

About Calypso Condo at Gentle Winds
At Calypso Condo at Gentle Winds, comfort and adventure come together in the heart of St. Croix’s stunning natural beauty. Nestled within a serene beachfront condominium community, this tropical retreat offers the perfect blend of relaxation and exploration. Whether it’s a romantic escape, a family vacation, or a getaway with friends, we provide everything you need for an unforgettable Caribbean experience.

Premier Beachfront Condominium
Staying in a beachfront condominium offers more than just a place to sleep. It’s your home away from home, providing a full house for less than the cost of many hotel rooms. Our prices are flexible, based on the number of guests, making it affordable for couples, honeymooners, and larger groups. Enjoy privacy, space, and the unique charm of a personalized vacation experience.
Private Paradise at Gentle Winds
Gentle Winds is a beautifully maintained private community surrounded by lush native vegetation and a protective reef. Far from crowded tourist hubs, this serene oasis features a pristine white sand beach, beautifully landscaped grounds, and diverse wildlife like deer, mongooses, cattle egrets, iguanas, and baby turtles during hatching season. Accessible only by sea or our private driveway, the property provides unparalleled security and tranquility.
Endless Amenities for Every Guest
Calypso Condo and the Gentle Winds community offer a variety of activities for guests of all ages, including:
- A gorgeous new saltwater pool and deck with special lighting and fountain features, open 24/7.
- A tennis court and a four-hole chipping golf course, free of charge.
- Shuffleboard, half-court basketball, and corn-hole for children of all ages.
- A recreation room with a lending library, game tables, ping pong, and space for children’s activities.
The condominiums are just a short walk across the lawn to the beach, pool, and Snack Shack. Guests can enjoy a crab racing court, and just beyond, there’s the Pirates’ Cove, a specially designed play area for children.
Perfectly Positioned on the North Shore
Centrally located between Christiansted and Frederiksted, our beachfront condominium is just steps away from world-famous scuba and snorkeling spots. Visit the nearby Salt River Preserve, where Christopher Columbus landed during his second voyage, or explore the many dining options along the North Shore.
Your Stay at Calypso Condo at Gentle Winds
Calypso Condo at Gentle Winds (C-2) is ideally situated directly facing the beach. This prime location captures the refreshing Trade Winds while offering easy access to the beach, pool, and recreation facilities.
Reasons to Visit St. Croix
St. Croix offers a unique blend of natural beauty, cultural richness, and exciting adventures, making it a must-visit destination. As a U.S. territory, the island is easily accessible to U.S. citizens, and no passport is required to enter. Visitors enjoy perks like twice the duty-free allowance of other Caribbean destinations and the convenience of using U.S. postage stamps.
Explore Underwater Wonders
The Wall at Cane Bay
Dive into one of the Caribbean’s most spectacular underwater sites. The Wall at Cane Bay plunges 3,000 feet, attracting divers from around the globe. St. Croix also boasts the largest living reef in the Caribbean, along with five shipwrecks within 100 yards of each other. For certified and non-certified divers, options like Snuba (breathing through a surface-connected hose) make this an unforgettable experience.
Explore scuba options with:
Buck Island Underwater National Park
Snorkel through a unique underwater trail with markers at Buck Island, where underwater plaques can identify reef fish. For non-swimmers, a glass-viewing window (Caribbean Sea Adventures) offers stunning views. Choose a half- or full-day tour to the island from Christiansted (Big Beard’s Adventure Tours) or take a smaller catamaran (Jolly Roger Charters) or a trimaran (teroro@msn.com).
Salt River Natural Historical Park
This ecological preserve offers both daytime and nighttime kayaking tours. Paddle through mangroves by day or witness the magical glow of phosphorescence by night. This is also where Columbus landed during his second voyage to America. Tour operators include:
Rum Distilleries
Visit the Cruzan Rum and Captain Morgan factories for engaging tours and complimentary samples. Even on rainy days, the tasting bars are always open. Learn more:
Wharf Dining & Tarpon Feeding
At the Christiansted Wharf, feed tarpon with chicken wing bones after enjoying a meal at one of the restaurants or pubs. The fish are lightning-fast and can reach nearly four feet long, adding excitement to the experience.
Family-Friendly Fun
Crab Races
Don’t miss the Monday evening crab races at the Brew Pub. For just $2, you can buy racing rights to a crab, with prizes for kids regardless of whether their crab wins.
Celebrate with Caribbean Music
Experience the joyful rhythms of steel pan drums featured in local parades, holiday celebrations, and Sunday brunches at waterfront restaurants. Sundays on the island are relaxing, as most stores close except for major department stores, which never charge sales tax.
St. Croix offers endless opportunities to relax, explore, and immerse yourself in Caribbean charm. From diving and snorkeling to cultural celebrations and family activities, it’s a destination that promises unforgettable memories.
Experience the Best of St. Croix
With only 66 units spread across 40 acres, Gentle Winds offers a rare combination of exclusivity and community. We provide a vacation like no other, whether you’re swimming under the stars, relaxing in the Pirates’ Cove, or enjoying a potluck BBQ with fellow guests.
Come stay at Calypso Condo at Gentle Winds and immerse yourself in the beauty and comfort of a premier beachfront condominium. Get in touch with us today for more details.