The Waypoints Spanish Virgin Islands Flotilla

St Thomas, USVI and Spanish Virgin Islands (SVI)

April 19-27, 2024

Starting Point: Waypoints USVI (St. Thomas)

If you love sailing, exploring beautiful destinations, and experiencing Caribbean Culture – you don’t want to miss the Waypoints Spanish Virgin Islands Flotilla – set to depart on April 19th, 2024.

The Waypoints SVI flotilla provides an ideal opportunity for families, friends, and couples to embark on a memorable vacation without the hassle of meticulous planning. Whether you’re an experienced sailor or a first-timer, the flotilla caters to like-minded individuals who share a passion for the sea. What makes it truly special is the sense of community fostered as participants sail together, anchoring at picturesque destinations along the way. This camaraderie extends to evenings spent dining together, where stories are shared, bonds are formed, and unforgettable memories are created. The Waypoints SVI flotilla is not just a sailing adventure; it’s a social and immersive experience that promises to leave you with a treasure trove of cherished moments.

What is a Flotilla?

A flotilla consists of a group of sailboats and yachts that travel together, led by an experienced lead boat or captain. This allows you to sail with a group of like-minded individuals, benefit from local knowledge, and have support and guidance throughout the journey.

Where Are the Spanish Virgin Islands?

The Spanish Virgin Islands are a relatively small cluster of islands and cays located between St. Thomas and Puerto Rico. They are a part of the United States, so no passport is required for US visitors.

Why the Spanish Virgin Islands?

Visiting the Spanish Virgin Islands can be a rewarding and unforgettable experience. Here are several compelling reasons to consider making a trip to these beautiful Caribbean islands part of your travel plans:

Stunning Beaches: The Spanish Virgin Islands are known for their pristine, white-sand beaches and crystal-clear turquoise waters. Beach lovers and sun seekers will find paradise on beaches like Flamenco Beach in Culebra and Sun Bay Beach in Vieques.

Bioluminescent Bays: Vieques is famous for its bioluminescent bays, such as Mosquito Bay and Mosquito Pier. Witnessing the water light up with bioluminescent microorganisms at night is a magical and rare experience.

Island Hopping: With several islands in close proximity, it’s easy to go island hopping in the Spanish Virgin Islands. Each island has its own charm and attractions, making it an adventure to explore them all.

Scenic Beauty: The islands offer breathtaking natural landscapes, from lush green hills to dramatic cliffs and rock formations. The scenery is perfect for hiking, photography, or simply taking in the beauty of the Caribbean.

Wildlife and Nature: The islands have protected natural areas where you can observe unique flora and fauna, including wild horses on Vieques and sea turtles nesting on Culebra’s beaches.

Local Culture: Immerse yourself in the vibrant local culture, influenced by a mix of Puerto Rican, Spanish, and Afro-Caribbean traditions. Explore local markets, try authentic Caribbean cuisine, and enjoy the friendly hospitality of the locals.

Snorkeling and Diving: The Spanish Virgin Islands are home to vibrant coral reefs and diverse marine life. Snorkeling and diving enthusiasts can explore colorful underwater worlds teeming with tropical fish, sea turtles, and more.

Relaxation and Tranquility: The Spanish Virgin Islands offer a more relaxed and less crowded atmosphere compared to some of the more popular Caribbean destinations, making it an ideal spot for those seeking tranquility and peaceful getaways.

Romantic Getaways: The Spanish Virgin Islands are a romantic destination, perfect for honeymooners and couples looking to escape to a serene and picturesque setting.

Water Activities: In addition to snorkeling and diving, you can enjoy various water activities like kayaking, paddleboarding, sailing, and windsurfing in the calm and clear Caribbean waters.

Adventure Opportunities: Whether it’s hiking through lush jungles, exploring hidden caves, or trying water sports, the islands offer plenty of adventure opportunities for thrill-seekers.

Eco-Tourism: The Spanish Virgin Islands are committed to sustainable tourism and conservation efforts, making it an excellent destination for eco-conscious travelers.

History and Heritage: Learn about the rich history of these islands, including their indigenous Taino heritage and their role in maritime history. Explore historical sites, such as old forts and lighthouses.

Most of all…you will experience unspoiled beauty!


Meet Greg Bammel, Lead Flotilla Captain

Greg’s passion for sailing began during his time at the University of Wisconsin’s Hoofer Sailing Club. Rather than opting for the typical spring break experience, Greg embarked on adventurous charters, sailing from the picturesque Florida Keys to the exotic Bahamas.

Over the past decade, Greg has emerged as a seasoned sailor and a leader in organizing flotilla expeditions. His nautical expertise has taken him and his crew to captivating destinations such as Antigua and Barbuda, the Bahamas, Thailand, the Spanish Virgin Islands, the British Virgin Islands, St. Martin, Anguilla, Saba, Florida, and Greece.

Looking ahead, Greg and his crew are gearing up for another exciting voyage to the Spanish Virgin Islands, known for their pristine beaches and stunning Caribbean beauty.

Sample Itinerary – St. Thomas and Spanish Virgin Islands April 19 – 27, 2024


Day 1 – Arrive at the Waypoints charter base in St Thomas USVI.  Finalize your provisioning, meet and greet with the team, and then get a good night’s rest after a full day of travel. 

Day 2 – Leave St Thomas and make your way for the vacation of your lifetime.  Rise and shine because it is time to make a downwind run. Typically, the next stop is Ensenada Honda on Culebra. It is roughly twenty miles from the west end of St Thomas to Culebra. You will carefully follow the ships’ channel into the harbor.  Once you are anchored in the harbor you can use the ROAM APP to clear your vessel and crew into customs. Then, it is time to explore the town of Dewey. Dewey is home to multiple dining and shopping options. The Dinghy Dock, Zaco’s Tacos, or Mamacita’s are just a few of the great options available. 

Day 3 – How about a little land-based excursion? You can rent street-legal golf carts from Jerry’s Jeeps in Dewey. Pack your beach gear and head out for the day. First stop – Zoni Beach! This is a turtle sanctuary located on the North Shore. A long stretch of white sand with views for miles. Then, you can drive to Flamenco Beach on the northwest side of Culebra and explore the large natural beach. With food vendors, pristine white sand, and even a photo op or two on old tanks used for target practice, it is an experience not to be missed. Leave yourself enough daylight to move the boat around to the anchorage Ensenda Dakity. This is a great snorkel spot tucked in behind a barrier reef.

Day 4 – Culebrita, the name sounds as pretty as the Cay. Culebrita is home to a spectacular beach, a historic lighthouse, and a natural “hot tub”. There is a lot to see and do here. Or you can choose to do nothing at all. Either way, it is not to be missed. You have your choice of several anchorages depending on the weather.

Day 5 – Set sail for Vieques. In most instances, you will run around the east end of Vieques, then work your way to any number of south side anchorages. Ensenada Honda, Sun Bay, or Esperanza just to name a few. If the moon is right, book a kayak tour of the Bioluminescent in Mosquito Bay. This is a protected harbor, and you must book with an authorized vendor.

Day 6 – Decisions, decisions. Hang out in town for a pub crawl. Rent a jeep and explore. Spend the day in Sun Bay enjoying the beautiful beach, the water, and the sun. There is no wrong answer.

Day 7 – Set a waypoint for the west end of Water Island just south of St Thomas. Drag a fishing line if you have one. Or just drop by Dinghy’s Beach Bar at Druif Bay on Water Island to provide you with the last dinner of the trip.

Day 8 – On the last day you will have a quick stop at a marina for fuel and return to our base in Frenchtown. Make sure to send us pictures of your charter trip and don’t forget #WaypointsWanderer on social media!

You don’t want to miss out on the experience of a lifetime. Space is limited so contact our charter experience specialists to reserve your spot today!