A Captain-Recommended Route Through St. Thomas & St. John

A week of sailing the U.S. Virgin Islands offers some of the most beautiful cruising grounds in the Caribbean. Calm turquoise waters, short sailing passages, and the protected shoreline of Virgin Islands National Park make this region ideal for both first-time charter guests and experienced sailors.

At Sail Makin’ Memories, we spend much of the season navigating these waters with guests aboard our luxury sailing charters. Over time, we’ve refined an itinerary that balances the best beaches, snorkeling spots, hidden anchorages, and island dining experiences the USVI has to offer.

This 7-day USVI sailing itinerary begins in St. Thomas and explores the breathtaking coastline of St. John, with a mix of adventure, relaxation, and quiet bays that feel like your own private paradise.

Day 1 — St. Thomas to Christmas Cove (Great St. James)

Your adventure begins with a short sail from St. Thomas to Christmas Cove, one of the most welcoming first stops in the islands.

This protected anchorage is famous for its calm water and vibrant marine life. Sea turtles glide through the grass beds, and the shallow reef makes snorkeling easy and enjoyable for all experience levels.

Spend the afternoon swimming, paddleboarding, or relaxing on the bow as the sun settles into the horizon.

For dinner, enjoy one of the most unique dining experiences in the Caribbean — Pizza Pi, the USVI’s floating pizzeria that delivers fresh, hot pizzas right to your boat.

It’s the perfect relaxed start to island life.

Day 2 — Christmas Cove to Caneel Bay (St. John)

Sailing north brings you into the stunning waters of Virgin Islands National Park, which protects nearly two-thirds of St. John.

Caneel Bay offers crystal-clear water and powder-soft sand — an idyllic setting for swimming, paddleboarding, or snorkeling along the shoreline.

Guests often enjoy exploring nearby hiking trails or visiting historic ruins that reflect the island’s colonial past.

If you’d like a lively evening, it’s a quick dinghy ride or taxi into Cruz Bay, where you'll find some of the best restaurants and beach bars in the Virgin Islands.

After dinner, returning to the quiet anchorage at Caneel Bay offers the perfect contrast — calm water, warm breezes, and a peaceful night aboard.

Day 3 — Exploring St. John’s North Shore

(Trunk Bay, Cinnamon Bay & Maho Bay)

St. John’s north shore is widely considered one of the most beautiful coastlines in the Caribbean.

Each bay has its own unique character:

• Trunk Bay: Known for its famous underwater snorkeling trail and postcard-perfect views.

• Cinnamon Bay: A wide stretch of beach ideal for swimming, paddleboarding, and long walks along the shore.

• Maho Bay: One of the best places in the Virgin Islands to swim with sea turtles. The shallow seagrass beds attract turtles year-round.

• Nearby, Maho Crossroads offers a fun beach-side hangout with drinks, snacks, live music, and local shopping.

With calm water and dramatic green hillsides meeting the sea, this stretch of coastline represents the USVI at its most breathtaking.

Day 4 — Leinster Bay & Waterlemon Cay

Tucked into the northeast corner of St. John, Leinster Bay is a favorite stop for experienced sailors and locals alike.

From here, a short swim or dinghy ride takes you to Waterlemon Cay, where drift snorkeling reveals thriving coral reefs, rays, starfish, and colorful reef fish.

On land, guests can explore the nearby Annaberg Sugar Plantation ruins, offering a glimpse into the island’s colonial history.

For one of the most memorable moments of the trip, take a sunset hike to the Windy Hill Greathouse ruins. The panoramic views over the bay are spectacular and provide an unforgettable vantage point of the surrounding islands.

Day 5 — Coral Bay to Salt Pond Bay

Next, sail toward the quieter and more rugged eastern side of St. John.

Before leaving Coral Bay, many guests stop at Lime Out, the famous floating taco bar known for its creative tacos and laid-back Caribbean atmosphere.

From there, continue to Salt Pond Bay, a peaceful anchorage surrounded by dramatic cliffs and rolling hills.

Adventurous guests often hike to Ram Head, where sweeping views stretch across the Caribbean Sea. The reward for the hike is well worth it.

At night, Salt Pond Bay offers one of the darkest and most peaceful anchorages in the USVI, making it perfect for stargazing from the deck.

Day 6 — Little Lameshur Bay

For those seeking true tranquility, Little Lameshur Bay is one of St. John’s hidden gems.

Protected by surrounding hills and rarely crowded, this anchorage offers excellent snorkeling with vibrant coral reefs and abundant marine life.

From the beach, guests can take the scenic hike to the Reef Bay Petroglyphs, where ancient carvings created by the Taino people sit beside a freshwater pool and seasonal waterfall.

Along the shoreline, historic stone ruins provide a fascinating reminder of the island’s past.

Little Lameshur offers a rare combination of natural beauty, history, and peaceful seclusion — the perfect place to savor your final full day in the islands.

Day 7 — Return to St. Thomas

Enjoy a relaxed morning swim or paddleboard session before beginning the sail back to St. Thomas.

The return journey offers one last opportunity to take in the vibrant blue water and dramatic coastline that make the Virgin Islands one of the world’s premier sailing destinations.

By the time you arrive back at the marina, you’ll have experienced a week filled with unforgettable views, hidden beaches, and moments that define the magic of sailing the Caribbean.

Why This USVI Sailing Itinerary Works So Well

This route has become one of our favorites because it combines:

• Short, easy sailing legs

• Protected waters ideal for all experience levels

• World-class snorkeling and marine life

• A blend of lively beach stops and secluded anchorages

• Easy access to hiking, history, and island dining

It’s the perfect balance of adventure, relaxation, and authentic Caribbean exploration.

Plan Your USVI Sailing Charter

If this itinerary has you dreaming about turquoise water, sea turtles, and sunset anchorages, we’d love to welcome you aboard Makin’ Memories.

Our charters are designed to provide a personalized sailing experience through the Virgin Islands, combining local knowledge, boutique hospitality, and carefully curated destinations that most visitors never discover on their own.

Whether you're planning a family vacation, a couples getaway, or a celebration with friends, we’ll help craft a sailing adventure that fits your travel style.

Start planning your Virgin Islands sailing charter today.

👉 Visit our inquiry page to begin designing your unforgettable week in the Caribbean.