Vacation of a Lifetime
Privacy, Adventure, Romance

Privacy Away fom the World

Unbelievable Adventure Every Day

Romance Like You’ve Never Experienced

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1,200+ Boats

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1,000+ Villas

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4,000+ Planes

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30 Private Islands

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50 Countries

USE THE APP

Use WAYPOINT to select the perfect vacation based on the activities you want to experience. We’ll suggest the best islands and the best villa/boat.

Sit Back

We’ll contact you to finalize your needs, then complete the reservations, and send you everything you need, including some extras to enhance your experience.

Enjoy Your Trip

You simply need to show up at the airport. We’ll have everything ready for you upon arrival. If you need anything during your trip we’re available 24/7.

CLICK OR CALL: 1-833-333-0203

Use the arrows to see just a few of our 1,000+ boats

No matter what your interest or style, we've got the perfect craft for you. Sail or power, our boats range from 42 feet to over 170 feet!

Epic Yachts

Our yachts cruise the Caribbean and the Mediterranean, with future voyages in Asia and the Indian Ocean. Spanning from 110 to 170 feet, we have a ship to match your lifestyle and budget. 

Traditional Monohaul

Beautiful sailing ships large enough for six passengers to explore and sleep comfortably. Take the helm and learn how to read the winds while your partner relaxes in the afternoon sun. 

Expansive Catamarans

Sail the seas with lots of elbow room. The catamaran is nearly as wide as it is long. The cabins and bathrooms are large and the higher sail allows access to the full ship, even at sail! Help raise the main sail and take the helm. You're in for one of the most relaxing experiences of your life. 

A Power Cat!

If you want the extra space of a catamaran, but cruise as fast as a mega yacht, then try a power cat. The power cat is even larger than a sail cat. Some even have hot tubs! You'll reach your destination faster, with more time to play. 

We like big boats and we cannot lie...

For a once in a lifetime adventure, or celebrating a major milestone in life, a trip in a mega yacht will allow you to touch any island in the sea. Sleeping up to 12 passengers, it's large enough to bring family and friends - and split the cost!

Quiet for two. Party for eight.

Our yachts are spacious and very well appointed. They are perfect for the couple who wants to escape the world in a discrete and private environment. Discover coves far from the crowd. Or gather up your friends for the most exciting party trip you've ever imagined, with endless beach bars to experience.

It's all about tranquility.

Relax in places most people only dream about. The water and air are always warm. Our boats are large and spacious with lots of room to relax, including the "trampoline" at the front of the catamarans. 

Start the next chapter of your life.

Sailing and yachting are a relaxing way to see the world, while providing the perfect environment to kindle romance and even envision your shared future of adventures together. Go wherever you want. You're in charge. 

Over 1,000 villas worldwide

From the Caribbean to the Mediterranean, and across the islands of the Pacific and Indian oceans, we have over 1,000 luxury villas. Cliffside villas with endless views and beachside villas to walk right into the sea. The villas range from two to over eight bedrooms, or go bigger with a compound or entire island!

Magnificent views

Part of the Waypoint process at Regatta is putting you on the right island for the activities that interest you. Anything from hiking to shopping to the perfect sunset, we consider all your interests, then place you on the island and with the villa to meet them.

An island to yourself!

Exploring the islands with a large party? How about your own island with a compound of villas? We have 30 islands around the world, including some very famous locations. Each island is equipped with all the amenities and provisions you'll need for a great adventure. Wanna make it a real surf and turf? Why not book a boat for a couple days as well!

Indoor-Outdoor Living

One of the wonderful attributes of island villas is how they open up! Walls become windows, and windows disappear. Feel the sea air flowing through all your rooms. Relax in the infinity pool on a cliffside villa or wander into the sea from a beachside villa. At night, close up the villa and let air conditioning lead you to a comfortable night’s sleep.

A brilliant end to the perfect day

Nothing is more awe-inspiring as a tropical sunset. There's no better place to witness it than from your villa's infinity pool. Watch the sky light up in all the colors of the spectrum. Maybe even see the elusive green flash. What you can guarantee is that it'll be the most romantic experience of your life. 

Versatile Living

Villas offer everything you'll need for the week. Wake up to the crisp clean air and gently rising sun. Spread out on the deck for fruit and pastries. Grill your own lunch or head into town to a local dining getaway. Hop in your car and head to one of many beaches on the island, then return to your pool for a relaxing cool-down. The main areas have enough room for grand meals (or really competitive board games).  

Breakfast is served.

Let us enhance your experience by delivering breakfast each morning! Local fresh fruit and pastries straight from the neighborhood patisserie are a great way to start the day. Make your own coffee or we can bring some local espresso. We're on hand to provide every detail for a perfect stay. 

Attention to quality

There are thousands of villas worldwide, but we've picked the ones that meet our high standards for luxury. Across the globe, we have an array of villas to meet your party size and lifestyle. Moreover, we are focused on the things you want to do, and ensure that the villas can meet those needs. 

Endless views from every room

Open the glass walls on a perfect day, close them on a bad day. Either way, you have amazing views of the sea. Our villas are designed to meet the conditions of all seasons. Encounter a rare storm, then sit back and watch from the safety and comfort of your villa, then open up the walls when the storm passes for a taste of that crisp post-storm sea air. 

A squadron of over 4,000 jets!

We have a wide range of jets that canvas the country and shuttle you to the Caribbean, or to the coast where you can transfer to a first class ticket on a commercial airline for your trip to the Mediterranean or Asia. This gives you a turn-key, luxury solution for your adventure.

Jets of all sizes

If you have a small party then try a cozy jet that gets you to the far reaches of the tropics in style, while saving some budget for on-island shopping! These jets are perfect for parties of two to four people. 

Only the best quality jets

We have the jet to match any lifestyle and party size. Need to travel across the US with your whole family, or just want to splurge on a once-in-a-lifetime adventure, then we have long-distance jets that offer the highest in-flight service available. You deserve to feel like royalty!

The fun starts right away!

Why lose precious hours of your vacation in airports and belted into your airplane seat? Charter your jet and start the party as soon as you leave home. Take off from a private hanger and avoid the crowds. Unbuckle, relax, and enjoy the flight and its full amenities. 

The perfect way for a family

Traditionally, an instant stress point of a vacation is getting the full family through the airport. The tickets, the bagage, the security lines, and trying not to loose anyone! Then spreading about the plane and trying to tend to everyone's needs. Avoid all this with your own accommodations! You're in charge. Wisk past all the baggage and security lines. Relax with your family and enjoy the ride. 

Because you've earned it.

You've worked your whole life to build your worth. This last year forced you to shelter inside and miss all the joys of travel. Make up for lost time and reward yourself. Grab your partner and head to your private villa or boat in your own private jet. It'll be an experience you'll always remember. You earned it.