7 nights, Miami to San Juan

Seven nights, seven calls, no repeats. This sailing runs one-way from Miami to San Juan and threads a tight set of Eastern Caribbean islands, with a different flag almost every day. The shape is busy rather than slow, so know that going in. Miami gives you contrast within a short rideshare, from bayfront museums to Wynwood and Little Havana. Then the smaller islands do the real work: Cruz Bay tenders you into Saint John, two-thirds of which is national park, built around protected beaches and reef. Gustavia keeps large ships out by design, so its red-roofed harbor never feels crowded. Road Town is a base camp more than a destination, with a short ferry to The Baths on Virgin Gorda that beats anything on Tortola itself.

This itinerary rewards a traveler who likes a port a day and one well-chosen thing ashore at each. It is not for anyone wanting sea days to decompress, because there are none. A few calls anchor and tender (Cruz Bay, Gustavia), so if swell is running the day turns on tender timing, not anything on the island. Basseterre and St. John's each force one choice between a fort and a beach or railway, so commit before docking. Pick a slower, fewer-port route if island-a-day pace tires you.

Both gateways, Miami and San Juan, put you near the good stuff on foot. The ship is all-suite and all-oceanfront.