My Cruise Checklist

Planning guides

Practical, opinionated long-form guides on the planning decisions that actually shape a good cruise — from booking to packing to which excursions are worth it.

When to Book — Cruise Pricing Windows, Decoded
Booking

When to Book — Cruise Pricing Windows, Decoded

Cruise pricing bottoms twice — at the opening of the booking window and again 30-60 days before sailing. Here's how to use both.

11 min read · April 25, 2026
Choosing a Cabin by Ship Class — A Deep Reference
Cabins

Choosing a Cabin by Ship Class — A Deep Reference

Cabin tier breakdowns by ship class for the major mainstream lines. Which categories actually deliver the upgrade.

14 min read · April 22, 2026
First-Time Cruiser? Everything They Don't Tell You at Booking
First-timer

First-Time Cruiser? Everything They Don't Tell You at Booking

The fifteen things a first-time cruiser actually needs to know — none of them about which excursion to book.

13 min read · April 20, 2026
Drink Packages — The Real Math
Dining

Drink Packages — The Real Math

The break-even on a beverage package is 5-7 alcoholic drinks per day. Here is how to read the line-by-line offer and decide.

11 min read · April 18, 2026
What to Pack for a 7-Night Caribbean Cruise
Packing

What to Pack for a 7-Night Caribbean Cruise

A category-by-category packing list developed across 40+ cruises. Trim ruthlessly — every traveler will overpack.

11 min read · April 15, 2026
Cruise Tipping — What Actually Goes Where
Etiquette

Cruise Tipping — What Actually Goes Where

Auto-gratuities, cash tips, and the line-by-line breakdown of who actually receives what.

9 min read · April 10, 2026
How to Book a Cruise Without Getting Fleeced
Booking

How to Book a Cruise Without Getting Fleeced

Cruise pricing is the most opaque corner of travel. Here is how to read a quote and what to negotiate.

12 min read · April 8, 2026
Accessibility at Sea — The Honest Guide
Planning

Accessibility at Sea — The Honest Guide

Cabin selection, embarkation, port-day logistics, and the lines that handle mobility, vision, and dietary needs the most adeptly.

12 min read · March 28, 2026
The Standout Caribbean Cruise Ports — Honest Rankings
Ports

The Standout Caribbean Cruise Ports — Honest Rankings

After 50+ Caribbean port days across the editorial team, a ruthless ranking of the major stops, with what actually works at each.

14 min read · March 22, 2026
Solo Cruise — Which Lines Actually Welcome Singles
Planning

Solo Cruise — Which Lines Actually Welcome Singles

Studio cabins, single supplements, and the lines that program for solo travelers rather than just charging the full cabin to one person.

10 min read · March 18, 2026
Repositioning Cruises — The Deep-Value Play
Planning

Repositioning Cruises — The Deep-Value Play

Trans-Atlantic and trans-Pacific repositioning sailings deliver more cruise per dollar than any other category. Here's how to use them.

11 min read · March 12, 2026
Alaska Cruises — Which Itinerary, Which Line
Destinations

Alaska Cruises — Which Itinerary, Which Line

Glacier Bay, Hubbard, Tracy Arm — the itinerary picked matters more than the line. Here is how to choose both.

14 min read · March 8, 2026
Embarkation Day — The 2-Hour Window
Planning

Embarkation Day — The 2-Hour Window

The boarding window is the difference between a 25-minute embarkation and a 90-minute slog. Use it.

8 min read · March 4, 2026
Main Dining Room vs. Specialty — Where to Eat Each Night
Dining

Main Dining Room vs. Specialty — Where to Eat Each Night

A line-by-line guide to which nights to skip the main dining room and what's worth the specialty cover charge.

11 min read · February 25, 2026
Photo Packages — When They Are Worth It
Onboard

Photo Packages — When They Are Worth It

The cruise photo package is the most over-marketed onboard add-on. Here is when the math actually works.

8 min read · February 18, 2026
Balcony vs. Inside Cabin — The Honest Math
Cabins

Balcony vs. Inside Cabin — The Honest Math

The price gap between an inside and a balcony cabin is rarely worth it — except in the four cases where it absolutely is.

10 min read · February 12, 2026
Teens on a Cruise — Line by Line
Family

Teens on a Cruise — Line by Line

The teen product on most lines is genuinely good. Here is what each line actually delivers for the 13-17 demographic.

10 min read · February 4, 2026
Mediterranean Cruise — The Itinerary Trap
Destinations

Mediterranean Cruise — The Itinerary Trap

Most Mediterranean itineraries pack 10+ ports into a 12-night sailing. Here's why fewer-port itineraries are usually the better trip.

12 min read · February 1, 2026
Port-Day Logistics — Cozumel, Nassau, and CocoCay
Ports

Port-Day Logistics — Cozumel, Nassau, and CocoCay

The three most-visited Caribbean cruise ports, with the editorial playbook for each.

11 min read · January 30, 2026
Formal Night — Is It Still a Thing?
Etiquette

Formal Night — Is It Still a Thing?

The dress code at sea has loosened. Here's what travelers actually need on which line.

9 min read · January 22, 2026
Private Islands Ranked
Ports

Private Islands Ranked

Castaway Cay, CocoCay, Half Moon Cay, Ocean Cay, and the rest — ranked by what they actually deliver.

11 min read · January 15, 2026
Shore Excursions — Book With the Line or Independently?
Ports

Shore Excursions — Book With the Line or Independently?

The line's excursions are 30-50% more expensive — but they include a real safety net. When that safety net is worth paying for.

11 min read · January 8, 2026
Wi-Fi at Sea — Is It Worth It Now?
Tech

Wi-Fi at Sea — Is It Worth It Now?

Starlink has changed cruise Wi-Fi. Here's what each line offers, what it costs, and whether travelers actually need it.

9 min read · December 30, 2025
Bringing Kids on a Cruise — Honest Line Rankings
Family

Bringing Kids on a Cruise — Honest Line Rankings

Six lines, ranked by what they actually deliver for families with kids — not by what their marketing says.

13 min read · December 15, 2025