St John Itineraries: Day Charters and Multi-Day Routes

Cruz Bay to Caneel Bay and Trunk Bay

Board your yacht at Cruz Bay by mid-morning. Pick up a mooring at Caneel Bay for a mid-morning swim on Honeymoon Beach and a hike through the national park trails on the peninsula. Your chef serves lunch on the aft deck as the yacht repositions east to Trunk Bay. Spend the afternoon on the famous beach and underwater snorkel trail. Anchor overnight at Trunk Bay or the nearby Cinnamon Bay – a wider beach with a campground ashore and a reef snorkel along the eastern headland. Dinner on board under a sky full of stars.

Maho Bay and Leinster Bay

An early cruise to Maho Bay for the morning turtle encounter. Green sea turtles graze in the shallows daily – wade in quietly and they’ll be within arm’s reach. After brunch, cruise east to Leinster Bay and the Waterlemon Cay snorkel – widely considered one of the finest reef snorkels in the Caribbean. Circle the small cay through a fringing reef teeming with eagle rays, stingrays, barracuda, angelfish and nurse sharks. In the afternoon, hike the short trail from Leinster Bay to the Annaberg Sugar Plantation ruins – an 18th-century Danish plantation with stone windmill towers, slave quarters and sugar-boiling works overlooking the bay and the BVI islands beyond. Anchor overnight in Francis Bay, the quietest anchorage on St John’s north shore.

Francis Bay and Return to Cruz Bay

A lazy morning at Francis Bay: swim ashore, walk the Mary Creek Trail through the salt pond, and birdwatch along the shore. After a chef’s brunch on the aft deck, cruise west along the north shore, pausing at Hawksnest Bay for a final snorkel along the rocky headlands. Return to Cruz Bay by mid-afternoon with time for a stroll through the village, a last rum punch at a waterfront bar, or the short ferry ride back to St Thomas.

Cruz Bay to Round Bay and Hurricane Hole

Depart Cruz Bay and cruise south, then east around St John’s southern tip to Round Bay (roughly 6 nautical miles, 30 minutes). Enter the narrow passage into Hurricane Hole – a network of mangrove-fringed inlets within the Virgin Islands Coral Reef National Monument. Kayak and snorkel through the shallow channels where mangrove roots are encrusted with vibrant corals, sponges and anemones – a phenomenon found in very few places on earth. Juvenile fish, rays and upside-down jellyfish inhabit the warm, sheltered water. Anchor in Round Bay for a chef’s lunch, then continue to Coral Bay for an afternoon ashore: cold beer and a burger at Skinny Legs, followed by a stroll through St John’s quieter eastern settlement.

Coral Bay to Salt Pond Bay and Ram Head

Cruise south from Coral Bay to Salt Pond Bay (2 nautical miles, 10 minutes). Pick up a mooring and swim ashore to a beach that is one of St John’s best-kept secrets: calm water, excellent snorkelling (nurse sharks, turtles, stingrays in the shallows) and the trailhead for the Ram Head hike. The 45-minute coastal walk through cactus scrub leads to a dramatic rocky headland 200 feet above the Caribbean, with panoramic views across to St Croix and the open sea. Return to the yacht for a late lunch, then reposition to nearby Lameshur Bay – a remote anchorage on St John’s south coast with exceptionally clear water and trails leading to the Yawzi Point viewpoint.

Lameshur Bay to Reef Bay and Privateer Bay

Cruise west along the south coast to Reef Bay (3 nautical miles). The Reef Bay Trail – one of St John’s most popular hikes – descends from the Centerline Road to the bay through dense tropical forest, passing plantation ruins and pre-Columbian Taino petroglyphs carved into streambed rocks. Your captain arranges to meet you at the bay after the hike (a wonderful way to experience the trail without retracing your steps). After a swim and a chef’s lunch, continue west and south to Privateer Bay or Haulover Bay on the island’s eastern tip – secluded anchorages with clear water, rocky snorkelling, and a genuine sense of Caribbean seclusion.

Privateer Bay to Lovango Cay and Return to Cruz Bay

An early morning snorkel at Privateer Bay’s reef, followed by a farewell brunch on the aft deck. Cruise north-west along St John’s east coast, passing Brown Bay (a secluded north-east cove) and rounding the island’s northern tip. Stop at Lovango Cay for a late-morning cocktail at the stylish resort, or anchor off the cay’s western side for a final swim. Continue to Cruz Bay by early afternoon, with time for a last wander through the village, a farewell drink overlooking the harbour, or the short crossing back to St Thomas.

Guests looking for a longer voyage can combine the 3-day north-shore route (Caneel Bay, Trunk Bay, Maho Bay, Leinster Bay, Francis Bay) with the 4-day eastern and southern route (Hurricane Hole, Coral Bay, Salt Pond Bay, Lameshur Bay, Reef Bay, Privateer Bay) for a comprehensive 7-day St John charter that circles the entire island without repeating a single anchorage.