Skip to main content

18-night Caribbean cruise: Bridgetown, Barbados to Caldera, Costa Rica on Wind Star

The Bridgetown to Puerto Caldera is a 18-night Caribbean cruise aboard Wind Star, operated by Windstar Cruises. Departing Bridgetown, Barbados on November 24, 2026 and arriving in Caldera, Costa Rica on December 12, 2026, the voyage visits 14 ports including Bequia, St Georges, Grenada, Kralendijk,Bonaire. Fares start from $12,551 per person.

Length
18 nights
Departs
Nov 24, 2026
Returns
Dec 12, 2026
Ports of call
14
Days at sea
4

Voyage code ST20261124-18D

Bridgetown, Barbados

18 nights · Caribbean

from $12,551 pp

via CruiseDirect

Book with CruiseDirect

Book direct with Windstar Cruises we may earn a commission

Why this route stands out

A closer look at the journey

Bridgetown, Barbados

When you arrive in Barbados on an MSC Caribbean and Antilles cruise, begin your exploration with the capital, Bridgetown. There are many attractions in this small Caribbean city, but by all means pause to admire its many colonial buildings, the Parliament Building and the statue of Lord Nelson standing in what is currently called the National Heroes Square. Barbados has retained somewhat of a British feel, with its place names, cricket, horse-racing and polo, Anglican parish churches and even a hilly district known as Scotland. But the Britishness can be exaggerated, for this is a distinctly West Indian country, covered by a patch-work of sugarcane fields and dotted with tiny rum shops. The Garrison Historic Area, a UNESCO World Heritage Site with magnificent 18th- and 19th-century buildings, is a must-see stop, featuring one of the world's finest collection of cannons. It also includes the George Washington House, where the American patriot spent six weeks of his life. The current St. John's Church, in the eastern parish of the same name, is the fifth reconstruction of the oldest local church, in Barbadian Gothic style. Perched on a cliff 800 feet above the sea, it dates back to 1836. Its interior hosts a sculpture by 18th-century British artist Richard Westmacott, while its churchyard contains the tomb of Ferdinando Paleologus, a direct descendant of the brother of Constantine XI, the last Byzantine emperor. Book an MSC excursion to discover the island’s history at the Barbados Museum and Historical Society in the St. Michael neighbourhood. And tour Sunbury Plantation House, located in the tranquil St. Philip countryside. Dating back to 1650, it’s a living monument to plantation life and a bygone era. Harrison’s Cave, in St. Thomas district, is a wonder of nature with its stalactites, stalagmites, streams, lakes and waterfalls. In one of the caverns, the play of light on the rocks is so in-tense that it has been nicknamed “The Crystal Room”. For some fun at the beach, head to Pirates Cove, one of the best beaches on Barbados. Featuring palm trees and chickee huts, white sand and crystal-clear water, it’s the perfect place to relax, just a stone’s throw from Bridgetown. If you’re brave enough to dive into the deep, set out on an MSC excursion inside a real submarine, the Atlantis, to explore the coral reef and discover the beauty that the depths reveal.

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.

Kralendijk,Bonaire

Bonaire's small, tidy capital city (population 3,000) is five minutes from the airport. The main drag, J.A. Abraham Boulevard, turns into Kaya Grandi in the center of town. Along it are most of the island's major stores, boutiques, and restaurants. Across Kaya Grandi, opposite the Littman’s jewelry store, is Kaya L.D. Gerharts, with several small supermarkets, a handful of snack shops, and some of the better restaurants. Walk down the narrow waterfront avenue called Kaya C.E.B. Hellmund, which leads straight to the North and South piers. View less In the center of town, the Harbourside Mall has chic boutiques. Along this route is Ft. Oranje, with its cannons. From December through April, cruise ships dock in the harbor once or twice a week. The diminutive ocher-and-white structure that looks like a tiny Greek temple is the produce market, where one can find plenty of fresh produce brought over from Venezuela. Pick up the brochure Walking and Shopping in Kralendijk from the tourist office to get a map and complete list of all the monuments and sights in the town.

Price tracking

Today’s fare, in context

Price history

All
Fare details

Fare details

Per person · taxes & fees included
Current fares
Verified 30 minutes ago
Oceanview
$12,551
Tracked range
2 days
Price history by cabin type
CabinCurrentLowestHighest
Oceanview $12,551 $12,551 on Sep 7 $12,551 on Sep 7
Cabin grades
5 total
StateroomOceanview · A
Deluxe StateroomOceanview · AX
StateroomOceanview · B
Deluxe StateroomOceanview · BX
Owner's SuiteSuite · OW

○ = last seen (sold out or delisted). · Verified 30 minutes ago.

Lowest fares with no residency, age, or service requirement — verify eligibility at booking. How our pricing works

Current prices

Per person · 2 guests · incl. taxes & fees

Inside

Not available

Oceanview

from $12,551

$697 / night

Fare rows

Stateroom

Cabin grade

Available

from $12,551

$697 / night

per person · incl. taxes & fees

Balcony

Not available

Suite

Not available

Prices verified Sep 8, 2026

This sailing

Catch the next fare drop

We’ll email you if this sailing drops below today’s $12,551 fare.

Free. Confirm by email. Unsubscribe anytime.

Advanced options Cabins & price targets

Choose a cabin, then select any price drop, a percentage, or a target price.

at or below $

The journey

18 nights, in order

Bridgetown, Barbados

Day 1 Nov 24, 2026

Bridgetown, Barbados

When you arrive in Barbados on an MSC Caribbean and Antilles cruise, begin your exploration with the capital, Bridgetown.

Explore Bridgetown, Barbados

Day by day

The full itinerary

20 scheduled calls
Wind Star

Your ship

Wind Star

Wind Star is a sleek, 4-masted sailing ship accommodating 148 guests. With four decks and a gross tonnage of 5,307, Wind Star feels like your own private small ship. Wind Star features wide open, teak decks—quite unusual for small ships. Guests will find hidden nooks for private moments giving them a feeling of being on their own private veranda. All staterooms have ocean views, queen beds, flat-screen TV with DVD player, and Bose SoundDock speakers for Apple iPods. The Owner’s Suite includes a sitting area. Wind Star offers two primary dining venues. Amphora restaurant offers gourmet, course-by-course cuisine in the evenings and Veranda restaurant offers casual buffet and full-service dining for breakfast and lunch. All dining is open seating. And, for dining under the stars, make a reservation for Candles which features steaks and skewers. Wind Star amenities include: WindSpa, Watersports Platform, Lounge, Library, Pool, and Hot Tub.

4★ 5,307 GT 148 Passengers Built 1985
Wind Star ship guide Search cruises on Wind Star

Deck plans

Deck plan for Deck 1

Scroll to explore · Double-tap to zoom

from $12,551 pp

via CruiseDirect

Book with CruiseDirect

Book direct with Windstar Cruises we may earn a commission