Islands of Bermuda Walk

From $2415 per person

****# (91%) Based on 25 customer reviews
  • Unspoilt pocket-sized paradise; perfect for independent discovery
  • Sugary pink sands, secret turquoise bays, sea grottoes and pastel villages; fabulous year-round climate
  • Gentle traffic-free trails, spectacular coastal paths, lush woodland tracks
  • Luxurious hotel with swimming pool, tennis court, panoramic ocean views and outstanding cuisine
  • Colourful flowers, birds and fish - look out for humpback whales!

What's included?

  • 7 nights, single centre
  • Departs Selected Sundays and Tuesdays from 22 Jan '17 to 3 Jun '18
  • All buffet breakfasts and evening meals included
  • Managed by Headwater appointed agent
  • Sustainability rating: 84%
  • Route notes and maps provided
  • 7 day travel pass

Excellent for...

Islands of Bermuda Walk

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 8 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'll stay in a deluxe ocean view room (with either balcony or terrace) at the exclusive 64-room 4-acorn Coco Reef Hotel on the edge of the best private beach on the island and just 15 minutes from the capital, Hamilton. Meals are taken either in the elegant Cafe Coco signature restaurant or on Tamara's Terrace overlooking the pool.

Day-by-day itinerary

Day 1 - Arrive in Bermuda

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

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 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 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 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.

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 a shaded path leads past cassava fields to the hotel, in time for a dip in the hotel's pool.

Day 6 - 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. Maybe savour a Dark 'n' Stormy cocktail after visiting the fascinating Crystal Caves, then take the bus back to the hotel.

Day 7 - Botanical Gardens and Spittal Pond 5km/3mi/1.5h 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

Walking information

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.

Where you stay

This single-centre holiday is based at the following hotel. If you'd like to extend your stay here, or upgrade your room, just let us know at the time of booking. You can call our sales team on 1-800-567-6286 to discuss accommodation options.

Coco Reef Resort, Bermuda   (4 Acorn)

Coco Reef Resort, Bermuda

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!

The hotel has 64 rooms divided between four pastel coloured buildings set over two floors. The rooms have a ‘tropical' feel utilising traditional Bermudian colours and are decorated with wicker furniture and floral furnishings.

All have private facilities with bathtub and shower as well as a balcony or terrace too equipped with furniture, mostly with good ocean views.

All the rooms are identical; the only difference is location. The Ocean View rooms are located at the top of the hill on the same level as the Lobby building and the beach front rooms are located at the bottom of the hill overlooking the main lawn with a staircase down onto the beaches. They offer panoramic views of the ocean and beach. Every room in both categories has a view of the ocean from the bed itself!

Further details on the hotel website, and independent reviews on Trip Advisor.

Local facilities:

  • Mastercard accepted
  • American Express accepted
  • Swimming pool
  • Hairdryer
  • Wifi hotspot
  • Television
  • Minibar
  • Air conditioning
  • Safe
  • Tea/coffee facilities

Nearby facilities:

  • Shops
  • ATM / Cash machine

Travel options

Transfers included from Bermuda airport at 18:30, and back to Bermuda airport at 17:45.

Please call our sales team on 1-800-567-6286 or email to arrange connecting flights.

Customer reviews

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, of course, an overall rating and comments about their holiday.

Any feedback collected is posted straight to our website - totally unedited. So, for the real tales, twists and turns of our holidays, look no further than the reviews from our previous travellers.

Reviewed by Sir Brooke on 25/11/2016

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.

Reviewed by Mr Brown on 18/11/2016

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.

Reviewed by Ms Kay on 02/06/2016

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.

Reviewed by Mrs Wallace on 28/03/2016

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.
Headwater response:
Dear Mrs Wallace, Thank you for taking the time to complete your post-holiday feedback and for your constructive comments. It was great to see you enjoyed your holiday overall. We were however sorry to read there were areas within the hotel that did not meet with your expectations. Firstly, we can advise there is a new Hotel Manager in place; she has already made noticeable improvements to the feel of the hotel and is keen to work with us to ensure our customers have a great holiday. The latest customer feedback is positive and a good reflection of the improvements she is making. In closing, we would like to thank you for choosing Headwater and look forward to welcoming you on another of our holidays in the future. Kind regards, Headwater Customer Service team

Reviewed by Mr Marsh on 20/11/2015

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.

Reviewed by Mr Beck on 22/05/2015

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).

Reviewed by Mrs Bishop on 18/05/2015

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

Reviewed by Mrs Greenhill on 29/04/2015

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.

Reviewed by Mrs Little on 13/04/2015

Generally very good.

Reviewed by Mrs Conaghan on 01/04/2015

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.

Reviewed by Mr Steinbock on 10/03/2015

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

Reviewed by Mr Walker on 02/03/2015

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

Reviewed by Mrs Hills on 13/02/2015

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.
Headwater response:
Dear Mrs Hills, Thank you for taking the time to provide your post-holiday feedback, it was great to see that you enjoyed the walking aspect of your holiday. Although, we were surprised to read of your disappointment with the Coco Reef. Ordinarily this hotel receives positive feedback. However, we realise that we cannot afford to let our high standards of accommodation and service slip, and have discussed your feedback with the hotel manager. He would like to offer an apology for the poor service you felt you received from the reception staff, and assures us this will be addressed immediately. There are also plans in the pipeline to replace the soft furnishings in the rooms and public areas. Whilst we realise this does not impact on your holiday, we hope that it goes some way to show we take the feedback we receive seriously. We would like to thank you for travelling with Headwater this summer and look forward to welcoming you on another of our holidays in the future. Yours sincerely, Headwater customer service team

Reviewed by Mr Neininger on 31/12/2014

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

Reviewed by Mr Pittam on 22/10/2014

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

Reviewed by Mr Stather on 04/06/2014

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

Reviewed by Dr Harrison on 01/06/2014

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.

Reviewed by Mr Wright on 18/03/2014

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. 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.

Reviewed by Mr Tuffill on 21/02/2014

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.

Reviewed by Mr Kirby on 09/11/2013

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!

Reviewed by Mrs Howells on 07/11/2013

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

Reviewed by Mr Fisher on 24/11/2012

The hotel has lovely beach front location and excellent food. Enjoyable, safe and mainly level walking with lots to see and do. Easy access to buses and ferries. Bermuda is a delight!

Reviewed by Mrs James on 05/05/2012

A lovely island with friendly people. The bus passes worked well but it was a shame that quite a lot of the walking was on road.

Reviewed by Mrs Kingston on 08/03/2012

Most enjoyable way to discover this island

Reviewed by Mrs Owen-Jones on 10/02/2012

Good restful break. Rather quiet as off season -we were alone in the restaurant at times

Departure dates & prices

October 2016 departuresTour only 
Oct 23$2785
Oct 30$2785
November 2016 departuresTour only 
Nov 6$2596
Nov 13$2596
Nov 20$2596
Nov 27$2596
December 2016 departuresTour only 
Dec 4$2596
Dec 11$2596
Dec 20$2854
Dec 27$2854
January 2017 departuresTour only 
Jan 8$2415
Jan 15$2415
Jan 22$2415
Jan 29$2415
February 2017 departuresTour only 
Feb 5$2460
Feb 12$2460
Feb 19$2460
Feb 26$2460
March 2017 departuresTour only 
Mar 5$2711
Mar 12$2711
Mar 19$2711
Mar 26$2711
April 2017 departuresTour only 
Apr 2$2708
Apr 9$2708
Apr 16$2708
Apr 23$2708
Apr 30$2708
May 2017 departuresTour only 
May 7$2928
May 14$2928
May 21$2928
October 2017 departuresTour only 
Oct 1$2757
Oct 8$2757
Oct 15$2757
Oct 22$2757
Oct 29$2757
November 2017 departuresTour only 
Nov 5$2711
Nov 12$2711
Nov 19$2711
Nov 26$2711
December 2017 departuresTour only 
Dec 3$2711
Dec 10$2711
Dec 17$2740
Dec 19$2740
Dec 26$2740
January 2018 departuresTour only 
Jan 2$2571
Jan 7$2571
Jan 14$2571
Jan 21$2571
Jan 28$2571
February 2018 departuresTour only 
Feb 4$2630
Feb 11$2630
Feb 18$2630
Feb 25$2630
March 2018 departuresTour only 
Mar 4$2880
Mar 11$2880
Mar 18$2880
Mar 25$2880
April 2018 departuresTour only 
Apr 1$2957
Apr 8$2957
Apr 15$2957
Apr 22$2957
Apr 29$2957
May 2018 departuresTour only 
May 6$3157
May 13$3157
May 20$3157
May 27$3157
June 2018 departuresTour only 
Jun 3$3157

Holiday details

Holiday type

Self-guided walking, single centre. Managed by Headwater appointed agent.


Selected Sundays and Tuesdays from 22 Jan '17 to 3 Jun '18, for 8 days (7 nights). Non standard departures are possible on this holiday.


All buffet breakfasts and evening meals included.

Other details

Please see our Planning your holiday and What's included in the price? pages for additional information. Please call us for single room supplements, room upgrade options and child prices.

Starting your tour

Transfers included from Bermuda airport at 18:30, and back to Bermuda airport at 17:45.

Enquire about this holiday

Simply complete the form below and a member of our sales team will contact you (when it's most convenient for you) to provide availability information, travel options and additional information.

We'd like to keep you informed of our latest news and special offers. Please tick here if you'd rather not receive our free e-newsletter.
We can call you when it's most convenient for you, or contact you by email if you'd prefer. Morning calls will be between 9:00-13:00, afternoon calls between 13:00-17:00, and evening calls after 17:00.
Let us know any queries you might have about departure dates, similar holidays or tailor-made options.


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  • ABTA Member (No. W1593)
  • Relaxed activity holidays since 1985

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