







Bermuda
Average customer rating 4.7 / 5(21 verified reviews)
This self-guided walking holiday explores the quintessential island paradise of
Bermuda, a sub-tropical gem, seemingly adrift in the North Atlantic Ocean. Warmed
by the temperate Gulf Stream, Bermuda is a stunning archipelago of 181 islands and
islets, the eight largest of which form the fishhook-shaped mainland. The oldest British
colony, this tiny treasure trove is packed with history and natural beauty. Famed for
its stunning turquoise waters in a whole rainbow of blues, incredible pink sands and
coral reefs home to hundreds of colourful fish, Bermuda is a beach-lover’s heaven.
Beyond the postcard-worthy bays, the islands offer a lush interior alive with a
multitude of birds and flowers, making it perfect to explore on foot. As Mark Twain
commented, ‘You go to heaven if you want. I’d rather stay here in Bermuda’.
Our travel specialists can arrange flights, rail and transfers to this holiday from wherever you are. Call us to plan your journey. +44 1606 720099


Arrive at your hotel in time for dinner overlooking the ocean.
You stay at Grotto Bay Beach Resort Bermuda

Your hotel for the duration of this holiday is the Grotto Bay Beach Resort, which sits within a lush tropical estate set along the water’s edge in Bailey’s Bay. It overlooks a secluded pink sand beach and comprises of 11 brightly coloured cottages which overlook the turquoise Bermudian waters.
The hotel boasts fantastic facilities including water sports and the ‘Natura Spa’ which is set within the atmospheric Prospero’s Cave – complete with stalactites and stalagmites – overlooking a crystal-clear ocean-fed lake.
The resort’s luxurious Great House offers cosy seating areas where guests can enjoy stunning views of the hotel grounds and turquoise ocean beyond. It’s home to the Rum House Bar – where there is regular live entertainment – and the resort’s 2 main restaurants: the relaxed Palm Court or the elegant Hibiscus Dining Room. The Bayside Grill is also available at lunchtime (seasonal), whilst the Bayside Bar serves tropical drinks poolside and along the water’s edge.
The bedrooms at the Grotto Bay Beach Resort are spacious and contemporary with marble bathrooms and either private balcony or private patio.
As your stay at the Grotto Bay Hotel is on a room only basis, please let us know if you would like to add breakfast, breakfast and evening meal or all inclusive to your stay. Please contact us for a quote.

Today’s route begins at Somerset Bridge, the world’s smallest drawbridge, to follow the Railway Trail lined with unusual screw palm and cedar, 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.
Elevation


You start the day in charming St George, a UNESCO World Heritage Site. There’s time to explore the tangle of colourful streets and pretty 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 fort and Corsican tower.
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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 the nature reserve of Cooper’s Island, a truly isolated and unspoilt area.
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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 savouring a Dark ‘n’ Stormy cocktail back at the hotel.
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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. Visit the fascinating Crystal Caves perhaps, before a leisurely dip in the pool back at the hotel.
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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.
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17.0
Kg CO₂e
per person, per night
Relative to other Headwater trips
We measure emissions from the parts of the holiday we organise — including accommodation, in-trip transport, meals and activities — and express them as CO₂e per person, per night. Our label doesn’t include your travel to and from the start of the trip. As a Certified B Corp, Headwater is committed to reducing this figure and to positively impacting local communities, the local environment and our staff. Learn more