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Dream Islands as Your Holiday Gift Caribbean Sailing Cruise

Escape the traditional winter festivities and celebrate Christmas beneath Caribbean skies on this seven-night sailing voyage from Barbados to Guadeloupe. Aboard an elegant tall ship, discover a collection of idyllic islands where turquoise waters, palm-fringed beaches, and warm trade winds replace snow and evergreen trees. Explore the lush rainforests and waterfalls of Dominica, the spice-scented streets of Grenada, the untouched beauty of Tobago Cays, and the relaxed charm of Bequia and Tobago. With opportunities for swimming, snorkelling, and simply unwinding under sail, this festive Caribbean escape combines tropical scenery, island culture, and the timeless romance of life at sea.

21 December, 2027 to 28 December, 2027
Category F Upper/Lower Beds. From €4,845 EUR pp
All the cabins have small sitting areas, a bright ambience, brightly coloured, spacious marble baths and plenty of space for all your personal belongings. No matter which cabin you choose, the cabin service will provide everything you need. Your pretty maritime home is tidied twice a day, the fruit bowl is refilled, and the daily programme is left out for you to read (not to mention all the extra little touches...). These cabins are in the traditional windjammer style with upper and lower beds. They are located on the Cabin Deck. Cabin size: Approx. 14 m². Furnishings: Two portholes, chair, table, TV with DVD player, mini-bar, dressing table, closet, safe, adjustable A/C Bed: Upper and lower single beds (90 cm x 200 cm) Bathroom: Approx. 3 m² with shower, WC, marble sink, golden fixtures, hair dryer, outlet for razor.
view cabin photo
Category E. From €5,627 EUR pp
All the cabins have small sitting areas, a bright ambience, brightly coloured, spacious marble baths and plenty of space for all your personal belongings. No matter which cabin you choose, the cabin service will provide everything you need. Your pretty maritime home is tidied twice a day, the fruit bowl is refilled, and the daily programme is left out for you to read (not to mention all the extra little touches...). The comfortable cabins in Category E are located on the Cabin Deck, where the hospital, sauna, swim platform and fitness area can be found. Cabin size: No. 207-210 approx. 19 m². No. 211-217, 224-231 approx. 20 m². Furnishings: Two portholes, sofa, table, TV with DVD player, mini-bar, dressing table, closet, safe, adjustable A/C Bed: Queen size bed (180 cm x 200 cm); can be separated into two single beds Bathroom: Approx. 3 m² with shower, WC, marble sink, golden fixtures, hair dryer, outlet for razor.
view cabin photo
Category D. From €6,477 EUR pp
All the cabins have small sitting areas, a bright ambience, brightly coloured, spacious marble baths and plenty of space for all your personal belongings. No matter which cabin you choose, the cabin service will provide everything you need. Your pretty maritime home is tidied twice a day, the fruit bowl is refilled, and the daily programme is left out for you to read (not to mention all the extra little touches...). The Category D de luxe double-bed cabins are located on the Cabin Deck, where the hospital, sauna, swim platform and fitness area can be found. Cabin size: Approx. 21 m². Furnishings: Three portholes, two chairs, table, TV with DVD player, mini-bar, dressing table, closet, safe, adjustable A/C. Bed: Queen size bed (180 cm x 200 cm) with two separate mattresses. Bathroom: Approx. 3 m² with shower, WC, marble sink, golden fixtures, hair dryer, outlet for razor
view cabin photo
Category C. From €6,741 EUR pp
All the cabins have small sitting areas, a bright ambience, brightly coloured, spacious marble baths and plenty of space for all your personal belongings. No matter which cabin you choose, the cabin service will provide everything you need. Your pretty maritime home is tidied twice a day, the fruit bowl is refilled, and the daily programme is left out for you to read (not to mention all the extra little touches...). The Category C deluxe double-bed cabins are located on the Promenade Deck, where the restaurant, boutique and the reception can be found. Cabin size: Approx. 20 m². Furnishings: Panorama windows, two chairs, table, TV with DVD player, mini-bar, dressing table, closet, safe, adjustable A/C. Bed: Queen size bed (180 cm x 200 cm) with two separate mattresses Bathroom: Approx. 3 m² with shower, WC, marble sink, golden fixtures, hair dryer, outlet for razor.
view cabin photo
Category B. From €7,463 EUR pp
All the cabins have small sitting areas, a bright ambience, brightly coloured, spacious marble baths and plenty of space for all your personal belongings. No matter which cabin you choose, the cabin service will provide everything you need. Your pretty maritime home is tidied twice a day, the fruit bowl is refilled, and the daily programme is left out for you to read (not to mention all the extra little touches...). The spacious junior suites are conveniently located on the Promenade Deck, where the restaurant, boutique, and the reception can be found. Cabin size: No. 303 approx. 22 m², No. 304 approx. 21,5 m², No. 305-319 approx. 23 m². Furnishings: Panorama window, seating area, decorative fireplace, console with TV/DVD and mini-bar, dressing table, walk-in closet, safe, adjustable A/C. Bed: Queen size bed (180 cm x 200 cm) with two separate mattresses; can be separated into two single beds. Bathroom: Approx. 3,2 m² with tub, WC, marble sink, golden fixtures, hair dryer, outlet for razor.
view cabin photo
Category A. From €8,577 EUR pp
All the cabins have small sitting areas, a bright ambience, brightly coloured, spacious marble baths and plenty of space for all your personal belongings. No matter which cabin you choose, the cabin service will provide everything you need. Your pretty maritime home is tidied twice a day, the fruit bowl is refilled, and the daily programme is left out for you to read (not to mention all the extra little touches...). The charming luxury owner suites are located on the Lido Deck where you can also find the library and the lounge. Cabin size: Approx. 27 m². Furnishings: Panorama window, sofa, table, chair, desk, decorative fireplace, TV and DVD player, mini-bar, dressing table, four closets, safe, adjustable A/C. Bed: King size canopy bed with two separate mattresses (90 cm x 200 cm). Bathroom: Approx. 4,2 m² with tub and separate shower, WC, marble sink, golden fixtures, hair dryer, outlet for razor
view cabin photo

Dream Islands as Your Holiday Gift Caribbean Sailing Cruise itinerary:

show reverse itinerary
Day 1 Bridgetown, Barbados

Departure 10:00 pm
More than 300 years of British rule have left their mark. The whole of Bridgetown, Barbados' historic center, with its colonial architecture surrounding Trafalgar Square, is a UNESCO World Heritage Site. A green hilly countryside and endless fields of sugar cane characterize the island's landscape. Old colonial houses are reminders of the high life of the plantation owners, while innumerable colorful chattel houses are evidence of their workers' moveable properties. The sweeping coastline is a picture postcard of fine sandy beaches and turquoise sea surrounded by vibrant coral reefs.

Days 2 - 3 Man-O-War Bay, Tobago

Arrival 9:00 pm
If you are looking for a sunny, dreamy Caribbean bay, the options are nearly endless in the northeast of Tobago. As soon as the windjammer enters Man-o-War Bay, smaller hidden bays are revealed. A real island paradise: From Hermitage Bay to Pirate's Bay, the tropical forest grows up to the golden sand beach, while under water colorful reef inhabitants cavort below the surface. Tobago is a pioneer in environmental protection: As early as 1764, the Main Ridge Rainforest was declared a nature reserve here, enabling it to preserve its impressive biodiversity.

Day 4 St. George’s, Grenada

Arrival 8:00 am, Departure 11:00 pm
Beautiful beaches, aromatic spice plantations, dense rainforests, waterfalls, and a volcano that has long been extinct define this stunning island. For many people, Grenada is the incarnation of a tropical paradise and St. George's the most beautiful little port in the Grenadines. All around the horseshoe-shaped bay there are numerous houses reminiscent of colonial times. There is good reason why nutmeg is immortalized on the national flag. Alongside cloves, cinnamon and ginger, it is one of the island's biggest exports.

Day 5 Tobago Cays, St. Vincent & Grenadines

Arrival 8:00 am, Departure 6:00 pm
Right in the south of the Grenadines are the Tobago Cays – four small uninhabited islands, surrounded by a protective horseshoe-shaped coral reef. The Horseshoe Reef holds the Atlantic swell at bay and its unique animal and plant life make it an ideal place for snorkelling. The lagoon between the islets shimmers in all shades from turquoise through to emerald green and invites you to take a dip at the fantastic beaches.

Day 6 Port Elizabeth, Bequia

Arrival 8:00 am, Departure 1:30 pm
Bequia is actually the largest island in the Grenadines, but still small and tranquil at just 87 square miles. Elegant sailing yachts sway in the natural shelter of Admiralty Bay, while in lovely Port Elizabeth, with its attractive beach bars, you are right in the heart of a lifestyle that likes to take things easy. You can find Princess Margaret Beach just nearby, named because it was once visited by the British royal. And on the eastern coast, you can find the Old Hegg Turtle Sanctuary focuses on rearing and caring for endangered turtles.

Day 7 Cabrits, Dominica

Arrival 1:30 pm, Departure 11:00 pm
Dominica, nicknamed the Nature Isle of the Caribbean, is one of the most untouched of the Windward Islands. It boasts some of the highest mountains in the Lesser Antilles, as well as many beautiful national parks. Its interior is characterized by thick forest, where rivers plunge into the depths and tiny streams wind through the jungle. Two extinct volcanoes are at the center of the Cabrits National Park and, recaptured by nature, the former strategically important Fort Stanley appears like a picturesque backdrop in the heart of the lush woodlands.

Day 8 Pointe-à-Pitre, Guadeloupe

Arrival 8:00 am
With a population around 15,000, Pointe-à-Pitre is the largest city in the French overseas region of Guadeloupe – and euros are common currency. If you want to splash out, visit one of its picturesque markets. The traditional Marché La Darse takes place around the harbor on weekdays, where local traders sell mainly vegetables, fruit, and fresh fish. The best place to find exotic jams and spices is around the Saint-Antoine Market in the market hall. The name Pointe-à-Pitre goes back to a Dutch fisherman named Peter, who settled there in the 17th century.

Please note:

Itineraries are subject to change. 

Dream Islands as Your Holiday Gift Caribbean Sailing Cruise reverse itinerary:

show main itinerary
Please note: *

Itineraries are subject to change. 

Day 8 Pointe-à-Pitre, Guadeloupe *

Arrival 8:00 am
With a population around 15,000, Pointe-à-Pitre is the largest city in the French overseas region of Guadeloupe – and euros are common currency. If you want to splash out, visit one of its picturesque markets. The traditional Marché La Darse takes place around the harbor on weekdays, where local traders sell mainly vegetables, fruit, and fresh fish. The best place to find exotic jams and spices is around the Saint-Antoine Market in the market hall. The name Pointe-à-Pitre goes back to a Dutch fisherman named Peter, who settled there in the 17th century.

Day 7 Cabrits, Dominica *

Arrival 1:30 pm, Departure 11:00 pm
Dominica, nicknamed the Nature Isle of the Caribbean, is one of the most untouched of the Windward Islands. It boasts some of the highest mountains in the Lesser Antilles, as well as many beautiful national parks. Its interior is characterized by thick forest, where rivers plunge into the depths and tiny streams wind through the jungle. Two extinct volcanoes are at the center of the Cabrits National Park and, recaptured by nature, the former strategically important Fort Stanley appears like a picturesque backdrop in the heart of the lush woodlands.

Day 6 Port Elizabeth, Bequia *

Arrival 8:00 am, Departure 1:30 pm
Bequia is actually the largest island in the Grenadines, but still small and tranquil at just 87 square miles. Elegant sailing yachts sway in the natural shelter of Admiralty Bay, while in lovely Port Elizabeth, with its attractive beach bars, you are right in the heart of a lifestyle that likes to take things easy. You can find Princess Margaret Beach just nearby, named because it was once visited by the British royal. And on the eastern coast, you can find the Old Hegg Turtle Sanctuary focuses on rearing and caring for endangered turtles.

Day 5 Tobago Cays, St. Vincent & Grenadines *

Arrival 8:00 am, Departure 6:00 pm
Right in the south of the Grenadines are the Tobago Cays – four small uninhabited islands, surrounded by a protective horseshoe-shaped coral reef. The Horseshoe Reef holds the Atlantic swell at bay and its unique animal and plant life make it an ideal place for snorkelling. The lagoon between the islets shimmers in all shades from turquoise through to emerald green and invites you to take a dip at the fantastic beaches.

Day 4 St. George’s, Grenada *

Arrival 8:00 am, Departure 11:00 pm
Beautiful beaches, aromatic spice plantations, dense rainforests, waterfalls, and a volcano that has long been extinct define this stunning island. For many people, Grenada is the incarnation of a tropical paradise and St. George's the most beautiful little port in the Grenadines. All around the horseshoe-shaped bay there are numerous houses reminiscent of colonial times. There is good reason why nutmeg is immortalized on the national flag. Alongside cloves, cinnamon and ginger, it is one of the island's biggest exports.

Days 2 - 3 Man-O-War Bay, Tobago *

Arrival 9:00 pm
If you are looking for a sunny, dreamy Caribbean bay, the options are nearly endless in the northeast of Tobago. As soon as the windjammer enters Man-o-War Bay, smaller hidden bays are revealed. A real island paradise: From Hermitage Bay to Pirate's Bay, the tropical forest grows up to the golden sand beach, while under water colorful reef inhabitants cavort below the surface. Tobago is a pioneer in environmental protection: As early as 1764, the Main Ridge Rainforest was declared a nature reserve here, enabling it to preserve its impressive biodiversity.

Day 1 Bridgetown, Barbados *

Departure 10:00 pm
More than 300 years of British rule have left their mark. The whole of Bridgetown, Barbados' historic center, with its colonial architecture surrounding Trafalgar Square, is a UNESCO World Heritage Site. A green hilly countryside and endless fields of sugar cane characterize the island's landscape. Old colonial houses are reminders of the high life of the plantation owners, while innumerable colorful chattel houses are evidence of their workers' moveable properties. The sweeping coastline is a picture postcard of fine sandy beaches and turquoise sea surrounded by vibrant coral reefs.

* = Indicative
Map for Dream Islands as Your Holiday Gift Caribbean Sailing Cruise
Sea Cloud II, the ship servicing Dream Islands as Your Holiday Gift Caribbean Sailing Cruise

Sea Cloud II

Vessel Type: Tall Ship (Sailing)

Length: 105 metres

Passenger Capacity: 88

Built: 2001

Sea Cloud II is a romantic tall ship that masterfully blends the elegance of classic sailing with the comfort and convenience of modern luxury. Inspired by her legendary predecessor from the 1930s, this three-masted barque is fitted with 23 sails and is hand-sailed whenever possible, adding a sense of theatre and tradition to every voyage. With 44 cabins accommodating just 88 guests, the atmosphere aboard remains intimate and relaxed, while the interiors evoke the charm of a bygone era—polished wood, sweeping staircases, and vintage nautical style—all paired with the contemporary standards of a premium expedition ship.

Guests aboard Sea Cloud II enjoy spacious decks for sun-soaked sailing days, al fresco dining on the Lido Deck, and a wellness area featuring a sauna, massage therapy, and fitness facilities. The ship’s welcoming indoor spaces include an elegant dining room and a comfortable lounge for evening Recaps hosted by expert field staff such as historians and photo instructors. Meals focus on locally sourced ingredients and regional cuisine, served in an informal yet refined setting. With an open Bridge policy and wide, accessible passageways, Sea Cloud II invites guests not just to relax, but to immerse themselves fully in the experience of life under sail.

Cabin layout for Sea Cloud II
• Trade Evergreens for Palm Trees: It’s the new way to holiday, with Caribbean rhythms as your Christmas soundtrack.

• Take a Deep Breath: Clove, nutmeg, cinnamon, and ginger grow in abundance on the spice isle of Grenada.

• Snorkel, Swim, Paddle: These stops are the most beautiful spots for water sports enthusiasts.

• Pure Nature, Pure Adventure: Dominica wows with thundering waterfalls, red cliffs, and a lush, unspoiled jungle.