THE WEEKENDER

St. Thomas

May 4 - 8, 2028

11 SPOTS ONLY!

Dates:

May 4 - 8, 2028
Arrive on: May 4th
Depart on: May 8th

Trip Type:

Weekenders:  Thursday–Monday experiences created to introduce you to the Sisters Traveling Solo.

Airport Code:

Up To Traveler
Arrival Airport: STT

Departure Airport: STT

Group Size

Min: 7 Travelers

Max: 11 Travelers

Travelers must be 21 years are older at the time of travel. 

Tour Highlights:

History of St. Thomas
Experience the best of St. Thomas on a guided island adventure through historic Charlotte Amalie, where colorful streets, local markets, and centuries of Caribbean history come together. Take in breathtaking panoramic views from Mountain Top and Drake's Seat before heading to the world-famous Magens Bay Beach to enjoy its crystal-clear turquoise waters and beautiful white-sand shoreline.
Catamaran Sail to St. John
Set sail aboard a catamaran for an unforgettable adventure across the Caribbean Sea to the beautiful island of St. John. Enjoy a complimentary open bar while taking in spectacular coastal views, then spend time exploring the charming boutiques, restaurants, and local atmosphere of Cruz Bay. Continue your sailing adventure into the pristine waters of Virgin Islands National Park.
Caribbean Cooking Class
Immerse yourself in the flavors, culture, and culinary traditions of the U.S. Virgin Islands during an interactive Caribbean cooking experience. Learn from a talented local chef as they demonstrate traditional cooking techniques and guide you through preparing your own island-inspired meal. Gather around the community table with your fellow Sisters to enjoy the delicious Caribbean feast you've created.
Sisterhood in Paradise

From our welcome dinner to our farewell celebration, enjoy meaningful moments around the table with women who share your love of travel and new experiences. Spend your evenings connecting, sharing stories, laughing, and creating friendships against the beautiful backdrop of St. Thomas. Because at Sisters Traveling Solo, the destination is only part of the experience. We meet as strangers, leave as sisters.

Destination Overview

Welcome to St. Thomas, where turquoise Caribbean waters, white-sand beaches, colorful island culture, and breathtaking coastal views create the perfect setting for a tropical escape.  Located in the U.S. Virgin Islands, St. Thomas offers the perfect blend of relaxation, adventure, history, and Caribbean charm. From the historic streets of Charlotte Amalie to the stunning shores of Magens Bay, this island paradise invites you to slow down, soak up the sunshine, and experience island life at its finest.

DAY ONE
WELCOME TO ST. THOMAS

Upon arrival at Cyril E. King Airport (STT), you'll be greeted and transferred to our hotel.  After checking in, take some time to settle into your accommodations, explore the resort, or simply relax and enjoy your first moments in St. Thomas. This evening, we'll gather for our Welcome Dinner, where you'll meet your fellow Sisters over delicious food, great conversation, and plenty of laughter. 

DAY TWO

DISCOVER ST. THOMAS

After breakfast, we'll begin our guided island adventure in historic Charlotte Amalie, the capital of the U.S. Virgin Islands. 

We'll have an opportunity to explore local shops, browse island treasures, and visit historic landmarks before making our way into the hills for some of the most spectacular views in the Caribbean.

Our journey continues to Mountain Top and Drake's Seat, where we'll take in panoramic views of the island, neighboring cays, and the sparkling turquoise waters below. 

Next, we're trading sightseeing for sunshine as we head to the world-famous Magens Bay Beach. Known for its calm, crystal-clear waters and beautiful stretch of white sand, Magens Bay is the perfect place to unwind, take a refreshing swim, or simply relax beneath the Caribbean sun.

DETAILED ITINERARY PROVIDED AFTER BOOKING
photo of colombian women with fruit standing in front of buildiing
photo of colombian women with fruit on their head walking down the street with stools in their left hand
photo of colombian women with fruit on their head walking down the street with stools in their left hand
photo of colorful colombian houses with a colombia flag handing over

Secure Your Spot!

BOOK NOW!

DOUBLE OCCUPANCY

(shared room = 2 ppl in a room: two beds)

TOTAL TRIP COST:  $2,595/pp  
NON-REFUNDABLE DEPOSIT: $295/pp
(8) MONTHLY PAYMENTS: $288/pm*
*plus 3% card (debt or credit) fee

No Credit Card Processing Fees
Travelers who have completed 6+ Sisters Traveling Solo trips and maintain their loyalty status per program terms will have credit card processing fees waived.

SINGLE OCCUPANCY

(my own room = 1 person in a room)

TOTAL TRIP COST: $3,595/pp
NON-REFUNDABLE DEPOSIT: $395/pp
(8) MONTHLY PAYMENT:  $400/pm*
*plus 3% card (debt or credit) fee

No Credit Card Processing Fees
Travelers who have completed 6+ Sisters Traveling Solo trips and maintain their loyalty status per program terms will have credit card processing fees waived.
What's Included

✓ 4 Nights Hotel Accommodations
      ✓ Welcome Dinner
      ✓ St. Thomas Island Sightseeing Tour
      ✓ Charlotte Amalie Historical Tour & Shopping
      ✓ Mountain Top & Scenic Overlooks
      ✓ Magens Bay Beach Visit
      ✓ St. John Catamaran Sailing Excursion
      ✓ Cruz Bay Exploration
      ✓ Snorkeling Adventure
      ✓ Complimentary Open Bar During Sailing
      ✓ Taste of St. Thomas Cooking Experience
      ✓ Caribbean Culinary Lunch
      ✓ Farewell Dinner
      ✓ Daily Breakfast

What's Not Included

✗ Flights to St. Thomas

✗ Airport Transfers

✗ Travel Insurance (Required)

✗ Meals Not Listed

✗ Gratuities for Guides & Drivers

✗ Optional Tours & Activities

✗ Personal Expenses & Souvenirs

✗ Baggage Fees Charged by Airlines

✗ Anything Not Specifically Listed as Included

Sisters Loyalty Rewards Program

Created for our most loyal travelers, the Sisters Loyalty Rewards Program rewards consistent travel with Sisters Traveling Solo. Status is based on your completed trips as of December 31, 2026 and is reserved for travelers who traveled with us in 2025 or 2026. If you have not traveled with us during that period, your status begins again at zero trips.


Review our website for full terms and conditions.

Hey Sis! Level

3 Trips Completed

Earn a $175 travel credit toward your 4th Sisters Traveling Solo trip.

Fly Girl! Level

6+ Trips Completed

Receive an exclusive Sisters Traveling Solo North Face Jacket and waived credit card processing fees while maintaining your status.

Founder's Circle

9+ Trips Completed

Receive a $350 travel credit on up to two eligible Sisters Traveling Solo trips per year and waived credit card processing fees while maintaining your status.

Awards & Recognitions: 

Our company has been featured in renowned publications such as Travel & Leisure, Essence, Black Enterprise, Money Magazine, and Sweet July (hard copy).


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2022 FedEx Global Entrepreneur of the Year
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2021 Forbes Next 1,000
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2022 Queen of Culture Honoree by Forbes
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2020 Goldman Sachs 10KSB Alumni

Life is a Journey!

Never get so busy making a living that you forget to make a life. 

COPYRIGHT 2018-2024 SISTERS TRAVELING SOLO. ALL RIGHTS RESERVED.

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