Top Advice and Tips for Cruises After Hundreds of Trips at Sea

  • Cruise ships and their destinations are overflowing with travelers this summer. 
  • Among them is “The Cruise Guy” Stewart Chiron, an industry expert who has been on over 300 cruises.
  • He shared 10 tips for travelers spending their summer vacations at sea. 

Cruise ships — and their destinations — are jam-packed with travelers this summer.

Among them is Stewart Chiron, an industry expert also known as “The Cruise Guy.” The travel agency founder has taken a total of 311 cruises in his lifetime, including 36 since since industry’s reopening and two voyages this summer. 

Cruising’s resurgence from pandemic ground-zero to record-breaking bookings hasn’t been without challenges,  including norovirus outbreaks, man-overboard incidents, overbooked ships, and large crowds

So we asked Chiron to share his top advice for travelers spending their summer vacations at sea this year — from how to avoid long lines and crowded pool decks to when you should buy travel insurance and how early you should arrive before the ship’s departure. 

“The ships are operating at full capacity. That’s a big difference,” he told Insider. “This year was my third consecutive summer at Mykonos and Santorini and the difference between this year and last year is significant. Not so much more ships, it’s just more people.”

Lessons from taking over 300 cruises around the world

Stewart Chiron Celebrity Beyond cruise ship

Stewart Chiron, “The Cruise Guy” has taken over 300 cruises in his lifetime.

Courtesy of Stewart Chiron

1. Pick a cruise line that matches your personality and expectations

Not all cruise lines, or cruise ships for that matter, cater to the same kind of clientele. Some brands are popular among young party-goers, while others may attract a more mature crowd. 

“You want to make sure that you get paired up and matched with the right cruise line. It can make a tremendous difference,” Chiron said. “You want to book something that is reminiscent of your likes and desires.”

2. Don’t get distracted by flashy sales and packages

Many cruises offer shipboard credit or package deals for food, drinks, or other items and services. Princess cruises, for example, charges $76.70 daily for a drink package that provides up to 15 alcoholic beverages daily.

“I think a lot of people get caught up with some of these sales. It’s the same offers and they’re just getting regurgitated and re-titled,” Chiron said. “But they’re creating distractions and sometimes they’re covering for higher prices.”

“It’s like with the drink package, when you calculate how much you’re going to have to drink in order to break even,” he added. 

3. If you’re traveling with children, look for family-friendly cruises 

“There’s a lot of ships that are just really incredible for kids and there are ships that aren’t,” Chiron told Insider. 

Some ships have amenities tailored for kids like water parks, teen clubs, kids menus, and day care options, while other ships are far less accommodating toward young travelers.

4. First-timers should consider booking through a travel agent 

The biggest advice Chiron said he gives first-time cruise-goers is to “research online, but don’t book online.” Unlike airfare, booking a cruise can be an overwhelming and manual process, he said, and travel agents who have a relationship with the cruise lines have access to special rates and can advocate on your behalf if something goes wrong. 

“You may not wind up in the type of cabin you want, you may not be able to get the reservation you want,” he said. “There’s a lot of things that could go wrong or things that [a travel agent] can help improve.”

5. Buy travel insurance if you’re going on an international cruise 

Chiron said he never travels internationally without purchasing trip insurance. But what’s even more important than buying insurance is understanding exactly what it covers, he said. 

From trip interruption and cancellation insurance to evacuation and property coverage, not all insurance policies are made equal. 

“There’s a lot of medical insurance that does not cover international travel which is very important for people to find out,” he said, adding that passengers who see a doctor abroad for something simple could end up footing a $500 bill.

6. Weigh the pros and cons of booking airfare through the cruise line

Some cruise lines have access to discounted flights and allow you to bundle your airfare with your cruise. But like all third-party booking platforms, the programs have their benefits and downsides. Chiron recommends comparing the flight prices and availability of booking directly with the airline to whatever the cruise line is offering before making a decision. 

7. Arrive at the port at least a day before the cruise departs

It’s always a good rule of thumb to arrive at least one day before your cruise departs, especially if you’re flying to the port. That way, you have more flexibility if your flight gets delayed or canceled. 

For domestic ports like Miami, Seattle, or Los Angeles, it’s fine to arrive a day before your cruise departs, Chiron said. But for cruises departing from international ports, you should consider arriving multiple days in advance, he said. That way, you can explore the area and adjust to the time difference. 

“It also depends where I’m going. I enjoy Rome, so sometimes I’ll go in two or three days before the cruise,” he said. “If you’re going to the Mediterranean, why wouldn’t you want to spend some extra time in whatever port you’re departing out of?”

8. Plan strategically to avoid long lines and crowded ports

Not only are cruise ships booked to capacity — the cities that they’re visiting are overflowing with tourists too. This congestion at cruise ports can cause some challenges as cruisers disembark, Chiron said. 

In Santorini, for example, he said cruise passengers are required to take a smaller tender boat to shore, and then hop on a tram in order to get to town. 

“When we got off the tender I saw thousands of people waiting in line to take a tram,” he said. “So we actually got back on the tender, went back to the ship, had lunch, waited a couple hours and then came back.”

His advice: “Take some time to do research on how some of these ports are handling cruise passengers and tourist traffic” and then plan strategically. 

9. Don’t feel pressure to disembark at every port

A potentially controversial travel hack of Chiron’s is to skip disembarkment at the ports he’s already been to in order to enjoy the amenities of the ship, sans crowds. This is prime time to eat at the most popular restaurants or relax at the pool, he told Insider. 

“On certain ships it can be overly crowded trying to find deck chairs. But when you’re at port, you have the ship to yourself. There’s no issues,” he said. 

10. Wash your hands — but don’t let norovirus scare you away

There have already been 13 norovirus outbreaks on cruise ships this year, but Chiron says the odds of getting a stomach virus on a cruise ship are in reality quite rare due to companies’ stringent sanitation policies and CDC reporting requirements

“After all those cruises, I’ve never had it [norovirus] on a ship,” he told Insider. 

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