St Thomas Itineraries: Day Charters and Multi-Day Routes

Charlotte Amalie to Magens Bay and Caneel Bay

Board at Yacht Haven Grande by mid-morning. Cruise north to Magens Bay for a morning swim and snorkel on the famous heart-shaped beach. Your chef serves lunch on the aft deck as the yacht repositions east across Pillsbury Sound to St John (15 minutes). Pick up a mooring at Caneel Bay – a sheltered anchorage on St John’s western shore with seven pristine beaches spread across a 170-acre peninsula. Swim ashore for an afternoon walk through the Caneel Bay ruins and surrounding Virgin Islands National Park trails. Dinner on board – the chef serves Caribbean lobster and coconut rice as the sunset paints the western sky.

Trunk Bay and Hawksnest Bay

A short morning reposition brings you to Trunk Bay – arguably the most famous beach in the Caribbean. Snorkel the underwater trail (225 metres of marked path through coral gardens), swim in the turquoise shallows, and spend a lazy morning on the white sand. After lunch, cruise a few minutes west to Hawksnest Bay for a quieter afternoon. This smaller beach offers calm water, good snorkelling along the rocky headlands, and a secluded feel with far fewer visitors. Anchor overnight in Hawksnest – your chef prepares a gourmet barbecue on the aft deck as the stars appear over St John’s dark, unpolluted skies.

Maho Bay, Francis Bay and Return to St Thomas

Cruise to Maho Bay for an early-morning turtle encounter. Green sea turtles graze in the shallows here almost every morning – wade in quietly and they’ll be within arm’s reach. After brunch on board, reposition to Francis Bay on St John’s north-west shore – one of the quietest and most protected anchorages on the island, with a sandy beach backed by salt ponds where migrating birds gather. Afternoon swimming and paddleboarding in the calm, crystal water. Depart Francis Bay in the mid-afternoon for the 30-minute crossing back to St Thomas, arriving at Yacht Haven Grande in time for a final stroll through Charlotte Amalie or a farewell dinner at The Old Stone Farmhouse.

Charlotte Amalie to Sapphire Beach and Lindquist Beach

Depart Yacht Haven Grande and cruise east along St Thomas’s south coast, rounding the island’s eastern end to Sapphire Beach (roughly 8 nautical miles, 30 minutes). This sandy beach on the island’s east end offers good snorkelling, soft sand and a beach bar with cold drinks and Caribbean plates. After lunch, continue to Lindquist Beach (Smith Bay Park) – widely considered St Thomas’s most beautiful east-end beach, quieter than Magens Bay with excellent reef snorkelling along the rocky headlands. Anchor overnight in the sheltered waters off Lindquist.

Christmas Cove and Lovango Cay

Cruise south to Christmas Cove on Great St James Island for a morning snorkel and a floating-pizza lunch at Pizza Pi. In the early afternoon, head north across Pillsbury Sound to Lovango Cay – a small island between St Thomas and St John that has been developed into a chic resort and restaurant destination. Tender ashore for a craft cocktail and a tour of the eco-conscious property, or simply anchor off the cay’s western side for a quiet afternoon swim. Overnight at Lovango or cross the short distance to Cruz Bay, St John, for dinner ashore at Morgan’s Mango (neo-Caribbean cuisine in a tropical courtyard) or Woody’s Seafood Saloon (famous fish tacos in the heart of town).

Round Bay, Hurricane Hole and Coral Bay, St John

Cruise south along St John’s east coast to Round Bay and the narrow entrance to Hurricane Hole – a network of mangrove-fringed inlets within the Virgin Islands Coral Reef National Monument. This is one of the most unusual snorkelling experiences in the USVI: the mangrove roots are encrusted with vibrant corals, sponges and anemones, and the shallow channels are home to juvenile fish, rays and upside-down jellyfish. After a morning exploring by kayak and snorkel, continue south to Coral Bay – St John’s quieter, more bohemian settlement on the eastern shore. Anchor in the wide bay and tender ashore for lunch at Skinny Legs (a beloved bar and grill, famous for its burgers and its zero-pretension atmosphere). Afternoon watersports in the bay’s calm water.

Salt Pond Bay, Ram Head Trail and Return to St Thomas

An early cruise to Salt Pond Bay on St John’s southern tip delivers one of the island’s best-kept secrets: a sheltered bay with superb snorkelling (nurse sharks, turtles, rays in the shallows) and a trailhead for the Ram Head hike – a 45-minute coastal walk through cactus scrub to a dramatic rocky headland 200 feet above the Caribbean, with panoramic views across to St Croix on a clear day. After the hike and a swim, your chef serves a farewell brunch on the aft deck. Cruise back across Pillsbury Sound to St Thomas (roughly 40 minutes from St John’s south coast), arriving at Yacht Haven Grande by mid-afternoon.

Guests looking for a longer voyage can combine the 3-day western route (Magens Bay, Caneel Bay, Trunk Bay, Maho Bay, Francis Bay) with the 4-day eastern route (Sapphire Beach, Christmas Cove, Lovango Cay, Hurricane Hole, Coral Bay, Salt Pond Bay) for a comprehensive 7-day charter that covers both St Thomas and the entirety of St John without repeating a single anchorage.