Cayman Islands Itineraries: Day Charters and Multi-Day Routes

The Cayman Islands offer two distinct charter experiences: the polished, dive-rich waters around Grand Cayman for day charters and short breaks, and the multi-island voyage to Cayman Brac and Little Cayman for guests with more time and a passion for wall diving and wildlife. 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

Stingray City, Starfish Point and Rum Point

Depart the marina mid-morning and cruise north into Grand Cayman’s North Sound – a 35-square-mile lagoon protected by barrier reef. Head to Stingray City for the marquee experience: wading into chest-deep, crystal-clear water to hand-feed roughly 90 wild Southern stingrays. Spend an hour with the rays, then cruise to nearby Starfish Point for a gentle wade among red cushion sea stars in ankle-deep water. Your chef serves lunch on the aft deck as the yacht repositions to Rum Point on the north coast – a palm-shaded beach with calm water and a relaxed island atmosphere. Return via the west coast with the late-afternoon sun painting Seven Mile Beach in gold.

Kittiwake Wreck and Seven Mile Beach

Cruise north from George Town to the USS Kittiwake wreck site off Seven Mile Beach – roughly 10 minutes. Moor above this 77-metre submarine rescue ship in 5–20 metres of water and spend the morning exploring her five decks: schools of tropical fish, eagle rays, sea turtles and a resident barracuda patrol the corridors. Snorkellers can appreciate the superstructure from five metres, while certified divers access the deeper levels. Surface for lunch on the aft deck, then anchor off Seven Mile Beach for an afternoon of swimming in calm turquoise water. Tender ashore for sundowners at a beach bar or stay aboard for a sunset champagne session on the flybridge.

North Wall Dive and Coral Gardens

Head north from the marina to Grand Cayman’s North Wall – one of the island’s most dramatic dive sites, where the reef shelf drops into abyssal depths just minutes from shore. Spend the morning drifting along the wall in 15–30 metres: sponge-covered ledges, swim-throughs and the occasional passing eagle ray. After lunch, cruise to the Coral Gardens in the shallow water of North Sound for an afternoon snorkel over healthy reef in just 3–6 metres – ideal for less experienced swimmers and families. Return to the marina by late afternoon.

Multi-Day Itineraries

3-Day Cayman Islands Yacht Charter Itinerary: Grand Cayman Highlights

Day 1: Seven Mile Beach, Stingray City and Rum Point

Board your yacht at the Barcadere Marina or the Cayman Islands Yacht Club by mid-morning. After a welcome briefing and champagne toast on the flybridge, cruise to Stingray City in North Sound for a morning of hand-feeding wild stingrays in crystal-clear, chest-deep water. Continue to Starfish Point for a gentle wade, then cruise to Rum Point for a relaxed beach lunch – soft sand, calm water and the genuine island atmosphere of Grand Cayman’s quiet north coast. Return to Seven Mile Beach in the late afternoon for a swim. Dinner ashore at Grand Old House – a waterfront 1908 plantation home with fine seafood and an award-winning wine list.

Day 2: Kittiwake Wreck, West Wall and Camana Bay

Depart early and moor over the USS Kittiwake wreck for a morning dive or snorkel on Grand Cayman’s most accessible shipwreck. Explore the five decks of this 77-metre submarine rescue ship in 5–20 metres, surrounded by tropical fish and eagle rays. After the dive, cruise north to a section of the West Wall for a second dive along the dramatic drop-off. Your chef serves lunch on the aft deck. In the afternoon, anchor off Camana Bay – Grand Cayman’s most stylish waterfront district – and tender ashore for shopping, gallery browsing and an evening out. Dinner at Blue by Eric Ripert at the Ritz-Carlton: tasting menu, 700-label wine list, AAA Five Diamond dining.

Day 3: North Sound, Coral Gardens and Farewell

Rise early for a final swim from the yacht, then cruise into North Sound for a morning snorkel at the Coral Gardens – healthy reef in 3–6 metres with colourful fish, sea fans and the occasional turtle. Visit the barrier reef on the sound’s northern edge for more advanced snorkelling. Your chef prepares a farewell lunch on the aft deck as the yacht cruises south along Seven Mile Beach, passing the white sand and turquoise water that define Grand Cayman’s western shore. Return to the marina by mid-afternoon.

4-Day Cayman Islands Yacht Charter Itinerary: Grand Cayman to the Sister Islands

Day 1: Grand Cayman to Cayman Brac

Depart George Town mid-morning and set course north-east for Cayman Brac – approximately 89 miles, roughly four to five hours at cruising speed. Your crew serves brunch and lunch on the aft deck as the open Caribbean rolls past. Arrive at Cayman Brac by late afternoon and anchor off the western coast. The dramatic limestone bluff, rising to 43 metres, is visible from miles away. Spend the late afternoon exploring a shoreline cave or hiking one of the marked trails over the bluff. Dinner aboard beneath the stars, or tender ashore to Captain’s Table for fresh seafood.

Day 2: Cayman Brac Diving and Little Cayman

Spend the morning diving Cayman Brac’s walls – healthy hard-coral formations, swim-throughs and passing pelagics on a reef that is wilder and less visited than Grand Cayman’s. After lunch, cruise the short five-mile crossing to Little Cayman – 15 minutes – and pick up a mooring off the west coast. Spend the afternoon snorkelling the shallow reef shelf above Bloody Bay Wall: green turtles, eagle rays and colourful coral in water so clear it barely seems real. Paddle a kayak to tiny Owen Island for a beach walk. Dinner aboard at anchor, with the quiet of one of the Caribbean’s least developed islands surrounding you.

Day 3: Bloody Bay Wall and Little Cayman

The day dedicated to world-class diving. Descend from the six-metre reef shelf and drift along a wall that Jacques Cousteau declared among the top three dive sites in the world: tube corals, sea fans, green turtles and black triggerfish against a backdrop that plummets beyond 300 metres into the Caribbean’s deepest water. Surface for lunch, then dive or snorkel a second site in Bloody Bay Marine Park – the park has 24 marked sites, each offering different topography and marine life. In the late afternoon, visit the booby-bird colony – over 20,000 nesting red-footed boobies, one of the largest colonies in the Caribbean. Overnight at anchor.

Day 4: Return to Grand Cayman

Depart Little Cayman mid-morning and set course south-west for Grand Cayman – approximately 75 miles, arriving by mid-afternoon. Your crew serves brunch and lunch on the aft deck as you cruise, with the deep blue of the Cayman Trench beneath you. Arrive at Seven Mile Beach by mid-afternoon – time for a final swim, a stroll through Camana Bay, or a farewell dinner at Taikun at the Ritz-Carlton, where real wasabi is grated tableside and the saké list is among the largest on the island.

Guests looking for a longer voyage can combine the 3-day Grand Cayman route with the 4-day Sister Islands crossing for a comprehensive 7-day charter covering the full spectrum of the Cayman Islands – from Stingray City and Seven Mile Beach to the caves of Cayman Brac and the legendary Bloody Bay Wall on Little Cayman – without repeating a single anchorage.