The WOMEN ON A ROLL Travel Experience

Women On A Roll offers boutique, luxury travel for lesbians and their female friends. Each journey brings 15 to 50 guests together to share beautiful destinations and unique experiences, customized to fit our desires and our lifestyle.

Whether you arrive alone, with a friend or with your significant other, the end result will be the same... you'll return with a whole new set of friends and shared memories to last a lifetime!

"We travel not to escape life, but for life not to escape us."


Get ready for an exciting year full of spectacular adventures and unique discoveries shared with new and old friends!

Spectacular South Africa Adventure April 24-May 3, 2019 - The trip is now closed and we can no longer accept bookings.

Pride of the Ocean LGBT Film Festival at Sea Cruise to Canada & New England! June 8 - 16 Women On A Roll is excited to be partnering with Pride of the Ocean! In honor of the 50th anniversary of Stonewall, the cruise/festival will be celebrating LGBT Military Veterans as well as Veterans of the Stonewall Revolution.

One Week in New York City! June 24 - July 1 But not just any week! Our second trip to New York is during Gay Pride! NYC is celebrating the 50th anniversary of Stonewall all week! In addition to many the LGBT Pride events, the trip will offer Broadway shows, luxury cruise, lesbian events, private tours, and so much more!

Glorious Greece Odyssey September 17-29, 2019 This trip is now sold out. if you'd like to be placed on a waitlist, please email

Women's Week in Provincetown October 14-20, 2019 Join us for our 22nd Women On A Roll trip to Ptown! This will be a very special year as it's the 35th anniversary of Women's Week!


Thoroughly Thailand ~ Tantalizing Tastes & Traditions February 18-29, 2020: Explore the country’s sparkling temples, tropical beaches, colorful market places, exciting urban life, picturesque countryside, rich culture and history, and of course, the mouth-watering cuisine! 

Italian Villa September 2020: Details announced soon.

Watch for more exciting destinations announced soon!

Women’s Week in Provincetown

This trip is currently sold out.  Please email if you’d like to be placed on a waitlist. October 14-20, 2019 Join us for th...
Statue of Liberty

New York City Gay Pride Week

Have you heard the exciting news about New York City Pride? Well, actually it's not just NYC Pride! It's WorldPride and Stonewall 50! Read ...

Thoroughly Thailand

Tantalizing Tastes & Traditions Bangkok, Chiang Rai, Chiang Mai, Phuket February 18-29, 2020 We have worked diligently with our travel part...
Santorini, Greece

Glorious Greece Odyssey!

Important Travel Update: Our Glorious Greece Odyssey is now sold out! If you'd like to be placed on a waitlist for a room, please email andrea@wom...

Spectacular South Africa Adventure!

Important Update: Please email as soon as possible if you'd like to join us. We will inquire about room availability once we re...