Regatta provides an activity-based desktop and mobile app, paired with white glove concierge service to produce unforgettable luxury vacations in 50 countries in the Caribbean, Mediterranean, and Indian seas, with the largest fleet in the market:

• 1,400+ Boats (Catamarans and Yachts)

• 1,000+ Island Villas

• 4,000+ Planes

• 30+ Private Islands 

Why Luxury Vacations?

The yacht and villa charter market was valued at US$12B in 2020 and set to grow at 5.4% CAGR through 2026. The market is highly driven by the rising inclination towards personalized luxury travel. Market growth is further complemented by the increasing number of affluent high net-worth individuals (AHNW) globally; increased by nearly 8% to a record 16.5M. This represents a large and growing market, yet the technology used in the travel industry are basic inventory search databases (triggering the psychological phenomenon called, Paradox of Choice). Regatta offers an end-to-end solution: an AI-base app, the largest inventory in the market, and white-glove concierge service.

The money spent on these vacations is extraordinary with sailing catamarans chartering at $25,000 to $80,000 per week, villas renting at $15,000 to $100,000 per week, and yachts pulling in $85,000 to over $500,000 per week. It is extraordinary, but these vessels and villas sell out every year. 

Every Year over 700 million vacation days go unused in the United States alone. The equivalent of 1.9M years worth of vacation. People want to go on vacation but many just don’t have the time to plan out all the little details. This is where Regatta comes in; with our technology and concierge service, our customers can create the vacation they always dreamed of (with less stress and more confidence). With our technology (Waypoint) our customers can quickly find the locations that provide the activities they desire, and the optimal villa and/or boat that enable them to enjoy those activities. Then our white-glove service guides them to/from their location and executes the perfect vacation.

Any vacation planning process is time consuming and wrought with frustrations. Tropical vacations are even harder. The selections can be frustrating with dozens of islands, each with hundreds of villas and boats, all of which look alike, and may or may not provide the activities they desire. Some locations have the activities you want to enjoy, but some don’t. The wrong island could ruin your vacation. The transportation process is complex. Not every island has an airport and today’s COVID travel restrictions make island transportation even harder.

Our solution eliminates the psychological burden referred to as the Paradox of Choice, the overwhelming feeling experienced with too many choices, often associated with travel planning. Our activity-based engine, Waypoint, allows our customers to choose the activities they want to experience, then finds the best islands, villas and/or boats to accommodate their preferences.  Waypoint then presents these choices in a fun and engaging manner. Once the user selects a vacation matching their desired activities, our concierge team confirms all logistics, prepares an itinerary, and the vacation is ready without any hassles. Just show up to the airport on time. Waypoint has all the addictive properties of dating apps, engaging the dopamine cycle that excite the customer and increase the odds of purchase.

Meet Our Founder

Our Captain is a successful entrepreneur of four start-ups, who has been a senior executive of three publicly traded companies and honored with 30 industry and 20 entrepreneurial awards, including seven INC. 500 awards. William West is making his next entrepreneurial voyage merging his passion for the sea with his love of building companies.

“Ten years ago, I took my son sailing in the Caribbean and it changed my life. I’ve gone back every year since to sail or stay in an island villa, but there’s been one consistent challenge: planning the trip. Making selections from dozens of islands, hundreds of villas and boats, arranging transportation, lodging, activities, dining, and making sure that the trip meets my original vision. After ten years and twelve islands, the planning has never gotten any easier. I formed Regatta to solve this problem and make these vacations readily accessible to the rapidly growing population of affluent, high net-worth individuals who desire them. “

“Join us – where life meets the sea, relaxation meets luxury, and where the wind will revitalize your spirit – I promise that a Regatta trip will change your life,” William

Regatta makes these truly unique and life-changing vacations readily accessible for busy, affluent families. There is nothing like experiencing life from a crisp infinity pool overlooking a sunset or peacefully riding the wind in our massive sailing and power boats. We enable our customers to share their vision, then our technology compares thousands of islands, villas/boats, and vibes until we find the perfect one for them.

Sifting through dozens of islands and hundreds of boats and villas is a wasted effort if the choices don’t provide the activities you wish to enjoy. Arrive on an island that doesn’t have beaches? Arrive to a town that doesn’t have shopping? Find yourself on a boat without scuba or fishing equipment? All these are possible, but Waypoint ensures you get to experience the tropics without heartbreak.

How Waypoint Works

Waypoint is our AI-based engine that provides the backbone to our activity-based approach to travel planning. It is radically different and makes the planning process enjoyable, simple, and highly effective.  Waypoint pulls from thousands of options to design a trip guaranteed to fulfill your dreams.

When first arriving at Waypoint, users are prompted to select the desired vacation activities they wish to experience. The user selects: the time frame, number of beds, target budget, and the activities they wish to partake in. Once you have selected your preferences, the search engine matches available yachts and villas detailing potential activities you can do. The results will detail the top 3 locations that most suit your desired activities and the optimal boat and/or villa to support your trip! They can tweak the options and compare results. From there, the user is prompted to create a consultation booking with one of our excellent concierge representatives and a custom itinerary will be created for you!

Head to www.regatta.travel to explore!

At Regatta Travel we offer the best sailing catamarans, sexy power-cats, out-of-this-world yachts, and the magnificent views and indoor-outdoor living of luxury villas. Using our unique activity-based approach to travel we get them to the places that excel in the activities they want to experience. Rather than the typical long list of vacation options, they choose the vacation experience they desire, then we identify the island destination and accommodations that meet their needs (and vibe) for a private, covid-safe, and truly unforgettable experience.

Help put wind in our sails so that we can radically change the travel industry. Help us make these life-changing getaways possible and you’ll earn discounts and free days for your own out of this world excursion!

We are seeking your help in raising $500,000 to help Regatta Travel:

• Reinforce our marketing campaign and expand our clientele.
• Establish the sales staff to build direct B2B relationships to attract our target audience.
• Refine our Waypoint app to expand its AI ability and expand the database of options.
• Improve our concierge services to include 24/7 on-call knowledgeable and high-quality representatives.
• Develop and enhance Regatta’s operations to make booking more efficient on the back-end

Your contribution will help us get people (maybe even you!) out of their traditional vacation and into a fantasy world of yachts, villas, and even private islands easily to create memorable experiences with a loved one, family, and friends.