Sailing Game Using Pretend Play

For kids: Sailing Adventure

If your kids love dressing up, adventure, and pretend play that takes them to faraway places, this sailing game is for you!

Create life on the high sea in your very own living room with some old-timey clothes, a little music, and your child’s limitless imagination. This sailing game is perfect for those who long to travel without leaving home for the adventure.

All activities in our pretend play Sailing Adventure can be completed with or without props. The boat, binoculars, tools, and other items mentioned can be imaginary or enhanced with physical objects and art supplies. It’s up to you how you play the game!

Come aboard! Let's set sail on in our pretend play adventure!

“THE SAILING Adventure!”

The sailing game

3 - 6


10 minutes


25 - 35 minutes

Coloring Sheets

Grab your ticket for the Creativity Cruiseline, navigate your way to find the hidden treasure, and bring to life sea friends. Below, available for free download, are our hand-drawn coloring sheets for your kiddos to color before or after their sailing adventure! 

Dressing Up

First, grab some old-timey clothes, or even a striped t-shirt and some white pants. You can’t play a sailing game without costumes! Ask your kiddo what they think a sailor wears and work with what you have at home. Complete the look with a hat for a more formal sailor look, or go barefoot if you’re a more rough and tumble sailor. There are no rules! Once your costume is complete, you’re ready for the next step.

mermaid themed pretend play kits

Building the Boat

Next, if you’re going to sail, you need a boat! This boat can be made from cardboard boxes, couch cushions, chairs and blankets, a clothes basket, or pure imagination. You and your child can decide. Building it is part of the fun!

Pretend that the boat has been sitting in the dock for quite a while. It needs to be fixed up before the adventure begins. Get out your hammer, nails, and paintbrushes to tackle some ship repair and maintenance before you set sail. The deck could use a good swabbing, too! Once the boat is seaworthy, hoist the sails and pull up the anchor. You’re on your way!

On the Water

Once you’re on the water, you, or another adult, will act as the captain and steer the ship. But let the little seafarers take turns steering, too, so they can help guide the sailing game.

As you set sail, listen to the “Sailing, Sailing” song and create movements to go with the music. This will help propel the boat through the water.

Have your sailors use binoculars (toilet paper rolls?) to find ocean creatures, other boats, or fantastic islands. When anyone spies an island, they should shout, “Land, ho!” That means it’s time to stop and explore, as that is what sailors do.


Your journey can take you anywhere, but here are a few places you can drop anchor. 

Lollipop Island:

Filled with lollipop flowers and magic beans, Lollipop Island is a sweet adventure waiting to happen. Perhaps your kiddos hop out of the boat and onto the Rainbow Dot Path until they reach Lollipop Fields, where they fill their pockets with lollipop flowers and other souvenirs. Each child can describe their lollipop flavors and treasures when they return to the boat. If you’ve decided to use real lollipops on this island, maybe your sailors can enjoy them as you float to your next destination.


Welcome to the land of all things animal! Here you can encourage your child to use their theater skills by playing Guess the Animal. Each child pretends to be a specific animal, acting it out with sounds and movement to the best of their ability. Everyone else gets to guess what kind of animal they are. When everyone’s had a turn, it’s on to the next port!

Dancing Island

No walking here, only follow-the-leader freeze dancing! Choose a dance leader (a child or an adult), and have them stand on one side of the room facing the followers (everyone else). Let the dancing begin! Freeze everyone occasionally to change dance leaders so everyone gets a chance to lead before returning to the boat.

Troll Island:

Do not disturb the trolls! The trolls are sleeping. Little sailors should tiptoe around the island without waking them. But maybe they’ll find one fun little troll to quietly invite back to the boat for storytime. If your child does invite a troll back to the boat, have them introduce their new friend to the rest of the group.

Thank you for coming aboard our sailing adventure!

Once you’re home from your sailing journey, you can start planning your next pretend play adventure game!

Dress-up games like this one don’t have to be perfect or too complicated. The most important thing is encouraging your child to play, imagine, and create with confidence. Enjoy your time at sea!

The Rabbit Hole Theater Products

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Mary Eriette Atanante

Teacher and Characters

  • Favorite Character:  Sabirel
  • Favorite Magic Powers: Flying
  • Favorite storybook land: Camelot

Mary has been a teacher at The Rabbit Hole Children’s Theater for the last four years. You can find her teaching a class, creating activity books, dressing up and performing for kids or jamming at a birthday party! 

A recent graduate from San Francisco State University studying Theater and Communications,  Mary  loves to help children unlock their imaginations and motivate them to create the wonderful ideas in their mind!

Chelsey Mony


  • Favorite Character:  Alice 
  • Favorite Magic Powers: Flying
  • Favorite storybook land: Wonderland

Chelsey is an actress, dancer, improviser and has an exuberant passion for musical theater. Her love of theater began when she was a little girl.

When she is not helping those in need, she found joy in performing in a community theater group in Las Vegas- having starred in multiple shows for the past 5 years.

Chelsey  moved to the Bay Area in 2019, and  joined the Rabbit Hole team. Her love of theater and wonder will be an excellent asset to the team as she encourages children to find their own unique love of theater and wonder.

Creating a safe space for children to exercise their imagination and creativity is her mission in this work.

Melania 'Mel' Rivas

Head of Product Development

  • Favorite Character:  Sailor Moon 
  • Favorite Magic Powers: Flying
  • Favorite storybook land: Neverland

Mel is an eclectic, curious and creative individual who has learned and experimented with many different arts & crafts forms since she was a little kid.

Fascinated by the healing power of art and its ability to express our inner worlds, she has pursued and completed studies in art, early childhood education and psychology.

Mel has taught bilingual exploratory art to children during the last 5 years and now she makes use of her passion for creativity and children’s education to bring The Rabbit Hole Children’s Theater ideas to life for kids all over the world to enjoy!

Strider Patton

Project management

  • Favorite Character:  Wizard Merlin
  • Favorite Magic Powers: Invisibility
  • Favorite storybook land: Middle Earth

Strider Patton is founder and director, Brooke’s husband, and partner in The Rabbit Hole. A third-generation self-taught artist, Strider grew up appreciating and making art.

He is a professional contemporary visual artist himself, specializing in sculpture, murals, and studio art. When he is not in his studio or on an installation, he is working with the Crew at The Rabbit Hole. Building sets, designing products, creative planning, and the occasional puppet show keep Strider involved with the company from many angles.

He has worked with youth and communities since he was young, valuing the role that creative expression plays in communities and individual lives.

Ariella Cooley

Head Creator.Sound Designer.Teacher

  • Favorite Character: Pirate
  • Favorite Magic Powers: Flower Power
  • Favorite storybook land: Narnia

Ariella Cooley has been teaching and creating at The Rabbit Hole since 2017. As a lead teacher, she uses theater games, song, dance, masks, puppetry, and crafts to tell stories with the kiddos in her class.

As sound designer, she pulls from her classroom experience to make the Rabbit Hole Queendom come to life aurally. Crafting whimsical underscores, creating kooky sound effects, and finding expressive character voices make her tasks endlessly enjoyable!

Ariella earned her B.A in Theatre Arts from UC Santa Cruz, focusing primarily on acting and directing. Her work as a vocalist and songwriter inspired her expansion to audio production and theatrical sound design.

At Rabbit Hole, she is able to tap into all of these artistic loves and fold them into her work with children.

Meryl Theo Press

Head Creator.Illustrator.Teacher

    • Favorite Character: A drowsy cat with a cupcake farm  
    • Favorite Magic Powers: Flying 
    • Favorite storybook land: Narnia not under the white witch’s rule

    Meryl Theo Press has an affinity for play. She brings humor, music, visual art, and empathy to her work with the Crew at The Rabbit Hole. With these tools, she enjoys creating magical worlds for kids to inhabit, in order to stimulate their imaginations, encourage self-expression, and nourish joy.

    In the classroom, her focus is on “seeing” the child. In her illustrations, Meryl appreciates detail and seeks a thread of storytelling. In summoning voices for The Rabbit Hole’s audio plays, she digs deep and scoops out the absurd characters within. She uses her longtime love of singing to bring musical elements to Rabbit Hole classes and productions.

    Meryl studied printmaking and painting at California College of the Arts and has performed with various bands in San Francisco, the United States, and Europe. She has been a part of The Rabbit Hole since 2016. Meryl’s 9-year-old daughter Vida is her most treasured and valuable collaborator.