San Juan to San Juan Cruise

Day 1 - San Juan

Arrive: Sun 20 December 2026 / Depart: Sun 20 December 2026 at 19:00

Day 2 - Jost Van Dyke

Arrive: Mon 21 December 2026 at 08:00 / Depart: Mon 21 December 2026 at 18:00

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 3 - Little Bay, Montserrat

Arrive: Tue 22 December 2026 at 09:00 / Depart: Tue 22 December 2026 at 19:00

As one of the Caribbean’s most dramatic islands, Montserrat has always done thing a little differently. While the rest of its neighbours were busy promoting tourism in its masses, Montserrat was content to sit back and stay in the (metaphorical) shadow. The island remains relatively undeveloped for the archipelago, with off the beaten path beaches, hidden creeks and so much natural beauty that we fully expect this little island to soon become the next go-to eco-tourism destination. View less Much of Montserrat’s discretion is because it is governed by seismic activity and has endured more volcanic eruptions than any other Caribbean island. These have earned it the nickname the “Pompeii of the Caribbean”, understandably so, as much of the main city was covered in ash after the 1995 eruption. The cause of this is the mighty Soufriere Hills volcano, dormant since 2010 yet still spewing sulphur and smoke. However, it is not all doom and gloom and Monserrat’s other nickname is “the emerald isle”, is not only because of its lush verdant forests lined with lime trees and palms, but because its coasts bear a certain similarity to Ireland. And yes, Guinness is available! Montserratians are optimistic and fun loving and Little Bay locals are the perfect example. Set at the very tip of the island, the town is intended as the new capital, and is being enhanced with the modernity once would expect of such an honour. Little Bay beach is without doubt one of the most beautiful in Caribbean, and is a tonic for the soul.

Day 4 - St John's, Antigua

Arrive: Wed 23 December 2026 at 08:00 / Depart: Wed 23 December 2026 at 18:00

Day 5 - Fort de France, Martinique

Arrive: Thu 24 December 2026 at 08:00 / Depart: Thu 24 December 2026 at 18:00

The largest of the Windward Islands, Martinique is 4,261 mi (6,817 km) from Paris, but its spirit and language are decidedly French, with more than a soupçon of West Indian spice. Tangible, edible evidence of the fact is the island's cuisine, a superb blend of French and creole. Martinique is lushly landscaped with tropical flowers. Trees bend under the weight of fruits such as mangoes, papayas, lemons, limes, and bright-red West Indian cherries. Acres of banana plantations, pineapple fields, and waving sugarcane stretch to the horizon. The towering mountains and verdant rain forest in the north lure hikers, while underwater sights and sunken treasures attract snorkelers and scuba divers. Martinique is also wonderful if your idea of exercise is turning over every 10 minutes to get an even tan and your taste in adventure runs to duty-free shopping. A popular cruise-ship excursion goes to St-Pierre, which was buried by ash when Mont Pelée erupted in 1902.

Day 6 - At Sea

Day 7 - Soper’s Hole, Tortola, Britische Jungferninseln

Arrive: Sat 26 December 2026 at 08:00 / Depart: Sat 26 December 2026 at 18:00

Day 8 - San Juan

Arrive: Sun 27 December 2026 at 07:00 / Depart: Sun 27 December 2026 at 19:00

Day 9 - St John, U.S.Virgin Islands

Arrive: Mon 28 December 2026 at 08:00 / Depart: Mon 28 December 2026 at 18:00

Like so many of the islands in the Caribbean, 2017’s double whammy of hurricanes Irma and Maria devastated much of St. John. However, as relief funds get funnelled into rebuilding, normality is gradually being restored, and St. John version 2.0 is emerging - bolder, brighter and better. St. John’s small size might just give it the edge over other desert islands. View less The US purchased the tiny landmass (at just nine miles long, the island is the smallest of the three American Virgin Islands) from the West India and Guinea Company in 1917 and it remains under US govern to this day. Historically speaking however St. John is Danish, who colonised it for almost 250 years before its sale to America. The Virgin Island Nation park covers almost two-thirds the island, meaning visually St. John is stunning, and will remain that way for generations to come. This ‘gift’ to the world comes thanks to Laurence Rockefeller who in 1956 gave the 5,000 acres of lush forest to the people of the island, with the caveat that it become a national park. Thus, velvety green hills slope into picture perfect white sand beaches, which are ringed by turquoise seas. One very definite winner of the tourism hiatus since 2017 has been the marine wildlife. Underwater life was barely affected by the storms and the subsequent lack of tourism has allowed the eco-systems to propagate. The island’s abundant coral reefs were not overly affected by the storms and today the waters are teeming with sea turtles, reef sharks and sting rays.

Day 10 - Basseterre, St. Kitts

Arrive: Tue 29 December 2026 at 08:00 / Depart: Tue 29 December 2026 at 18:00

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.

Day 11 - Guadeloupe

Arrive: Wed 30 December 2026 at 08:00 / Depart: Wed 30 December 2026 at 17:00

This small group of islands lies opposite the western part of Guadeloupe. They were discovered in November 1493 by Columbus, who named them Los Santos. French settlers established themselves in 1648 and changed the name to Iles des Saintes, commonly known as Les Saintes. Since then the islands have been closely connected with Guadeloupe.

Day 12 - Bequia

Arrive: Thu 31 December 2026 at 08:00 / Depart: Thu 31 December 2026 at 18:00

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.

Day 13 - At Sea

Day 14 - St. Thomas (US Virgin Islands)

Arrive: Sat 02 January 2027 at 08:00 / Depart: Sat 02 January 2027 at 18:00

The steep, spectacular hills that surround St Thomas's exquisite harbour provide a fitting entry point for this island of overwhelming natural splendour. The jungled-mountains reach up above tempting beaches and scuba diving sites, while Charlotte Amalie - the island's capital - sprawls down towards the water, bedecked with shops and tasty restaurants. Part of the beautiful U.S. Virgin Islands - together with St John and St Croix - these lands were purchased by the US in 1917. View less Nowadays, St Thomas is a patchwork of cultures, and a lively welcome to the islands, serving as a gracious host to the many visitors who linger - as well as those who jump on ferries, yachts and catamarans to explore the blessed beaches of the Caribbean's other retreats. A stunning island of dramatic jungled-scenery, keep your camera close to hand as you swing up the Skyride to Paradise Point, to look down over the natural amphitheatre of the dock and city below. Snap some more postcard-perfect shots at Drake’s Seat - said to be Sir Francis Drake's lookout point, where he could survey for approaching enemy ships. Nowadays, the views over Magens Bay and the infinite sea are always peaceful, and this is a great spot to catch a fiery Caribbean sunset spilling across the sky. Take catamaran cruises to explore the shining coastline, or seek out the glorious coves and caves that are hidden along the island's perimeter. Land on the secluded shores of tiny islands, before scuba diving and snorkelling above the twisted boughs of lost ships, reclaimed by the waters and inhabited by curious tropical fish life. Kayak over still lagoon waters, or take the chance to lay back on soft beaches strewn with tiny shells, as St Thomas's beauty washes over you.

Day 15 - San Juan

Arrive: Sun 03 January 2027 at 07:00 / Depart: Sun 03 January 2027