Islands of Bermuda Walk

Trip code: W07BM 4.6 (34 reviews)

Self-guided walking

7 nights,
single centre

Level: 1

17.0Kg CO2e

Stop press! Book between 21st June and 11th July for any departure between 10th November and 26th December 2024, and get a discount of £200 per person! Quote BER24 at time of booking.


  • 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!


  • 7 nights accommodation
  • Room only
  • Briefing at the start of your holiday
  • Comprehensive route directions
  • 7 day travel pass
  • Local taxes, resort levy and service charge


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'.

A traffic-free trail spans Bermuda's diminutive 21-mile length; we've split it into 6 diverse sections to offer gentle walks exploring every corner. 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 7-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 the Grotto Bay Beach Resort, which sits within a lush tropical estate, with 3 private beaches and a wealth of excellent facilities.


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.

Read more about this holiday in our Meet the Expert blog with Megan.




Day 1: Arrive in Bermuda

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

You stay at Grotto Bay Beach Resort.

hotel details


Grotto Bay Beach Resort Bermuda,



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.

The hotel boasts fantastic facilties including tennis courts, 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 comes with dark wood floors and tropical colours, as well as 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 restaurants: the relaxed Palm Court or the elegant Hibiscus Dining Room. The Bayside Grill is also available at lunchtime, whilst the Bayside Bar serves tropical drinks along the water's edge.

The newly renovated 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.

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.

Day 2: Somerset to the Dockyard 7km/4.5mi/2hr or 8km/5mi/3hr

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.

Day 3: Exploring the East End 7km/4.5mi/2hr

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.

Day 4: 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.

Day 5: 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.

Day 6: Coast and Caves 9km/5.5mi/3hr

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.

Day 7: 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.

Day 8: Leave Bermuda


Show prices including flights?  


These tour only prices are based on two people sharing. Single supplement from £691.

These flight inclusive prices are based on two people sharing. Single supplement from £691.

  • Flights from Gatwick to Bermuda with British Airways
  • Other flights, including regional departures
  • Alternative flights, including regional departures
  • Business/club/first class fares
  • Room upgrades and extra nights at selected hotels
  • Breakfast
  • Half Board

Our aim is to provide holidays that are unbeatable for choice and flexibility. We've listed our most popular travel options below, however you aren't limited to these - we can tailor-make virtually any holiday to suit.

Air prices include our standard flights/transfers
Out: British Airways Heathrow to Bermuda transfer to the hotel, 25 minutes, provided Return: Transfer to airport then British Airways Bermuda to Heathrow

Business/club/first class seats are available on request.

Alternative Air Travel
Alternative flights, onward rail to your holiday area, and connecting private transfers can be arranged from most UK airports. If you would like to use one of the many 'low cost' airlines, we can book these on your behalf. We can also book UK shuttles to connect with your onward flight, please call for details and prices.

Alternative transfers
If you require alternative transfers (because you will be arriving at a different time to our standard flights), then we can usually arrange these for you (there may be an additional charge).

To find out more about the travel options available call our sales team on 01606 720199, use our live webchat (we open again 9am Monday) or email

Should you require overnight airport accommodation, airport parking or even a uniformed chauffeur to take your car from your departure terminal and park it for you, we can arrange this for you through Holiday Extras. You can book airport parking, airport hotels and executive lounges through their website or contact us for further details. Early booking is recommended to obtain the best availability and prices.


The holiday was very well organised with only one hitch, the failure of the pickup to turn up to the airport. However I managed to share a taxi with others quite easily. The walks detailed were all excellent though I did not do the Cooper's Island walk as the buses were not running the whole way. I did, however, enjoy a shorter walk at St Davids. The weather was very good, which helped. The small nature reserves were impressive as were the local museums and colonial architecture. The views were tremendous, the flora along the Railway Trail was amazing ,lush and very varied, and the birdlife wonderful, especially tge nesting Longtails. But above all it was the exceptionally friendly and helpful Bermudians which made this trip special for me.

Michael Degraeve, 1 Mar 2024


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, 22 Dec 2023


A safe pair of hands

Marian Lewis, 23 Nov 2023


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, 21 May 2023


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, 19 Jan 2020


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, 29 Dec 2019


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, 14 Apr 2019


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, 27 Jan 2019


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, 6 Jan 2019


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, 11 Nov 2018


Just as advertised, and just what we needed

Dr Howden, 4 Nov 2018


For UK travelers, make sure they take a lot of money. At least 3 times as expensive as this country. In our hotel, when not 'happy hour' £ 14 a £12 for a small bottle. Therefore forced to go to a small supermarket. Cheapest bottle of wine £11. even then.

Mr Elias, 18 Feb 2018


A very good holiday but in all honesty Bermuda is not really a walking destination. Once you accept that this is really a sight seeing holiday on foot and that most of the walking will be on roads it's fine. Fabulous coast and beaches and excellent accommodation.

Mrs Westall, 26 Feb 2017


Bermuda is a delightful place and absolutely ideal in November: lovely climate, beautiful beaches, historic interest, luxuriant vegetation, helpful people, more British and Britain. There is even a Marks & Spencer. and an excellent hotel.

Sir Brooke, 13 Nov 2016


Bermuda is slightly off the beaten track, the air temperature is good for walking but also swimming etc. Bermudans are exremely friendly and not once did we feel threatened or have to stop people trying to sell us goods.

Mr Brown, 8 Nov 2016


Bermuda is a first class holiday destination. Walking round much of the island is a great way to experience the culture of the island first hand. Headwater enabled us to do that.

Ms Kay, 22 May 2016


Really enjoyed holiday in Bermuda. Beautiful island. Excellent walks. It is an EXPENSIVE destination, and therefore (for us) Special, But we don't regard Coco Reef as meeting 'special'. Fabulous location, but it's a bit tired, could do with freshening up, and no apparent sign of management involvement- maybe that's the Bermudian way? Furthermore its close to a Bermuda College, and during our stay a group of students were also resident, who although decent kids, kept different hours to us, and on 2 occasions kept us awake into the early hours. I don't think hotel management is doing itself any favours by mixing them with holidaying guests.

Restaurant food excellent, but menu needs regular update, a bit 'samey'after a week.

Mrs Wallace, 13 Mar 2016


Bermuda is friendly, beautiful and relaxing. We followed all walks but one and wished we had had longer to do more (the walks didn't leave enough time for visiting museums etc). Coco Reef was a lovely place to stay.

Mr Marsh, 8 Nov 2015


Thank you, Headwater: we would never have thought of visiting Bermuda if your brochure had not suggested it as a base for a walking holiday, and we would have missed a treat. A delightful destination, with friendly and helpful people, a comfortable hotel in an attractive beach-side setting, some lovely walks along the old railway trail and the stunning coastline, and a range of places to visit and learn about Bermuda's fascinating history, customs and society.

The accessibility of all parts of the island and its excellent (and entertaining) bus and ferry service make it easy to 'pick and mix' elements of the recommended walking routes. We made full use of this flexibility so we could spend time in some of the museums and historic houses that help bring Bermuda's rich history and culture to life, as well as exploring the various nature reserves that feature in some of the walks.

Highly recommended (and we found May a perfect time to go - warmth and stunning flora).

Mr Beck, 3 May 2015


Beautiful location, average breakfasts, excellent evening meals although limited menu.

Mrs Bishop, 3 May 2015


Walking in Bermuda was described well in the brochure and ideal for those of us who don't want a sun/beach /pool holiday. The bus/ferry service was excellent for getting around either before walking or after, we sometimes split the walk over 2 days as we stayed an extra 3 days and decided that to go to the end point (often a sightseeing place) and walk back, rather than start by walking. Everyone was very friendly and willing to show us the way if we were unsure. The maps and the guide notes were good. We added in going on the glass bottom boat and swimmimg with the dolphins as extras but readily available.

Mrs Greenhill, 17 Apr 2015


Generally very good.

Mrs Little, 29 Mar 2015


We really enjoyed our holiday with you. We didn't meet our rep which was unfortunate ( he was unwell) . I had hoped that he may contact us later in the week. We followed all the walks which we enjoyed. We both thought that the Island was rather more suburban than rural. Really enjoyed the bus trips and Bermuda.

Mrs Conaghan, 22 Mar 2015


Lovely island with great walks. Eating and drinking out can be expensive

Mr Steinbock, 22 Feb 2015


Bermuda was excellent

Costa Rica was a rushed experience rather than a holiday; there was too much road walking!

We were disappointed with the Flora content

Mr Walker, 4 Feb 2015


The walking aspect of the holiday was great but the Coco Reef was a disappointment. The hotel needs to be refurbished and better maintained and the main hotel receptionist who was on duty during our stay was disinterested to the point of rudeness. Bermuda in the winter is an ideal walking holiday destination, but visitors need to be ready for a virtually empty hotel with a skeleton staff.

Mrs Hills, 3 Feb 2015


I can put in one word GO It`s worth it

Mr Neininger, 21 Dec 2014


Bermuda was an excellent choice for a walking holiday & Coco Reef a great hotel. The food was better than our expectation. Walking was very easy just unfortunate that the storms had blocked the Railway Trail & paths. Just very unfortunate to have 2 storms hit within one week but cannot fault the care , help & advice given to us by Headwater - esp Lisa - & Tim who arranged taxi to airport etc

Mr Pittam, 12 Oct 2014


Walks were slightly different to those in brochure, not a problem, but needs up dating. Very relaxing and enjoyable holiday. Bermudan people are extremely friendly and helpful, why can't we all be like that? Buses and ferries very reliable.

Hotel looked a bit dated and the food was poor on Tues and Thurs - Island and Buffet night, so we went out as had read the headwater previous visitors book comments. Other nights the food was fantastic. Beach is rather small could be busy at peak times. Ran out of towels on 2 occasions. Can be very busy when the cruise ships are in.

Overall, the walks were longer than advertised but very enjoyable. We had a great time. Lovely way to see Bermuda and some bits that others may not get too - Coopers Island.

Dr Harrison, 20 May 2014


May is a good time to go for wildlife - and weather not too hot

Mr Stather, 10 May 2014


Walking pretty much as described, care needs to be taken on switching from rail track to road and vice versa Avoid multiple bus changes at weekends as they run less frequently. The hotel has large parties of sporty types out of season, try to find out if any are there while you plan to stay, if there are, don't book. They are loud, boorish and their behaviour is totally unacceptable. Dont expect the shop to be open out of season. Do take the ferries, though only one runs out of season. Do explore apart from your route notes, there are many other nature reserves to visit and also ramble around headlands, Simson's island particularly rewarding. The friendliness of the local people and the great hotel staff contribute to making this a really special destination and the stunning scenery everywhere is overwhelming.

Mr Wright, 2 Mar 2014


The walking is pretty good but it especially suited us because there are good places to visit including the Aquarium, the Underwater Exploration Institute, the Museum at the Dockyard and the town of St George. The food at the hotel was very good quality and value as was the combined bus/ferry ticket which takes you everywhere on the islands. You can minimise the waiting times for the transport with some careful pre-planning. And you can walk straight from the hotel onto the sandy beach and swim in the warm ocean, even in February.

Mr Tuffill, 7 Feb 2014


We found the route notes were a times lacking in information, distances from one point to the next for example, and at others over complicated when there was a perfectly good way mark to guide us. The hotel was excellent, very friendly, the food was very good, I did not repeat a dinner main course selection in the 11 days we were there!

Mr Kirby, 27 Oct 2013


Walking is a great way to see a country, and Headwater provides a good service for doing so.

Mrs Howells, 27 Oct 2013


Self-guided walking

7 nights,
single centre

Level: 1

17.0Kg CO2e

7 nights from £1749


Call: 01606 720199