Caribbean Cruising 101 - A Guide For Your First Time

Cruise ships are essentially cities at sea -- these massive floating towns not only have enough cabins to sleep hundreds and thousands of passengers, but they sail equipped with restaurants, cafes, bars, mini golf courses, basketball courts, ice skating rinks, theaters, zip-lines, and more all for you to enjoy in between island stops. They are so much fun! 

 The Caribbean Islands boast impressive natural beauty, delicious food, warm clear beaches, and the undeniable aura of relaxation. It’s no wonder that the likes of Jamaica, Aruba, and Barbados are such popular vacation destinations for us Americans. A cruise through this region can give you the opportunity to explore the Caribbean and enjoy the fun atmosphere of sailing the high seas, and usually at a lower total cost than an island resort stay.

I’m thankful to have a cruise-enthusiast as a mom, who was always planning cruises and finding the best deals for our yearly family vacation. My 11-year-in-a-row cruise streak ended when I skipped out on the family cruise to go on a girls’ trip to Cancun a few years ago, but this summer I got back into the cruise flow on a 5-day voyage aboard the Carnival Conquest to Ocho Rios, Jamaica and Grand Cayman Island. It wasn't hard to fall back in love with the seduction of life on the sea. 

 I unexpectedly popped up and surprised my aunts and cousins, who had no idea I was coming because my original plan was to have been in Thailand by then. I hadn’t seen my Pittsburgh-based fam in a while since moving to LA, so we were beyond psyched to see each other and vacation for the first time together.

I’m sooo so happy my mom suggested I come -- the 11 of us had a blast the entire time. The quality time spent with my family before moving overseas, where I have NO family, was priceless. It felt like a brand new experience traveling alongside first-time cruisers, and watching them fall for the joys of cruising was amazing. The icing on the cake -- turning up with my dad on his birthday, who got to ring it in this year on a ship, with his sisters, nephews, and nieces too. A litany of litness indeed.

We’re already talking about our next one, and we’re making sure we get more family on board for next time. Needless to say, they loved their first cruise!

If you haven’t yet set sail, but are interested in doing so, check out these 7 tips below to get you on your way to planning your first vacation at sea.

1. Choosing Your Ship, Itinerary, and Budget

Now that US-based cruise lines have expanded globally, you can sail all around the world -- Europe, Asia, the Middle East, South America -- it’s a great way to get a glimpse of several spots in one region in a short period of time. Choosing where you’re going to sail is the first step in planning your vacation at sea. Of the 15 cruises I’ve sailed on since being a second-grade little tike -- with missing front teeth and head full of tiny fake braids -- all but three have been through the Caribbean. This expansive group of islands is a popular starting point for first time cruisers.

Most itineraries are 3-7 nights. I say go for the 7 day all the way! A week is a perfect amount of time to soak up ample servings of both the sand & sea. However, if you’re not sure whether cruising is your thing yet, or you’re just looking for an extended weekend getaway, 3-5 day jaunts are a great alternative. 

Next, choose your ship and your itinerary -- which islands you want to visit. One may hold more importance than the other. When determining which cruise to sail on, we usually factor in ship features, itinerary, and price equally. Royal Caribbean and Carnival dominate this region, so you’ll most likely be picking one from their plentiful fleets.

If you’re yearning for fanciness, look towards Royal Caribbean and Princess, who have the most beautifully constructed ships (I have not sailed Norwegian, but their ships look amazing as well).   

Royal Caribbean brings the wow factor like none other, and it's the first choice for adventurers. The ice skating rinks and zip-lines I mentioned earlier? You’ll find those features, along with rock climbing walls, surfing simulators, exotic solariums, and more (I haven’t even covered the half of it) only on Royal Caribbean’s megacruises. Royal is bae; it’s by far my favorite line to sail on.

Carnival has less frills, however, they are understandably a lot more budget friendly. Their ships do have basketball courts, putt-putt golf, and at-sea entertainment, so there’s enough to keep you busy when you’re not enjoying cocktails poolside. It lives up to its catchphrase as the “Fun Ship.” Carnival passengers, in my experience, are usually the younger, more laid back, social, and dance-like-no-one’s-watching crowd. The pool deck parties, dining room song & dance sessions, and nightclubs on Carnival are always popping.

Since it is the less expensive line, it can be easier to plan large group cruises and/or family reunions on Carnival. I’ve always had the best times on cruises when I went with a group of family members/friends.

Now, when deciding between itineraries you can choose to sail between the:

Eastern Caribbean - which includes the U.S. Virgin Islands, British Virgin Islands, St. Maarten, and Puerto Rico.
Southern Caribbean - St. Lucia, Dominica, Grenada, Aruba, and the French West Indies
Western Caribbean - Grand Cayman, Cozumel, Jamaica, and sometimes Belize and Honduras!

My favorite ports of call so far have been St. Maarten, St. Thomas, San Juan, and St. Lucia. Each island has something a little different to offer, with some being known for idyllic beaches, snorkeling, and scuba diving, while others are known for being rich in historic sights and land adventures.

Grand Cayman and its GORGEOUS crystal water

2. Packing & Sailing

Always plan for two outfits per day. Your afternoon ensemble should be beach appropriate -- swimsuit, coverup, shorts and a tank, or an easy sundress. Your evenings will typically include dinner in the dining room, the only place onboard where a dress code applies. You don’t have to dress up, but smart casual wear is expected (no jeans, shorts, or hats). A helpful thing to remember: laundry rooms are available on most ships if you need clothes cleaned during your trip. 

There is usually one dedicated Formal Night, where you can dress as elegantly as your heart desires. I’ve seen it all from ball gowns to freakum dresses. The guys can break out sharp tuxedos and suits or go for slacks with a jacket -- either choice is equally acceptable. Carnival cruises are the most laid back in regards to ship style. 

When choosing your outfits, keep in mind you’ll have nightly professional photo opportunities, so you may just want to bring out your finest threads. Some days photographers make their rounds through the dining room and snap you where you sit. You can also choose from multiple backdrops to pose in front of for solo or group photos. Take as many pictures as you want during the cruise; they’ll all be printed for you to view in the photo shop. You can purchase whichever ones you want to keep.

Grand Cayman 7-Mile Beach

Carnival Conquest at port in Grand Cayman

Making a friend & cooling off in the pool

Almost all itineraries include at least one full day at sea without any ports of call. For me, sea days are always the most relaxing. You can sleep in without missing anything, order free room service, lay out and read, or have pitchers of margaritas delivered to you by the pool. If that sounds like the life, trust me, it is.

You get a lot for your money on cruises. When you’re onboard, you can enjoy dancing lessons, attend adult comedy skits and Broadway-style shows, party well into the morning hours, do arts & crafts, work out in the gym, take behind-the-scenes ship tours, participate in fun game shows and friendly competitions, and more -- pretty much at no additional cost. And my favorite part…?

3. Food. Eat as much as you want.

Need I say more? (Yes.)

The thing that excites me most about cruising is the food, and the ability to have as much of it as I want without looking at the price, because the price doesn’t exist. (That’s a lie, you already paid for it in your cruise fare, but that’s besides the point.)

Diets do not exist on vacation, and especially not on cruises. Now, don’t go ordering everything on the menu just to taste a bite and waste the rest, but if you’re hungry enough for three appetizers and two main courses, by all means, have them and eat them too. I’ll always fondly remember one cruise night I shamelessly devoured a delicious Thai BBQ chicken and three buttery lobster tails. Mmm mmm mmm.

Breakfast buffets, freshly grilled lunches, being served by attentive waiters every evening, and late night pizzas are all at your disposal. It’s common for ships to have specialty restaurants now, too (sushi, Italian, steakhouses). Reservations at these venues might cost about $20-$30 per person; you can decide if you want to have a more upscale dinner when you’re onboard.

The quality of food varies from line to line. If the company has a higher luxury value, their recipes are likely more well-crafted and their dishes tastier than lower-fare cruise companies. Carnival’s cuisine wasn't always that impressive. Nonetheless, if you’re not picky, you’ll be fine and never hungry.

We love our lobster

4. Save on Excursions

Each cruise line has a list of land activities and tours that they offer for each port of call, which all come at different prices. You can book directly through the cruise, or venture out on your own and take independent excursions.

My family tends to save a lot of money by going for the latter option. When we disembark the ship at an island stop, we hire a taxi/tour driver on our own to take us where we want to go (the beach, jet skiing, parasailing, on a tour, etc). We usually negotiate a price that’s always better than the ship’s offer.

During our Ocho Rios stop this summer, we hired a van to take us horseback riding and to Dunn’s Rivers Falls for only $40 each. This was an incredible deal, butttttt, admittedly, our horseback riding wasn’t exactly what we expected.

We got dropped off to a group of Jamaican guys (one was only in the 7th grade!) with a team of horses seemingly right on the side of the road. We each mounted our own horse -- mine was named Playboy and apparently had a vendetta against one of the other big guys, so they couldn’t be near each other -- and the young horse keepers led us up through a small local neighborhood on a hill. The poor horses seemed so tired marching upwards with us on their backs. We thought we’d be galloping along the shoreline, but when they led us down to the beach, we only got a quick tease of a walk in and out of the water.

Our horseback riding adventure was a little bootleg, but we got a kick out of it and still enjoyed the experience. There’s never a dull moment with my family. The lesson here: if you want a guaranteed legitimate, well-organized excursion, book it through the cruise line. If you’re more price sensitive, book tours independently, but be aware you may just get what you pay for.

Aren't they so cuuuute!?

We conquered Dunn's River Falls! - The falls is always crowded, but it's an Ocho Rios must

Waterfall chillin'

You only get several hours at each island before having to re-board the ship by 4:00 or 5:00PM. Get out as early as possible in the morning and plan your day full of adventuring, relaxing at the beach, and shopping accordingly.


5. Leave Room in Your Budget For…

  • Land excursions, as mentioned earlier, which range on average from $50-$150/per person depending on what you do. Jet skiing, parasailing, speedboat rides, snorkeling, and ATV rides are popular island activities all around the Caribbean.
  • Shopping. There are shops and jewelry/watch sales onboard, as well as duty-free stores at almost all of the ports of call, waiting for ships to unload thousands of passengers right to their front doors. You may want to buy silver, gold, gemstones, cologne, local handicrafts, or souvenirs to take back home with you. Eating on the islands comes at your own expense as well. 
  • Sodas and alcoholic drinks onboard. While food is nearly all inclusive, soft drinks and those fancy poolside cocktails are not. You can buy prepaid beverage packages if you think you’ll drink a lot, or just order and add drinks and anything you buy onboard to your tab. You pay for everything purchased onboard at the end of the cruise.
  • Gratuities! Most lines automatically add service charges on top of your fares, or offer the option of prepaid gratuities at booking. The waitstaff works around the clock serving three meals per day, and room stewards clean cabins twice per day, every single day for months on end. With the low wages typical in the cruise industry, tips are very important. Feel free to add any additional gratuity at the end of the cruise for exceptional service. For more in-depth cruise tipping etiquette, click here.
  • The onboard casino - if gambling is your thing
  • Phone & wifi charges. It's okay to disconnect completely while you're out at sea. Trust me, you don't need the wifi. But if you absolutely must, be prepared to pay for internet packages.

6. Get The Best Deals Early (Or Last Minute)

You can find truly lustworthy cruise deals if you book early enough. Cruise lines offer attractive prices about 8 months to a year prior to the sailing date to encourage advanced bookings. However, you can also find last minute cruise deals of up to 50%-80% off of brochure fares only a few weeks or a couple months before -- is your go-to for finding these deals. You can book through the cruise line itself, through a travel agent, or a third-party site like Vacations To Go. Some third parties offer perks like onboard credit or special discounts; do explore your options!

Summer and spring break are peak Caribbean travel seasons, so I suggest booking summer & spring trips early so you don’t run the risk of your desired itinerary being sold out. If you’re planning a group trip, booking early is necessary. If your group is large enough, you can usually secure discounted fares. This also gives you more time to plan and save up for your vacation spending.


With the ship as your playground, you never want to spend too much time in your cabin. But when you are in your room, there’s nothing better than being able to recline back on your private balcony and enjoy the gentle waves in peace as you sail. It’s the most relaxing thing. You can wake up to beautiful island views and watch the ship pull out from the port as you’re getting dressed for dinner.

You may even get treated with a dolphin sighting! Towards one of our last days on the cruise, we peeked out and caught a few dolphins swimming alongside the boat, jumping through the air and showing off for us. It was definitely one of the trip highlights to see these beautiful sea dwellers, graceful, stunning, and free in their natural habitat. 

Wake up to this view on your balcony!

Ocho Rios, Jamaica

8. Spend a couple of days on land.

If you have any more vacation days to spare, it’s great to spend some time on land, before or after you sail, in the ship’s embarkation city. Our starting and ending point this time was Ft. Lauderdale/Hollywood, in line with a lot of Caribbean cruises that depart from Florida ports.

We spent some time in Miami before and after the cruise, relaxing in the warm waves and enjoying the eclectic vibe of my beloved South Beach. I was flooded with smirk-inducing memories when riding across the bridge into SoBe, where I spent three spring breaks in a row and Dri’s 21st birthday. It’s a lot different being there when you’re no longer a carefree  college kid, and with parents, but I’ll always love the ‘Yayo’ for those priceless times and for providing me with memories to reminisce on with friends ‘til we’re old.

This time around, I checked out an area of Miami I hadn’t yet seen: The arts district. The Wynwood Walls and its gorgeous street art were fun to admire.

Notorious South Beach streets

Hanging out on Ocean Drive like old times

Miami street art - Wynwood Walls

Have you cruised before? Let me know about your cruise experiences below. If you have yet to go, are you ready to try your first vacation at sea!? 

Kristen Noelle

I consider myself a softly eccentric urbanista. I’m quiet by nature, and I’ve generally always had a mellow laid-back vibe. However, when it comes to my preferences for fun, my style, and my overall thought process, I get a bit more eccentric. I like stepping out of the box of normalcy -- but without forcing anything. I’m a thrill junkie and I live for things that get my adrenaline pumping, such as riding on top of party buses in New York City and hanging off of skyscrapers in Vegas. I spring for bold hues, colorful prints and patterns, and a relaxed look that gives effortless-chic. I like exploring new places and capturing exciting sites. I’m a creative, with a million different ideas running through my mind each day. Whether I’m designing waistbeads, imagining up new clothing concepts, envisioning my next business venture, or planning my next adventure abroad, I’m always thinking of how I can create something great. Being raised in the suburbs but not far from the city and constantly traveling, I developed a love for the best of worlds. The calm and the crazy. The easy-going and the always-buzzing. The soft and the eccentric.