The Caribbean is the place for cruising and Princess Cruises offers more than 90 itineraries across the Caribbean for 2026. Here, a veteran cruiser who has spent two months sailing aboard Princess cruise ships, highlights just a few of the Princess cruises sailing the Caribbean in 2026.
Princess Cruises Itinerary Highlights
- Solo Travelers: Cruise itineraries that feel safe but open up a world of culture, adventure and experiences.
- Grown-Ups: Which trips to take with the ones you love, whether they’re romantic partners or besties.
- Families: What’s best for littles, middles and teens.
This post is sponsored by Princess Cruises..
How to Choose the Right Caribbean Cruise for You (Quick Cheat Sheet)
- Short on time? → 4–6 day Bahamas/Eastern Caribbean
- First cruise? → Eastern Caribbean
- Want something unique? → Southern Caribbean (ABC islands: Aruba, Bonaire, Curacao)
- Explore different cultures → Western Caribbean (Mexico, Honduras, Belize)
- Traveling with little kids → Princess Cays
- Traveling with teens → Bigger ship
- Girls’ trip? → Short + easy Eastern Caribbean
Best Princess Cruises for Romantic Couples
Cruises hit the real sweet spot for my husband and me. We both love the all-inclusive aspect of cruising from a budget standpoint and low-stress-on-the-planning-front standpoint. Hubby knows I won’t get too worked up about anything once we step on board a ship.
Tips for Romantic Cruisers
- Choose smaller ships for a more laid-back cruise
- Look for itineraries with more sea days to allow for sleeping in
- Budget for an extravagant extra, such as a couples’ massage or a long romantic dinner at a specialty restaurant
Top Itineraries for Couples
8-Day Southern Caribbean with Aruba aboard Regal Princess
This round-trip cruise from Fort Lauderdale offers four sea days and three port days, including a stop in another of my favorite Caribbean islands: Aruba. Definitely book an ATV adventure to explore the history and wild terrain of this tiny island.
Regal Princess is small enough to feel intimate but big enough to have all of the features you want in a full-service ship, from exemplary entertainment to a luxurious spa.
Why it works:
- These islands are less crowded and more colorful
- Late-night departure in Aruba = built-in date night on shore
- More sea days = more time for unstructured time together
14-Day Eastern Caribbean Adventurer Aboard Caribbean Princess
OK, two weeks might feel like a long time, but don’t you deserve it? When hubby and I did our 20-day Caribbean cruise aboard Enchanted Princess in 2025, we worried we might get bored after so much time on the same ship.
We were so wrong!
When you lead busy Type A lives, it can take a week or longer just to settle into vacation mode. All that time on the ship left us feeling relaxed, recharged and ready to return to real life.
This round-trip cruise from Port Canaveral includes six sea days and seven ports, with two stops each in the Dominican Republic, Puerto Rico and Turks and Caicos.
Why it works:
- Classic Caribbean beauty (turquoise water, white sand)
- Lots of downtime to spend together
- A ship that is small enough not to be overwhelming but big enough to offer all of the entertainment, dining and fun you can handle
Best Princess Cruises for Girlfriend Getaways
For a girls’ trip, you want something that feels easy, flexible and celebratory. And, because it’s hard to coordinate schedules, shorter is usually best when you’re trying to get the besties together for fun.
You can choose a big ship with lots to do every minute of every day on the cruise, or a smaller ship for a more intimate, laid-back vibe.
Tips for Planning a Cruise with Girlfriends
- Aim for 4– to 6-day sailings
- Buy the drinks package
- Splurge on a spa day on board
SheBuysTravel Tip: My standard cabin on Enchanted Princess was very comfortable for two people. I think, however, that it would feel very crowded with more than two adults, so book more than one cabin if you’re traveling with three or more friends!
Top Itineraries for Girlfriend Trips
5-Day Caribbean Getaway with Grand Turk Aboard Enchanted Princess
My 20-day cruise in 2025 was spent aboard Enchanted Princess, so I can assure you that you will find plenty to do on board. The entertainment is first-rate, the bars are hopping and the staff is attentive.
This round-trip itinerary includes a stop at Princess Cays, the cruise line’s private island resort, where you and your friend can spend the day on the gorgeous beach, sipping mai tais in a lounger.
Why it works:
- Perfect long weekend trip
- Private island = zero-stress beach day
- Plenty of things to do to keep everyone happy
4-Day Caribbean Getaway Aboard Star Princess
Star Princess debuted in October 2025. And that’s the reason to take this round-trip from Fort Lauderdale: There’s only one stop, at Grand Turk, so you can spend the rest of the cruise exploring the ship, the newest in the Princess fleet.
Why it works:
- A shiny new ship is always fun
- It’s a bigger ship, so there are more things to do on board
- There’s a spa
Families: Match the Itinerary to Your Kids’ Ages
My kids ALWAYS loved cruising and I loved taking them. When they were little, it was fun to explore the ship through their eyes. And when they got bigger, it was easy to give them more freedom because there was only so much trouble they could get into on a cruise ship with a 2:1 passenger-to-staff ratio.
All Princess ships offer:
- Dedicated kids club spaces for kids ages 3-12. Kids must be potty-trained to participate without a parent.
- Beach House Teen Lounge for teens ages 13-17.
- Drop kids off during the day for free while you explore ashore, visit the spa or just chill.
- Babysitting is available in the evenings for a fee.
Best Princess Cruises for Little Kids (Ages 3–7)
This is the time to keep things simple. Shorter trips, fewer ports, more beach time and definitely a stop at Princess Cays, the cruise line’s private island resort. And remember to book a little grown-up time, too.
7-Day Eastern Caribbean with Princess Cays Aboard Caribbean Princess
Why it works:
- Private island = easiest beach day of your life
- Kids club for the littles, middles and big kids
- Lots of cruise dates available
Best Princess Cruises for Middle Kids (Ages 8–12)
Bigger kids want more stuff to do and have the stamina for more port days.
8-Day Eastern Caribbean with Puerto Rico
Why it works:
- A holiday cruise over the winter break will give your kids bragging rights when they return to school in January.
- A day on Princess Cays.
- Port stops in Puerto Rico, Dominican Republic and Grand Turk offer broad cultural exposure.
Best Princess Cruises for Teens
Oh-so-grown-up teens are ready to explore more. Expose them to new cultures, sights and sounds with ports that go beyond the typical island scene.
7-Day Western Caribbean Aboard Star Princess
Why it works:
- Stops in Honduras, Mexico and Belize
- Dedicated teen space for hanging out and meeting new people
- Wide choice of sail dates and ships, so you can choose the bigger Star Princess or Sun Princess to give teens more space to roam and more activities to try
Best Princess Cruises for Solo Women Travelers
When I cruised the Caribbean aboard Enchanted Princess, I met two women who I thought were long-time besties. When I asked how long they had been friends, they responded, “We met on the ship two days ago.”
It drove home to me how easy it is to travel solo on a cruise. You have a deep and immediate connection to other solo women travelers. You both love to travel and who doesn’t love talking about all of the places they’ve been and what’s still on the bucket list?
But, where to go first as a solo cruiser?
Tips for Solo Women Cruisers
- Book excursions through Princess so you know you’re in good hands.
- Check the Princess app or daily planner to find opportunities to meet other solo cruisers.
- Choose to eat at a shared table in the complimentary dining venues to meet fellow travelers.
- Princess has a few solo cabins on some ships, so you may be able to save the solo supplement.
Top Itineraries for Solo Women
7-Day Eastern Caribbean with Turks & Caicos Aboard Regal Princess
Any cruise that sails to Turks and Caicos gets a thumbs-up from me. I’ve explored a lot of the Caribbean and I have yet to find an island with clearer aqua blue water or softer white sand.
Plus, this round trip cruise from Fort Lauderdale includes a stop at Princess’ gorgeous private island resort, Princess Cays (pronounced “keys”). There, you can while away the day in a beach lounger, rent a floaty to lounge in the gentle surf or book an excursion to explore farther afield.
Plus, it’s easy to feel safe on a private island that is staffed by Princess employees and open only to Princess passengers.
Why it works:
- Short and manageable for a first solo cruise
- Beach-heavy ports = easy DIY exploring
- Mid-sized ship gives you plenty of chances to meet people in a more intimate setting
7-Day Eastern Caribbean with Puerto Rico (Caribbean Princess)
This round-trip sailing from Port Canaveral starts with two sea days so you can really get to know the ship. Stops offer the opportunity for rich cultural exploration in Puerto Rico, a sunny beach day close to the ship in the Dominican Republic and a glimpse of Caribbean history in Grand Turk.
Why it works:
- Adds cultural depth
- Sea days offer time to get to know the ship and meet other passengers
- 3 distinctly different ports provide a real taste of Caribbean diversity
To learn more about Princess cruises for all types of travelers, visit Princess.com.
FAQs
While Princess is known for a more relaxed atmosphere, Sun Princess and Discovery Princess are top choices for families. These newer ships feature the most expansive “Camp Discovery” youth centers and “The Catch by Rudi,” which offers approachable seafood options for all ages.
Yes! Solo travelers often prefer Caribbean Princess or Enchanted Princess . Beyond the “Singles and Solos” meetups held early in the sailing, the MedallionClass technology makes solo travel much smoother — you can order food or drinks to your exact location on the ship via the app, and the wearable device allows for touchless cabin entry and easy navigation.
Princess is ideal for group trips because of the balance between relaxation and entertainment. The Lotus Spa is one of the best at sea for group treatments, and the Sanctuary, an adults-only retreat, is the spot to claim a group of cabanas for the day. For evening fun, the “Movies Under the Stars” deck parties and the high-end cocktail menus at Good Spirits at Sea provide a great social backdrop.
For couples, the ultimate experience is the Ultimate Balcony Dining , where a meal is served privately on your stateroom balcony. Larger ships also feature “The Enclave,” an extra-large thermal suite with a hydrotherapy pool, which is a favorite for couples looking to unwind together between port visits in the Virgin Islands or the Bahamas.
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