy Tower which houses historical findings from the city dating from ancient times to the period of World Wars. Another institution worth visiting is the National Maritime Museum located inside Château de Brest containing a real submarine. To start your tour of Brest, you can walk along Rue de Siam, a lively commercial district. The look of the road is severe, in full 1950s style. Both here and the entire district found between Pont deRecouvrance and the Town Hall is filled with large multi-story residential buildings, symmetrically arranged on a perfectly straight axis. Pont de Recouvrance, which dominates the docks and military port, was built in 1954 with a vertical lifting device. For a long time, it was the largest lifting bridge in Europe and is undoubtedly a stop not to be missed on your visit to Brest during an MSC cruise. Another really interesting place found at the docks is Les Ateliers des Capucins, a series of buildings that face the sea, built during the 19th century. In 2009, they were converted into a cultural and commercial center. In the bay of Brest, you can also see the delightful Phare du Petit Minou, a lighthouse built in 1848 that stands in front of the fort with the same name and is connected to the mainland by a stone bridge in the commune of Plouzané. Aligned with the Portziclighthouse, the Petit Minou had guided ships for over one hundred and fifty years along the safest route to make their way through the natural channel that unites Brest to the Atlantic Ocean. Brest port guide Search cruises visiting Brest

Day 17 Apr 19, 2028 Amsterdam Arrives 08:00 Few can resist the grand beauty of Amsterdam’s famous canals, which thread through this place of evocative beauty and thrilling contrast. Open-minded and tolerant, Amsterdam is a place for history buffs and hedonists alike, and its diverse neighbourhoods have something for everyone - whether it’s the beachside relaxation of Bloemendaal, nocturnal thuds of Buiksloterham, or characterful charm of Jordaan. 160 serene canals serve as the arteries of this city, imbuing it with its unique essence. Cruise along concentric waterways, past cherry red and oak-wood cladded houseboats, as you learn of its Golden Age history. Culture is also deep in Amsterdam’s DNA, and the Van Gogh Museum – which pays tribute to the tortured genius of the Dutch post-impressionist artist - stands out among its leading museums and galleries. One of history’s greatest tragedies is also rendered in heart-breaking clarity at Anne Frank House. Visit the site where the precocious teenager hid from the Nazi regime for so long, and the room where she penned the most famous diary ever written. Compact and easily walkable, Amsterdam remains consistently postcard-perfect as you watch bright bicycles trundling over ornate bridges, and stumble across hidden, tulip-decorated courtyards. ‘Gezellig’ is the local word for Amsterdam’s unhurried outlook on life. No translation can quite do the concept justice, but you’ll recognise it instinctively as hours float by in a happy haze browsing De Negen Straatjes street’s independent shops, or as you sip coffee with gooey stroopwafel. Broodje haring - a raw herring sandwich - is Amsterdam’s must-try delicacy, but many visitors find tompouce, a delicious pastry topped with vivid pink icing, a little more to their taste. Amsterdam port guide Search cruises visiting Amsterdam

Amsterdam photo — Day 17 Apr 19, 2028 Amsterdam Arrives 08:00 Few can resist the grand beauty of Amsterdam’s famous canals, which thread through this place of evocative beauty and thrilling contrast. Open-minded and tolerant, Amsterdam is a place for history buffs and hedonists alike, and its diverse neighbourhoods have something for everyone - whether it’s the beachside relaxation of Bloemendaal, nocturnal thuds of Buiksloterham, or characterful charm of Jordaan. 160 serene canals serve as the arteries of this city, imbuing it with its unique essence. Cruise along concentric waterways, past cherry red and oak-wood cladded houseboats, as you learn of its Golden Age history. Culture is also deep in Amsterdam’s DNA, and the Van Gogh Museum – which pays tribute to the tortured genius of the Dutch post-impressionist artist - stands out among its leading museums and galleries. One of history’s greatest tragedies is also rendered in heart-breaking clarity at Anne Frank House. Visit the site where the precocious teenager hid from the Nazi regime for so long, and the room where she penned the most famous diary ever written. Compact and easily walkable, Amsterdam remains consistently postcard-perfect as you watch bright bicycles trundling over ornate bridges, and stumble across hidden, tulip-decorated courtyards. ‘Gezellig’ is the local word for Amsterdam’s unhurried outlook on life. No translation can quite do the concept justice, but you’ll recognise it instinctively as hours float by in a happy haze browsing De Negen Straatjes street’s independent shops, or as you sip coffee with gooey stroopwafel. Broodje haring - a raw herring sandwich - is Amsterdam’s must-try delicacy, but many visitors find tompouce, a delicious pastry topped with vivid pink icing, a little more to their taste. Amsterdam port guide Search cruises visiting Amsterdam

Pricing

Lowest fare we've tracked over the observed 91-day span: $2,720 · range $2,720–$999,999

Lower than 100% of peers This extended sailing's from-price per night is lower than 100% 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 $2,720

$170 / night

Fare rows

Star Porthole Suite

Cabin grade

Available

from $2,720

$170 / night

per person · incl. taxes

Ocean View Suite

Cabin grade

Available

from $2,960

$185 / night

per person · incl. taxes

Ocean View Suite

Cabin grade

Available

from $3,200

$200 / night

per person · incl. taxes

Star Ocean View Suite

Cabin grade

Available

from $3,440

$215 / night

per person · incl. taxes

Ocean View Suite

Cabin grade

Available

from $3,600

$225 / night

per person · incl. taxes

Ocean View Suite

Cabin grade

Available

from $3,920

$245 / night

per person · incl. taxes

Balcony

from $4,000

$250 / night

Fare rows

Balcony Suite

Cabin grade

Available

from $4,000

$250 / night

per person · incl. taxes

Star Balcony Suite

Cabin grade

Available

from $4,160

$260 / night

per person · incl. taxes

Balcony Suite

Cabin grade

Available

from $4,480

$280 / night

per person · incl. taxes

Star Balcony Suite

Cabin grade

Available

from $4,720

$295 / night

per person · incl. taxes

Suite

from $5,760

$360 / night

Fare rows

Deluxe Suite

Cabin grade

Available

from $5,760

$360 / night

per person · incl. taxes

Classic Suite

Cabin grade

Available

from $8,800

$550 / night

per person · incl. taxes

Owner's Suite

Cabin grade

Available

from $9,200

$575 / night

per person · incl. taxes

Prices verified Jun 23, 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