CRUISE PLANNING TIPS

Planning a cruise should be exciting, not overwhelming. Over the years, we’ve sailed with different cruise lines, explored countless ports, and picked up plenty of tricks along the way. From packing essentials to embarkation day hacks, we’ve learned what works (and what doesn’t) when it comes to cruising.

At High Seas Escapades, our goal is simple: help you cruise smarter, stress less, and enjoy every moment at sea. Whether you’re a first-time cruiser or a seasoned sailor, our tips will make planning easier so you can spend more time soaking up the sunsets and sipping cocktails on deck.

How We Book Our Cruises

Over the years we’ve found a booking style that suits us best. It gives us the freedom to shape our vacation exactly how we want it — while still leaving room for a little spontaneity.

Our Step-by-Step Approach

Pick the Cruise – These days, our choice often starts with the itinerary. Having cruised much of the Caribbean and Mediterranean, we sometimes select sailings for new ports we haven’t visited yet — but just as often, we’ll happily revisit familiar places if the ship itself excites us or if we know we can discover something new in a port we’ve been to before.

Book Direct with the Cruise Line – We like the simplicity of going straight to the source. It makes it easy to manage our reservation, handle upgrades, and keep everything in our own hands.

Sort Flights Separately – We prefer arranging flights ourselves for more flexibility. That way, we can choose the best routes, best prices, and even arrive a few days early if we want extra time in the embarkation city.

Choose Accommodation – Instead of taking what’s bundled, we pick hotels that suit our plans — whether that’s a convenient stopover near the port or a boutique stay for a mini pre-cruise adventure.

Other Options to Consider

Travel Agents (Popular in the US): Many cruisers use agents for the convenience and potential perks like onboard credit or group discounts.

Travel Companies (Common in the UK): Large operators often bundle cruises with flights, hotels, and transfers. It’s a stress-free option if you prefer everything in one package.

For us, booking directly and building the trip piece by piece gives us the flexibility to cruise the way we want. But whichever method you choose, the real win is getting out to sea.

Flights

When it comes to booking flights, we like to keep things simple (and wallet-friendly). Our go-to tools are Skyscanner and Kayak, where we can set up price alerts and let the apps do the hard work of spotting deals. It’s a great way to play around with destinations too—perfect if you’re still daydreaming about where to jet off from.

Not sure which airlines actually fly your route? That’s where FlightConnections comes in. Pop in your departure airport and it shows you every destination served from there. Or, if you already know where you want to go, enter both airports and it’ll map out the direct flights and any possible connections. Basically, it takes the guesswork out of flight planning so you can focus on the fun part—getting to your cruise.

Travel Insurance

When it comes to cruises, travel insurance isn’t just a nice-to-have—it’s essential. Unlike land-based vacations, cruises involve multiple countries, ports, and a floating hotel in the middle of the ocean. Standard travel insurance may not always cover situations unique to cruising, such as missed port stops, shipboard medical care, or emergency evacuation at sea.

Why Cruise Travel Insurance Matters

Cruise-specific travel insurance can protect you against:

• Medical expenses at sea – onboard medical facilities can be costly, and your regular health insurance may not apply outside your home country.

• Trip interruptions or cancellations – if illness, bad weather, or other issues force a change in plans.

• Missed connections – such as flights or transfers that cause you to miss your ship’s departure.

• Lost or delayed luggage – especially important when your suitcase may be on one side of the ocean and you on the other.

In short, cruise travel insurance provides peace of mind so you can focus on what matters: enjoying your voyage.

We personally use and recommend Just Travel Cover because they offer some of the most comprehensive cruise travel insurance policies we’ve found. Cruise insurance isn’t just “regular” travel insurance with a fancy label — it often covers things like missed ports, cabin confinement, medical emergencies at sea, and even repatriation from a ship.

There are also plenty of myths about cruise insurance — from “I’m super careful, so I won’t need it” to “the cruise line will look after me if something goes wrong.” Spoiler: they won’t. Whatever provider you choose, always read the policy carefully to be sure you’re covered for the activities and destinations you’re planning.

Accommodations 

Once the cruise and travel insurance are sorted, the next big decision is where to stay before or after your sailing. Unlike a land trip where you can be spontaneous, cruises run on a fixed schedule — so we recommend booking hotels well in advance, especially in busy embarkation ports like Miami, Barcelona, or Rome.

Staying flexible is great when you’re backpacking, but when it comes to cruising, securing a convenient and reasonably priced hotel ahead of time saves a lot of stress. This is especially true during peak season when the best options near the port get snapped up quickly.

When it comes to pre- and post-cruise stays, we turn to trusted booking sites like Expedia to track down the best deals. To make things easier, we’ve put together guides for the departure ports we know well, highlighting convenient hotels, budget-friendly options, and comfortable stays close to the action. You’ll find these recommendations throughout our port guides and planning pages, so you can start your cruise relaxed and stress-free.