Caribbean Cruise Retreat(s) 2026

CRUISE WITH ME TO THE CARIBBEAN!

CHOOSE ONE
OF THESE SHORTER CARIBBEAN CRUISES
OR
JOIN ME FOR BOTH,
BACK TO BACK, FOR AN EPIC 9-NIGHT VOYAGE!

oPTION 1:
5-NIGHT CRUISE TO GRAND TURK AND THE BAHAMAS
from MIAMI, FLORIDA
ON VIRGIN VOYAGES: SCARLET lADY 
JANUARY 16-21, 2026

AND

oPTION 2:
4-NIGHT CRUISE TO KEY WEST AND THE BAHAMAS
from MIAMI, FLORIDA
ON VIRGIN VOYAGES: SCARLET lADY 
JANUARY 21-25, 2026

 

For general information about retreats, like inclusion, traveling solo, group size, activity level, and more, click here.

For information about our 2026 Caribbean Cruises, read on!

I chose Virgin Voyages in the Caribbean for my 50th birthday, and I knew immediately I wanted to bring you along on the next one! After living in Southeast Asia and experiencing some of the best beaches in the world, I was stunned at the azure water in Grand Turk. It was the best snorkeling location I’ve visited with calm, sunny weather, crystal clear seas, and a huge variety of sea creatures in comfortingly shallow water because some of us like to play in the ocean AND see the bottom. 😉 I’ve been longing to get back ever since, and now’s our chance!

 

 

GRAND TURK ITINERARY:

  • Day 1: Depart Miami
  • Day 2: Day at Sea
  • Day 3: Grand Turk, Turks & Caicos
  • Day 4: Day at Sea
  • Day 5: Day in Bimini, Bahamas at Virgin’s Private Beach
  • Day 6: Arrive in Miami (and depart on cruise #2!)

KEY WEST ITINERARY:

  • Day 1: Depart Miami
  • Day 2: Day at Sea
  • Day 3: Key West, Florida
  • Day 4: Day in Bimini, Bahamas at Virgin’s Private Beach
  • Day 5: Arrive in Miami

 

CRUISE COST and INCLUSIONS: Cruise costs vary based on your stateroom selection and when you book (hint: the earlier, the better). You can see the latest rates, room types, and book with our group directly on the Virgin Voyages website using this link for Cruise 1: Grand Turk and this link for Cruise 2: Key West. Virgin Voyages “Always Included Luxury” policy means your cruise cost includes lodging, meals at all 20+ dining locations (honestly, the BEST food at sea), unlimited wifi, shipboard entertainment and activities, all gratuities, essential drinks (soda, sparkling water, coffee, tea), group fitness classes, taxes, and fees.

ADDITIONAL COSTS: 

  • Alcoholic Beverages, Mocktails, and Specialty Coffees: If you need your morning espresso or an evening tipple, Virgin Voyages has you covered! You can purchase these beverages on board or, if you want the most bang for your buck, you can purchase a “bar tab” ahead of time which nets you bonus dollars to spend.
  • Spa Treatments: Virgin ships have a lovely thermal spa and many spa treatment options you can purchase onboard as well as a hair salon, nail salon, and tattoo parlor. You can also purchase “sailor loot” (onboard credit) ahead of time if you’d like to prepay for these services. 
  • Shore Excursions: Approximately three months before our departure, we will also plan group shore activities for an added fee. Past Caribbean excursions include snorkeling, swimming with nurse sharks, feeding manta rays, simply sunning on the beach, cultural and food tours, e-bike tours, hiking, and more. You can choose from our group excursions, Virgin Voyage’s excursions, or no excursions at all. Feel free to curate exactly the type of trip you want.

 

RETREAT GROUP SIZE: 45 maximum retreat participants

HOW TO BOOK THE CRUISE: You can directly book Cruise 1: Grand Turk with this link and Cruise 2: Key West with this link. Each link automatically connects you to our group. If you have questions or need help booking, feel free to contact me at beth@bethwoolsey.com.

GOT ANY OTHER INFO, BETH?
As a matter of fact, I do!

  • What about travel arrangements before and after the cruise? If you need assistance with ground transportation to the cruise ship, hotels before and after the cruise, travel insurance (inexpensive and highly recommended), etc., just let me know! As a certified travel advisor, I’m happy to assist. You can contact me at beth@bethwoolsey.com.
  • If you’re nervous about booking this far in advance, it’s important to note that Virgin Voyages allows you to change your sail date with no penalty up to 45 days before you sail. They also allow you to make name changes on your tickets (transfer your reservation) up to 48 hours before departure. In addition to travel insurance, which is there to protect your investment should you not be able to travel (surprisingly inexpensive and highly recommended), these policies help by giving you maximum flexibility.
  • Want to bring your family and friends? Want to ditch them and come solo? Either is fine! Virgin Voyages is an adults-only (age 18+) cruiseline, so as long as your humans fit that criterion, sign ’em up! If, however, you’re attending solo, you should know you’re not alone! Loads of folks have attended my retreats on their own and found themselves fast friends with my crew. We can even help you find a cabin-mate, so if you’re looking to share costs, just let me know.

I do hope you’ll join me!

 

OUR INCLUSION POLICYWe welcome all adult humans (who are welcoming of all humans) to all of our retreats. We are LGBTQ+ friendly and an inclusive space. We’d love to have you attend!

For general information about retreats, like inclusion, traveling solo, group size, activity level, and more, click here.