A Journey of Paradise Coves and Puerto Rican Spirits

Day

Date

Arrival

Departure

24th Feb 2026 Tuesday

Miami, Florida

17:00

25th Feb 2026 Wednesday

At Sea

26th Feb 2026 Thursday

At Sea

27th Feb 2026 Friday

Charlotte Amalie, Saint Thomas

08:00

21:00

If you cruise regularly to the Caribbean, chances are you'll end up in St. Thomas. Its popularity as one of the world's most heavily trafficked cruise ports is well-earned. The island offers something for just about everyone and has the infrastructure that can accommodate a huge daily population influx. In addition to a duty-free shopping scene that's virtually unparalleled, other on-the-beaten-track sites include the world-famous beach at Magens Bay. In September 2017, the Virgin Islands -- along with many other islands in the Caribbean -- were rocked by Hurricanes Irma and Maria. While St. Thomas worked to quickly recovered its most popular tourist destinations, some have sadly closed their doors indefinitely -- including the SkyRide to Paradise Point. Beloved restaurants like Cuzzin's shut down. However, new restaurants and attractions have popped up in their place, solidifying the island's commitment to welcome visitors. Nearly every ship sailing an Eastern Caribbean itinerary includes St. Thomas as a port of call, as do many Southern Caribbean voyages. You'll even see St. Thomas on the Panama Canal and South American itineraries (when a Florida port such as Fort Lauderdale or Miami serves as a port of embarkation or debarkation). It's not uncommon, particularly during the Caribbean's winter high season, to see six ships or more docked or anchored in a day -- and that can mean an extra 20,000 people mixing into a population hovering in the mid-50,000s. Believe it or not, it's easy to find some respite from the inevitable crowds by exploring St. Thomas' quieter, more undiscovered side -- a lovely historic district trips to Water Island (the "fourth" and youngest, U.S. Virgin Island), beaches all over the island and fabulous restaurants in Frenchtown. It's also an easy jaunt via a 20-minute ferry to tranquil St. John from the town of Red Hook. Even this town has local character (this is where ex-pat residents of St. Thomas spend their time) that's a far cry from Charlotte Amalie's shopping mall vibe. Just taking transportation to the eastern end of the island will give you emotional distance from the hectic pier. Even if it's your first time on St. Thomas, don't be afraid to explore. Although locals drive on the left side of the road, the island has an American familiarity that makes it a perfect introduction to the Caribbean style of life. Attractions, beaches, shopping, golf, water sports -- the island offers a wide variety of activities, with new ones added every year. Even if it's your tenth trip, you're bound to find something fun to do, even if that just means discovering a new beach.

28th Feb 2026 Saturday

Jost Van Dyke

09:00

18:00

1st Mar 2026 Sunday

Saint John's, Antigua

09:00

20:00

Antiguans like to boast that they have 365 beaches -- one for each day of the year. And while no one counts to ensure the accuracy of this catchy marketing claim, the squiggly shaped island indeed is full of beachy gems, each with its own unique appeal. Part of the West Indies, Antigua was first occupied by the peaceful Arawak Indians around 200 B.C. They stayed until the arrival of the Caribs, an Amazonian tribe, whose name was derived from the Spanish word "caribal," meaning "cannibal." Then, the island was known as Wadadli until 1493 when Columbus, who never made landfall, sailed by and named the island in honor of Maria de la Antigua, a saint he worshipped in Seville. The English arrived in 1632, establishing sugar plantations and bringing African slaves; slavery was fully abolished in 1838. Great Britain held the island until 1981, when Antigua (pronounced "An-tee-gah") achieved independence. The island was an important colonial base of the Royal Navy, with English Harbour serving as its headquarters. The remains of the navy's presence represent some of the most fascinating attractions -- a walk around historic Nelson's Dockyard and the grounds of Shirley Heights reveals remnants of a working Georgian-era harbor, old forts and officer's quarters, as well as a multitude of crumbling sugar mills from the days when sugar plantations ruled the island. In more recent years, English Harbour has become the capital of international yachting and sailing, and those activities are responsible for a surge in population during the winter months. The season opens in December with the Antigua Yacht Show and ends in May with Antigua Sailing Week, one of the largest annual regattas in the Caribbean. Since gaining independence, Antigua has all but abandoned its agricultural heritage in favor of a tourist economy. The island can hold its own in the duty-free shopping category, but the real highlights lie well beyond the capital and port town of St. John's. And if all those beaches aren't enough, Antigua's sister island, Barbuda, is accessible by ferry for day-trippers. The ferry drops you in the middle of 14 miles of unspoiled pink shell beaches -- including one that used to be a favorite of Princess Diana; it's now named in her honor. Antigua owns an average high temperature of a pleasant 81 degrees, but it's a slightly less hospitable climate in the summer when the trade winds die down. Antiguans celebrate these slower summer months with the annual Carnival at the end of July and beginning of August. The island is susceptible to hurricanes and tropical storms, with a direct hurricane hitting about every seven years on average. The highest risk is in early September -- so there's little need to worry during peak cruising season. Bring your umbrella, though, because more than half of the days in November through February experience rainfall.

2nd Mar 2026 Monday

Gustavia (St. Barts)

08:00

18:00

3rd Mar 2026 Tuesday

San Juan

07:00

As an anchor on Eastern and Southern Caribbean itineraries -- not to mention a turnaround port for many ships -- San Juan is a place where just about all cruisers, at some point or another, are going to wind up. Puerto Rico is a U.S. territory, and San Juan is its urban hub. The city, by and large, is divided into new and old. The new includes a business district and outlying neighbourhoods, concentrated with hotel chains like Isla Verde. The old is, of course, the historic city within ancient walls. Both offer many Americanisms. (Senor Frog's has a prime outpost, and you'll never want for a McDonald's Big Mac.)

Get beyond that, though, because of all America's Caribbean islands, Puerto Rico offers the most exotic aura. The melange of indigenous Taino culture, combined with European and African influences in San Juan (and all of Puerto Rico, for that matter), is one major factor. Add to that its own unique influences in areas ranging from cuisine and music to history and art. And there's more: folks who have travelled to Cuba say that Old San Juan reminds them more of Cuba, at times, than Cuba itself! It's also very Spanish (think Seville) and even a bit Italian (reminiscent of Naples). Finally, the city evokes just a wee taste of South America (like Buenos Aires).

For those who visit San Juan as a day-stop on a Caribbean itinerary or embark or disembark there, the island's biggest appeal is the old city. Most cruise ships dock right in the heart of Old San Juan, which dates back to the 16th century. The old, walled city has been exquisitely preserved, and its sprawling forts, cobblestone streets, antique shops and art galleries make it an ideal first stop. Its mainstream attractions include the imposing El Morro fort, which dates back to 1539; the Cathedral of San Juan, where the island's first governor, Ponce de Leon, is buried; La Fortaleza, the oldest governor's mansion on U.S. soil; several colonial plazas; and the triumvirate of Calle del Cristo, Calle San Jose and Calle Fortaleza for shopping. Calle del Cristo, in particular, is chock-full of art galleries, artisan studios and distinctive boutiques.

But, if you're a "been there, done that" visitor to Old San Juan, there's much more to explore.

And there's one more thing to keep in mind: many cruises stay in port until late at night. That makes it possible to sample some of the city's vibrant restaurants and nightlife (as long as you keep an eye on the clock).