THE WINDWARD ISLANDS, 2026
Voyages
12°38'50.1"N 61°23'22.7"W[ SAILDEEP VOYAGES ]SailDeep runs small liveaboard trips where you spend several days living on the water.
We move under sail, anchor in sheltered bays and keep life on board simple. Diving and other experiences can be added if they fit you and the conditions, but the core of every trip is time at sea.
Day Passage
For those who want a full day on the water without the commitment of an overnight.
[ THE DAY PASSAGE ]The Day Passage gives you a full day on the water aboard Nayru, a 36 ft Beneteau Oceanis.
You step off the beach into the dinghy and leave the shore behind. By the time you climb aboard Nayru, shoes off and bag stowed, the concerns on land already feel further away.
The day settles into a steady rhythm. We hoist sail and you take a turn on the helm, feeling the boat lean and settle under your feet. You start checking the wind, the shape of the sails and the colour of the water instead of a screen.
Time falls into the gaps between small tasks such as easing a sheet, coiling a line and keeping an eye on a landmark as we move along the coast.
At anchor the boat eases back and forth on her chain in a gentle pattern. You swim, snorkel or sit in the shade and watch the surface change with the breeze.
We may go ashore to a quiet beach to walk or to try a small local restaurant. Conversations come and go, and there are long quiet patches where nobody feels the need to talk.
On the sail home the light has shifted, the sea looks different and you feel different too.
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You spend the day as part of the action on-board our 36 ft Beneteau Oceanis “Nayru”, and get back to shore before nightfall
It is a great way way to:
Enjoy a full interactive day under sail in Barbados
See whether a longer voyage might suit you
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Meet ashore by Pebbles Beach at 08:30
Take the dinghy out to Nayru at anchor
Safety and boat briefing, then hoist sail and leave the bay around 09:00
Let out the fishing line and see if we can catch lunch
Learn and practice basic sailing manoeuvres:
tacking, gybing and feeling the different points of sailTake turns on the helm and work together on trimming and easing the sails
Drop anchor in a sheltered spot for a swim and snorkel, then have lunch
Sail back along the coast and return to our starting point by 16:00.
The exact route and stop depend on conditions and what makes sense on the day.
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You are invited to:
Steer the boat under guidance
Pitch a hammock on deck while we are at anchor
Try your luck with the fishing rod
Help with sail trim and basic manoeuvres
Assist with sweating the main or weighing anchor
You do not need any sailing experience. You do need to be able to swim, feel comfortable in the water, and be reasonably fit and steady on your feet.
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No overnight: You do not sleep on board. Cabins and night routines are part of the liveaboard trips.
Less gear, less packing: You bring a day bag, not a full kit for several days.
Lighter safety and systems tour: You still learn the essentials, but not the full long-voyage routine.
Lighter interaction: You’ll get a little taste of being at the helm, trimming the sails and help with anchoring or mooring,
No deep immersion: You will not fully drop into the rhythm of sea life in one day but by the end of the day passage you will know whether the motion, the tasks and the style of trip feel right to you.
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Who the Day Passage suits
Those who are curious about sailing and want more than a sightseeing cruise
Couples or small groups who want a full, active day at sea as part of a trip to Barbados
Sailors or divers who want to see whether SailDeep feels like a fit before booking a longer voyage
If you are already thinking about a Coastal, Island, Deep or Horizon Voyage, a Day Passage is a good first step. It gives both you and the skipper a real sense of how you move and how you like to learn before you commit to more days offshore.
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We provide light snacks and soft drinks on board.
Lunch is not included in the charter fee. When we drop anchor we can head ashore to a small local spot where you choose and pay for your own meal. You are welcome to bring your own food and drinks on board, and if the fishing is kind to us, we might even turn a fresh catch into ceviche.
Alcohol is not served on board, but you may bring your own to enjoy in moderation.
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Small soft bag or backpack
Swimwear and a towel
Light clothing that dries quickly (shorts, t-shirt, sun shirt or rash guard)
Reef-safe sunscreen (SPF 30 or higher)
Hat and sunglasses with good UV protection
Your preferred seasickness remedy
Flip-flops for going ashore, and light non-marking shoes if you prefer not to be barefoot on deck
Packed lunch or enough cash to get some food from a local spot
Coastal Voyage
Live aboard Nayru for 3 days and 2 nights, sailing and diving along Barbados’ sheltered west coast.
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The Coastal Voyage is a short liveaboard. You sleep on Nayru for two nights, stay on Barbados’ sheltered west coast and get enough time for the rhythm of life at sea to start to make sense.
It is the first real step up from a Day Passage. You move from “a day sail” to living on the boat for a few days, sharing space, tasks and routines.
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Day 1
09:00 Meet at the designated location, stow your gear and settle into your cabin.
Safety and boat briefing, then leave harbour and sail north along Barbados’ west coast.
You share the helm, practice a few sailing manoeuvres in calm waters
Take some time for a snorkel / swim / shore excursion, or perhaps a dive depending on your booking
Anchor in a sheltered spot for the night
Go ashore for dinner or a sundowner
Head back on board and settle in for the night
Day 2
Your skipper is an early riser & will likely go ashore for an early morning walk or swim
Enjoy a shared Breakfast in the cockpit,
Check the forecast and plan the day
A longer sail along the coast, working on tacking, sail trim and reading the water
Anchor for lunch and swimming
If your voyage includes diving, go for one or two guided dives
A relaxed evening at anchor, with time to talk, read or sit and watch the sun go down
Day 3
A comfortable start to the morning
Set sail for the home anchorage
Stop for a dive or two depending on your booking
A light lunch under sail
Pack-up personal belongings
Return to our home anchorage by mid to late afternoon.
Disembark by 16:00
Exact anchorages dive sites and timings depend on wind, sea state and how the crew is feeling. We stay within the west coast where conditions are usually kinder, especially for newer sailors.
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You sleep on board and share cabins, the galley (kitchen), the head (bathroom) and living space.
You move through full days and nights and start to get accustomed to the sound, motion and routines.
You take on more responsibility around the boat and get a clearer sense of how Nayru sails
You get a better idea of whether
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Shorter and more comfortable. You stay on one coast, in more sheltered water.
No long passages, sailing against the swell or night watches.
Enough time get a sense of life on board
No blue water sailing, night sailing or crossing international boundaries
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People who have done a Day Passage or similar and want to try sleeping aboard
Couples, mixed families, friends who want a simple three day adventure that mixes sailing, swimming and quiet
Divers interested in a short & sweet liveaboard experience where they’re as involved in getting to the dive sites as they are in doing their pre-dive safety checks
Guests who are new to sailing and want calm conditions and a gentle learning curve
Anyone thinking about an Island, Deep or Horizon Voyage who wants to test how they handle shared space and movement over a few days
If you want more than a day out and less than a full week offshore, the Coastal Voyage is the right place to start.Item description
[ A DAY ON BOARD ]Add any other details here.
Island Voyage
The Island Voyage is where the trip starts to feel like a way of living rather than a break.
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Five days aboard gives enough time for the boat, the motion and the routines to become familiar.
You see more of the island from the sea, sail both the sheltered west coast and the more exposed south, and get a clearer feeling for how the sails, wind & swell all come together at the helm.
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On the Island Voyage you settle in. Cabins, galley, head, deck and cockpit all become familiar.
You get used to waking with the sun, watching the sails, and reading the surface of the water
We usually begin along the protected west coast to give smooth reaching and comfortable sailing while everyone finds their feet.
We anchor where conditions allow, swim and snorkel and, if your booking includes diving we’ll visit some of the better spots on the south & west coast
As confidence builds we work south into livelier water. You feel the difference between reaching, beating and running, learn to trim the sails in stronger breeze and feel to what the boat needs
There is time for stretches of sailing, time at anchor, shore excursion and quiet time on board
By the end of the voyage you start to feel it all at once: the tension in the sails, the angle of heel, the pressure on the rudder.
Your hands and body know how to move before you think
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Longer and more varied sailing. You see both west and south coasts rather than staying in one sheltered area.
More time for skills to stick and routines to feel natural.
A clearer sense of whether you enjoy being at sea for several days in a row
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Still coastal. You remain within reach of safe harbours and do not commit to long blue water crossings.
No night sailing. You may experience a little sailing at dusk but we won’t be doing any night navigation
A strong step up in confidence without the demands of a ten day passage
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Guests who have sailed or lived aboard for a few days and want more time on the water
People who want to see what it feels like when life at sea becomes a steady rhythm, not a one-off
Small groups or pairs who want a solid block of time on the water without stepping straight into a week or ten days offshore
Anyone considering the Deep or Horizon Voyage who wants to test how they handle a longer stretch aboard and more varied conditions
If you want enough time for the boat and the sea to feel familiar but are not ready for blue water yet, the Island Voyage is the middle ground.
[ A DAY ON BOARD ]Add any other details here.
Deep Voyage
The Deep Voyage is a full week aboard. It is long enough for land routines to fall away and for the boat, the sea and the crew to become a new frame of reference
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We work along the south and west coasts and, if conditions allow, up into the more secluded north and north-west.
Explore some of the most untouched parts of Barbados’ coastline, where you see more fishing boats than tour boats and fewer signs of the usual hustle and bustle
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Over seven days you stop “visiting” the boat and start living on it.
You move through days where sailing, anchoring, cooking, early morning walks on the beach, daytime naps and simple conversation set the rhythm
Forecasts and sea state matter more than the day of the week
You feel changes in wind and swell in your body before you need to check a screen
This voyage allows for longer tacks, more time under sail, and more chances to handle the helm in different conditions
When the forecast and crew readiness line up, we reach further north into less trafficked waters
If your voyage includes diving, this is often where it feels most special. You have time to choose sites by conditions instead of squeezing them into a tight schedule and to dive places that fewer people get to see
By the second half of the week most people notice how simple things have become.
You know where everything lives on board
You know the difference between a halyard and a sheet
You move around the boat without thinking and feel more part of a crew than a guest
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More time: seven days gives extra depth and repetition so skills and routines really stick.
More range: we are more likely to reach the north and north-west coasts, away from the busier areas.
More variety: you see a wider spread of conditions and adjust plans to weather in real time, not just once or twice.
More immersion: where the Coastal Voyage tests whether life aboard suits you, and the Island Voyage lets the rhythm take hold, the Deep Voyage lets that rhythm become normal for a while.
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You remain in Barbados’ coastal waters within reach of safe harbours and won’t be committing to the longer blue water crossings that define the Horizon Voyage.
No night sailing. You may see early starts or late arrivals, but full overnight passages are kept for Horizon.
Demanding in a steady way rather than by long offshore legs.
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Those who already know they enjoy being at sea for several days and want a fuller immersion
People who want quiet stretches of coastline and anchorages away from crowds
Divers who want time for conditions to line up for better sites, not a rush through a fixed checklist
Anyone thinking seriously about the Horizon Voyage who wants to see how they respond to a week of continuous boat life and longer periods under sail
If you want the time and range for the island and its waters to feel familiar, but are not yet ready for long open crossings, the Deep Voyage is where that happens.
[ A DAY ON BOARD ]Add any other details here.
Horizon Voyage
Let’s Cross That Horizon
[ OVERVIEW ]A longer journey for those ready to go beyond familiar shores .
The Horizon Voyage is an open-ended sailing and diving trip where we cross between islands, following weather, crew, and sea conditions rather than a fixed plan.
You’ll live aboard Nayru for ten days as part of the crew — sailing, diving, keeping watch, and sharing the effort of life at sea. Each leg offers something different, and no two voyages are ever the same.
It’s a shared crossing — time to disconnect, and see where the horizon leads.
The Horizon Voyage isn’t for everyone.
Living aboard a sailboat for ten days and crossing open water takes commitment, teamwork, and comfort with unpredictability. It asks you to be present, adaptable, and ready to take part in every aspect of life at sea.
To be considered, you’ll need to provide:
Proof of recent sailing experience or participation in one of our other SailDeep voyages.
Proof of travel and medical insurance that covers sailing and diving activities.
Experience alone doesn’t guarantee a spot — we’ll talk through your background, expectations, and readiness to make sure it’s the right fit for you and for the crew.
Because this voyage crosses international waters, we’ll also need to discuss timing, documentation, and weather windows before setting dates. Every Horizon Voyage is unique, shaped by season, conditions, and crew readiness.
If you’re serious about joining, reach out and we’ll start the conversation. The application process is part of the journey.
[ HIGHLIGHTS ]A Few Spots We Keep Coming Back To
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