From Puerto Rico To Five Islands: A First-Time Cruise Guide

A first cruise is a crash course in what you value when you travel. From a lively launch in San Juan to five Caribbean ports in seven days, we share the joy of bioluminescent kayaking, the calm of a French-side beach on Saint Martin, and the green, mountainous bliss of Grenada and Dominica. We also get candid about a tougher moment in Saint Lucia, where constant vendor pressure cut a solo city walk short—and how a simple plan with a vetted driver could have changed the day.

We dig into the money side most people underestimate. Solo supplements can double a fare, but there are smart workarounds: Virgin Voyages frequently offers better pricing and social programming for singles; Norwegian and select Royal Caribbean ships have limited studio cabins; Silversea reduces single supplements on some sailings. Beyond the sticker price, budget for gratuities, specialty dining, fitness classes, laundry, Wi‑Fi, and excursions—or pick a more inclusive line to avoid the nickel-and-dime feeling. If you’re wondering whether to book excursions at every stop, learn from our missteps: sometimes one well-chosen experience or a simple plan with a trusted local driver beats a packed bus and crowded viewpoints.

The real key is matching the cruise to who you are. If big crowds drain you, consider smaller ships or river cruises like AmaWaterways. If sand isn’t your happy place, look to Alaska or Scandinavia for fjords, hikes, and cooler air. Traveling with a friend? Set expectations upfront—sleep rhythms, alone time, and activity choices—so the cabin is shared but the day can be flexible. We close by looking ahead to Scandinavia as a better fit for our hiking-first style and invite you to think about your own 2026 plans.

If this helped you plan smarter, follow the show, share it with a friend who’s cruise-curious, and leave a quick review to tell us where you want to sail next.

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