Ultimate Guide to the Best Sailing in St. John

St. John, nestled in the U.S. Virgin Islands, is celebrated for its stunning beaches, rich biodiversity, and tranquil waters, making it a haven for sailing enthusiasts. With its crystal-clear waters and picturesque coastline, the island offers countless hidden gems perfect for exploring by boat. In this guide, we will traverse 25 of the most captivating sailing spots in St. John, each promising breathtaking views and unforgettable experiences.

Travel Guide: St John

1. Trunk Bay

Wide angle view of Trunk Bay's pristine beach and turquoise waters — Trunk Bay, a quintessential tropical paradise

Trunk Bay is often regarded as one of the most picturesque beaches in the world. With its soft white sand and vibrant coral reefs just off the shore, it’s an ideal spot for both sailing and snorkeling. The calm waters are perfect for anchoring and soaking in the island’s natural beauty.

The bay is accessible only by boat, adding to its allure as a secluded paradise. Sail here to enjoy a day of swimming, sunbathing, or exploring the underwater snorkeling trails, which make it a must-visit locale.

2. Cinnamon Bay

High angle view of Cinnamon Bay's lush greenery and gentle waves — Cinnamon Bay’s lush backdrop and inviting waters

Cinnamon Bay offers a blend of natural beauty and historical significance. The bay is known for its historical ruins of sugar plantations, providing a glimpse into the island’s past. This family-friendly destination is perfect for those sailing with children.

The bay’s gentle winds and calm waters make it an excellent spot for beginners to practice sailing or for families to enjoy a leisurely day on the water.

3. Leinster Bay

Eye-level view of the serene waters of Leinster Bay surrounded by hills — The tranquil waters of Leinster Bay provide a serene sailing experience

Leinster Bay is a tranquil spot ideal for those looking for a peaceful retreat. The bay features stunning scenery with rolling hills and lush vegetation all around, making it a perfect backdrop for a serene day on the water.

Here, you can anchor and explore the nearby Waterlemon Cay, a small islet that’s famous for its snorkeling opportunities, filled with vibrant life beneath the waves.

4. Coral Bay

Close-up view of boats gently rocking in the calm waters of Coral Bay — Boats peacefully anchored in the calm waters of Coral Bay

Coral Bay is a quieter alternative to the bustling Cruz Bay, offering an authentic Caribbean sailing experience. This area is dotted with colorful boats and sailboats, providing a picturesque setting for a sailing adventure.

Enjoy the calm waters and nearby restaurants that serve local cuisine, making it a great spot to spend the day with friends after sailing.

5. Virgin Islands National Park

Eye-level view of the lush trails within Virgin Islands National Park — Lush trails and untouched nature within the Virgin Islands National Park

No visit to St. John would be complete without exploring the Virgin Islands National Park. Spanning over 7,000 acres of land and sea, this park is a treasure trove of natural wonders.

Sailing through the park allows you to appreciate the diverse flora and fauna, with several protected areas that offer excellent opportunities for snorkeling and swimming.

6. Salt Pond Bay

Wide angle view of Salt Pond Bay's serene waters and sandy beach — Salt Pond Bay showcases the perfect blend of tranquility and beauty

Salt Pond Bay is the perfect escape for sailors looking to experience a less crowded area. The bay features a sandy beach, surrounded by dramatic cliffs and lush vegetation, creating a stunning view from the water.

Not only is this an excellent spot for sailing, but it’s also known for its unique salt pond, which adds an extraordinary ecological feature to explore.

7. Caneel Bay

High angle view of Caneel Bay showcasing its luxury resorts and marina — Caneel Bay merges luxury with natural beauty

Caneel Bay is home to some of the most luxurious resorts on St. John and offers a unique experience for those who wish to sail in style. The bay’s clear waters are perfect for a leisurely sail or a more upscale dining experience after a day on the boat.

The surrounding landscapes provide a beautiful contrast to the pristine blue water, making it a popular spot for sunset sails.

8. Brown Bay

Eye-level view of Brown Bay’s golden sands and rolling hills — Brown Bay offers a secluded beach experience away from the crowds

Brown Bay is known for its secluded atmosphere, making it a great choice for those looking to get away from the more tourist-heavy areas. The serene environment allows for peaceful anchoring and relaxation.

The beach is complemented by lush greenery and rolling hills, providing excellent hiking opportunities nearby, making it perfect for an adventurous sailing trip.

9. Hawksnest Bay

Wide angle view of Hawksnest Bay with its inviting beach and serene waters — Hawksnest Bay features inviting waters perfect for a day on the sailboat

Hawksnest Bay is a charming spot that combines clear waters and pristine beaches, offering an ideal location for both sailing and swimming. With gentle breezes and a serene atmosphere, it’s perfect for a relaxing day on the boat.

The nearby snorkeling spots are also outstanding, making it an ideal backdrop for a day filled with aquatic adventures.

10. Maho Bay

High angle view of Maho Bay's crystal-clear waters filled with colorful boats — Maho Bay is famous for its crystal-clear waters and tranquil anchorages

Maho Bay is a vibrant bay that attracts sailors and water sports enthusiasts alike. Its clear waters provide an excellent opportunity for snorkeling, with an abundance of marine life just beneath the surface.

This bay is also well-suited for sailing due to its sheltered nature, making it a safe haven regardless of wind conditions.

11. Johnson Bay

Eye-level view of Johnson Bay's calm waters and surrounding greenery — The calm waters of Johnson Bay create an inviting atmosphere for sailors

Johnson Bay is a stunning and tranquil bay known for its picturesque landscapes. Surrounded by verdant hills and palm trees, it’s an idyllic setting for sailing enthusiasts who appreciate natural beauty.

Visitors can enjoy a peaceful day anchored, with the option of exploring nearby hiking trails that lead to scenic viewpoints.

12. Waterlemon Cay

Close-up view of the vibrant marine life near Waterlemon Cay — Waterlemon Cay is a snorkeling paradise teeming with vibrant marine life

Waterlemon Cay is a small yet beautiful islet known for its remarkable underwater experiences. Accessible by a short sail from Leinster Bay, it offers some of the best snorkeling opportunities in the region.

With vibrant coral reefs and diverse marine life, this spot is perfect for sailors looking to dive into the underwater wonders of St. John.

13. Francis Bay

Wide angle view of Francis Bay featuring its soft sandy beach and turquoise waters — Francis Bay invites visitors with its soft sands and beautiful surroundings

Francis Bay is widely regarded as one of the most beautiful beaches on St. John. Its peaceful, sheltered waters create a calm environment, ideal for sailing and swimming.

The beach’s soft sands and scenic surroundings invite visitors to spend a day soaking in the sun, making it a popular spot for both locals and visitors alike.

14. Great Cruz Bay

High angle view of Great Cruz Bay showcasing a bustling marina — Great Cruz Bay is alive with activity and sailing adventures

Great Cruz Bay is a bustling hub of activity and a well-known spot for sailors looking to take advantage of the vibrant local culture. The marina here plays host to various boats and offers various amenities for sailors.

This bay also serves as the primary access point for ferries, providing easy connections to other Virgin Islands, making it an important location for sailing adventures.

15. Pastory Point

Eye-level view of the rocky shoreline at Pastory Point — Pastory Point features stunning rocky coastlines and rolling waves

Pastory Point serves as a landmark for sailors navigating the waters around St. John. The rocky coastline is visually striking and provides a unique sailing experience.

This area is known for its dramatic views and is a fantastic spot to anchor and take in the natural surroundings or enjoy a picnic along the coast.

16. Little Cinnamon Bay

Wide angle view of Little Cinnamon Bay's tranquil waters mirror the sky — Little Cinnamon Bay’s tranquil waters provide a secluded escape for sailors

Little Cinnamon Bay is a hidden gem that offers a serene atmosphere perfect for those looking for a quiet getaway. This bay provides a secluded environment away from the crowds.

Sailors can enjoy peaceful anchoring, with opportunities for snorkeling and exploring the vibrant marine life just off the shore.

17. Rams Head

High angle view of the rugged cliffs at Rams Head with the sea in the background — Rams Head offers dramatic cliffs and stunning ocean views

Rams Head showcases St. John’s rugged coastline and provides an impressive sailing experience. The cliffs rise dramatically from the ocean, presenting a stunning landscape that is perfect for photography.

This area is ideal for experienced sailors looking for thrilling conditions or those wanting to enjoy a beautiful sunset sail.

18. Annaberg Bay

Eye-level view of the historic ruins at Annaberg Bay — Annaberg Bay is a site of historical significance with stunning views

Annaberg Bay is home to the ruins of sugar plantations, providing a unique interplay of history and natural beauty. Sailors can immerse themselves in the area’s history while enjoying the beautiful scenery.

The bay’s easy access from the water makes it a perfect stop for sailors interested in diving deeper into St. John’s cultural heritage.

19. Coki Point Beach

Close-up view of the inviting sand and clear water at Coki Point Beach — Coki Point Beach is a delightful spot for sunbathing and sailing

Coki Point Beach is another luxurious beach spot, perfect for those who want to enjoy a vibrant beach atmosphere. The lovely sands and lively beach scene make it a popular stop for those sailing around St. John.

Sailors can enjoy swimming, sunbathing, or even partake in local beachside dining options.

20. Lind Point

High angle view of the lush landscape from Lind Point — Lind Point provides spectacular views of St. John’s coastline

Lind Point is a unique spot that offers stunning views of St. John’s coastline from above. The nearby trails allow sailors to explore the surrounding area, leading to jaw-dropping vistas of the sea and foliage.

This area is great for those who want to combine sailing with hiking and photography, creating an unforgettable experience.

21. Salt Pond

Close-up view of the serene water of Salt Pond with silhouettes of nearby shrubs — Salt Pond features quiet waters that reflect the surrounding landscapes

Salt Pond is a unique body of water that provides a tranquil spot away from the typical tourist areas. Sailors can anchor here to enjoy the peace and quiet, perfect for a relaxing afternoon.

The surrounding landscape features stunning plant life and wildlife, making it a great location for nature enthusiasts.

22. Cruz Bay

Wide angle view of the lively Coral Bay area — Cruz Bay is the bustling heart of St. John with vibrant activities

Cruz Bay is the hub of activity on St. John, providing ample opportunities for sailors to explore shops, restaurants, and bars. The busy marina welcomes various vessels, making it a perfect starting point for sailing adventures.

Enjoy local cuisine, shop for souvenirs, or simply enjoy the vibrant atmosphere after a day on the water.

23. Water Island

Eye-level view of the tranquil beach at Water Island — Water Island offers a serene beach experience away from the main island

Water Island is a lesser-known spot that provides a tranquil space for sailors looking for peace. The beaches here are pristine, surrounded by clear waters ideal for swimming.

Accessible by sailboat, this island invites visitors to enjoy an unhurried day of relaxation and exploration.

24. B caracteer Bay

Wide angle view of the hidden B caracteer Bay surrounded by cliffs — B caracteer Bay is nestled among dramatic cliffs and lush vegetation

B caracteer Bay is a hidden treasure, showcasing stunning landscapes with dramatic cliffs on one side and serene waters on the other. This area offers excellent protection from the winds, making it a great anchorage for a sailboat.

The stunning scenery here complements a peaceful day of exploration, with opportunities for hiking along nearby trails.

25. East End

Eye-level view of the shimmering waters at East End with distant islands — East End presents glittering waters and scenic views of surrounding islands

The East End of St. John is a picturesque sailing destination that leads to awe-inspiring views of surrounding islands. The protected waters allow for a smooth sailing experience, perfect for both novice and seasoned sailors alike.

Explore the various small coves and sparkling beaches, each offering a distinct ambiance and beauty, ideal for a final day of sailing around the island.

Conclusion

Sailing in St. John is more than just a pastime; it’s a gateway to experience the natural beauty and rich culture that the island has to offer. From pristine beaches to secluded bays and historical sites, each of the 25 spots listed above promises a unique adventure waiting for sailors of all levels.

Whether you are an experienced sailor or a first-timer, St. John’s diverse sailing spots ensure that each journey on its turquoise waters is one that will create cherished memories. So grab your sailing gear, set course for the Virgin Islands, and discover the hidden gems of St. John.

KW Adventure Explorer