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
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.
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.
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.
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.
Depart San Juan at 10:00 PM
St. Thomas has something for everyone who loves the outdoors. Magen’s Bay, the island’s most popular beach with its heart-shaped protected bay, the incomparable view of the Caribbean found climbing the famous 99 steps of Charlotte Amalie, world-famous Mahogany Run Golf Course, the Skyride that soars 700 feet above the city, and snorkeling and sailing, Sightsee the St. Thomas Synagogue, built in 1833, Fort Christian, built in 1680, Blackbeard’s Castle, a 1679 watchtower, and the childhood home of French Impressionist Camille Pissarro, now an art gallery.
Pastel-colored buildings and shops filled with tempting souvenirs herald your arrival to bustling Philipsburg. Situated near the harbor on the Dutch side of St. Maarten, Philipsburg owes its discovery to Christopher Columbus in 1493. Today, celebrated Front Street is home to a number of local Creole restaurants as well as jewelry stores, stylish boutiques, and lively casinos for visitors seeking an upbeat island experience.
Affectionately known as St. Barts, the Caribbean’s most chic island adds a French flair to Riviera-like beaches and duty-free boutiques. Walk past gingerbread cottages in search of celebrities, shop for designer fashions, or sip the island’s signature ti punch as kite surfers fly by.
With Georgian architecture situated against an irresistible backdrop of emerald green hills, Basseterre is one of the loveliest of the Caribbean’s small capitals. Beyond town, more than a quarter of St. Kitts has been set aside as Brimstone Hill Fortress national Park, a UNESCO World Heritage Site.
For an island comprised of a mere eight square miles, it’s amazing how much there is to do on Jost Van Dyke. Visit the national park on nearby Diamond Cay, snorkel among swaying sponges and angelfish at Sandy Spit, or pilot your own boat around Sir Francis Drake Waterway. After all that, you’ll be ready for an evening drink on the beach —where you can admire your Windstar ship aglow in the harbor.
The beautiful Bank Barrier coral reef wavers just beneath you as your ship makes the break to the bird sanctuary of Prickly Pear Island, so named because it is dotted with prickly pear cacti. Although uninhabited, it does have a beach bar and water sports facilities. Not far away lies the curious assembly of house-sized boulders called “The Baths,” which form huge underground pools and caverns.
The imposing façade of El Morro fortress is just one of the many UNESCO World Heritage Sites in San Juan. Admire the colorful colonial buildings from your casually elegant ship, docked right in the heart of Old San Juan.
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:
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.