How to Choose Your Caribbean Cruise?

Exploring the eastern and western Caribbean aboard a ship can be an incredible travel experience. Finding the perfect cruise among all the options, however, can be a real headache.

With all the beautiful islands and their crystal-clear waters to discover, plus the range of ships and routes available, an informed choice lets you get the most out of your vacation.

Here are the key points to weigh when choosing your southern cruise, so you can plan a getaway at sea that matches your preferences perfectly.

We’ll also suggest several cruise lines and ships, whether you’re travelling with family or among adults.

How to Choose Your Caribbean Cruise? - pixabay

Caribbean Cruise – Travel With Points

To save or pay for a cruise with points, simply use travel rewards points from certain credit cards. Here are a few of them:

Taking the Scotiabank Passport^™ Visa Infinite +* Card and the Cobalt American Express Card as examples, they offer a redemption rate of 1,000 points for a $10 credit. This can be applied to the cruise payment transaction to obtain a credit to your account.

Our credit card selection
Credit card	Annual fee	Welcome offer
SponsoredTD First Class Travel^® Visa Infinite* Card Apply NowCompare	Annual feeFirst Year Annual Fee Rebate$139 $0First Year Annual Fee Rebate	Welcome offerAfter $7,500 in 6 months Up to 160,000 points After $7,500 in 6 months	Apply NowCompare
Scotiabank Passport^® Visa Infinite +* Card Apply NowCompare	Annual fee$150	Welcome offerAfter $2,000 in 3 months Up to 35,000 pointsEnds Nov 1, 2026 After $2,000 in 3 months	Apply NowCompare
ExclusiveNational Bank World Elite^® Mastercard^® Apply NowCompare	Annual feeFirst Year Annual Fee Rebate$150 $0First Year Annual Fee Rebate	Welcome offer$150 annual fee rebated First Year Annual Fee RebateEnds Nov 4, 2026 $150 annual fee rebated	Apply NowCompare
American Express Cobalt^® Card Apply NowCompare	Annual fee$191.88	Welcome offerGet 1,250 points after $750 in purchases per month for 12 months Up to 15,000 points Get 1,250 points after $750 in purchases per month for 12 months	Apply NowCompare

You can also book your cruise directly with loyalty programs such as Aeroplan (with Air Canada Vacations), AIR MILES and Marriott Bonvoy.

It’s essential to define your objective and the type of cruise you want, then move on to the game plan with your credit card points.

Here’s our guide with tips for cruise with points :

Caribbean Cruises – Tips for Planning Your Trip

Choosing the Right Route

To choose an itinerary that matches your expectations, define your travel priorities, be they cultural richness, coral reefs, secluded beaches or sporting activities.

Some itineraries focus on cultural exploration, while others emphasize seaside delights.

Take into account the length of your stopovers. Are you aiming to maximize your adventures on each island? Does the sheer number of destinations visited appeal to you? Are full days of on-board travel a problem for you?

How to Choose Your Caribbean Cruise? - Caribbean cruise Unsplash

The Best Time to Go for Good Weather

In the Caribbean, the hurricane season from June to November presents risks, consequently rates are lower.

The ideal cruising season is generally from December to April, with pleasant temperatures and optimal conditions.

However, the popularity of this period can lead to higher rates. By planning according to the weather, you can avoid potential climatic hazards and maximize the enjoyment of your cruise.

How to Choose Your Caribbean Cruise? - St Thomas -unsplash

Choosing the Right Ship: Criteria to Take Into Account

Choosing the right cruise ship is vital for an experience tailored to your preferences. Evaluate the size of the ship for ambience, choose between interior cabins and suites according to your budget. Do you prefer more intimate or lively settings?

Consider the activities on board, from spas to entertainment, and the variety of restaurants on offer.

Check out the itineraries and ports-of-call, as some ships specialize in specific destinations.

Assess the company’s reputation in terms of service, safety and overall experience by consulting traveller reviews to make an informed decision.

How to Choose Your Caribbean Cruise? - MSC-Seascape

Caribbean Cruises – Our Suggestions for Families

Holland America Line

Among the best family cruise options in the Caribbean, Holland America stands out for its commitment to passenger comfort and enjoyment.

The Nieuw Statendam and Koningsdam ships, in particular, offer spacious cabins that sleep four people, large lounge areas and generous verandas.

How to Choose Your Caribbean Cruise? - Nieuw-Amsterdam--12174119244

Their popular ports-of-call include destinations such as Half Moon Cay, Ocho Rios, Grand Cayman and Cozumel, where you can enjoy magnificent coral reefs.

This is one of the 8-day Nieuw Statendam itineraries:

Day 1 Fort Lauderdale

Day 2 At sea

Day 3 Grand Turk

Day 4 San Juan

Day 5 Charlotte Amalie

Day 6 At sea

Day 7 Half Moon Cay

Day 8 Fort Lauderdale

Royal Caribbean

Royal Caribbean is ideal for many families, thanks to its age-appropriate facilities.

The company’s exclusive cruise, Perfect Day at CocoCay in the Bahamas, aboard the Freedom of the Seas, is particularly popular with young passengers for its water-slides and play areas.

How to Choose Your Caribbean Cruise? - perfect-day-at-coco-cay

The Icon of the Seas is specially designed for families. Featuring the Surfside outdoor area at the rear of the boat, this tropical paradise offers a water play area with slides and an infinity pool for adults.

Facilities include a themed carousel, arcade, several family-friendly restaurants and a relaxing “Mommy and Me” bar.

MSC Cruises

MSC Cruises has a variety of leisure activities specially designed for children, from water parks to Broadway-style shows.

MSC Seaside offers fun family excursions and a Lego Experience On Board event on every cruise.

Its kids club, named Doremi Land, offers separate areas for different age groups, from 6 months to 11 years. The child-care staff can take children to the onboard water park, accompany them in parades around the ship and even take them to lunch and dinner at the buffet.

How to Choose Your Caribbean Cruise? - msc seaside

Popular ports of call on the MSC Seaside include Ocean Cay MSC, Nassau, San Juan and Puerto Plata.

Here is one of the itineraries offered aboard the MSC Seaside in the Caribbean:

Day 1 Fort-de-France

Day 2 Pointe-à-Pitre

Day 3 Roseau

Day 4 Saint-Martin

Day 5 Saint Johns

Day 6 Basseterre (St. Kitts)

Day 7 Sailing

Day 8 Fort-de-France

How to Choose Your Caribbean Cruise? - fort saint louis saint-martin

Here are some other popular family ships in the Caribbean:

MSC Seascape
Wonder of the Seas, from Royal Caribbean
Disney Wish
Celebrity Ascent (for teens)
Sapphire Princess
Norwegian Prima

How to Choose Your Caribbean Cruise? - Disney Wish au port

Caribbean Cruises – Our Adult Suggestions

Celebrity Cruises

A good option is Celebrity Cruises.

With its home port in Fort Lauderdale, the Celebrity Equinox is a great choice for sophisticated relaxation in the Caribbean. It is beautifully decorated and offers gourmet cuisine, a variety of suites with exclusive benefits and a green deck for relaxation.

Without being an excessively expensive cruise, it’s perfect for couples and lovers of fine cuisine and cocktails.

The 2850-passenger ship’s varied destinations include Nassau, Bimini, Cozumel, Aruba, Bonaire, Curacao, Grand Cayman, St. Thomas, Sint Maarten, Tortola, Puerto Plata and San Juan.

How to Choose Your Caribbean Cruise? - Celebrity Equinox

Virgin Voyages

Based in Miami, Virgin Voyages ‘ Scarlet Lady stands out for its innovative approach that breaks with the conventions of traditional cruises. For example, you can forget about queues and classic booths. It’s ideal for fun-loving cruisers, single travellers, and groups of friends.

The Scarlet Lady offers several distinguished features, such as the Razzle Dazzle vegetarian restaurant, the Beach Club in Bimini, and the Shake for Champagne option, which lets you order champagne from anywhere on the ship via an app.

Destinations include Bimini in the Bahamas, Puerto Plata, Key West and Cozumel.

How to Choose Your Caribbean Cruise? - Lady Scarlet

Viking Cruises

If you have the pleasure of sailing on Viking’s West Indies Explorer, you’ll discover that this is not a cruise for the young. You’ll benefit from captivating lectures in conferences.

A Caribbean itinerary aboard the West Indies Explorer looks like this:

You’ll spend 11 days in 9 countries, starting in San Juan and stopping in Tortola, St. Maarten, and St. Martin. St. Kitts and Nevis, St. Lucia, Barbados, Dominica, Antigua and Barbuda, St. Kitts and Nevis Thomas, back to San Juan.

On such a trip, you’ll have the chance to hike to the top of Sage Mountain in the Virgin Islands and end your journey on the beach or visiting historic sites.

In Roseau, Dominica, a visit to Morne Trois Pitons National Park is a must, as is snorkelling at the famous Champagne Reef.

In Saint-Martin, enjoy unique opportunities such as creating your own perfume at a perfumery class or taking a chairlift ride to the top of Sentry Hill.

Defining leadership: 7 tips for becoming an inspiring leader - Sentry Hill

Other popular adult cruises in the Caribbean include the Sky Princess, Enchanted Princess and Discovery Princess with their magnificent Sky Suites; and the Pomp Romance in Paradise cruise with Regent Seven Seas.

Caribbean Cruises – Conclusion

Choosing the perfect Caribbean cruise can be a challenge, but with the right information, you can plan a maritime getaway that meets all your expectations.

From cultural itineraries to coral reefs, white sandy beaches, and age-appropriate vessels, you’re rich with choices. By exploring key criteria such as itinerary, weather, and ship, you can make informed decisions for a luscious vacation.

Discover our travel guides for the Caribbean and West Indies:

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American Express Cobalt^® Card

American Express Amex Membership Rewards

Annual fee: $191.88
Our valuationMilesopedia first-year estimate First-year valueWelcome bonus$255Total$255Rewards on your spending are not included. The calculator that adds them from your own profile is on the card's page.: $255
Welcome offerGet 1,250 points after $750 in purchases per month for 12 months: Up to 15,000 points

The American Express Cobalt^® Card is a versatile American Express card, whether you want points for travel or cash back.

American Express Cobalt^® Card welcome offer

The welcome bonus is paid out monthly over your first 12 months. You earn 1,250 Membership Rewards points for each monthly billing period in which you charge $750 in net purchases to your card, in any category (1X, 2X, 3X or 5X). That adds up to 15,000 Membership Rewards points over the year, a welcome offer valued at $255.

Earning the full bonus means $9,000 in net purchases spread across 12 monthly billing periods. This offer rewards steady monthly spending rather than one large purchase.

You can use these points as statement credits on everyday or travel purchases, at the same rate either way: 1,000 points = $10.

You can also transfer them to Aeroplan, Avios (British Airways and Qatar Airways), Flying Blue, Marriott Bonvoy or Hilton Honors. With the full welcome bonus, that is a choice between:

15,000 Aeroplan points
15,000 Avios points
15,000 Flying Blue Miles
18,000 Marriott Bonvoy points

American Express Cobalt^® Card benefits

Here is what the card gives you, starting with the benefits cardholders use most.

5X points on eligible eats and drinks in Canada: groceries, restaurants and bars, and home food delivery. A spend cap applies.
3X points on eligible streaming subscriptions in Canada.
2X points on eligible gas, public transit and ride sharing purchases in Canada.
1 additional point on eligible hotel and car rental bookings made through American Express Travel Online.
1X point per dollar on everything else, with no category restrictions.
Points that hold the same value either way: 1,000 points = $10 as a statement credit, or a 1:1 transfer to several airline and hotel loyalty programs.
No minimum income requirement, as with every American Express Canada card.
Additional cards at no extra cost: the first and every other supplementary card is $0.
The Hotel Collection: a room upgrade when available, 12pm check-in and late check-out when available, and up to $100 USD in hotel credit on amenities charged to the room for a stay of two or more consecutive nights, booked through American Express Travel.
Front Of The Line^® presale and reserved tickets for concerts and theatre performances, plus offers and events curated for cardmembers through Amex Experiences.
A soft credit check before you apply: you can see whether you will be approved with no impact to your credit score. This applies to American Express personal card applications.

The 5X categories and where they apply

The 5X rate is the reason most people carry this card. In Canada it covers three kinds of merchants:

Groceries: Metro, IGA, Sobeys, Super C, Safeway, Whole Foods.
Restaurants and bars: sit-down meals, takeout and drinks.
Home food delivery.
Convenience stores (Couche-Tard, 7-Eleven): not part of 5X, 1 point per dollar.

The 2X rate covers gas stations such as Esso, Shell and Petro-Canada, along with public transit and ride sharing.

With the American Express Cobalt^® Card, you earn between 1 and 5 points per dollar:

Category	Points per dollar
Grocery (Metro, IGA, Sobeys, Super C, etc.)	5
Home food delivery	5
Restaurants and bars	5
Convenience stores	1
Streaming services	3
Service station	2
Transport	2
Travel	1
Other	1

That works out to a 1 to 5% return on those purchases. For example, if you spend $1,000 per month across groceries, restaurants and food delivery, you earn $50 back per month, or $600 per year from that category alone. Transfer the points to a program such as Aeroplan instead and the return can be higher.

You can also stack these categories with the hundreds of stores that offer 5x points.

American Express Cobalt^® Card insurance coverage

The card comes with a broad insurance package. The amounts below are the coverage limits; conditions, age limits and exclusions are set out in the certificate of insurance linked in the Insurance section above.

Travel insurance

Emergency medical: up to $5,000,000 for the first 15 days of a trip.
Travel accident: accidental death and dismemberment of up to $250,000 for you, your spouse and dependent children under age 23 when travelling on a common carrier (plane, train, bus or ship) and the tickets are charged to your card. Supplementary cardholders and their families are covered too.
Flight delay: up to $500 for necessary hotel, meal and sundry expenses bought within 48 hours when you are delayed or denied boarding for four hours or more and no other transportation is available. This $500 is an aggregate limit per occurrence, shared with missed connection and delayed baggage coverage.
Delayed baggage: up to $500 for essential clothing and sundries bought within four days when your outbound luggage is delayed six hours or more. This $500 is an aggregate limit per occurrence, shared with missed connection and flight delay coverage.
Lost or stolen baggage: up to $500 per occurrence for all insured persons combined, for checked or carry-on baggage and personal effects in transit, when the airline tickets are charged to your card. Within that limit, jewellery is capped at $300 per occurrence and golf clubs, including golf bags, at $250 per occurrence.
Hotel and motel burglary: up to $500 against the loss of most personal items if your hotel or motel is burglarized, when the stay is charged to your card.

Rental car insurance

Theft and damage coverage is included for a rental car with an MSRP, for its model year, of up to $85,000 excluding all taxes, for rentals of up to 48 days. To use it, decline the Loss Damage Waiver (LDW) or any similar option from the rental company and charge the full rental to your card. There is no cost for this coverage, and it replaces the daily insurance the rental company charges, usually $16 to $23 per day.

Mobile device insurance

Your device is covered for up to $1,000 per occurrence when it is charged to the card, for up to two years from the date of purchase. The payout is based on the depreciated value of the device, which falls by 2% of the purchase price for every completed month, less a 10% deductible. Theft and accidental damage coverage starts on the 91st day after purchase, because the first 90 days are covered by purchase protection.

Purchase protection and extended warranty

Eligible items charged to your card are insured against accidental physical damage or theft for 90 days from the purchase date, up to $1,000 per occurrence for all items combined. The card also extends the original manufacturer’s warranty by up to one additional year on eligible items, with indemnification limited to $10,000 per insured item and $25,000 per Cardmember per policy year for all items combined.

American Express Cobalt^® Card fees

Card fee: $15.99 per month, which equals $191.88 per year, for residents outside Quebec. Quebec residents are billed $191.88 per year.
Additional cards: $0.
Purchase interest rate: 21.99%.
Cash advance interest rate: 21.99%.
Foreign transaction fee: 2.5%.
Minimum income required: none.

Because the fee is billed monthly rather than in one annual charge, you can stop and restart the cost in step with how much you are actually using the card.

Legal

American Express is not responsible for maintaining or monitoring the accuracy of information on this website. For full details and current product information, click the Apply Now link. If you apply and get approved for an American Express Card, we may receive compensation from American Express, which can be in the form of monetary payment.

Annual fee

Primary card$191.88

Additional card$0

Annual income required

Individual$0

Household$0

Conversion fees

2.5%

Earning rate

5xRestaurants
5xGroceries
3xStreaming
2xTransit
2xGas
1xAll spending

Value

1st Year Value$1,675

2nd Year Value$799

Transfer partners

AeroplanAirline
British Airways ClubAirline
Cathay Asia MilesAirline
Etihad GuestAirline
Flying BlueAirline
Hilton HonorsHotel
Marriott BonvoyHotel

Travel insurance

Travel medical (under 55)Up to $5,000,000 / 15 days

Travel medical (55-64)Up to $5,000,000 / 15 days

Delayed BaggageUp to $500

Lost BaggageUp to $500

Flight DelayUp to $500

Hotel BurglaryUp to $500

Travel AccidentUp to $250,000

Purchase protection

Purchase ProtectionUp to $1,000 / 90 days

Extended Warranty+1 years

Mobile DeviceUp to $1,000 / 2 years

Auto Rental Collision (primary)Up to $85,000 / 48 days

Frequently Asked Questions

What is the average price of an all-inclusive package on a cruise ship?

It all depends on the company you choose, and the length and itinerary of your cruise. You could save on your getaway with travel points. We invite you to consult our guide How to get a low-cost cruise with your credit card points?

How can I find a cheap cruise with an good discount?

Black Friday, Cyber Monday, Boxing Day and Labor Day are days when you can find the best deals and discounts from cruise lines.

What's the best line for a southern cruise?

Royal Caribbean was named “Best Cruise Line in the Caribbean” in the 2023 Travel Weekly Readers’ Choice Awards.

When is the best time to cruise the Caribbean islands?

The ideal time to enjoy a cruise in the West Indies is from December to May, since the hurricane season is in full swing from June 1 to November 30.