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 another exciting year full of spectacular adventures and unique discoveries shared with new and old friends!
New Orleans: The Big Easy Trip June 8-15, 2020: This trip as been cancelled and refunds have been issued.
Bella Italia: Under the Tuscan Sun - This trip has been postponed until May 2022 We have worked diligently with our travel partner, Destinations & Adventures, to offer a trip to Italy like no other! Exclusive, Enchanting, Exceptional.  
Women’s Week in Provincetown October 12-18, 2020 Details have been announced. At this time, we are still planning to go and will notify you if that changes.


Rhine River Cruise July 31- August 7, 2021: This trip is still on as planned! Rolling on the River with Women On A Roll! We have chartered an 83-room riverboat cruising from Switzerland to Amsterdam. And we land in Amsterdam just in time for Pride! It’s time to book your cruise,  Only 14 rooms remaining! We will be adding an optional two-night stay in Switzerland prior to boarding the riverboat cruise and a two-night stay in Amsterdam after the cruise to enjoy all the Pride festivities! Pre and post-cruise itineraries will be announced soon.

Europe Lovers Special: Guests who join us in Italy in 2020 and on the Rhine River Cruise in 2021 will receive a $100 per person discount on the Rhine River Cruise!

Looking for a roommate? We are happy to assist our solo travelers find roommates on any of our trips. Please feel free to let us know if you're looking to room with someone. The process is simple: we arrange a conversation, you ask all the necessary questions, and if you both think you'll be compatible, you have a roomie and a new friend! Email if interested.

Rhine River Cruise 2021

Rolling...Rolling... Rolling on the River! Rhine River Cruise July 31 - August 7, 2021 This trip is still on as planned! We will need this time t...

New Orleans: The Big Easy Trip

New Orleans: The Big Easy Trip! June 8-15, 2020 This trip as been cancelled and refunds have been issued.   Laissez les bon temps roule...

Bella Italia

Bella Italia: Under the Tuscan Sun featuring a Roman Holiday Pre-Tour! This trip has been postponed until May 2022.   We ...

Women’s Week in Provincetown 2020

Women’s Week in Provincetown will be a bit more special this year... The year 2020 marks the 400th anniversary of the 1620 voyage from Plymouth, U....

Thoroughly Thailand

Tantalizing Tastes & Traditions Bangkok, Chiang Rai, Chiang Mai, Phuket February 18-29, 2020 This trip is sold out. Please email andrea@wom...