San Juan, Puerto Rico: before the ship — Trip Report

Overview

San Juan is where the winter Caribbean sailings begin, and it is worth arriving a day or two early rather than flying in on embarkation morning. Old San Juan is seven square blocks of sixteenth- and seventeenth-century streets inside a city wall, and in December it is strung with lights end to end. This is the stay before the ship; the sailing ended at St. Barthélemy.

Where we stayed

Hotel El Convento, a Carmelite convent of 1651 that has been a hotel since the 1960s, on Calle del Cristo opposite the cathedral. Rooms open onto a galleried courtyard around an old nispero tree. We stayed in the Gloria Vanderbilt Suite, named for the designer, who was a regular, and we would book it again.

The lamplit yellow facade and arched door of El Convento at night — El Convento after dark, on Calle del Cristo.

The galleried courtyard at El Convento, around the old nispero tree

The old city

The Cathedral of San Juan Bautista is across the street from the hotel: begun in 1521, rebuilt in the nineteenth century, and, on this visit, hung with banners for the 2025 Jubilee. Ponce de León is buried in it, under a marble monument in the north transept. A block down Calle del Cristo is the Capilla del Santo Cristo, a chapel the size of a garden shed with a baroque bell-gable over an iron gate, and beside it the pigeon park with its banyan.

The Cathedral of San Juan Bautista with Jubilee banners at the doors — The cathedral, banners up for the 2025 Jubilee.

Down the nave of the cathedral, black and white marble underfoot — Down the nave. The floor is black and white marble.

An iron cross on a gate below a painted chapel dome — The Capilla del Santo Cristo: an iron cross on the gate, the painted dome behind it.

The Capilla del Santo Cristo de la Salud: a stone bell-gable above an iron gate at the foot of Calle del Cristo — The Capilla del Santo Cristo de la Salud, at the foot of Calle del Cristo: the bell in its gable, the iron gate, and pigeons on the top.

Walk downhill and the streets are blue cobbles, adoquines, cast as ballast in Spanish foundries. The city gate on Paseo de la Princesa is the last of the original five; the wall runs from it around to El Morro.

A painted street in Old San Juan with decorations strung overhead — Painted houses and strung decorations.

Fortress-wall gate and royal palms, Old San Juan — The city gate, with the palms of the Paseo behind it.

An old banyan spreading over the city wall walk — The banyan by the wall.

The bastions of Castillo San Cristóbal above the road at dusk

The tomb of Juan Ponce de León in the cathedral

A bronze figure with a rosary at its neck, against the old city wall

Christmas in the old city

Puerto Rico keeps the longest Christmas season anywhere, from late November through the Fiestas de la Calle San Sebastián in the third week of January. In December the plazas carry trees, the streets carry lights, and La Fortaleza, the governor's residence and the oldest executive mansion still in use in the Americas, is dressed with wreaths, garlands and nutcrackers at the gate. On Plaza Colón, at the top of Calle Fortaleza, the Columbus monument of 1893 stands in a ring of lit trees.

A Christmas tree on a street in Old San Juan under strung lights — The tree on Calle Fortaleza.

White colonial facade dressed with wreaths, ribbons and nutcrackers — La Fortaleza, dressed for Christmas.

Steve and Jeannie in front of the Christmas tree in Old San Juan — Us, at the tree.

The Columbus monument on Plaza Colón, ringed with lit trees

Before the ship

The cruise terminals are at the bottom of the old city, a few minutes from El Convento, so embarkation day is a short walk or a shorter taxi rather than an airport transfer. Ilma sailed from here; St. Barthélemy, the last stop of the cruise, has its own report.

Pro tips

Fly in at least a day before the cruise. San Juan is worth two nights on its own, and it removes the risk of a missed sailing.
No passport for US travellers, and the dollar. Puerto Rico is domestic.
Stay inside the old city. El Convento puts the cathedral across the street and the cruise pier a short walk downhill.
Old San Juan is walkable. End to end on foot, though the streets are steep and the blue cobbles are uneven; wear something with a sole.
Shop duty free. Old San Juan has the luxury houses, and they sell at the duty-free rate.
Book the pre-cruise hotel through the same advisor as the cruise. One person holds the dates if the ship’s schedule moves.

Book a trip like this

Jeannie can research and book a trip like this one, cruise and pre-cruise stay together. See Book with Jeannie.