Friedman recommends several Caribbean island combinations, including the ABC islands (Aruba, Bonaire and Curacao); the many islands of the Bahamas; and St. Lucia, Martinique, Guadeloupe and Dominica, all of which are connected by ferry service L'Express des Iles.

Traveling between Caribbean islands can be notoriously difficult due to "hub-and-spoke" flight patterns, but certain clusters are very easy to navigate. The US Virgin Islands and British Virgin Islands are perhaps the easiest, with frequent, short ferry rides connecting St. Thomas, St. John, Tortola, and Virgin Gorda. Similarly, St. Maarten/St. Martin serves as a major hub with high-speed ferry connections to the chic islands of Anguilla (20 mins) and St. Barthélemy (45-60 mins). In the southern Caribbean, the "ABC Islands"—Aruba, Bonaire, and Curaçao—are physically close, but travel between them is mostly handled by small regional airlines like Divi Divi Air or EZAir rather than ferries. Another easy "twin-island" trip is St. Kitts and Nevis, which are separated by a narrow channel and linked by a regular 20-minute water taxi. For 2026 travelers, these clusters offer the best "island hopping" opportunities without the need for long, expensive connecting flights through major hubs like San Juan or Miami.