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Group Travel Planning for Busy Women

Small Group & Girlfriend Trips for Women 50+
 

Mexico • Caribbean • South America and beyond

Dreaming about sipping wine in Mexico, relaxing on a Caribbean beach, or exploring South America with your favorite people?

I help busy women plan stress-free group trips, hosted travel experiences, and unforgettable girlfriend getaways — so you can focus on the memories, not the logistics.

Expert Planning for Group Travel
Small Group & Hosted Travel for Women
Luxury Experience 
Without the Overwhelm

When was your last adventure?

Annual vacations are for every year, not every five!

Planning the perfect trip can feel like a part-time job.  Before you realize it, you’ll be overdue for a getaway. But don’t worry! I’m here to take charge. Embrace the escape and dive into travel!

Ways We Can Work Together

Girlfriend Getaways, Group Trips & Hosted Adventures

Whether you're planning a trip with friends, celebrating a milestone with family, or traveling solo but want the comfort of a group,

I design travel experiences that are easy, memorable, and values driven. Travel that helps women reconnect with themselves and the people they love.

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Girlfriend Getaways

Planning a trip with your favorite people should be fun — not a logistical nightmare. I help groups of friends plan unforgettable escapes to Mexico, the Caribbean, and beyond.​ Perfect for: 
 

  • Milestone birthdays

  • Girls trips

  • Retreats

  • Food and wine tours

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Family and Celebration Trips

From anniversary trips to family reunions, I coordinate every detail so everyone in your group can simply relax and enjoy the experience.

Just because you're mom doesn't mean you have to be the designated trip planner!

Let's make this the year you enjoy the WHOLE vacation.

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Solo No More

Traveling solo but don’t want to travel alone? Join one of my hosted small-group trips designed for women who want adventure, connection, and incredible destinations.

Can't wait for one of my escorted trips? I can help you find the perfect tour for you. 

Tara Woodbury, Travel Advisor

Are You Ready To Take a Group Trip?

Hi there!
 

I’m Tara — founder of Escape Into Travel.
 

Although I love all kinds of travel and travelers, I specialize in helping women 50+ plan incredible travel experiences with the people they love most.
 

Many of my clients are:

• women planning girlfriend getaways
• women organizing group trips with friends or family
• solo travelers who want escorted trips they can join
 

If you have your group of travel besties already, whether it’s a beach escape in the Caribbean, a food and wine adventure in Mexico, or a bucket-list trip to South America, let's talk! I handle the planning so you can simply enjoy the experience. And if you're a solo traveler looking for a community to travel with, I can help you find escorted tours to join, and I also host my own trips a few times a year for travelers just like us!

Not yet 50, but you want to go on a group trip or form a group? That's ok, we can still work together! My goal is to make travel fun and stress-free for every generation.

Until our next adventure,

Tara

About

Escape the Group Trip Planning Chaos

Escape the Research Black Hole

Planning a trip to Mexico, the Caribbean, or South America can mean hours of comparing resorts, reading reviews, and second-guessing every decision.

 

I narrow it down to the best options for your travel style so you can say yes with confidence.

Escape the Drama

Coordinating a trip with friends or family can quickly turn into a logistical headache. I manage the details, track reservations, and keep everything organized so your group can focus on having fun.

And on my escorted trips, I'm there to take 

care of every detail in real time.

Escape the Boring

You didn't invest in your trip so you could 

take the same vacation everyone else is talking about on Instagram and TikTok.

My escorted tours are exclusive and unique, and always include personalized touches you won't get anywhere else. 

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FREE DOWNLOAD

Get Your Girlfriends Trip Planning Checklist

Whether it’s a milestone celebration, a much-needed escape, or just an unforgettable adventure, you’re about to create memories that will last a lifetime. But before you hit "book now," make sure you’re checking off all the essentials to make the experience as seamless, fun, and relaxing as possible!
 

This guide is designed for group leaders like you who want to ensure everyone in your group has an unforgettable, stress-free luxury vacation.

  

Click the button below to enter your name and email address to receive your guide today.

Friends Hiking

Escapes My Clients Love

Mexico

  • Riviera Maya adults-only resorts

  • Cabo food and wine trips

  • San Miguel de Allende cultural escapes

Caribbean

  • St. Lucia romantic escapes

  • Jamaica girls trips

  • Barbados beach & food experiences

South America

  • Costa Rica exploration trips

  • Peru & Machu Picchu adventures

  • Chile wine country

Services
Image by Shreyas Malavalli

 THE PROCESS 

– STEP 1 –
Let’s Connect

Before we begin planning your perfect vacation, we'll have a consultation so I can learn more about you, the people you are traveling with, and what your expectations are. 

– STEP 2 –
Your Perfect Itinerary

After you've paid your planning fee, I’ll begin researching and planning your next favorite vacation. You will be presented with a few different itinerary options that I can modify to make sure everything is just right.

– STEP 3 –
Book Your Trip!

Once I have finalized your itinerary, it’s time to book your trip! I will help you prepare for your vacation, and we will stay connected to ensure everything goes smoothly. My contacts in destination will also be there to take care of your every need!

Women Laughing Together

Many of my clients love to travel but don’t always have someone ready to go at the same time. That’s why I offer small-group and hosted trips where you can travel with like-minded women and enjoy the experience together. The best way to stay up to date on the next hosted trip is to follow me on Instagram and subscribe to my get my emails.

Dreamworthy Destinations

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