6 nights, San Juan to Miami

Six nights, one direction: San Juan to Miami, with five Caribbean calls in between and no doubling back. The pace is brisk but not punishing. One island per day, each close enough to the dock that you spend the time ashore, not in transit. San Juan sets the tone well: the ship ties up at the Old San Juan piers themselves, so the cobbled colonial grid, the cathedral, and the Paseo de la Princesa start a few steps from the gangway, with El Morro a climb uphill for harbor light. In Road Town the town is beside the point. The real move is the ferry from near the pier across to The Baths on Virgin Gorda, a far better sight than anything on Tortola. Gustavia is the quiet standout: St Barths keeps big ships out by design, so you anchor and tender into a small Swedish-era harbor that never feels crowded. Grand Turk closes the island run with a leeward beach steps from the ship and a dramatic offshore reef wall for snorkeling.

This rewards a traveler who wants a different island every morning and is happy to read each port for its best single thing rather than chase a checklist. Skip it if you want long, slow days in one place, or if tendering gives you pause: Gustavia is anchor-and-tender only, and swell is the real constraint there, not anything ashore. Miami is a disembarkation city more than a destination, so plan your time around the departure rather than expecting a full day.

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