Are you ready to travel and make lasting memories?
Wandering Women Sets Sail
Our First-Ever Cruise Through Spain, France & Italy
April 19–27, 2027 - 8 night cruise on Windstar Cruises
Imagine waking up each morning in a new breathtaking destination... with a community of women ready to explore it with you.
For the very first time, Wandering Women is taking to the sea —and we couldn’t be more excited to invite you aboard.
Join us for an unforgettable luxury small-ship cruise with
Windstar Cruises sailing through some of the most beautiful
and iconic ports in Spain, France, and Italy from April 19–
27, 2027.
This is more than a vacation.
It’s an experience designed for women who crave
connection, adventure, beauty, and the joy of discovering
new places—without having to plan it all alone.
Why Women Love Wandering Women
There’s something powerful about traveling with women
who are open to connection, laughter, adventure, and new
experiences.
Women join us because they want:
✨ Meaningful connection and instant community
✨ The confidence and ease of traveling with a trusted group
✨ Beautiful destinations without the stress of planning
* Knowing there is a dedicated Trip Leader
✨ Shared experiences that become lifelong memories
✨ Time to recharge, explore, and enjoy life fully
And cruising adds an entirely new level of ease and wonder.
Unpack once.
Wake up somewhere new each day.
Enjoy luxurious accommodations, incredible dining, and
effortless travel—all while sharing it with women who may
begin as strangers and leave as friends.
Why Windstar?
This isn’t your typical mega-cruise experience.
Windstar’s elegant small ships offer a more intimate and upscale way to travel—with fewer crowds, personalized service, and access to charming ports larger ships simply can’t reach.
Think:
• Boutique luxury at sea
• Open deck sunsets and ocean breezes
• Incredible food and thoughtful service
• Beautiful ports and immersive experiences
• A relaxed atmosphere perfect for connection
* Curated shipboard activities
It’s sophisticated, comfortable, and perfectly aligned with the Wandering Women experience.
The Journey
Together, we’ll sail through stunning coastal destinations like Tarragona and Pallamos, Spain, Collioure, Cannes, Toulon
and Monte Carlo, France and Portofino, Portoferraio and Citavecchia Italy—exploring vibrant cities, charming seaside
villages, historic landmarks, and unforgettable Mediterranean culture.
Be Part of Our First-Ever Cruise
This is a milestone moment for Wandering Women—and we would love for you to experience it with us.
Because this is a small-ship experience, space will be limited and expected to fill quickly.
Save the date:
April 19–27, 2027
Yachtsman’s Harbors of the Rivieras
Come sail with us for an unforgettable Mediterranean adventure.
Our Trip Leader
Cheryl Grasso is honored and delighted to be your trip leader for this wonderful Yachtsman Cruise with Windstar.
Originally from Connecticut, Cheryl has been a resident of the Tampa, Florida area for 27 years. She recently retired after a distinguished 40-year career in the healthcare insurance industry, where she traveled extensively to consult with large employers on employee benefits. Cheryl now happily gets to enjoy time with her new grandson as well as traveling more for pleasure!
As an experienced traveler, she has explored the U.S. from coast to coast as well as Hawaii, the Caribbean, and Europe. Cheryl is very familiar with Windstar’s intimate, small-ship style. Having enjoyed several past
Wandering Women trips, she looks forward to fostering new connections, friendships, and memorable experiences with all of you.
All-Inclusive
For this sailing, we will have an All-Inclusive package included:
*All beer, wine and cocktails
*All gratuities
*Shipboard wifi
To find out all of the details about our cruise, see the itinerary, the cabins, the extras, click the button below.
