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Join us for our

Wandering Women San Antonio Holly Days Getaway

December 4-7, 2026

Celebrate the magic of the holiday season with an unforgettable Wandering Women getaway to San Antonio.

This special Holly Days trip combines holiday cheer, culture, history, dining and connection. From a magical evening river cruise under holiday lights to strolling through charming historic districts, this weekend is designed to help you relax, connect, and celebrate the season together.

Picture twinkling lights along the famous San Antonio Riverwalk, festive decorations around every corner, delicious food, and the joy of exploring a vibrant city with an incredible group of women.

We'll stay right on the Riverwalk at the beautiful Westin Riverwalk, San Antonio, putting us steps away from the holiday magic.

Perfectly placed on the famous San Antonio Riverwalk, The Westin Riverwalk offers an urban retreat with extraordinary experiences right in the heart of downtown. Capturing the authenticity of the city, this hotel will be our home base for this exciting trip!

Whether you're coming solo or with a friend, you’ll be welcomed into the warm and supportive community that makes Wandering Women trips so special.

"I loved both Amy and the women in the group. I knew only one of them before the retreat, and by the end I had created special friendships with each of them. That was beyond my expectations.”

-LEAH GOERKE

Save the date:

December 4-7, 2026

Join Us

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.

Our Dates

Friday December 4, - Monday December 7, 2026

Our Hotel

Our home for the weekend is the beautiful Westin Riverwalk located right on the iconic San Antonio Riverwalk in the heart of downtown. This elegant riverside hotel puts us steps away from holiday lights, restaurants, shops, and San Antonio’s most famous attractions, including the historic Alamo. With comfortable rooms, beautiful river views, and the festive atmosphere just outside our door, it’s the perfect home base for our Holly Days getaway. We’ll be right in the heart of charming streets, beautiful shops as well as interesting restaurants.

You can join us alone, bring a friend along or be paired up with one of the exceptional women in our group. All rooms will be single occupancy for this trip — enjoy your own space and time.

Our Activities

Experience an iconic area during a festive holiday time. You’ll gather the first evening for a Welcome Reception to meet and greet each other. Each morning we will connect for a full breakfast to get the day started off in the best way possible.

We’ll enjoy a walking food tour to sample the food and history of San Antonio. We’ll ride on the fun Hop on Hop Off Trolley, share a private evening Holiday Lights river cruise, visit the cultural shops and stores in La Villita and more.

Our Leader

Diane Tamango is our trip leader. By day, Diane collaborates with organizations to achieve their marketing strategies. Outside the office, she is passionate about helping make a difference within her community. As a Wish Granter and Volunteer Captain with Make-A-Wish Massachusetts and Rhode Island, she helps spread hope and joy to critically ill children and their families. Diane is a well-traveled adventurer whose journeys span both personal exploration and professional endeavors. Her adventurous spirit has fueled trips spanning the U.S., Caribbean, and European destinations. She's enjoyed several past Wandering Women adventures. As a Wandering Women trip ambassador, Diane is excited to help facilitate connections, friendship, memorable experiences, exploration and fun!

“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

What's Included

LODGING

4 Days/3 Nights at The Westin Riverwalk, San Antonio

EXCURSIONS

3 Hour walking food tour of San Antonio
Hop on Hop Off Trolley Tour
Private evening Holiday Lights River Cruise

MEALS

Opening night Welcome Reception
Full breakfast every morning
1 group lunch
1 group evening meal

BONUSES

2 Pre-trip Zooms to meet the women attending
Unique welcome gift

Single Room

$2697/Per Person

Double Room

$2167/Per Person

*To Be Paid in 3 Installments

Sign Up Now

Trip Itinerary

Friday, December 4

Welcome to San Antonio!

Welcome Reception with the Wandering Women group • Evening stroll along the Riverwalk

Saturday, December 5

Breakfast at the hotel

Hop-On Hop-Off Trolley Tour of San Antonio’s most iconic sites, including views of the historic The Alamo

Free time to explore the River Walk shops and cafes • The Magic Saloon Magic Show

Sunday, December 6

Breakfast at the hotel

La Villita Historic Arts Village for shopping and art • Group Lunch together

FlorVino Wine Tasting experience

Evening Private Holiday Lights River Cruise along the beautifully decorated San Antonio River Walk

Monday, December 7

Breakfast at the hotel

Farewell hugs and departures

*Itinerary is subject to change

Stay With Us An Extra Day

Bonus Day and Night:

Monday December 7th to Tuesday December 8th

Including:

Overnight stay at The Westin on Monday December 7th
Taste of Fredericksburg: visit two Hill Country wineries before our final stop in the charming historic German town of Fredericksburg
Breakfast at The Westin Tuesday December 8th

Additional Pricing:

Single Room: $667/per person

Double Room: $477/per person

AN AMAZINGLY UNIQUE EXPERIENCE

You Won’t Want To Miss

Join Us

Space Is Limited

“My first trip with Amy was more than I hoped for. I don't think I have laughed and danced that much in a long time. I feel like I have made bonds with new people that will last a lifetime. Amy, I can't express enough how grateful I am to you for facilitating this incredible experience! You've been such an inspiration to me!”

- DEBBIE WESSMAN

Meet Your Coach, Amy Goober

Action Coach, Amy Goober, has helped over 800 clients in the last 10 years to create the lives they are looking for. She has strived to help those she works with find happiness and success in all possible ways. Her passion for connecting with women and helping them improve their lives led her to create the unique Drive Your Life™ program, a 5 step process that teaches clients how to get back in the driver’s seat of their lives.

As a young woman, Amy opened, ran and later sold a successful cake bakery in Boston, learning first-hand about entrepreneurship. After raising her 3 children as a stay at home mom, she wanted to put her Cornell psychology degree to use by developing and growing a health coaching practice. Taking lessons from all of these phases in her life, Amy has created a path for other women to learn from their past experiences and to propel themselves into doing in the now.

Comments about previous trips with Amy

“I loved defining a new goal for myself and getting into action with Amy’s guidance. Having an opportunity to be with other women, away from home and Zoom, that want the same things as I do was incredible.”

“The group showed such love and support. It was an experience like no other.”

“I always feel Amy is available to support me. This retreat combined wonderful women, a great location and a unique program to help me reach my goal.”

“I loved the intentionality of the program and the authenticity of the interactions with both Amy and the women in the group. I knew only one of them before the retreat, and by the end I had created special friendships with each woman in the group. That was beyond my expectations.”

“This was my first retreat, and now I’m hooked. I look forward to being on Amy’s next retreat wherever and whenever it is.”