Windstar 22 Nights Caribbean

Star Collector: Caribbean Beats & Transatlantic Treats

Star Legend • Embarkation: Malaga

Voyage Overview

Embark Date 12-Nov-2026
Disembark Date 04-Dec-2026
Duration 22 Nights
Vessel Star Legend

Day-by-Day Itinerary

Day 1: MALAGA

Here, on the shores of Costa del Sol, the Andalusian spirit thrives. Be sure to include an optional visit to see the brilliant and comprehensive collection of Picasso's work at Museo Picasso Málaga, a tribute to this artistic genius in the city of his birth. Or you may choose to opt for a visit to the beautiful village of Mijas, where picturesque Andalusian country life creates some of the world's best wines. 

Day 2: TANGIER

Fascinating Tangier is a traveler's delight with beautiful vistas, lovely unspoiled beaches, intriguing history and friendly people. Separated from Spain by only 20 miles across the Strait of Gibraltar, Tangier is considered by many to be the gateway to Africa. With its cosmopolitan mix of African and European influences, there are many interesting sites in Tangier.  The two UNESCO sites of the Medina (the old-walled city) a bustling place, and the Kasbah which offers beautiful views and fine Moroccan art, and the Place de France in the heart of the new city is an entertaining place to sip mint tea and enjoy the view.

Day 3: CASABLANCA

The siren call of Morocco is irresistible. Amid the whitewashed alleyways and stunning ocean views, make time for an optional excursion to the medina of Marrakech, a UNESCO World Heritage Site.  Explore the souks and medinas in the footsteps of Sir Winston Churchill and Yves St. Laurent, who both called this extraordinary blend of east and west their home.

Day 4: SEAD

SEAD

Day 5: FUNCHAL, MADEIRA

Considered one of Portugal's main tourist attractions and home of world-famous footballer Cristiano Ronaldo, Funchal is known for its style and beauty.  Visit Cabo Girao, the highest sea cliff in Europe or take a trip to the Pica da Torre for an incredible view of Camara de Lobos, a delightful fishing village. With a long history of Madeira winemaking, there'll be time here for a little wine tasting, a meal at one of the many 5-star restaurants, sightseeing to 15th century Cathedral of Our Lady of the Assumption, shopping the bargains to be found here, or experiencing the vibrant night life.

Day 6: SEAD

SEAD

Day 7: SEAD

SEAD

Day 8: SEAD

SEAD

Day 9: SEAD

SEAD

Day 10: SEAD

SEAD

Day 11: SEAD

SEAD

Day 12: SEAD

SEAD

Day 13: SEAD

SEAD

Day 14: SEAD

SEAD

Day 15: SEAD

SEAD

Day 16: BRIDGETOWN, BARBADOS

Jolly old England comes to life in the city and its garrison, both UNESCO World Heritage Sites. Further afield, you'll find historic sugar plantations and the fairyland magic of Harrison's Cave.

Day 17: ANSE MITAN, MARTINIQUE

Martinique offers a delightful and distinctive blend of French and Caribbean influences, with a bounty of historical sites, museums and a wide array of excellent shopping. Be sure to take a tour of the beautiful Jardin de Balata Botanical Gardens with exotic plants from around the world and a treetop walkway affording mountain views.

Day 18: RODNEY BAY

Rodney Bay, Saint Lucia

Day 19: RODNEY BAY

Rodney Bay, Saint Lucia

Day 20: CASTRIES, ST LUCIA

The capital and largest city of St. Lucia is a bustling port where shoppers flock.  Most of the city's historic buildings were destroyed in major fires between 1785 and 1948 but you'll see the beautiful, scenic backdrop of Morne Fortune (elev. 2,795 ft.) and the bustling harbor.  Visit the Castries Market for handicrafts, fruits and vegetables, see the murals painted by a local artist and housed in the Cathedral of the Immaculate Conception, and check out one of the many restaurants or Derek Walcott Square.

Day 21: SUNSET CRUISING PITONS

Located near the town of Soufriere, St. Lucia the Pitons are a UNESCO World Heritage Site and a spectacular landmark. Gros Piton is 2,619 feet high (798 meters) and Petit Piton is 2,438 feet high (743 meters). Gros Piton is home to at least 148 plant species and 27 bird species (5 of them endemic) and Petit Piton has 97 plant species with 8 rare tree species.

Day 22: MAYREAU

Mayreau is the smallest inhabited island of St. Vincent and the Grenadines, covering just about 1.5 square miles with a population of only a few hundred people. Tucked between Union Island and the Tobago Cays in the southern Grenadines, it's known for its laid-back, off-the-grid charm—there are no airports, no banks, and only one small village (Old Wall) perched on a hillside.

Day 23: ST GEORGES, GRENADA

Inhale the intoxicating aroma of the "Isle of Spice" as your eyes feast on what is widely claimed to be the most beautiful city in the Caribbean. Spend the day on 2-mile-long Grand Anse beach, and before you go, a taste of nutmeg ice cream is a must.

Day 24: BEQUIA

The only ships in port are those small enough to anchor alongside the yachts and fishing boats in Admiralty Bay. Bequia's whaling heritage is on display in the museum in pretty Port Elizabeth, or watch the island's famed model boat builders at work on their miniature masterpieces.

Day 25: BRIDGETOWN, BARBADOS

Jolly old England comes to life in the city and its garrison, both UNESCO World Heritage Sites. Further afield, you'll find historic sugar plantations and the fairyland magic of Harrison's Cave.

About Star Legend

Star Legend
  • Cruise Line: Windstar
  • Guest Capacity: 3 guests
  • Vessel Type: Ocean Liner / Mega-Cruise Ship
  • IMO Registration: 9008598
Starting From
$6,047
per person / based on double occupancy
Category Estimates
Inside Cabin: Call
Oceanview Cabin: $6,047
Private Balcony: $9,944
Luxury Suite: $6,047
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