Travel Planning Made Personal

Cruise season always brings the same first question: “which cruise line should we go with?” Honestly, that’s usually the wrong starting point. Here’s how I actually help clients narrow it down.

Start with the itinerary, not the ship. It’s tempting to pick based on which ship looks nicest in photos, but the itinerary matters more. Caribbean cruises are relaxed and beach-focused, Alaska is scenery and wildlife, Mediterranean is culture and history. Figure out what kind of trip you actually want first — the ship follows from there.

Think about cabin category honestly. Interior cabins are fine if you’re not going to spend much time in the room. But if you want to actually wake up and see the ocean, a balcony makes a real difference — especially on scenic routes like Alaska. I always ask clients how much time they actually plan to spend in their cabin before recommending a category, because it’s one of the easiest places to overspend or underspend.

Read the fine print on what’s included. “All-inclusive” means different things on different lines. Some include drinks and gratuities, some don’t. Some charge extra for basically every specialty restaurant onboard. This is honestly one of the biggest reasons I still book cruises for clients rather than have them do it themselves — the pricing structures are genuinely confusing, and it’s easy to end up paying more than expected once you’re onboard.

Consider who you’re traveling with. Family cruises with kids’ clubs and pools are a different experience than an adults-only sailing built around quiet lounges and spas. Both are great — they’re just not the same trip, and picking the wrong one for your group can sour an otherwise good cruise.

If you’re staring down a list of cruise lines and itineraries and not sure where to start, tell me what kind of trip you’re picturing and I’ll narrow it down from there.