Plan a Trip to St. John: Four-Day Outdoor Itinerary

Nearly every bit of shoreline on St. John is either a sunny white-sand beach, a snorkeling spot brimming with schools of colorful fish — or both. Small towns lined with Danish colonial architecture offer plenty of places to eat Caribbean cuisine, sip traditional drinks, dance to vibrant live music plus shop at boutiques and buy a perfect souvenir from your adventures. Follow this fun-filled four-day itinerary to plan a trip to St. John.

Day 1 in St. John

Get a sense of your surroundings by spending your first day strolling colorful downtown villages, shopping in unique boutiques and eating some local fare.

Morning

Hop aboard the 45-minute, air-conditioned ferry from St. Thomas to St. John, docking in Cruz Bay. Spend a bit of time wandering around. Perch at an open-air bar, sip a freshly brewed coffee, and watch locals and visitors go about their day at a relaxed island pace.

While in Cruz Bay, admire the mosaic of stone walls and shaded courtyards in Mongoose Junction. In its collection of stores you’ll find lots of local galleries filled with arts and crafts. Made in St. John sells clothing designed and screen-printed on the island. The St. John Experience Gallery showcases large prints of local landmarks and lush landscapes.

Afternoon

Break for lunch at The Tap Room on Mongoose Junction’s second floor, where you can sample St. John Brewers‘ craft beers — with names like Tropical Mango Pale Ale  and Cruz Bay Session IPA — plus sweet craft sodas made on-site to go with your burger, garlic cheesy bread or a seared mahi sandwich.

After lunch, get more retail therapy at the shops in Wharfside Village on the Cruz Bay waterfront, including several stores specializing in handmade jewelry and gifts. Pink Papaya displays island-inspired art of St. John resident Lisa Etre, in addition to other artists and craftspeople.

Evening

Dine at The Lime Inn, the land-based outpost of floating Coral Bay taco shack Lime Out. Try the Cowabunga taco, stuffed with slow-braised short ribs, blackened shrimp and feta cheese, alongside a craft cocktail with hand-squeezed juice.

After dinner when the stars emerge, it’s time for the day’s main outdoor event: a Night Kayak GLOW Tour. Departing from The Westin St. John Resort Villa near Cruz Bay, this guided paddle takes you through the bay in clear-bottom kayaks outfitted with underwater LED lights. As you move through the water, watch it come alive with tarpons and sting rays moving gracefully beneath you.

Day 2 in St. John

Devote your second day to reveling in the quiet beauty of one or more of our island’s stunning North Shore beaches. You can easily begin your explorations of St. John’s coastal wonders within a few minutes of town.

Morning

You’ll soon discover why Trunk Bay has a permanent spot on any list of the world’s most beautiful beaches. Bask in the sun and float in the warm, clear water. Then, don snorkel gear and follow the sea-bottom markers on the Trunk Bay Underwater Snorkel Trail. Bob along, reading the signs along the trail to learn interesting facts about the reef and its resident sea life.

Afternoon

Refuel with lunch at the Rain Tree Cafe at Cinnamon Bay Beach & Campground, just a few minutes up the road. Then, explore the island’s history on an easy, shaded half-mile walk through 18th-century plantation ruins. Afterward, return to Cruz Bay and get pampered with a massage at Mango Bliss Spa, one of the top-rated spas on St. John.

Evening

Dine on French-inspired dishes that make the most of fresh local seafood at The Terrace Restaurant overlooking the boats moored in Cruz Bay. A standout is the seared yellowfin tuna with fingerling potatoes, roasted-red-pepper confit and a nicoise olive vinaigrette. Then wind down — or up — with drinks and casino-style gaming at the Parrot Club, located in Wharfside Village on the water in Cruz Bay.

Day 3 in St. John

Feel the wind in your hair, hear the waves lapping at the bow and watch the islands slowly pass by. Spend the day enjoying a sail and follow it up with a sumptuous dinner.

Morning

Sail in St. John’s balmy trade winds, with stops to snorkel in azure waters among swirling schools of sergeant majors and parrotfish. Outfitters like Seas the Day Charters & Tours and Dream Yacht Worldwide host guided adventures that stop at stunning snorkeling spots and dreamy beaches.

Afternoon

After cruising around on the water, dock and visit Lime Out VI — a floating bar and taco stand in Coral Bay where your feet dip in the ocean while you dine — for lunch and drinks. The name refers to both its bright-green color scheme and the island slang “to lime” — meaning to chill and hang out.

Evening

Enjoy an early dinner at Ocean 362, an airy terrace just above Cruz Bay at Gallows Point Resort. The third-story bar has panoramic views of the bright, cotton candy-colored sunset over the horizon, with tiny cays and St. Thomas in the distance. Watch the glittering lights of St. Thomas appear as daylight fades.

Day 4 in St. John

Spend your final day exploring St. John history and taking a drive through the island’s lush interior in Virgin Islands National Park.

Morning

Drive out to North Shore Road, keeping an eye out for roaming wild donkeys and picture-perfect ocean vistas. If your route includes Centerline Road, stop for fresh fruit drinks at Colombo’s Smoothies, a roadside stand.

Read informational signs at the Annaberg Sugar Plantation ruins and learn how sugar was produced back in the 17th century when wind and animals were the main sources of power for the sugarcane mills. Take photos of picturesque Leinster Bay and pint-size Waterlemon Cay to share with your friends back home.

Afternoon

Before boarding the ferry to St. Thomas to catch your flight home, lunch on Baja fish tacos or a jerk mahi-mahi sandwich at Cruz Bay Landing, a short walk across Powell Park near the ferry dock.

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