Twenty years ago, the pristine shores of Trunk Bay in St. John witnessed our wedding vows. This small Caribbean island wasn’t just a picturesque backdrop; it was our home for the initial, carefree years of our marriage. This summer marked a special milestone – our anniversary – and we chose to celebrate it with a month-long return to this cherished island. St. John has evolved into our sanctuary, our happy place, the home we long for when away, and a haven we frequently revisit with our three children. It’s where we disconnect, recharge, and embrace life at a gentler, saltier rhythm.
Trunk Bay's pristine beauty, St. John Caribbean
St. John, Caribbean, boasts an unparalleled natural beauty, largely thanks to approximately two-thirds of its land being protected as Virgin Islands National Park. This designation has preserved its lush green hills, untouched white-sand beaches, and crystal-clear turquoise waters, a stark contrast to many overdeveloped Caribbean destinations. On this 19-square-mile island, home to around 4,000 residents, you won’t encounter towering resorts, bustling highways, or even a single traffic light. Driving here is a unique experience – navigating narrow, winding roads on the left side, with a friendly honk preceding each hairpin turn, and frequent pauses to yield to the island’s diverse non-human inhabitants: donkeys, goats, mongoose, chickens, deer, and iguanas.
Donkeys peacefully coexisting with beachgoers on Honeymoon Beach, St. John
St. John, the smallest and most unspoiled of the U.S. Virgin Islands, offers a true escape from the everyday pressures of life. Each day begins with vibrant sunrises, serenaded by rooster calls, and concludes with breathtaking sunsets and gentle trade winds. In between, you’ll find us immersed in the natural saltwater pools of the Caribbean Sea.
Reaching St. John from Austin is an adventure in itself. The absence of an airport on St. John means there are no direct flights from Austin to neighboring St. Thomas either. Our journey typically spans around 16 hours, involving two or three flights, a shared taxi van from St. Thomas airport to the Red Hook ferry dock, a 20-minute ferry ride to Cruz Bay in St. John, and finally, a Jeep ride to our island destination. However, the moment we step onto this island paradise, the travel fatigue instantly vanishes. Our children, now aged 9, 13, and 16, have each visited St. John more times than their years, taking the journey in their stride, knowing the reward that awaits is well worth the effort.
My own love affair with St. John began during a college trip. Shortly after graduating, I traded my office job for a work-exchange program under the Caribbean sun. For six weeks, I worked as a housekeeper at an eco-resort, cleaning tents in exchange for accommodation, spending my free time exploring the island’s stunning beaches. Leaving after the program felt impossible. I found a job at the island’s newspaper, spending years writing about island life and enjoying weekends on beaches and boats.
Over two decades, my affection for St. John has deepened, especially as it has become a cherished escape for our own family. If you’re considering a trip to St. John, this guide offers an insider’s perspective on the best beaches, hikes, activities, and accommodations this Caribbean gem has to offer.
Turquoise waters and white sand of Trunk Bay, a world-renowned beach in St. John
Beaches: Discover a New Bay Each Day in St. John
Our family motto on St. John is simple: every day is beach day. St. John boasts an incredible number of stunning bays, more than you could possibly explore in a single trip. I always recommend starting with the pristine beaches along the island’s North Shore.
Trunk Bay, famous for its crescent of soft white sand and incredibly clear water, consistently ranks among the world’s top beaches. It’s undoubtedly St. John’s most popular and photographed beach. While it can get busier by mid-morning, arriving early or later in the day often rewards you with a more private experience. During the low season (late August to mid-November), you might even find yourself completely alone on its sands, regardless of the time.
Green sea turtle swimming in the clear waters of Maho Bay, St. John
Maho Bay, with its calm, shallow waters, is perfect for families with young children. It’s also the best spot on St. John for observing sea turtles. The seagrass beds just offshore provide a rich habitat for green sea turtles. You’ll likely see numerous turtles while swimming, but remember to maintain a respectful distance and never touch any marine life.
For a quieter beach experience, Francis Bay is just a short drive further down the road. This peaceful stretch of golden sand is the last beach on St. John’s North Shore. Its clear, glass-like water is ideal for swimming and snorkeling. Here, we often encounter sea turtles, schools of juvenile fish, and stingrays, and occasionally even octopus, starfish, baby blacktip reef sharks, and squid near the shore.
Secluded beauty of Gibney/Oppenheimer Beach, St. John
Gibney Beach, also known as Oppenheimer Beach, is a true hidden gem and our children’s absolute favorite. This secluded, sugar-sand beach, framed by lush sea grape trees and vibrant turquoise waters, is like stepping into a postcard. Parking is extremely limited at Gibney and Oppenheimer, ensuring that those fortunate enough to find a spot will enjoy a truly uncrowded beach experience.
Hiking Trails with Refreshing Rewards in St. John
Exploring the extensive network of trails within Virgin Islands National Park is a fantastic way to exercise while immersing yourself in the island’s history and natural beauty. A major bonus? Many of the best trails conclude with a refreshing dip at a nearby beach.
For a challenging hike, the 6-mile roundtrip Reef Bay Trail takes you through some of St. John’s oldest and tallest trees. A detour leads to ancient petroglyphs, carved between 900-1500 AD by the Taino people, and the ruins of the Reef Bay Sugar Mill, which operated until 1916. After your hike, cool off in the waves of the secluded Reef Bay on St. John’s south shore before the uphill return journey.
Panoramic views of Maho and Francis Bays from America Hill, St. John
The Cinnamon Bay Trail offers a glimpse into history, passing the remnants of the Cinnamon Bay Sugar Plantation before a short, steep climb to the America Hill Great House Ruins from the 19th century. The uphill path winds through a shaded forest of mango, genip, and guava berry trees. At the summit, you’re rewarded with stunning views of Maho and Francis Bays. Afterwards, relax and cool down at Cinnamon Bay, St. John’s longest beach.
The Lind Point Trail leads to Honeymoon Beach, starting near the National Park Visitor Center in Cruz Bay. This less than 2-mile round trip hike is manageable even for young children. Honeymoon and its neighboring beach, Salomon, are accessible only by foot or boat, making them more secluded, especially in the early morning before charter boats arrive.
Honeymoon Beach, a secluded paradise accessible by hiking in St. John
Venture to the quieter side of St. John and hike to the summit of Ram Head, the island’s southernmost point. Starting at tranquil Salt Pond Bay, the mile-long trail follows a rocky beach, steep inclines, and dramatic cliffs to reach panoramic 360-degree ocean views. Afterward, swim in the clear waters of Salt Pond Bay, or explore Drunk Bay, known for its beach art made from rocks and driftwood.
Luxurious and eco-friendly Calichi at Picture Point, St. John
Accommodation Options: Splitting Your Stay in St. John
St. John’s unspoiled beauty distinguishes it from many Caribbean islands marked by overdevelopment. Here, you’ll find a range of accommodations, from luxury boutique hotels and charming inns to spacious villas and Caribbean cottages. We prefer to divide our time between the two main areas of the island: Cruz Bay and Coral Bay.
Breathtaking view from Out of the Blue villa, St. John
On our recent trip, we returned for the third time to Calichi at Picture Point, an eco-luxury villa retreat perched high on Bordeaux Mountain, overlooking Coral Bay. From the Tower Villa, we enjoyed views of sailboats in the harbor and panoramic vistas of neighboring islands – St. Thomas, Puerto Rico, and Vieques to the west, Tortola and Jost Van Dyke to the north, and St. Croix to the south. For the other part of our stay, located just 10 minutes from Cruz Bay, we chose the expansive Out of the Blue villa, offering stunning views of Rendezvous Bay and Ditliff Point on St. John’s South Shore.
Island Roots Boat Charters for unforgettable sea adventures in St. John
Boating Adventures to the British Virgin Islands from St. John
A significant advantage of vacationing in St. John is its proximity to the British Virgin Islands (BVI). If your itinerary and budget allow, island hopping to the BVIs is a must-do. Private charters between the USVI and BVI are available, offering a premium experience.
We booked a full-day BVI private charter with Island Roots Charters, a local company known for personalized itineraries in the Virgin Islands. Captain Ryan met us at the National Park Dock in Cruz Bay, ready to take us on a luxurious 32-foot power catamaran. After customs in Tortola, we swam in the incredibly blue waters of Sandy Spit, a tiny uninhabited islet resembling a movie set. We then explored Tortola’s North Shore, stopping at Rogues Bay for wave jumping and rock climbing on a secluded beach.
Sandy Spit, a picturesque islet near Jost Van Dyke, BVI, accessible from St. John
Our main destination was The Baths at Virgin Gorda – colossal granite boulders creating natural grottos and pools. After lunch at Devil’s Bay, we snorkeled at The Indians, a group of islets teeming with marine life. We concluded our day with Painkiller cocktails at White Bay on Jost Van Dyke, a stunning white beach with turquoise water and lively beach bars, as the sun set. This boat trip was a highlight of our return to our beloved St. John, Caribbean.
