Islands of Bermuda Walk

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It was the perfect holiday in Bermuda with everything organised. Walking with the app was easy.

A Valued Customer, 19 Mar 2025

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Bermuda was an unusual destination for a walking holiday but it worked really well. Picturesque island, very friendly locals and a very well organised transport system.

Mr Dick, 12 Feb 2025

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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

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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

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A safe pair of hands

Marian Lewis, 23 Nov 2023

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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

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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

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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

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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

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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

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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

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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

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Just as advertised, and just what we needed

Dr Howden, 4 Nov 2018

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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 glass...beer £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

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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

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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

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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

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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

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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

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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

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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

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

Mrs Bishop, 3 May 2015

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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

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Generally very good.

Mrs Little, 29 Mar 2015

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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

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

Mr Steinbock, 22 Feb 2015

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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

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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

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

Mr Neininger, 21 Dec 2014

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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

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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

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

Mr Stather, 10 May 2014

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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. Don’t 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

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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

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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

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

Mrs Howells, 27 Oct 2013