This self-guided walking holiday is the perfect mix of gentle walking and independent exploring allowing you to discover the quintessential island paradise of Bermuda at your own pace. Warmed by the temperate Gulf Stream, this sub-tropical gem, seemingly adrift in the North Atlantic Ocean is a stunning archipelago of 181 islands and islets, the eight largest of which form the fishhook-shaped mainland. 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 and, as Britain's oldest colony, it is packed with history too. 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'.
A traffic-free trail spans Bermuda's diminutive 21-mile length and we provide detailed routes for 6 different walks, each exploring it's own diverse sections of the islands. From hidden sea grottoes to panoramic forts, lush flower-speckled fields to the sun-kissed sands of the South Shore Trail, the kaleidoscope of colour is unforgettable and the diversity of flora and fauna unbeatable. To help you get around, a 14-day travel pass is included, allowing unlimited access to the modern and efficient bus and ferry networks. Our local partner, Tim Rogers, will brief you about how everything works; he has a wealth of knowledge about Bermuda's flora, fauna and history.
You stay at either the Coco Reef Resort or the Grotto Bay Beach Resort. The Coco Reef is on the edge of the best private beach on the island and just 15 minutes from the capital, Hamilton. The Grotto Bay Beach Resort sits within a lush tropical estate, with 3 private beaches and a wealth of excellent facilities.
From either hotel, you're free to pick and choose your itinerary each day and with stunning beaches, fabulous golf courses, outstanding natural beauty and fascinating history to discover there's plenty of interest for your 'rest days'.
We also offer a 7-night itinerary on our Islands of Bermuda Walk
The walking is predominantly flat with no real ascents or descents. Terrain varies between asphalt, gravel, and earthen surfaces as well as some sandy trails. Walking boots are recommended.
You stay at the exclusive 64-room 3* Coco Reef Hotel in a deluxe ocean view room (with either balcony or terrace). The hotel is just 15 minutes from the capital, Hamilton and perfect for independent exploring.
Bermuda is the perfect destination for a mix of relaxation and gentle walking. We provide six detailed walking routes to help you discover the historic, cultural and natural highlights of the island, but there's no set itinerary so you're free to choose when and where to walk - you are on holiday after all!
To help you get around, a 14-day travel pass is included, allowing unlimited access to the modern and efficient bus and ferry networks. Our local partner, Tim Rogers, has a wealth of knowledge about Bermuda's flora, fauna and history, and will brief you about how everything works.
You're free to choose when and where to walk:
Somerset and Ireland Island 7km/4.5mi/2hr or 8km/5mi/3hr
Begin at Somerset Bridge, the world's smallest drawbridge, and follow the Railway Trail lined with unusual screw palm and cedar, reaching C19 Fort Scaur, with stunning views to Hamilton. Onwards to sleepy Somerset Village for lunch by pretty Mangrove Bay, you then follow a coastal track out along Ireland Island to Bermuda's most westerly end.
Exploring the East End 11km/7mi/4.5hr
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 C17 forts and Corsican tower.
St David's and Cooper's Island 4km/2.5mi/2hr or 5km/3mi/2.5hr
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.
Sights of the South Shore 13km/8mi/3.5hr
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.
Coast and Caves 12km/7.5mi/4.5hr
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.
Botanical Gardens and Spittal Pond 5km/3mi/1.5hr or 4km/2.5mi/2.5hr
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.
There's plenty to see and do for the remainder of your stay, with the hotel's private beach an obvious attraction! The island boasts many other beautiful beaches, such as Elbow Beach and Horseshoe Bay, and several excellent golf courses too.
Pay a visit to the island's capital, Hamilton, and stroll along the harbour where pastel-coloured colonial buildings mix with high-end shops. Perhaps visit the stone Cathedral of the Most Holy Trinity and climb the tower for glorious city views befroe relaxing in one of the many harbour-side cafes for a spot of people watching.
The Royal Naval Dockyard is also well worth a visit: once the largest naval base outside the UK, the beautifully restored buildings now house a museum that offers a fascinating glimpse into the UK's and Bermuda's naval past. Nearby you'll also find the National Museum of Bermuda where you can discover more about the island's history and wildlife and pay a visit to Dolphin Quest to learn more about these fascinating animals, while the Bermuda Aquarium and Zoo on the shores of Harringston Sound, offers the chance to see seals, turtles, fish, monkeys, birds, and the first living coral reef exhibit in the world.
NEARBY:The Grotto Bay Beach Resort sits within a lush tropical estate set along the water’s edge in Bailey’s Bay. It comprises of 3 private beaches and 11 brightly coloured cottages which overlook the turquoise Bermudian waters.
Room upgrades: Ocean View Deluxe and Ocean Front Superior
Ocean View Deluxe Rooms offer spectacular views from the hillside near the main clubhouse. They are on the second or third floors and come with balcony and views across the bay and beyond. Ocean Front Superior Rooms are located closest to the pool and waterfront. On the ground floor, they have a walk out patio with a partial view of the calm waters of the bay.
Extra nights: Please contact us for details.
NEARBY:Coco Reef enjoys one of the best locations in Bermuda, right on the edge of one of the most stunning beaches of the South Shore with pink sands, several reefs and quintessentially Bermudian azure waters!
Room upgrades: Beachfront Double Room.
The beach front rooms are located closer to the beach than the standard rooms.
Extra nights: Please contact us for details.
Everyone who goes on a Headwater holiday will be emailed a link to our post-holiday questionnaire where they can give us an honest assessment of all aspects of their holiday - everything from how quickly we answer the phone to how clean the hotels were - plus an overall rating and comments about their holiday.
Any feedback collected is posted to our website, so that people can make an informed decision based on past experiences before heading off on holiday. We don’t edit the reviews, the only thing we do is proofread them and alter any typos, where necessary, to ensure they are easy to read for everyone. All reviews will be published (except in certain extreme circumstances), and a member of the Headwater team will respond to any constructive criticisms/comments under the reviews, at their discretion. So, for the real tales, twists and turns of our holidays, look no further than the reviews from our previous travellers.
Excellent holiday but very expensive destination, it would be nice to offer some self catering accommodation.
You can be confident that our pricing includes all the standard requirements of your holiday and many additional extras. Always ensure that you are comparing like for like when booking your holiday.
This 14 night self-guided walking holiday includes:
Single-centre accommodation in a hotel
Management by your local Headwater-appointed agent
Route directions and maps
Standard transfers to/from your hotel (if booking inclusive flights)
14 day travel pass
Local taxes, resort levy and service charge
How to book:
Minimum group sizes
No minimum group size, however transfers are subject to at least 2 people (in total) booked on each departure.
This holiday is unsuitable for children.
Self-guided walking Managed locally by Headwater appointed agent.
Prices are based on the 3* Coco Beach; please call us for prices for the Elbow Beach Resort and Spa
This holiday does not include any flights or rail.