Hiking

Peace Hill Easiest hike, best reward

Short and sweet — this is less than a quarter mile, but the payoff is spectacular. A quick uphill walk takes you to a beautiful old sugar mill windmill ruin set on a grassy hilltop, with sweeping views of Hawksnest Bay, Denis Bay, and Trunk Bay stretching out below you. You can also spot Jost Van Dyke and Tortola on the horizon. I bring every visitor here. It takes 15 minutes and feels like you've discovered something secret.

Heads up: Wild donkeys roam freely near the top. They're harmless — and very charming.

Caneel Hill Go for the views, earn them with a real hike

This one requires some effort — 2.4 miles and a serious climb to 719 feet — but the panoramic views of Cruz Bay and the surrounding islands from the top are absolutely worth it. Continue up to Margaret Hill (848 ft) for an even broader view. Start early in the morning when it's cooler, bring plenty of water, and wear real shoes. The trail connects Cruz Bay with North Shore Road and can be done as a loop.

Good to know: Moderate to difficult. Best in the early morning before it gets hot.

Cinnamon Bay Trail History and nature all in one

This trail begins right across from Cinnamon Bay Campground and follows an old Danish plantation road uphill through lush tropical forest. Along the way you'll pass through genuine sugar plantation ruins — the horse mill, the boiling house, stone columns — all reclaimed by jungle. It's a beautiful, shaded walk with real historical depth. At about a mile up, it connects to Centerline Road. You can make it a full loop by combining it with the American Hill Trail for extraordinary views over Maho Bay.

Get out on the water

Either BVI or beach hopping on the best spots.

The British Virgin Islands are just across the channel, and spending a day island hopping over there is one of the best things you can do from St. John. There are two ways to go.

Boat Charter to the BVI ⭐ Highly Recommended

For a full BVI day, I always recommend On The Sea Charters ask for Ryan and please mention Kelly sent you. They do private and group day trips out to some of the most beautiful water in the Caribbean: Virgin Gorda, The Baths, Norman Island, Willy T's floating bar, Cooper Island, and Jost Van Dyke. The boat will hit multiple stops, or if you just want Jost, that's possible too (though a private trip just for one stop can get pricey).

📞 Ryan: 850-339-8113 | ontheseacharters.com

For sailing, Dulce Vita Sails offers beautiful catamaran charters, a more relaxed, scenic way to get on the water. 🌐 dulcevitasails.com

And if fishing is your thing: Just Fish, they know these waters. 📞 340-201-9329 ask for Danny.

Ferry to Jost Van Dyke For a taste of the BVI without booking a charter.

There is a public ferry that runs Tuesday, Friday, and Sunday, departing St. John at 8am, returning from Jost at 3:30pm. The ride takes about 35 minutes and drops you into one of the most laid-back, beautiful spots in the Caribbean. Spend the day at White Bay, grab a Painkiller at the Soggy Dollar Bar, and wander.

Note: A passport or passport card is required. this is a different country. 🔗 Book the ferry here

Getting to Anegada A trek, but worth every minute

Anegada is not easy to get to and that's part of why it's so special. You can take a fast boat if the water is calm (about 1.5 hours), or catch one of the infrequent ferries (which take closer to 2.5 hours). It's a remote, flat coral island with world-class lobster, pink flamingos, and beaches that look untouched. Not a day trip kind of place, worth planning ahead for. 🔗 BVI Ferry Schedules