Bermuda Itineraries: Day Charters and Multi-Day Routes

Bermuda’s compact archipelago – just 22.5 kilometres from end to end – makes it ideal for both single-day outings and multi-day voyages that cover the full spectrum of the island’s beaches, wrecks, harbours and cultural landmarks. The itineraries below are designed to be combined: a guest booking the 3-day and 4-day routes can stitch them together into a comprehensive 7-day charter without repeating a single anchorage. Every itinerary is fully customisable – your Boatcrowd charter specialist and onboard captain will tailor stops, pacing and activities to your group’s interests and the conditions on the day.

Day Charter Routes

South Shore Pink-Sand Beaches

Depart Hamilton Harbour or the Royal Naval Dockyard mid-morning and cruise south to Horseshoe Bay – roughly three nautical miles from Hamilton, a gentle 15-minute run. Anchor in 8–12 metres over sand and tender ashore for a morning swim on Bermuda’s most famous pink-sand beach, with shallow reef snorkelling just offshore. Your chef serves lunch on the aft deck as the yacht repositions to Warwick Long Bay – 800 metres of quieter, equally beautiful pink sand. In the afternoon, continue east to Church Bay for the best shallow-water snorkelling on the island: coral heads rising within metres of the beach, parrotfish, angelfish and the occasional sea turtle. Return to harbour in the golden late-afternoon light.

Wreck Diving: Cristobal Colón and the Mary Celestia

Head north from Hamilton to the Cristobal Colón wreck site – roughly 20 minutes. Spend the morning exploring this 152-metre Spanish luxury liner in five to 18 metres of water: engines, propellers, turbines and a vast coral-encrusted debris field alive with reef fish. Your chef serves lunch on the aft deck while the yacht repositions to the south shore. In the afternoon, dive or snorkel the Mary Celestia – a Civil War blockade runner sitting upright in 17 metres, with both paddle wheels and boilers clearly visible. Surface to sundowners as the yacht cruises back to Hamilton.

St George’s Heritage and Tobacco Bay

Cruise east from Hamilton to St George’s Harbour – eight nautical miles, roughly 30 minutes. Drop anchor in Convict Bay (five metres, excellent holding) and tender ashore to explore the oldest English settlement in the Americas. Walk the cobblestone streets, visit St Peter’s Church (1612), browse the Globe Museum and take in the colonial architecture. After lunch at Wahoo’s Bistro (the island’s signature fish chowder), tender to nearby Tobacco Bay for an afternoon snorkel in the calm, rock-pool waters. Return to Hamilton via the north shore, passing Fort St Catherine and the eastern wreck sites.

Multi-Day Itineraries

3-Day Bermuda Yacht Charter Itinerary: South Shore and Wrecks

Day 1: Hamilton, Horseshoe Bay and Warwick Long Bay

Board your yacht at Hamilton Harbour or the Royal Bermuda Yacht Club by mid-morning. After a welcome briefing and champagne toast on the flybridge, cruise south to Horseshoe Bay for a late-morning swim on Bermuda’s most iconic pink-sand beach. Your chef lays out lunch on the aft deck – fresh fish, tropical salad and chilled rosé – as the yacht repositions to Warwick Long Bay for an afternoon of swimming and paddleboarding on 800 metres of quieter pink sand. As the sun drops, cruise back towards Hamilton for dinner ashore at the Waterlot Inn – Bermuda’s premier steakhouse, operating for nearly 350 years.

Day 2: Cristobal Colón, Church Bay and Elbow Beach

Depart early and cruise north to the Cristobal Colón wreck – the morning light filtering through the water creates the best visibility for exploring this 152-metre hull. Spend two hours on the wreck, then cruise south to Church Bay for a late-morning snorkel over the shallow reef – coral heads, parrotfish, blue angelfish and the occasional sea turtle just metres from shore. Your crew anchors for a long, lazy lunch on the aft deck. In the late afternoon, cruise to Elbow Beach for a final swim in calm, sheltered water, then return to Hamilton for the evening. Dinner at Blue by Eric Ripert at the Ritz-Carlton – tasting menu and a 700-label wine list.

Day 3: Mary Celestia, South Shore and Farewell

Rise early for a swim from the yacht, then cruise to the Mary Celestia wreck on the south shore for a morning dive or snorkel over this Civil War blockade runner in 17 metres. Both paddle wheels, the bow, stern and boilers are clearly visible – a piece of living history beneath the waves. Continue east along the south shore, stopping at a quiet pink-sand cove for a farewell picnic. Your chef prepares a final lunch on the aft deck as the yacht cruises back to Hamilton, passing the gentle limestone cliffs and turquoise water that make this coastline unforgettable. Return to harbour by mid-afternoon.

4-Day Bermuda Yacht Charter Itinerary: Full Island Circuit

Day 1: Royal Naval Dockyard and the Western Reefs

Board your yacht at Pier 41 Marina in the Royal Naval Dockyard. Spend the morning exploring the 19th-century fortress: the National Museum of Bermuda (gold bars and jewellery from century-old shipwrecks), the Clocktower Mall and Snorkel Park Beach. After lunch aboard, cruise east along the north shore to a sheltered anchorage near Fort Scaur – one of Bermuda’s most beautiful and private spots, flanked by high, wooded cliffs and sheltered from the prevailing breeze. Snorkel the nearshore reef in the late afternoon. Dinner aboard beneath the stars, with the lights of the Great Sound reflected in calm water.

Day 2: North Shore Wrecks and Hamilton

Depart early and cruise to the Cristobal Colón wreck on the north shore for a morning dive over the largest shipwreck in Bermuda. Continue east to the Hermes – a fully intact wreck with her mast pointing towards the surface, one of the most photogenic dive sites in the Atlantic. After lunch, cruise into Hamilton Harbour and moor at the Royal Bermuda Yacht Club or Hamilton Princess Marina. Spend the afternoon exploring the capital: pastel-painted shops, the Bermuda National Gallery at City Hall, and the harbourside produce market. Dinner ashore at Fourways Inn – the grande dame of Bermuda’s restaurants, with first-class European cuisine and a candlelit colonial setting.

Day 3: St George’s and the East End

Cruise east from Hamilton to St George’s Harbour – eight nautical miles, roughly 30 minutes. Anchor in Convict Bay and spend the morning walking the UNESCO World Heritage town: cobblestone lanes, St Peter’s Church (1612), the Globe Museum and the colonial architecture of King’s Square. After lunch at Wahoo’s Bistro (the island’s signature fish chowder and fresh wahoo), tender to Tobacco Bay for an afternoon snorkel in the calm rock pools. In the late afternoon, cruise south to explore Castle Harbour – a large natural harbour on the east end, excellent for a sunset paddleboard or tender exploration. Overnight at anchor in the calm waters of Castle Harbour.

Day 4: South Shore Beaches and Return

Rise early and cruise south-west along the coast to the Mary Celestia wreck for a morning snorkel. Continue west along the south shore, stopping at Church Bay, Warwick Long Bay and Horseshoe Bay – the island’s finest pink-sand beaches, each offering different snorkelling and swimming experiences. Your chef prepares a farewell lunch on the aft deck as the yacht cruises past the south-shore cliffs. Return to the Royal Naval Dockyard by mid-afternoon – time for a final visit to the National Museum, a sundowner at a waterfront café, or a stroll through the marina.

Guests looking for a longer voyage can combine the 3-day south-shore route with the 4-day full-island circuit for a comprehensive 7-day charter covering every major anchorage, wreck site, cultural landmark and pink-sand beach on the island without repeating a single stop.