Your itinerary
Day 1
Arrive in Bermuda
Arrive at your hotel in time for dinner overlooking the ocean. You stay at the Coco Reef Resort for 7 nights on a Room Only basis. Breakfast and evening meals are available at a supplement – please request prices at time of booking.
Day 2
Somerset to the Dockyard
Today’s route begins at Somerset Bridge, the world’s smallest drawbridge, to follow the Railway Trail lined with unusual screw palm and cedar trees, reaching 19th century Fort Scaur, with stunning views to Hamilton. Onwards to sleepy Somerset Village for lunch by pretty Mangrove Bay, you then follow a coastal track to the Royal Naval Dockyard at Bermuda’s most westerly end. Maybe visit vibrant Hamilton before meeting Tim Rogers at the hotel who will talk you through the suggested programme for the rest of your walking week. Two options: 7km/4.5mi/2hr or 8km/5mi/3hr
Day 3
Exploring the East End
You start the day in charming St George, a UNESCO World Heritage Site. There’s time to explore the tangle of colourful streets and picturesque harbour before a dazzling path lined with prickly pear and casuarina leads to Gates Bay where Sir George Somers first came ashore in 1609. You continue along a herb-scented coastal track to Ferry Reach, with its 17th century forts and Corsican tower.
Day 4
St David’s and Cooper’s Island
At tranquil St David’s, fragrant hibiscus scents the salty ocean air as you visit Red Hole bay. Then it’s on to St David’s Battery, with cliff views stretching infinitely across the ocean, before heading over to Cooper’s Island, Bermuda’s newest nature reserve, a truly isolated and unspoilt area. Two options: 4km/2.5mi/2hr or 5km/3mi/2.5hr
Day 5
Sights of the South Shore
From Gibbs Hill Lighthouse, balcony views span the entire west end across the azure waters of Great Sound, dotted with white sailboats. From here you descend to the sugary pink sands of the South Shore Trail, a string of nine gorgeous bays linked by a scented path of flowering morning glory and oleander. There’s time for a dip at Chaplin Bay before a shaded path leads past cassava fields to the hotel, in time for a dip in the hotel’s pool.
Day 6
Coast and Caves
Colourful prickly poppies dot the sparkling coastal route towards Flatts Village, where friendly locals cast their nets into the azure expanse of Harrington Sound, an inland lake littered with sea grottoes. It’s then onwards with views over the northern shore to reach Blue Hole Park, a tiny treasure trove of caves filled with aquamarine waters. Maybe savour a Dark ‘n’ Stormy cocktail after visiting the fascinating Crystal Caves, then take the bus back to the hotel.
Day 7
Botanical Gardens and Spittal Pond
Alive with the noisy chatter of yellow kiskadee, a gentle allspice-scented trail brings you to Paget Marsh, a wetland oasis, home to herons and warblers. Then it’s on to the Botanical Gardens – John Lennon’s Double Fantasy album is named after the purple flower he spotted here – before heading to Spittal Pond; maybe spot herons, egrets and flamingos before following the coastal path, vibrant with sea lavender, looking out for humpback whales basking in the warm Atlantic waters. Two options: 5km/3mi/1.5hr or 4km/2.5mi/2.5hr
Day 8
Leave Bermuda
The British Airways flight leaves in the early evening, so you have most of the day at leisure.
What’s included
What’s not included
Additional information
St George’s UNESCO Lanes & Gates Bay Coastal Walk
On day 3, wander the pastel lanes of St George’s, a UNESCO World Heritage Site, pausing in King’s Square and by St Peter’s Church, one of the oldest Anglican churches in continuous use outside the British Isles. Then follow a coastal path lined with prickly pear and casuarina to bright Gates Bay, where Admiral Sir George Somers made landfall in 1609.
Continue toward Ferry Reach, tracing bluff-top trails past minor forts and a squat defensive tower that once secured the narrows. With sea breeze, salt spray and seabirds wheeling overhead, the walk connects Bermuda’s early settlement to today’s lively harbourside rhythms.
St David’s Island & Cooper’s Island Nature Reserve
On day 4, breathe in hibiscus-scented air at tranquil St David’s as you walk to Red Hole Bay, then on to the cliff-top guns of St David’s Battery with horizon-wide Atlantic views. Crossing low causeways, the path reaches Cooper’s Island Nature Reserve, a restored sanctuary of pale sand and shallow coves.
Here, dunes rustle with sea oats and the cry of white-tailed tropicbirds (“longtails”) rides the wind. Once a restricted military site, the headland now protects turtle-grazed seagrass meadows and calm beaches that invite a quiet pause and a cooling paddle before you return.
Gibbs Hill Lighthouse & South Shore Pink-Sand Bays
Day 5 opens atop the 1846 cast-iron Gibbs Hill Lighthouse, where balconies survey the Great Sound, Little Sound and the reef-rimmed South Shore. From here, descend to the South Shore Park trail and drift between coves of rose-tinted sand and sculpted limestone, including Horseshoe Bay, Warwick Long Bay, Jobson’s Cove and Chaplin Bay.
Oleander and morning glory scent the path while translucent surf breaks in gentle cylinders. Take time to pause for photos and reflection, and, if conditions suit, wade into sheltered shallows before a shaded inland path leads you back toward the hotel for an afternoon swim.
Flatts Village, Harrington Sound & Blue Hole Park Caves
On day 6, trace the shoreline from colourful Flatts Village, where fishermen tend nets beside the jade waters of Harrington Sound. Follow lanes sprinkled with prickly poppies and sea grape toward Blue Hole Park, a pocket of mangroves and limestone where forest shade gives way to azure sinkholes.
Pick your way through leafy tracks to hidden grottoes and glass-clear pools that mirror stalactites above. The soundtrack is wind through casuarina and the echo of your footsteps on coral stone—a cool, contemplative counterpoint to the island’s sunlit beaches.
Paget Marsh Boardwalk, Botanical Gardens & Spittal Pond
Day 7 begins amid the whispering reeds of Paget Marsh, where wooden walkways cross peat bog and bird calls carry—kiskadee, heron, warbler. Continue to the Bermuda Botanical Gardens, whose orchids and breadfruit shade quiet paths; John Lennon named Double Fantasy after a flower he noticed here while writing on the island in 1980.
Finish at Spittal Pond Nature Reserve, a coastal amphitheatre of limestone ledges and blowholes. In spring, scan the horizon for migrating humpback whales; year-round, watch longtails carve white arcs over deep blue water. The day’s gentle gradients foreground Bermuda’s wilder moods and living natural heritage.
Evening Orientation with Route Host Tim Rogers
On day 2 in the evening, meet your route host, Tim Rogers, at the hotel for a friendly rundown of the walking week. Together you’ll review your route notes and maps, discuss daily options and terrain, and learn how to make the most of your 7-day transport pass across buses and ferries.
Tim shares local know-how—trail etiquette, weather tips, swimming spots and favourite cafés—so you can walk with confidence. This relaxed briefing frames the island’s geography and history, helping you choose the right pace and linger where the light, tide and mood are best.
National Museum of Bermuda at the Dockyard
While at the West End on day 2, step inside the National Museum of Bermuda within the stone bastions of the Keep Fort. Explore maritime galleries in the Commissioner’s House, learn about shipwrecks and the Royal Navy’s Atlantic station, and stroll ramparts overlooking the Great Sound.
This visit deepens the context of earlier fortifications you’ve seen along the trail. Allow an hour or two to trace Bermuda’s nautical lifelines from sail to steam. This is an optional experience at additional cost, bookable on tour and easily paired with your Railway Trail walk.
Crystal Caves Guided Tour & Swizzle Inn Tasting
Near Blue Hole Park on day 6, join a guided tour of the Crystal Caves, descending wooden walkways above sapphire underground lakes where slender stalactites reflect in still water. Guides share the caves’ 1907 discovery and explain how Bermuda’s limestone was carved by ancient seas.
Afterwards, stroll to the island’s storied pub to sample a Rum Swizzle or Dark ’n’ Stormy in a breezy garden. The pairing of geology and island flavor captures Bermuda’s twin identities—coral rock and Caribbean-tilted conviviality. This is an optional experience at additional cost, bookable on tour.
Seasonal Humpback Whale-Watching Cruise
In spring (typically March–April), board a small vessel to cruise the South Shore in search of migrating humpback whales. Naturalist guides help you read blows, tail slaps and fluke patterns as the Atlantic rolls in long swells beyond the reef line.
The outing complements day 7’s coastal walk at Spittal Pond, where you scan from shore; here you’re out on the water, feeling the scale of the migration and the clean salt wind. Sightings are never guaranteed, but the mood of open ocean is its own reward. This is an optional experience at additional cost, bookable on tour.
Gibbs Hill Lighthouse Tower Climb
Before starting your South Shore walk on day 5, climb the 185 steps inside Gibbs Hill Lighthouse to the lantern gallery. From here, the island spreads like a chart—Great Sound studded with sails, reefs tracing pale ribbons, and the pink fringe of beaches below.
It’s a brief, satisfying ascent through cast-iron ribs to one of Bermuda’s finest photo vantage points. This is an optional experience at additional cost, bookable on tour and perfectly timed for morning clarity.
Somerset Bridge to Royal Naval Dockyard Railway Trail
Begin on day 2 at the petite Somerset Bridge, often called the world’s smallest drawbridge, and follow the Bermuda Railway Trail through stands of screw palm and aromatic Bermuda cedar. Climb to Fort Scaur for sweeping views over the Great Sound and Hamilton’s harbour before descending to sleepy Somerset Village for lunch beside Mangrove Bay.
Continue along the coast to the Royal Naval Dockyard, whose stone ramparts once guarded Britain’s Atlantic fleet. Stroll past historic storehouses and the Keep’s battlements as turquoise water laps the quays. The varied terrain and layered history make this an ideal first walk, framing Bermuda’s maritime story against endlessly shifting ocean light.
