Windward Islands Highlights: The Best Spots You’ll Explore on a Caribbean Voyage

By: Bethany Remington, Broadreach HQ April 16, 2026 High School Adventures, Middle School, Scuba, Sailing

If you’ve ever dreamed of sailing through turquoise water, diving remote reefs, and discovering islands that feel completely untouched, welcome to the perfect Caribbean Windward Islands trip for teens.

Stretching from St. Lucia to Grenada, this region is one of the most diverse, adventurous, and underrated parts of the Caribbean. And when you explore it by liveaboard sailboat? You don’t just visit these places, you experience them.

Most Broadreach Caribbean voyages take place in the Leeward Islands, where calm anchorages and ideal sailing conditions create the perfect environment for learning to sail, dive, and live aboard a catamaran.

But for students looking to go further—literally—there’s the Windward Islands.

Our 21-day Advanced Scuba Voyages venture into this more remote region, with one session sailing from St. Lucia to Grenada and the other sailing in reverse. Either way, students experience the full arc of the Windward Islands: longer sails, wilder landscapes, and some of the most adventurous diving in the Caribbean.

And for those who want it all, our 24-day High School Sailing Voyage explores both the Leeward and Windward Islands in one unforgettable journey.

So what makes the Windwards so special?

Here are some of the best spots and can’t-miss highlights 👇

St. Lucia: Iconic Landscapes + Caribbean Highlights

For some students, the journey begins in St. Lucia, where dramatic volcanic peaks rise straight out of the ocean. For others, it’s the final stop on the voyage—and a pretty unforgettable way to wrap up.

🌟 Highlights:

• The Pitons (Anse des Pitons): Sail and anchor between these UNESCO-listed peaks—one of the most iconic views in the Caribbean.
• Hot Springs Hike: A short adventure inland leads to natural geothermal pools, a total “wow” moment.
• Marigot Bay: Often described as “the most beautiful bay in the Caribbean,” this lush, sheltered harbor is surrounded by steep green hills and a distinctive palm-lined sand spit. Today, it’s known as a “hurricane hole”: a calm, protected anchorage that’s perfect for sailboats and one of the most scenic places to drop anchor in the Windwards.

💡 Why it stands out: Whether it’s your first stop or your last, St. Lucia delivers an unforgettable mix of adventure, culture, and iconic Caribbean scenery.

St. Vincent: Wild Beauty + Adventure Diving

St. Vincent is rugged, less developed, and packed with adventure.

🌟 Highlights:

• Smuggler’s Cove (Student Favorite!): A secluded bay perfect for swimming, cliff jumping, and hanging out with your crew.
• Bat Cave Dive: A unique dive site used for buoyancy training and exploration.
• Wallilabou Bay: Famous as a filming location for Pirates of the Caribbean (yes, really!).
• Waterfalls & Volcano Hikes: From hidden waterfalls to La Soufrière volcano, this island is made for exploration.

💡 Why it stands out: This stop is one of the highlights of the route: remote, raw, and unforgettable.

Bequia + Petit Nevis: Culture, Community + Coral Reefs

Bequia offers a deeper cultural connection and some seriously beautiful beaches.

🌟 Highlights:

• Port Elizabeth Town Time: A charming waterfront town with local shops, food spots, and Caribbean culture.
• Princess Margaret Beach: White sand, turquoise water, and the perfect spot for beach games and downtime.
• Petit Nevis: A tiny, uninhabited island with fascinating history and incredible views.
• Coral Restoration + Community Service: (when available) Hands-on conservation work that connects students to the local environment.

💡 Why it stands out: It’s where adventure meets impact—students connect with both the ocean and the community.

🐢 Tobago Cays: Snorkeling Paradise

If there’s one place that feels like a postcard come to life, it’s the Tobago Cays. No matter which direction you’re sailing, this is one of those places that feels like the heart of the trip.

🌟 Highlights:

• Swim with Sea Turtles: Snorkel in protected waters and spot turtles, rays, and vibrant reef life.
• Petit Tabac (aka “Rum Island”): A remote, uninhabited island perfect for beach games and exploring.
• Beach BBQ Nights: Dinner under the stars with your group—one of the biggest trip “glow” moments.

💡 Why it stands out: No roads, no crowds, just crystal-clear water and pure Caribbean magic.

🌊 Union Island + Chatham Bay: Off-the-Grid Adventure

Union Island offers a more rugged, authentic Caribbean experience.

🌟 Highlights:

• Chatham Bay: A peaceful, wide-open bay perfect for watersports, beach games, and relaxing.
• Happy Island: A one-of-a-kind manmade island bar built from conch shells—great for photos and local flavor.
• Open-Air Markets + Local Culture: A chance to experience island life beyond the typical tourist path.

💡 Why it stands out: It feels remote and real, like you’ve discovered a hidden corner of the Caribbean.

Carriacou + Grenada: Epic Diving + Culture

Depending on your session, this is either where the adventure begins or where it all comes together. Whether your first dives or your final ones, this part of the voyage brings some of the best diving in the Caribbean.

🌟 Highlights:

• Isle de Ronde: Advanced, world-class diving with dramatic underwater landscapes.
• Molinere Underwater Sculpture Park: A surreal dive/snorkel experience among submerged sculptures.
• Sandy Island (Carriacou): A tiny sandbar island perfect for beach days and group bonding.
• Seven Sisters Waterfalls: A scenic rainforest hike leads to a series of cascading waterfalls where you can swim in cool freshwater pools—one of Grenada’s most rewarding inland adventures.
• Spice Island Tour: Explore why Grenada is known as the “Spice Island,” with visits to local plantations, markets, and farms where you’ll see (and smell) nutmeg, cocoa, and other spices firsthand.
• St. George’s, Grenada: A colorful capital city rich in history and Caribbean culture.

💡 Why it stands out: It’s a true highlight of the voyage, combining adventure, diving, culture, and some of the most unforgettable moments of the trip.

Why the Windward Islands Are So Special

Unlike more tourist-heavy Caribbean destinations, the Windward Islands offer something different:

• 🌊 Remote, less crowded islands
• 🤿 World-class diving and snorkeling
• ⛵ Constant movement—wake up somewhere new
• 🌱 Opportunities for conservation and real-world learning
• 🤝 Stronger group bonding through shared adventure

As your itinerary shows, this isn’t just a vacation, it’s a progression of experiences, from first sails and dives to advanced skills and independent exploration.

Final Thoughts: One Trip, Endless Highlights

The best part of the Windward Islands?

There isn’t just one highlight.

It’s:

• jumping off the boat in Smuggler’s Cove
• spotting your first sea turtle in Tobago Cays
• hiking above the Pitons at sunset
• and laughing with your crew during a beach BBQ

All of it adds up to something bigger: a once-in-a-lifetime experience you can’t replicate anywhere else.

Want to explore the Windwards? Check out our middle school and high school advanced scuba trips in the Windward Islands.