Six key questions to help you book a cruise that actually fits your travel style.
Thinking about booking your first cruise but not sure where to begin? You’re not alone. Cruising sounds simple: book a ship, show up. But the options can quickly spiral.
There are multiple cruise lines with different styles, countless itineraries, a maze of cabin categories, and endless opinions online. Before you dive into forums or start comparing 47 balcony options (what does “8% obstructed” even mean?), let’s take a step back.
Here are the key questions to ask before you book, so you can make confident, low-stress decisions from the start.
3. Where Do You Want to Go? Cruises sail to just about every region on the planet, but some are better for beginners or easier to reach if you’re starting from the East Coast.
Caribbean: Warm weather, beach time, and relaxed vibes. Great for families, couples, and friend groups. Most sailings are 3–7 nights, typically departing from Florida, New York, New Jersey, or occasionally Boston.
Alaska: Scenic and nature-heavy. Think wildlife, glaciers, and excursions like dog sledding or whale watching. Best from May to September. Cruises depart from Seattle, Vancouver, or (less often) San Francisco.
Europe: Culture, history, and lots of port stops. Great for travelers who want to see many cities without constant packing and unpacking. Flights and time zones make these better for longer or once-in-a-lifetime trips.
New England & Canada: Great in the fall, with sailings from Boston or New York visiting Bar Harbor, Halifax, and Quebec City. Expect foliage, lighthouses, lobster, and cool weather.
You don’t have to commit yet, but having a region in mind helps shape your planning.
How Long Can You Travel? Cruise lengths vary widely, so consider what fits your schedule.
3–5 Nights: Great for first-timers, younger families, or those testing the waters. Common on Carnival and Disney.
7 Nights: The sweet spot. A mix of sea days and port days, and the most common format across most lines.
10+ Nights: More immersive but better for seasoned cruisers or those with flexible time. You’ll find fewer crowds but also more sea days and complex itineraries.
Tip: If you’re flying to the port, add a buffer day before your cruise. Ships won’t wait for a delayed flight.
4. What Departure Ports Are Convenient? Your departure port impacts everything: which cruise lines you can choose, which ships sail there, and where you can go.
Here are the major East Coast and Gulf Coast options:
Boston, MA
Cruise lines: Norwegian, Holland America, Celebrity, and Royal Caribbean (limited sailings)
Good for: Bermuda, Canada/New England
New York, NY / Cape Liberty, NJ
Cruise lines: Royal Caribbean, Celebrity, Norwegian, MSC
Good for: Year-round access to Caribbean, Bahamas, Bermuda
Baltimore, MD
Cruise lines: Carnival, Royal Caribbean
Good for: Accessible port for Mid-Atlantic travelers; smaller selection but convenient
Florida (Miami, Fort Lauderdale, Port Canaveral, Tampa)
Cruise lines: All major lines
Good for: The widest range of ships and itineraries
Galveston, TX / New Orleans, LA / Charleston, SC
Cruise lines: Carnival, Royal Caribbean, Disney (seasonal)
Good for: Western Caribbean, shorter and regional sailings
5. Who’s Going With You? Cruises can work for families, couples, solo travelers, or groups—but your priorities change depending on the group.
Traveling with kids? You may want kid-friendly ships (like Royal Caribbean or Disney) and shorter itineraries.
Going as a couple? Consider adult-focused amenities, balcony cabins, and quieter ships like Celebrity or Holland America.
Cruising with a teen? You’ll want enough to keep them entertained without feeling trapped. (More on that in our Teen Corner.)
What’s Your Vacation Style? Do you like packed days or a slower pace? Are you more poolside or port explorer?
Some cruises are party-forward with nonstop entertainment. Others are more relaxed and refined. Knowing your style helps match you with the right ship.
(Spoiler: For some, the drink package is unnecessary. For others, it’s a must-have. Know your vacation style.)
6. How Much Planning Do You Want to Do Later? Cruising can be low-effort—or very DIY—depending on how much you want to plan.
Do you want:
Pre-paid drink packages and excursions?
Specialty dining or stick to what’s included?
Guided tours or explore ports on your own?
Think about how involved you want to be. Some people want full control. Others just want to show up and enjoy.
Final Thoughts Cruise planning doesn’t have to leave you feeling overwhelmed. If you start by asking the right questions, you’ll narrow your choices faster and avoid decision fatigue.
Once you know your preferred region, trip length, and travel group, the rest starts to fall into place.
Explore our other cruise posts for comparisons, port guides, and packing tips. Whether you’re sailing next month or just daydreaming for now, we’ll help you cruise smarter.
— Angelica Marino
Optimized Trips | Plan Smart. Travel Easy.