St John Itineraries: Day Charters and Multi-Day Routes

St John’s compact coastline and abundance of mooring buoys make it ideal for both day charters and multi-day explorations. The 3-day and 4-day itineraries below cover different stretches of coast and can be combined into a 7-day voyage that circles the entire island without repeating a single anchorage. Day charter routes offer standalone outings from Cruz Bay, the most common arrival point. Every itinerary is fully customisable – your captain reads the wind and swell each morning and adjusts accordingly.

Day Charter Routes from Cruz Bay

Cruz Bay to Trunk Bay and Hawksnest Bay: The Beach Day

Depart Cruz Bay mid-morning and cruise east along St John’s north shore to Trunk Bay (2 nautical miles, 10 minutes). Pick up a mooring buoy and swim ashore to the famous crescent of white sand. Spend the morning on the underwater snorkel trail – 225 metres of marked path through coral gardens, with informational plaques identifying brain coral, sea fans and parrotfish. After a chef’s lunch on the aft deck, reposition a few minutes west to Hawksnest Bay for a quieter afternoon: good snorkelling along the rocky headlands, calm water, and a fraction of the visitors. Return to Cruz Bay for sundowners at a waterfront bar. Duration: 7–9 hours.

Cruz Bay to Caneel Bay and Honeymoon Beach: The Heritage Route

Cruise the short distance north from Cruz Bay to Caneel Bay (1 nautical mile, 5 minutes). Pick up a mooring and tender ashore to explore the 170-acre peninsula – seven beaches, the ruins of Laurance Rockefeller’s former resort, and trails through the Virgin Islands National Park. Honeymoon Beach (within the Caneel Bay property) is a quiet crescent of sand with a small beach bar. Snorkel the reef at the bay’s western edge, then enjoy lunch on board. Afternoon swimming, paddleboarding and exploring. Duration: 6–8 hours.

Cruz Bay to Maho Bay and Francis Bay: The Turtle Run

Head east from Cruz Bay to Maho Bay (4 nautical miles, 15 minutes) for a morning swimming with green sea turtles in the calm shallows. The turtles graze on the seagrass beds daily and are remarkably unfazed by snorkellers. After brunch on board, cruise a short distance west to Francis Bay – one of St John’s quietest anchorages, with a sandy beach, a salt pond popular with birdwatchers, and good snorkelling along the western headland. Return to Cruz Bay in the late afternoon. Duration: 7–8 hours.

3-Day St John Yacht Charter Itinerary: The North Shore and National Park

Day 1: 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.

Day 2: 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.

Day 3: 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.

4-Day St John Yacht Charter Itinerary: East Coast, Coral Bay and the Southern Shore

Day 1: 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.

Day 2: 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.

Day 3: 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.

Day 4: 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.