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A Modern Girl's Guide
to Fun Sailing


Get a taste of
the cruising lifestyle!


Celebrating the strength,
resilience and spirit of woman sailors


Our Services

GirlsSailing.com offers empowering services tailored for women sailors, including Girls Weekends Getaways, Sunset Sails, and Captained Charters. Our experiences promote camaraderie, skill-building, and gender inclusivity, empowering women to navigate the waters with confidence and sisterhood. Join us for unforgettable adventures, expert guidance, and a supportive community dedicated to celebrating the strength and spirit of women on the water.

Cruise in Style!

Embark on an all-female-led sailing adventure! Join our experienced female captain for a unique blend of sailing education, camaraderie, and exclusive activities. Immerse yourself in the empowering spirit of this unforgettable journey.

An exclusive all-female crew
Girls Getaways

An All-Inclusive Sailing Adventure

Get a taste of the cruising life! Enjoy the camaraderie and comfort of an all-girls sailing experience full of sailing education and unique activities, led by a female captain.

Blissfully unplug and soak up the ocean






Read What Our Customers are Saying About Us

Cherisse was so calm and confident - I felt like I was in good hands the whole time, and she took the time to educate those on board who wanted to learn how to sail. She was really good at assigning tasks to people based on their interests, skill level, and experience with boating.
- Katie

- Jess

- Shauna

Sailing with Cherisse was an unforgettable experience, filled with stunning views of Florida's coastline, laughter and bonding with like-minded women, and unexpected healing from sciatica pain by feeling weightless in the water. Cherisse's expertise, passion for sailing, and genuine hospitality were evident in every aspect of our trip. I highly recommend her charters for an unforgettable sailing adventure!
- Claudia

- Lindsey


The adventure starts now


Answers to common questions.

Have another question? Contact us or send a message on Whatsapp to 727-238-7715.


Where will I sleep?

The sailboat has sleeping quarters (berths) for 8 people. We will arrange berth assignments so friends will be grouped together. Specific sleeping arrangements will be provided to guests during the planning process for your charter.

How much does it cost?

  • For a 2-day, 2-night all inclusive sailing charter, the cost is $1,000.
  • For a 3-day, 3-night all inclusive sailing charter, the cost is $1,600.

Rates can fluctuate depending on the duration of your charter and any customizations you’d like for your itinerary. For full pricing details by season and charter length, please see the Pricing Page on our website. And as always, feel free to reach out if you have any other questions as you plan your seafaring vacation with us! We’re happy to provide you with a customized quote.

Where will we go?

We will cruise along the gorgeous West Coast of Florida. Our route will cover 50-100 miles along remote stretches of coastline, marshes, and islands. We will sail through a combination of open Gulf waters, sheltered anchorages, marinas, and along the Intracoastal Waterway (ICW). While we’ll venture out away from land at times, you’ll always be able to see land on the horizon during our charter. Get ready for beautiful beaches, abundant wildlife sightings, and island-hopping adventure!

What if I follow a specific diet?

Not to worry! We understand many guests may follow specialized diets. During the initial intake survey, we will ask you to share any dietary needs, restrictions, or preferences you may have. As we develop the detailed plans for your charter, we will work with you to ensure the menu and provisions are customized to provide foods compatible with your diet. Please let us know if you have any strict dietary requirements or allergies so we can make sure you are well taken care of and satisfied throughout your sailing adventure with us!

What are the captains rules?

Your safety and enjoyment are our top priorities when you charter with us. To prevent seasickness, we kindly request all guests wear scopolamine patches or take other anti-nausea medication so you feel your best out on the water. We also ask that alcoholic drinks be enjoyed only when docked or at anchor, rather than while sailing. We want everyone alert and capable of lending a hand with sailing if needed. Other than that, our captains will create a relaxed environment focused on giving you the best possible experience. If any other special rules or protocols come up, our captain will let you know in a friendly, clear way. Most of all, we want your charter to be safe, pleasant, and full of adventure from start to finish!

Do you only do charters for women?

While we specialize in charters for female groups looking to sail the Gulf Coast, we welcome any type of group – families, friends, corporate outings, couples getaways or weddings, and more. We have captains to accommodate anyone’s needs and no matter the makeup of your group, we pride ourselves on delivering exceptional service tailored to each client’s needs. Contact us to start planning your own dream sailing getaway, no matter who you hope to bring along!

Can I bring my pet?

We apologize, but pets are not allowed on board our sailing charters at this time. This policy helps ensure the safety of your pet as well as provides an enjoyable experience for all guests. Though we cannot accommodate pets currently, we’d love to hear if this is important to you. Let us know your Feedback.

What Should I Pack?

Not to worry about all the essentials – we have you covered there! We stock basic amenities onboard such as shampoo, soap, sunscreen, linens, and towels – even yoga mats!

As for clothing and accessories, the coastal Florida climate calls for breathable, quick-dry options. We suggest prioritizing comfort over style – you’ll be busy on your nautical adventure after all! Recommended items include:

  • Rash guards & bathing suits
  • Coverups, shorts & tank tops
  • Boat shoes or strapped water sandals
  • Sunglasses, hat & flip flops
  • Battery pack & headphones
  • Seasickness remedies & medications

For Nov-Feb, toss in some warmer long sleeve layers too. No fancy cocktail dresses or anything you don’t want to get the salty ocean on – just laidback days focused on the simple pleasures of sea, sun, and sisterhood!

Don’t stress about forgetting something. We’re always near shops to grab sundries.

Above all, the best things to pack for your getaway are an easygoing spirit of adventure and an empty camera roll waiting to overflow with amazing coastal memories!

What if I don't know how to sail?

Not a problem! Our charters are perfect for anyone looking to dip their toes into sailing, regardless of your experience level. Even if you’ve never stepped foot on a sailboat before, this is your chance to discover the joy of life on the water.

While aboard, you can simply sit back and relax taking in the sights if you’d like. Or, lend a hand with sailing under the supportive guidance of a fantastic captain ready to teach you the ropes. You’ll only ever have to assist with tasks you feel totally comfortable doing. Whether you want to master sailing basics or just try your hand at handling the sails or anchor, our charters allow you to gently expose yourself to this adventurous activity at your own pace.

Is there Cell Service / Wifi Onboard?

There is cellular service and WiFi availability on board. However, we cannot guarantee constant access, but you’ll have coverage for a good portion if not all of your charter.

Are there any age restrictions?

Our charters welcome adult guests ages 18 and over. However, we also happily accommodate mother/daughter charters for younger girls looking to be introduced to the joy and empowerment of sailing. These trips allow precious bonding time focused on creating lifelong memories out on the open waves. The minimum age for our family-oriented charters is 5 years old – contact us to discuss particular ages and arrangements.

No matter your age or sailing skill level, our charters aim to provide a welcoming environment for females hoping to expand their horizons. Teens gain confidence mastering sailing fundamentals. Working moms recharge and destress in nature’s tranquility. Retirees relish the camaraderie and adventure with lifelong friends. We believe women of all ages, backgrounds, and aspirations deserve to experience the magic aboard our sail charters along the Florida coastline. Please reach out so we can help turn your nautical dreams into reality!

Do crew members live aboard full-time?

No, there are no full-time inhabitants aboard our charter sailboats. While you enjoy your sailing getaway, your group and captain will have the boat all to yourselves with no other overnight occupants. Our captain will stay aboard to expertly operate the vessel and provide sailing instruction. But in terms of cooking, cleaning, and basic onboard duties – that becomes the happy responsibility of you and your first mate friends! Consider it part of the adventure.

By taking an active role together running the boat, you get to learn the ins and outs of life at sea. You’ll quickly bond over preparing gourmet meals in the galley, keeping your floating accommodation ship-shape, and trying your hand at sailing under the captain’s seasoned guidance. Get ready to build treasured memories cruising Florida’s glorious Gulf Coast!