San Juan to Miami Cruise: A Caribbean New Year

Arrive in Puerto Rico and transfer privately to your five-star hotel for the night. The afternoon and evening are yours to explore Old San Juan, the oldest city under US jurisdiction, where pastel façades and blue cobblestone streets sit within formidable Spanish fortifications.

Walk towards El Morro and San Cristóbal, explore the old city at your own pace and settle into the Caribbean before tomorrow’s sailing.

Enjoy a relaxed morning in San Juan before transferring to the port and boarding Silver Nova. Settle into your Classic Veranda Suite before sailing out from Puerto Rico and into the Caribbean.

Silversea is one of OROKO’s trusted cruise partners, and this is a sailing we would choose on the strength of the route itself. Five very different Caribbean islands are brought together in little more than a week, with New Year falling at exactly the right point in the journey. Onboard, Silver Nova brings all-inclusive dining and drinks across eight restaurants, the Otium Spa and a private veranda for every suite.

Much of St. John remains protected within Virgin Islands National Park, preserving a landscape of forested hills, coral reefs and extraordinarily clear bays. Spend the day exploring its coastline, where beaches such as Trunk Bay and Cinnamon Bay sit between tropical forest and calm Caribbean water.

Shore excursions offer different perspectives on the island, from snorkelling among coral and tropical fish to sailing along its protected coast or exploring the national park ashore.

Arrive in Charlestown on Nevis, an island of old plantation estates, volcanic landscapes and an appealingly unhurried rhythm. Explore its historic capital and the countryside beneath Nevis Peak, play a round of golf, or spend the day discovering the island’s coastline before returning to Silver Nova.

As evening falls, the focus shifts back aboard for dinner, drinks and celebrations as the ship carries you into the New Year.

Wake on New Year’s Day in Dominica, perhaps the most dramatically beautiful island of the journey. Beyond Roseau, rainforest climbs into a volcanic interior of waterfalls, hot springs, deep gorges and the mist-covered peaks of Morne Trois Pitons National Park.

Head inland towards Trafalgar Falls and the island’s geothermal landscapes, swim through the narrow rock walls of Titou Gorge or take to the water in search of the whales that inhabit the deep waters surrounding Dominica.

Antigua’s coastline is a succession of sheltered bays and pale-sand beaches, while inland, the island’s maritime history survives around Nelson’s Dockyard and English Harbour.

Spend the day sailing along the coast, exploring the UNESCO-listed dockyard and viewpoints above English Harbour, or head for one of the island’s quieter beaches before returning to the ship.

Small, mountainous and wonderfully relaxed, Jost Van Dyke is an idyllic final Caribbean call. White Bay is the island at its most recognisable, where brilliant white sand meets clear turquoise shallows and small beach bars sit beneath the palms.

Explore by boat, spend the morning swimming and snorkelling or simply settle into the easy rhythm of the island before sailing north towards Miami.

After five contrasting islands, the next two days are spent at sea as Silver Nova makes her way towards Miami. It is an opportunity to enjoy the ship properly, from long lunches and evenings across its eight restaurants to the expansive pool deck, Otium Spa and destination-led S.A.L.T. culinary programme.

The all-inclusive nature of Silversea comes into its own on these slower days. Dining and drinks are included throughout, leaving the rhythm of the day entirely open — breakfast overlooking the water, time by the pool or in the spa, followed by dinner and drinks as the ship continues north.

Arrive in Miami and disembark Silver Nova. Transfer onwards for your return flight, or extend the journey with a few nights in the city.

A short stay works particularly well after the cruise, allowing time to discover Miami beyond the beach — from the Art Deco architecture of South Beach to contemporary art, Cuban culture and the restaurants of Little Havana.