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San Juan and the Virgin Islands

november 16 - 23, 2024
A blonde woman with a pink shirt smiling
hosted by

Meredith Calloway

chief visionary officer

Permission to Indulge: Sail and Share Hosted Experience with Windstar

To sell luxury travel you must know luxury travel. To me, the true essence of luxury travel lies in granting yourself permission to indulge in life’s pleasures. One of life’s greatest joys, in my opinion, is sailing. I fell in love with the indescribable beauty of the Virgin Islands during a sailing trip there many years ago. From world-class snorkeling to exploring stunning islands with great food, dynamic cultures, and rich history, this experience was unforgettable. Join me for a retreat where we can indulge in rest, relaxation, exploration, exquisite cuisine, fine wines, and excellent company

Bring Your Favorite +1 for Same Price

Speaking of excellent company … the only thing better than giving yourself permission to indulge in life’s pleasures is doing it with your favorite people.  I am so excited to share you can bring a guest of your choosing at the same rate, whether this person is a travel advisor or not.  So pick your partner and let’s all indulge in the beauty of the Caribbean together.

Get a Much Needed Mindset Boost

And if you feel like you need a little mindset boost, there’s even more reason to join me. Many years ago, when I set a goal to sell ultra-luxury travel and attract high-net-worth clients, I faced serious self-doubt. It wasn’t until I set this ambitious goal, one that pushed me far beyond my comfort zone, that I recognized those doubts. However, I also learned how to replace those uncertain thoughts with empowering beliefs. Since then, I’ve transformed every aspect of my life. During the “Sail and Share Hosted Experience with Windstar,” I’ll be an open book, ready to answer any and all questions you might have. Whether it’s about attracting financial abundance, healing after a significant change, or maintaining a healthy and balanced lifestyle, feel free to ask. While this isn’t a structured mindset retreat, I believe that the relaxed atmosphere, surrounded by the pleasures of the Caribbean Sea, will provide exactly what you need.

Why Windstar?

Windstar’s tagline, “180 Degrees from Ordinary,” perfectly captures the spirit of indulgence. If I’m allowing myself to indulge, it must be far beyond the ordinary. Windstar’s ships strike the perfect balance—they’re large enough to pamper and entertain, yet small enough to navigate delightful tiny harbors and hidden coves that larger vessels can’t reach. In this Caribbean paradise for sailors, we’ll explore places that big ships simply cannot access. Our ship, the Star Pride, is an all-suite yacht that has undergone a complete renovation to enhance the guest experience. With new public areas, two additional dining venues, a spa, infinity pool, and fitness area, the Star Pride offers everything guests love. Plus, every suite now features brand-new bathrooms. Carrying only 312 guests, the Star Pride is the ideal vessel for experiencing Windstar’s exceptional luxury.

Itinerary and Shore Excursions

The best on land brought to you by the best at sea. Get to the heart of local cultures with Windstar shore excursions. You don't want to just dip a toe in local culture, you want to dive into the deep end, and that's exactly what Windstar shore excursions are designed to do. All of our excursions are created to provide authentic local experience - the kind travelers like you are looking for. And with more than 2,500 excursions to choose from, you can experience your destination in whatever way is most meaningful to you. Whether you're an outdoor enthusiast, a foodie, a history buff, or someone who loves to get to know the faces behind the many places we travel.

A map of the Virgin Islands and Puerto Rico


Simply click on the date below for more detailed information regarding that day.

Are you ready to indulge?

Trip Details


Double Occupancy: $289 PER PERSON per day for a total of $2,023
Single Occupancy: There is an additional $250 per day

Your payment includes:

  • Cruise Fare: Experience the luxury and comfort of a top-tier cruise line.
  • Taxes and NDAs: All government and port fees are covered.
  • All-inclusive Package: Enjoy unlimited drinks, daily gratuities, and Wi-Fi throughout your cruise.
Cancellation policy
  • The above deposit is NON-REFUNDABLE.
  • Any cancellations after final payment is processed on July 31, 2024, are non-refundable.
  • Please email to confirm single/double occupancy and guest name (if applicable) no later than July 31, 2024. Final payments will be processed on that date using the card information provided.

Airfare, transfers, excursions and incidental expenses are not included. Travel insurance is mandatory and must be arranged independently. We also recommend arriving at least a day prior to departure to ensure a smooth start to your adventure.