Wandering Women Sets Sail

April 19-27th 2027

Are you ready to travel and make lasting memories?

Join Wandering Women for our First-Ever Cruise to Spain, France & Italy

Journey with us on an 8 night cruise with 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 travel with Wandering Women?

We provide you with the community and connections you are longing for but can’t easily create on your own.
You’ll have fun and feel safe as a single traveler with opportunities to explore new places and adventures.
Your lodging, meals and itineraries are planned for you with our curated travel experiences.
You’ll save time and money as all the research and reservations are taken care of for you.
You will have peace of mind because we provide on-site management to make any real time changes needed and to work out any issues.

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.

• 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

• Ship capacity: 342 Guests

• Crew Onboard: 210

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.

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’s 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 our Windstar sailing, we will have the BONUS benefits of an All-Inclusive package which includes:

*All beer, wine and cocktails

*All gratuities

*Shipboard wifi

* $100 Shipboard Credit

Our Itinerary

DAY 1 - TARRAGONA (BARCELONA), SPAIN

DAY 2 - PALAMOS, SPAIN

DAY 3 - COLLIOURE, FRANCE

DAY 4 - TOULON, FRANCE

DAY 5 - MONTE CARLO, FRANCE

DAY 6 - CANNES, FRANCE

DAY 7 - PORTOFINO, ITALY

DAY 8 - PORTOFERRAIO, ITALY

DAY 9 - CIVITAVECCHIA, ROME

PRICING AND CABINS

See below the All-Inclusive Pricing for this 8-night Cruise

There are SINGLE and DOUBLE Cabin options based on your cabin selection.
We will help you with all of this when you contact us to learn more.

To be part of our Wandering Women Cruise and receive a 5% cruise discount,
fill out the form below, and we will get back to you to
answer any questions or register you for our cruise.

“I felt stronger connections with the women I had just met on this trip than I do with some that I’ve known for years! I highly recommend traveling with Amy and any group she puts together.”

Maddy Manza

“I have been on every trip Amy has planned! What I love is that no matter who I’m sitting next to I know that by the end of the trip I am sitting next to a friend.”

Susan Holding

“One of the best parts of our Wandering Women trip was knowing it was going to be perfectly organized and I didn’t have to do a thing. This trip has done so much for me in so many ways and I’m so happy I came!”

Patty Viaro

“We’ve done nothing but smile and laugh! It was life changing and so empowering to go on a trip with 12 strangers. The energy was just amazing, and we’re already planning where we want to go next year!”

Deb Harvey

“This was my 4th trip with Wandering Women and the best part of the trips is the people you travel with. I walked away with some amazing new friendships.”