Twenty years ago, the pristine shores of Trunk Bay in St. John provided the idyllic backdrop for our wedding, a cherished memory from our early years living and working on this gem of a Caribbean island. This summer marked a special occasion – our anniversary – and we chose to celebrate it with a month-long return to St. John’s Caribbean Island. This island is more than just a destination; it’s our happy place, a second home where we frequently escape with our three children to reconnect, rejuvenate, and embrace a slower, more relaxed pace of life, infused with the salty air of the Caribbean.
Trunk Bay's global acclaim as a top beach.
St. John distinguishes itself within the Caribbean, with approximately two-thirds of its land protected as Virgin Islands National Park. This designation safeguards its breathtaking natural beauty – from verdant, undeveloped hills and immaculate white-sand beaches to incredibly clear turquoise waters. Unlike many Caribbean islands, St. John remains unspoiled, free from sprawling all-inclusive resorts, bustling highways, and even traffic lights on its modest 19 square miles. Home to around 4,000 residents, the island maintains a unique charm, where driving on the left side of winding roads, a friendly honk before blind turns, and pausing for local wildlife like donkeys, goats, mongoose, chickens, deer, and iguanas are all part of the everyday experience.
Donkeys enjoying the tranquility of Honeymoon Beach in St. John.
As the smallest and most naturally preserved of the U.S. Virgin Islands, St. John offers an effortless escape from the pressures of daily life back home. Each day begins with vibrant sunrises and the sound of roosters, transitioning to evenings marked by stunning sunsets and gentle trade winds. In between, you’ll likely find us immersed in the refreshing embrace of the Caribbean Sea.
Traveling to St. John from Austin is an adventure in itself. The absence of an airport on St. John means reaching this paradise requires a journey. Typically, it’s a 16-hour travel day involving multiple flights, a shared taxi van from St. Thomas airport to Red Hook ferry dock, a swift ferry ride to Cruz Bay, St. John, and a final Jeep ride to our island destination. Yet, the moment we arrive on St. John’s Caribbean Island, the travel fatigue fades into insignificance. Our children, seasoned St. John travelers despite their young ages (9, 13, and 16), now handle the journey with ease, knowing the reward that awaits is well worth the effort.
My personal connection with St. John ignited during a college trip. Shortly after graduating from The University of Texas, I traded an office job for a work-exchange program on the island. Working as a housekeeper at an eco-resort, I spent mornings cleaning in exchange for accommodation, with afternoons free to explore the stunning beaches. The initial six weeks transformed into years as I found a role at the island’s newspaper, documenting island life and spending weekends enjoying the natural beauty of St. John.
Over two decades, my affection for St. John has deepened, especially as it has become a cherished family escape. If you’re considering a visit to St. John’s Caribbean Island, this guide offers insights into its best beaches, hikes, activities, and accommodations.
Trunk Bay's iconic white sands and crystal-clear waters.
Beaches: Discover a New Bay Each Day on St. John
Our family motto on St. John is simple: every day is beach day. With a stunning array of bays, St. John offers more beaches than days in a typical vacation, especially along its famed North Shore.
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Trunk Bay, celebrated for its crescent-shaped, powdery white sand and clear aquamarine waters, frequently ranks among the world’s best beaches and is undeniably St. John’s most popular and photographed location. While it attracts visitors, arriving early or later in the day provides a more secluded experience. During the low season (late August to mid-November), you might even find yourself alone on its beautiful sands.
Maho Bay, a prime location for sea turtle sightings in St. John.
Maho Bay, known for its tranquil, shallow waters, is perfect for families with young children. It’s also renowned for sea turtle sightings, thanks to the seagrass beds just offshore. Swimming in Maho Bay often means encountering these gentle creatures, but remember to observe them respectfully and never touch any marine life.
For a quieter beach experience, Francis Bay, a short drive from Maho, offers serenity. This golden sand beach, the last on St. John’s North Shore, boasts calm, clear waters ideal for swimming and snorkeling. Here, we often spot sea turtles, juvenile fish, and stingrays, with occasional sightings of octopus, starfish, and even reef sharks.
Gibney/Oppenheimer Beach, a secluded gem in St. John.
Gibney Beach, also known as Oppenheimer Beach, is a hidden gem and a family favorite. Its secluded, sugar-sand shore, framed by lush sea grape trees and turquoise waters, is truly picture-perfect. Parking is limited, which helps maintain its tranquility, making it feel like a private escape.
Hiking Trails with Rewarding Coastal Views on St. John
Exploring St. John’s extensive network of over 20 hiking trails within the Virgin Islands National Park is a fantastic way to exercise while immersing yourself in the island’s history and natural beauty. A significant bonus? Many trails lead to stunning beaches, offering a refreshing cool-down after your hike.
For a challenging hike, the 6-mile roundtrip Reef Bay Trail takes you through old-growth forests. A detour leads to ancient petroglyphs carved by the Taino people between 900-1500 AD, and further along, you’ll find the ruins of the Reef Bay Sugar Mill. Conclude your hike with a swim in the waves of Reef Bay before the uphill return.
Panoramic views of Maho and Francis Bays from America Hill.
The Cinnamon Bay Nature Trail and America Hill Trail combine history and views. Wander through the ruins of the Cinnamon Bay Sugar Plantation before a short, steep climb to the America Hill Great House ruins. The trail passes through a shaded forest of mango, genip, and guava berry trees, culminating in panoramic views of Maho and Francis Bays. Cinnamon Bay beach is perfect for a post-hike swim.
The Lind Point Trail to Honeymoon Beach is accessible and rewarding, even for families with young children. Starting near the National Park Visitor Center in Cruz Bay, this less than 2-mile round trip hike leads to Honeymoon and Salomon beaches. Accessible only by foot or boat, these beaches are more secluded, especially in the early morning before boat tours arrive.
Honeymoon Beach, accessible via hiking trails in St. John.
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Venture to the quieter side of St. John and hike to Ram Head, the island’s southernmost point. Starting at Salt Pond Bay, the mile-long trail traverses rocky shoreline, steep inclines, and dramatic cliffs, culminating in 360-degree ocean views. Afterward, relax in the clear waters of Salt Pond Bay or explore the driftwood art at nearby Drunk Bay.
Calichi at Picture Point, offering luxurious and eco-friendly lodging in St. John.
Accommodation Options: From Villas to Boutique Inns in St. John
St. John’s unspoiled beauty sets it apart from many overdeveloped Caribbean destinations. Accommodation options range from luxurious boutique hotels and intimate inns to spacious villas and charming Caribbean cottages. We often split our stays between Cruz Bay and Coral Bay to experience both sides of the island.
The breathtaking view from Out of the Blue villa in St. John.
During our recent trip, we returned to Calichi at Picture Point, an eco-luxury villa nestled high on Bordeaux Mountain overlooking Coral Bay. From the Tower Villa, the views encompass sailboats in the harbor and surrounding islands, including St. Thomas, Puerto Rico, Vieques, Tortola, Jost Van Dyke, and St. Croix. On the other side of the island, near Cruz Bay, we stayed at Out of the Blue villa, offering stunning views of Rendezvous Bay and Ditliff Point on St. John’s South Shore.
Island Roots Boat Charters, your gateway to unforgettable sea adventures in St. John.
Island Hopping to the British Virgin Islands from St. John
A significant advantage of a St. John vacation is its proximity to the British Virgin Islands (BVI). If your itinerary and budget allow, a boat trip to the BVIs is highly recommended. Private charters between the USVI and BVI are available, albeit at a higher cost since recent events.
We chose Island Roots Charters for a full-day BVI excursion. Captain Ryan met us at the Cruz Bay National Park Dock, ready to take us on a 32-foot power catamaran. After clearing customs in Tortola, our first stop was Sandy Spit, a picturesque islet that epitomizes Caribbean beauty. We then explored Tortola’s North Shore, stopping at Rogues Bay for swimming and rock climbing on a secluded beach.
Sandy Spit, a quintessential Caribbean islet near Jost Van Dyke.
Our main BVI destination was The Baths on Virgin Gorda, a remarkable geological site with massive granite boulders forming grottos and natural pools. After lunch at Devil’s Bay, we snorkeled at The Indians, known for vibrant marine life. The day concluded with Painkiller cocktails at White Bay on Jost Van Dyke, a stunning white sand beach with turquoise waters and lively beach bars, as the sun set on a perfect day at sea, a highlight of our St. John’s Caribbean Island retreat.
