St. John: Private Island Safari Tour with Local Guide & Pickup

Summary

Open-air island drive, local stories and quiet bays on St. John

You’ll ride an open-air safari truck around St. John with a local guide who shares real stories—not just facts—while you stop at places like Trunk Bay overlook, Annaberg Sugar Plantation, and Maho Bay. Expect laughter, ocean breezes, photo stops, and plenty of chances to ask questions or just take it all in.

What’s the experience like?

We rolled away from the Loredon Boynes Ferry Terminal in this bright open-air safari truck—every seat had a view, which was lucky because the first thing I noticed was just how green everything looked after that salty ferry ride. Our guide, Marcus, waved at someone every few minutes (I think he knew half the island) and pointed out Caneel Bay before I’d even gotten my camera out. He had this way of telling stories—sometimes pausing to let us actually look, not just listen. The air smelled faintly of sea grape and sunscreen, which is probably how I’ll remember St. John.

I didn’t expect to laugh so much on a day trip St. John private tour—Marcus teased me for mispronouncing “Annaberg” (I tried), but then he handed me a cold bottle of water and told us about his childhood running around those same ruins. We stopped at overlooks above Trunk Bay and Hawksnest Bay—honestly, photos don’t do it justice; there’s this weird hush when you see all that blue from above. Kids from our group kept leaning over the railings, trying to spot turtles in Maho Bay below.

At Annaberg Sugar Plantation, the stones felt warm under my hand and you could see Tortola hazy in the distance—British Virgin Islands just sitting there like it’s no big deal. The breeze picked up as we walked Reef Bay Trail for a bit; I’m not much of a hiker but even that short stroll made me wish we had more time here. We ended looking down at Coral Bay Harbor, everyone kind of quiet for a minute except for one guy who realized he left his hat behind (Marcus doubled back for him). So yeah—two and a half hours went fast.

Step-by-step itinerary

Day 1 — St. John Island Tour Highlights

• Depart from Loredon Boynes Ferry Terminal
• View Caneel Bay Resort and nearby beaches
• Pass by Hawksnest Beach local hangout
• Stop for photo of multiple beaches from above
• Pass by a smaller St. John beach
• Stop at Trunk Bay overlook for views
• Relax at Cinnamon Bay Beach
• Pass by Maho Bay tourist spot
• Visit Annaberg Sugar Plantation ruins
• Enjoy view of Coral Bay Harbor and British Islands
• Pass by Reef Bay Trail to Petroglyphs

Top questions

How long is the private island tour on St. John?

The tour lasts approximately two and a half hours.

Does the tour include hotel pickup?

Yes, hotel pickup and drop-off are included for selected hotels only.

Where does the tour start?

The tour departs from Loredon Boynes Ferry Terminal on St. John.

Is this a private tour or shared with others?

This is a private tour just for you and your party.

Are drinks provided during the tour?

Complimentary soft drinks and bottled water are included throughout the island tour.

What attractions are visited during the tour?

You’ll see Caneel Bay, Hawksnest Bay, Trunk Bay overlook, Cinnamon Bay, Maho Bay, Annaberg Sugar Plantation, Coral Bay Harbor view, and part of Reef Bay Trail.

Is this tour suitable for children or people with limited mobility?

The tour is suitable for all fitness levels; infants can ride in laps or strollers and collapsible wheelchairs can be accommodated with assistance.

Can cruise ship passengers join this tour?

Cruise ship passengers can join but must provide ship details when booking.

What’s included

Your day includes pickup from selected hotels or meeting at the ferry terminal in Cruz Bay; an open-air safari ride with window seats for everyone; guidance by a native St. Johnian who shares personal stories along each stop; complimentary bottled water and soft drinks; plus time to explore historic sites like Annaberg Sugar Plantation before returning to your starting point.