St John USVI
Family Vacation - Sample Flow Itinerary
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Arrival Day
Arrival & Settling In
DAY 1 — Arrival & Settling In
Your arrival experience is personalized to align with your flight schedule. Upon landing in St. Thomas, your transfer will be arranged to coincide with the most convenient ferry option based on your arrival time.
Once you arrive in St. John, your villa will be fully prepared with pre-arrival provisioning, ensuring all your essentials are ready and waiting.
Spend your evening unwinding and embracing island life with a casual dinner in Cruz Bay or a relaxed meal in the comfort of your villa.
The Perfect Day
North Shore Beaches & Iconic Sunset
Begin your St. John experience with two of the island’s most beautiful beaches: Trunk Bay and Cinnamon Bay.
If you’re feeling energized, an optional Caneel Hill hike offers sweeping views over the North Shore.
In the evening, enjoy sunset and live music at The Windmill Bar — a local favorite with panoramic views and the occasional Kenny Chesney sighting.
Dinner tonight can be a simple grill‑out at the villa or casual dining in Cruz Bay.
Say next when you’re ready for Day 3.
Island Rhythm
Turtles, Calm Water & Island Rhythm
Spend the morning at Maho Bay, renowned for its tranquil waters and frequent sea turtle sightings.
In the afternoon, head to Hawksnest Beach for a peaceful swim in a serene setting.
For a more refined beach experience, the Caneel Bay Beach Club is available as an optional serviced beach day.
In the evening, enjoy the option of live music in Cruz Bay to conclude your day.
Coral Bay & the East End
Discover the East End
Today, you will discover the quieter, more authentic side of the island.
Explore Salt Pond Bay and the rugged coastline of Drunk Bay, with the option to hike Ram Head for breathtaking panoramic views.
Enjoy lunch at Skinny Legs, a beloved Coral Bay establishment, followed by a relaxed dinner on the island’s east side.
Private Boat Day (USVI or BVI)
Explore
A full day on the water is often the highlight of a St. John trip. Your private charter will be customized to suit your preferences and comfort level—whether that means snorkeling at Waterlemon Cay or exploring secluded coves and vibrant reefs.
Lunch options include Lime Out, the floating taco bar, or Pizza Pi in Christmas Cove.
If you choose to visit the British Virgin Islands, a stop at the iconic Soggy Dollar Bar on Jost Van Dyke provides an authentic island experience.
Cruz Bay
Cruz Bay
Enjoy a leisurely morning at the villa or choose a beach that suits your mood for some relaxation.
In the afternoon, explore Cruz Bay’s charming boutiques, cafés, and local shops. Later, unwind at Honeymoon Beach by lounging in the chairs, swimming in the calm waters, or trying optional watersports.
End your day with dinner in Cruz Bay, with the option to experience live music at Beach Bar or The Windmill Bar for a vibrant island atmosphere.
Reef Bay
Reef Bay Trail & Final Beach Afternoon
Reef Bay Trail & Final Beach Afternoon
Begin the day with the Reef Bay Trail, one of the island’s most scenic hikes, featuring petroglyphs and historic sugar mill ruins.
After the hike, unwind at Gibney or Francis Bay — two of St. John’s most peaceful and picturesque beaches.
Your final evening includes an elevated dinner to celebrate your week on the island and soak in one last Caribbean sunset.
