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Bermuda

Islands of Bermuda Walk

Trip code: W07BM

Average customer rating 4.7 / 5(21 verified reviews)

Self-Guided Walking
7 nights single centre
Leisurely
Flights available
CO₂ rating 1/5
Headwater Navigation app

Trip highlights

Unspoilt pocket-sized paradise, perfect for independent discovery; fabulous year-round climate

Sugary pink sands, secret turquoise bays, sea grottoes

Gentle traffic-free trails, spectacular coastal paths, lush woodland tracks

Colonial towns, pastel coloured villages, panoramic forts, vibrant Hamilton

Colourful flowers, kiskadees, tree frogs, sea turtles and humpback whales!

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Trip details

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’.

What's included

Included

  • 7 nights in 4-star accommodation
  • Management by local hotelier
  • Headwater navigation app
  • 7 day travel pass
  • Local taxes, resort levy and service charge

Not included

  • Flights
  • Travel insurance

Travel options

Flights

Our air prices include standard flights and transfers.

Itinerary

Route map, with each night's stop marked
The full route, night by night. Select the map to view it full screen.

Day 1 · —Arrive in Bermuda

Arrive in Bermuda

Arrive at your hotel in time for dinner overlooking the ocean.

You stay at Grotto Bay Beach Resort Bermuda

Grotto Bay Beach Hotel
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Grotto Bay Beach Resort Bermuda

  • Air conditioning
  • American Express
  • Hairdryers
  • Mastercard
  • Minibar
  • Safe
  • Swimming pool
  • Television
  • Visa cards
  • Wifi access

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.

Day 2 · 10km/6.2miSomerset to the Dockyard

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, 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

Somerset to the Dockyard elevation profile

Day 3 · 7km/4.3miExploring the East End

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 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.

Elevation

Exploring the East End elevation profile

Day 4 · 6km/3.7miSt David's and Cooper's Island

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 the nature reserve of Cooper’s Island, a truly isolated and unspoilt area.

Elevation

St David's and Cooper's Island elevation profile

Day 5 · 11km/6.8mi or 13km/8.1miSights of the South Shore

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 savouring a Dark ‘n’ Stormy cocktail back at the hotel.

Elevation

Sights of the South Shore elevation profile

Day 6 · 6km/3.7miCoast and Caves

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. Visit the fascinating Crystal Caves perhaps, before a leisurely dip in the pool back at the hotel.

Elevation

Coast and Caves elevation profile

Day 7 · 3km/1.9mi or 3km/1.9miBotanical Gardens and Spittal Pond

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.

Elevation

Botanical Gardens and Spittal Pond elevation profile

Day 8 · —Leave Bermuda

Leave Bermuda

What our travellers say

Just as advertised, and just what we needed

Dr Howden

The holiday was very good the free bus & ferry pass excellent,we found the notes accurate the map also good but large,because we are getting older we reduced some of the walks which worked well,allowing more swimming time. The people were very friendly and would stop if we looked lost. Overall a very good holiday well done Headwater. When we booked I was looking for maybe a different way to Bermuda I got no help from the sales girls, so we stayed with your holiday guide.

Mr Gittins

Bermuda is beautiful and interesting if you like history. There wouldn’t be time to see everything and hike every day. I chose the things I wanted to see and organised my walking around that.

Miss Mellor

Very enjoyable holiday Jan/Feb 2019. Great weather apart from 1 day of thunderstorms, not at all humid and lovely temperature for walking. Hotel was just as described, with excellent food. Worth bearing in mind that the hotel is very quiet in winter (we had the breakfast room to ourselves most days, and just a couple of other tables at dinner). As previous reviewers have said, this is more of a sightseeing holiday on foot, but very enjoyable. The walks vary in length (and are very flat) and some are quite long (we managed 30,000 steps one day) but there’s lots of flexibility with the local buses (which work very well). A good trip for us to get away from the UK winter, followed by a few days in Miami on the way back.

Mrs Marchant

The Headwater walking holiday in Bermuda is an excellent way to see the beautiful coastline, explore the various historical sites and travel on the local buses and ferries. The Coco Reef Hotel is a good base for the holiday, staff are friendly and keen to please.

Ms Barnwell

This self-guided walking holiday in Bermuda was fabulous in every way. The hotel was a luxurious island paradise, with fine dining from a large a la carte menu every night. It was well worth having the inclusive meals package suggested. We enjoyed the trip immensely. Everything was good!

Mr Anderson

This is a "full-on" holiday to try and complete all the walks in a week, especially if you have bad weather, so would recommend booking extra days to include other sightseeing options. Hotel was pleasant enough, and a great location if you like a beach view, but somewhat remote – you need to familiarise yourself with other bus routes/directions if you want to return any later than 9.15pm! The food there is reasonably good but limited, we chose to eat out a lot of the time and there are plenty of good eateries in Hamilton. My personal suggestion would be to book room only to maximise your dining options. Tim provides a wealth of information at the briefing and we didn’t need to contact him for anything else during the week – the route notes are fairly straightforward and it’s relatively easy to find your way around. And if you do get lost it won’t be long before a friendly local approaches you offering help and directions! Overall a good intro to Bermuda, its history and its people.

Mrs Meusz

Bermuda is simply stunning. Fantastic coastlines & colours. Very friendly people. It was easy to get about via bus & ferry services, with not too challenging, scenic walking. The itinerary enables you to see most of the island in all it’s glory.

BRENNAN

A safe pair of hands

Marian Lewis

Very well thought out visit to Bermuda. I felt we got a good introduction to the island and explores the key areas. Clear and unambiguous guidance made the self guided walking straightforward. I would strongly recommend the trop to any walker wanting to visit Bermuda.

John Corfield
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Positive impact

Carbon score for this trip

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

From the journal

From£1,459per person