Your Cruise, Your Way: How to Actually Enjoy Every Sailing

If you've ever stepped off a cruise ship feeling more exhausted than when you boarded, you're not alone. And if you've been on one cruise, didn't love it, and decided cruising just wasn't for you — I want to gently push back on that.

Because here's what I've seen time and time again working with cruising clients: a disappointing cruise experience usually isn't about the ship or the destination. It's about not knowing how to make the cruise work for you. And that's exactly where having the right travel advisor makes all the difference.

I've helped hundreds of clients plan cruise vacations across dozens of ships and itineraries, and I want to share some of the most valuable things I've learned along the way.

You Don't Have to Do Everything

This is the number one thing I tell every cruise client before they board: the daily program is a menu, not a to-do list.

Every ship is packed with activities from morning to midnight. Trivia, cooking demos, live music, pool parties, spa treatments, specialty dining, Broadway-style shows. It can feel like you're supposed to squeeze every single thing in. But trying to keep up with a packed schedule of dining reservations, show times, and activity sign-ups can leave you more frazzled than relaxed — and that defeats the whole purpose.

Give yourself permission to skip things. Sleep in. Spend three hours by the pool doing absolutely nothing. That is a completely valid and wonderful way to spend a sea day. I always remind my clients: you're on vacation, not an itinerary.

Formal Nights Are Optional (Sort Of)

This one surprises a lot of people. Many cruise lines have formal or elegant nights in the main dining room, and while some guests love the excuse to dress up, others simply don't feel like it. And that's completely fine.

Most ships offer alternatives — from the buffet and casual dining venues to specialty restaurants with a more relaxed dress code. One of the things I do before any client steps onboard their ship is make sure they fully understand what to expect, including all of their dining options, so they can feel confident and enjoy their vacation without any last-minute surprises.

Talk to Your Travel Partners Before You Go

One of the best things you can do before a cruise is have an honest conversation with the people you're sailing with about what everyone actually wants out of the experience. Some people want adventure in every port. Others want to sleep late and spend the day at the spa. Neither way is better — the best vacation is the one that feels right for you.

One of the greatest advantages of cruising is the freedom it provides for different travel styles to coexist. You don’t have to spend every moment together to have an incredible shared experience. I help my clients think through preferences, expectations, and priorities before they sail, creating a trip that feels personalized and enjoyable for every traveler — not just the loudest voice in the planning conversation.

Get Off the Ship — But Don't Overdo the Ports

Port days are exciting, and it's tempting to pack them with excursions and sightseeing. But I've watched so many travelers come back from a full port day completely wiped out, only to do it all again the next day.

My advice: pick one or two meaningful things to do in each port and leave room to wander. Some of the best travel moments happen when you're not rushing to the next item on the list. Sit at a café, explore a market, walk without a destination. Those are often the memories that stay with you.

Book Shore Excursions Thoughtfully

Not all shore excursions are created equal, and this is one of the areas where working with a travel advisor can make a real difference. Some excursions are fast-paced and packed, which is great if that's your style. Others are more relaxed and immersive.

I match my clients to excursions based on their energy level, interests, and what they truly want to experience in each port — not simply what’s the most popular or highest rated. I also help clients understand the difference between ship-sponsored excursions, which come with the guarantee that the ship will wait if your tour runs late, and independent options, which are often more personalized but carry more risk. Understanding those differences before booking helps my clients make confident choices and enjoy their time ashore without unnecessary stress.

Use Sea Days to Actually Rest

Sea days are a gift. Don’t overlook them.

I know it can feel like you should be doing something when the ship is full of options. But sea days are the perfect opportunity to sleep in, read a book, try the spa, or simply sit on your balcony with a coffee and watch the water go by. When I'm helping clients plan their cruise, I always encourage them to protect at least one sea day for true, unstructured rest. It changes the whole tone of the trip.

Get to Know the Ship Early

On embarkation day, before the crowds arrive and before you're expected anywhere, take a walk around the ship. Find your dining room, locate the pool deck, figure out where the specialty restaurants are, and get a feel for the layout. This small investment of time makes the whole sailing feel less overwhelming and more like home.

This is one of those little tips I pass along to every client, because the travelers who do it almost always say it made their first day so much smoother.

Don't Skip Travel Insurance

I know this isn’t the glamorous part of cruise planning, but it’s an important one. With flights, ports, and unexpected situations at sea, the right travel insurance provides peace of mind so you can relax and enjoy your trip without worrying about the “what ifs.”

Every client I work with gets a thoughtful conversation about the right level of coverage for their specific trip. It's one of the most important things we do together before anyone sets sail, and it's one of the things my clients consistently tell me they're grateful for.

Make It Yours

At the end of the day, the best cruise is the one that fits you. Whether you're the first one off the ship at every port or the person who hasn't left the pool deck in four days — there’s no wrong way to cruise. Whether you dress up for formal night or eat at the buffet in your flip flops — both are valid.

The secret that experienced cruisers know is simple: stop trying to have someone else's cruise. Have yours.

And if you're not sure where to start — which ship, which itinerary, which line matches your travel style — that's exactly what I'm here for. There’s so much that goes into finding the right cruise, and I love helping travelers discover the one that feels made for them.

Ready to Find Your Perfect Cruise?

Whether you're a first-time cruiser or someone who wants to fall back in love with sailing, I'd love to help you plan a voyage that feels completely and wonderfully yours. From choosing the right ship and itinerary to excursion planning and travel insurance, I take care of the details so you can focus on enjoying every single moment.

Reach out to Toastable Travel + Events today and let's start planning your perfect sailing.

Source: Cabey, Melissa. "The Secret Trick to Actually Enjoying Every Cruise, According to Long-Time Cruisers." Parade, October 17, 2025.