When you think of cruising with kids, most families look to cruise lines like Princess, Disney, or Royal Caribbean, which offer huge ships with roller coasters, waterslides, nightly shows, and massive 24-hour buffets. While these ships certainly have lots to offer families, there’s something magical about the relaxed atmosphere and personal attention provided by small-ship cruises.

I recently took my 16-year-old daughter on Windstar’s Naturally Costa Rica, a seven-day sailing that promised lots of wildlife spotting, sunny beach days, and delicious food. This cruise appealed to me as my daughter is a huge nature girl, and I loved the idea that the ship could take us to smaller ports that are not typically frequented by cruise ships.

While my daughter was the youngest guest by at least two decades, we found the experience perfectly aligned with our preference for a slower pace of travel that’s more focused on nature. Here are six reasons you should take your teen on a Windstar cruise:

1. You get to know everyone on the ship.

Windstar Cruises
Windstar Cruises

We sailed aboard the Wind Star, one of the three sailing yachts owned by Windstar Cruise Line. On our sailing, 135 guests and just over 100 staff were onboard. This small group meant that you got to know the staff, and they got to know you. When I’d show up at breakfast with just a book to keep me company, the staff would ask about my daughter and tease her later in the day for sleeping in and missing breakfast. We loved feeling like they were looking out for us and that they really wanted us to have the best time possible on the cruise.

There was a community feel on the ship, and we made friends with other travelers while on excursions, hanging out in the lounge, and during dinner. While you can certainly request a private table during dinner service, part of the fun was getting to know fellow travelers. Hearing everyone discuss their different excursions was the perfect way to end the day.

2. The on-staff naturalist teaches you about the ports you’ll visit and the animals you might see there.

Windstar Cruises | Kate Loweth

We were visiting Costa Rica for the first time on this cruise, and part of what drew us to this specific sailing was the opportunity to see sloths, monkeys, and other native animals. Each afternoon, we’d attend a presentation by the on-staff naturalist who talked about the Costa Rican rainforest and animals we might see on our shore excursions. We’d also get tips about what to do in the towns we were visiting in case we had some extra time on-shore.

While you won’t find all the comedy shows and theatrical performances that other cruise lines offer, these naturalist presentations suited our interests much better and were an excellent way to learn about the area we were visiting. The small number of guests allowed us as much access to the naturalist as we wanted, with plenty of opportunities to ask follow-up questions.

3. The small ship means you can access ports unavailable to other ships.

One of our favorite things about sailing with Windstar was the tender ports. On these days, we boarded one of the emergency lifeboats, and they took us to port. The ship was anchored just offshore, and it was quite exciting to make our way to port aboard this small tender.

One day, we even had a “wet landing,” which means you board a rigid inflatable boat called a “Zodiac.” That boat took us to the sandy beach, where crew members were waiting to assist us in hopping out of the boat. These were quite exciting and part of the adventure!

Visiting the small towns on the Costa Rican coast was quite a different experience from other cruises I’ve been on, where you are docked at a port town with tons of souvenir shops and t-shirt vendors. Here, we were immediately immersed in the town’s action when we got to shore in towns like Quepos and Playa Flamingo. We spent our free time on shore trying the local cuisine and even doing a little thrift shopping (a favorite teen activity). It felt like we really got to see the culture of Costa Rica instead of a typical cruise port.

4. The cabins felt quite roomy for two people. 

Windstar Cruises
Windstar Cruises

While you won’t have a balcony on a Windstar Cruise, the cabins were quite spacious, providing a comfortable space for my teen to have some privacy while I spent time on deck. The benefit of being on such a small ship is that you’re never very far from your room, but there are also plenty of common areas where you can grab a coffee or a cocktail and enjoy a book.

5. The watersports platform. 

Windstar Cruises
Windstar Cruises

For a few days while we were anchored, the ship’s watersports platform was available for guests. This meant that you could swim right off the back of the ship! We spent some time lounging on the floating mats attached to the ship while other guests took the kayaks out. This was a highlight for my daughter, and I loved how you could do this activity for as long as you wanted, and then you were just a two-minute walk to your cabin when you were done.

6. Ease and variety of dining options. 

Cruises are typically known for the volume of food they serve but not necessarily the quality of those offerings. We knew that the Windstar offerings would be at a higher level, being that Windstar is the official cruise line of the James Beard Foundation.

My daughter appreciated the complimentary room service that was always available (including nightly popcorn!), and I enjoyed the ease of not having to wait through long meals as hundreds of guests were served. There was no need to sign up in advance for meals, and there were no specialty restaurants charging additional fees.


Costa Rica with @WindstarCruises #costarica #costarica🇨🇷 #windstar #windstarcruises #travel #travelbucketlist

♬ A Summer Place – Hollywood Strings Orchestra

We would highly recommend Windstar to any families traveling with teens. It offers a personalized experience that you won’t find on larger cruise lines. While some cruises might leave you feeling exhausted when they are over, our Costa Rica cruise was very relaxing, the perfect pace for a mother-daughter adventure.

More to come from Windstar Cruises:
Windstar Cruises is planning many exciting developments, from the refresh and redesign of its three sailing yachts to first-time cruises in South America beginning in December 2025 onboard the all-suite yacht Star Pride. New cruises in the Canary Islands kicked off this year, and Windstar will expand its usual Tahitian cruise stops (where the line has sailed for more than 35 years and is the small ship expert) to include the extremely remote Marquesas Islands.

Windstar Cruises
Online: windstarcruises.com

Editor’s note: This trip was hosted by Windstar Cruises but all opinions belong to the writer. 

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