There are many ways to spend time on the water in the Caribbean. Some offer comfort and service. Some offer courses or certifications. Others give you a quick dose of ocean time. Each has its place.
Why SailDeep
12°37'45.1"N 61°21'28.6"W[ LARGE LIVEABOARDS ]Large Diving Liveaboards
What they are like
16–20 guests on a large motor vessel
Fixed schedule with several dives each day
Clear divide between crew and guests
Route planned in advance and followed closely
Life on board feels closer to a small cruise with scuba as the main activity
Good fit if
You want to log as many dives as possible
You prefer to be a passenger
Comfort and predictability matter more than shared work
How SailDeep differs
Small groups, no more than 5 people on one sailing yacht
Everyone takes part: steering, lines, meals, anchoring
Diving is optional and shaped by weather, timing and the crew
The focus stays on life at sea, not on hitting a dive count
SailDeep suits divers who want to be on the water and to dive in intimate groups at a pace that allows for things to sink in.
[ LIVEABOARD CLASSROOMS ]Sailing Schools and Certification Courses
What they are like
Multi-day courses with a syllabus and required skills
Skipper is primarily an instructor
Several students learning toward the same qualification
The trip is shaped around a tight schedule of drills, checklists and teaching goals
Good fit if
You want a formal sailing certification
You prefer a structured learning environment
You enjoy group training and assessment
How SailDeep differs
No courses, no exams, no certificates
You learn by participating in the operation of the boat at a natural pace
The skipper runs a voyage, not a classroom
The aim is to feel comfortable on a small vessel, not to pass a test
SailDeep suits people who want hands-on experience without the pressure of a course or the desire for certifications.
[ HARDCORE PASSAGES ]Hardcore Offshore Adventure Passages
What they are like
Long passages in exposed conditions
Night watches in rotation
Aimed at sailors seeking challenge or high-mileage training
The story of the trip often centres on difficulty and distance
Good fit if
You want to push your limits
You already identify strongly as a sailor
You prefer demanding conditions
How SailDeep differs
Warm-water coastal and inter-island sailing when conditions allow
Enough movement for a sense of passage without extreme conditions
Simple, steady days rather than endurance
Space for swimming, diving and quiet time at anchor
SailDeep is for people who want a stretch of days living at sea, not a test of toughness.
[ PARTY BOATS ]Social / Party-Style Sailing Holidays
What they are like
Several boats travelling together
Big social scene, bar stops, busy nights
Sailing is often secondary to the group dynamic
Lots of photos, playlists and shared events
Good fit if
You want a lively holiday with new party friends
Late nights matter as much as the sailing
You enjoy big-group energy
How SailDeep differs
Single boat, small group, mixed ages
To sleep and wake with the sun, early dinners, conversation
No organised party atmosphere
No expectation to perform socially
SailDeep suits people who enjoy small groups, early evenings and that feeling of physical tiredness at the end of the day.
[ DAY-TRIPS ]Day-Trip Excursions
What most day-trip tours are like
Short sessions lasting a few hours on a tight schedule
Typically structured around one main activity: snorkelling, lunch, sundowners, etc.
Quick contact with the water before returning to shore
Great for people who want a focused ocean hit without changing pace
Good fit if
You have limited time
You prefer a single activity
You want a half-day on the water
The SailDeep "Day Passage"
You take part in sailing tasks aboard a monohull sailboat
We get away from the typical tour-boat spots
Time to sail, do a little fishing, swim, snorkel, go ashore, and if booked, dive
Calm, steady pacing rather than a packed activity schedule
Who the Day Passage suits
People curious about a multi-day voyage who want to try one day first
People interested in a doing a variety of activities at sea
Anyone interested in active participation over passive interaction
Divers who prefer a small-group environment
Anyone needing a day on the water, or a quiet reset.
The Day Passage is the on-ramp to life at sea, not an single-activity tour.
[ LUXURY ]Luxury Crewed Charters
What they are like
Large, comfortable yachts with a host of professional crew
Guests are looked after; crew handles all work
Predictable, polished service
Sailing is more of a backdrop than a shared task
Good fit if
You want to relax without responsibility
Luxury and privacy matter most
You prefer to be served rather than get involved
How SailDeep differs
Simple but comfortable boat
Little separation between skipper and guests, everyone gets to participate
The value comes from taking part, not being catered to
SailDeep is for people who enjoy involvement over indulgence.
[ WELLNESS RETREATS ]Wellness and Retreat-Style Trips
What they are like
Trips framed around transformation or healing
Guided circles, reflection, yoga or breath sessions
Sailing as a setting for inner work
Good fit if
You want structured emotional or therapeutic guidance
You enjoy group reflection
You are seeking a curated process rather than an adventure
How SailDeep differs
No coaching or therapy elements
No promises about transformation
The offer is days on the sea, shared time and simple living
Any clarity you gain comes from your engagement with the rhythm of the trip
SailDeep is not a wellness retreat, but it does offer a chance to use your body, share with others, and step away from the overstimulation of contemporary life.