Website & Operations Proposal — Prepared for Calypso Charters Anguilla
Calypso
Booking & Operations Platform
A purpose-built digital platform that handles customer-facing reservations and internal operations — replacing fragmented tools with one connected system.
Calypso Charters Anguilla
Evoluut
12 weeks to go-live
March 2026
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Project Overview

More than a booking website.

Calypso Charters requires more than a standard booking website. The goal is to create a digital platform that supports both customer-facing reservations and the day-to-day operational needs of the business.

The proposed platform will serve as the front-facing entry point for bookings while connecting directly into an internal operations system for managing reservations, passenger manifests, vessel scheduling, customer communication, and reporting. This project is intended to replace a fragmented workflow currently handled through multiple tools — website forms, spreadsheets, Google Calendar, WhatsApp, and manually prepared confirmation documents.

Project Objective

A modern booking and operations platform.

Design and develop a connected system that allows Calypso Charters to accept and manage online bookings efficiently, organise daily passenger reservations by trip and vessel, generate and distribute manifests automatically, and provide better visibility into departures, passenger readiness, and trip activity — while supporting internal staff, agents, and operational viewers through role-based access.

What the platform replaces

Current pain points

No central boat registry

Vessel assignments live entirely in staff memory. One resignation and it's gone — one mistake and a vessel is double-booked.

Manifest built by hand every day

45–90 minutes of avoidable manual work each afternoon, assembled from Google Calendar, spreadsheets, and memory.

WhatsApp carries safety data

After the 4PM send, all headcount changes flow through WhatsApp — producing no auditable souls-on-board record.

Vendors operating in the dark

SXM and AXA vendors have no live availability. Every booking requires a phone call or Google Sheet workaround.

What the platform delivers

The new system

Customer-facing booking

Online booking for shared transfers — branded interface connected directly to the internal operations system.

Internal operations hub

Reservations, manifest generation, passenger management, and fleet visibility — all in one system.

Role-based access

Six user roles with precisely scoped access for every person in the operation — staff, agents, captains, immigration.

Reporting & visibility

Monthly boat usage, transfer counts, excursion totals, and departure dashboards — generated automatically.

System Architecture

The modernised system — one connected platform.

The new platform consolidates every tool in the current workflow into a single system with three clear layers: booking intake, operations management, and automated distribution.

Booking channels
Website
Shared transfers
Online payment
Phone / Hotel
Excursions &
private transfers
Vendor Portal
Hotel Guest Services & Destination Agents
Email enquiry
Manual entry
by clerk
↓   ↓   ↓   ↓
Calypso Operations Platform
Booking Engine
Fleet Registry
Passenger Manager
Manifest Engine
Flight Feed
Reporting
↓   ↓   ↓   ↓   ↓
Automated distribution
Captains
Mobile manifest + SOB count
Desk Clerks
AXA + SXM terminals
Immigration
Auto-export, both ports
Vendors
Live portal, own bookings
Customers
Confirmation + reminders
Notifications & Communication

Automated notifications — email, WhatsApp, and in-app.

The platform handles automated communication at every touchpoint. The app does not replace WhatsApp — your team's existing WhatsApp groups continue as-is. The platform sends automated notifications into WhatsApp, supplementing rather than replacing the channel your team already relies on.

Daily manifest — sent automatically via WhatsApp + Email

Every day, the manifest is sent automatically to all relevant recipients — no manual sending required. Both WhatsApp and email are used so every recipient gets it through their preferred channel.

Admin Reservations Clerk Desk Clerk Captain Immigration / Police
Email
  • Booking request confirmation to customer (excursion & private)
  • Shared transfer payment confirmation to customer + admin
  • Approved booking confirmation to customer
  • Declined booking notification to customer
  • Daily manifest to all recipients
  • 24hr pre-departure reminder
WhatsApp (Automated)
  • Daily manifest to all recipients
  • New booking request alert to admin
  • Booking approved / declined notification
  • Flight delay alert linked to affected bookings
  • Daily summary report to super admin / stakeholders (add-on)
In-App Alerts
  • New booking request pending admin review
  • Missing passport data flag per booking
  • Manifest not-yet-sent warning (before deadline)
  • Vessel in repair — booking conflict
  • SXM flight delayed — affected bookings listed
  • Pending cancellation awaiting approval
Daily Summary Report
  • Sent via WhatsApp to super admin / stakeholders
  • Total departures and passenger count for the day
  • Revenue summary by service type
  • Vessel utilisation snapshot
  • Any alerts or issues flagged
Smart Vessel Movements

See what's available — before the customer hangs up.

Smart vessel movements is not GPS tracking — it is a real-time availability view. When a reservations clerk receives a call for a same-day excursion, she can instantly see which vessels are free, when, and for how long. No phone calls to find out. No double-booking. No guessing.

What the clerk sees in real time

Sea Dancer
Cap.30 · Dual use
Available now
Free 10:30am – 3:00pm
Lady Lina
Cap.24 · Shared only
In use until 11:30
Free from 12:00pm
Island Star
Cap.14 · Dual use
In Repair
Not available
Calypso I
Cap.10 · Fishing only
Fishing only
Not eligible for excursions

Why this matters

  • Clerk answers the phone and checks availability in seconds — no hold, no callback
  • System filters by service type — a fishing-only vessel won't show for an excursion request
  • Vessels in repair or retired are clearly marked and excluded from selection
  • Gaps between bookings are visible — easy to see if a vessel has a free window for a same-day booking
  • Replaces the mental map that currently lives only in experienced clerks' heads
The Platform — Booking Flow

How bookings move from enquiry to calendar.

Every booking starts with the same six steps. After submission, the flow splits based on service type — shared transfers confirm automatically on payment, while excursions and private transfers go through an admin approval step before confirmation is sent.

1
Date
Departure date and time slot
2
Service
Shared · Excursion · Private
3
Vessel
System shows available vessels
4
Passengers
Lead name · PAX count · Hotel
5
Flight
Linked to live SXM arrivals
Submit
Flow splits by service type
Shared Transfer Online payment flow
1
Customer fills out form + pays online
Card taken at time of booking. No manual follow-up needed.
2
Auto-confirmed immediately on payment
No admin approval required. System confirms instantly.
Booking added to calendar
Confirmation email sent to customer and admin automatically.
Customer email Admin email
Excursion Private Transfer
1
Booking request submitted
Request email sent to customer and admin. No payment yet.
2
Admin reviews request
Admin views request, checks vessel availability, assigns captain and vessel.
3
Approve or Decline
✓ Approve ✗ Decline
Decline sends a notification to the customer.
Auto-confirmation sent + added to calendar
Approved confirmation emailed to customer. Booking added to the calendar with captain and vessel assigned.
Approved confirmation
New booking screen
app.calypso.vc/bookings/new
CC
Dashboard
Bookings
Calendar
Manifest
Passengers
Fleet
Reports
New Booking
Step 2 of 6Submit request
1 Date
2 Service
3 Vessel
4 Passengers
5 Flight
6 Submit
Select service type
Shared Transfer
Pay online → auto-confirm
Excursion
Request → admin approves
Private Transfer
Request → admin approves
Fishing Charter
Request → admin approves
Shared Transfer: Customer pays online → confirmed immediately. No admin step required.
Departure date
27 March 2026
Time
08:30 AM
Lead passenger name
Johnson, Robert
Total passengers
4
Hotel / resort
Cap Juluca
Booking summary
Date27 Mar 2026
ServiceShared
After submitAuto-confirm
Passengers4
Available vessels
Filtered · 27 Mar · Shared
Sea Dancer
Cap.30 · 12 seats free
Blue Horizon
Cap.22 · 15 seats free
Lady Lina
Cap.24 · 24 seats free
Continue →
The Platform — Module 01

The Command Dashboard

Module 01 — Dashboard

Your full operation at a glance.

Every departure, vessel, alert, and incoming flight in one real-time view. No more piecing together the day from multiple sources.

  • Today's departure schedule with live status — pending, ready, check-in
  • SXM flight arrivals with delay flags — know before passengers do
  • Alerts: missing passports, unsent manifests, vessel service due
  • Full fleet status grid — active, repair, retired per vessel
  • Passenger headcount across all today's departures
app.calypso.vc/dashboard
CC
Dashboard
Bookings
Calendar
Manifest
Passengers
Fleet
Reports
DashboardThu 26 March 2026+ New Booking
8
Departures today
142
Total passengers
3
Pending action
6
Vessels active
Today's departures
08:30 Sea Dancer · Shared Transfer · 18 paxReady
09:00 Blue Horizon · Shared Transfer · 18 paxPending
10:00 Miss Anguilla · Private Transfer · 6 paxReady
11:30 Lady Lina · Shared Transfer · 19 paxCheck-in
14:00 Calypso I · Fishing Charter · 8 paxReady
16:30 Sea Dancer · Excursion · 24 paxPending
SXM flight arrivals
DL 902 · Atlanta → SXM · 10:40Delayed +35m
B6 384 · JFK → SXM · 13:20On time
UA 521 · Newark → SXM · 15:55On time
AA 204 · Miami → SXM · 17:10On time
⚠ Alerts requiring action
Blue Horizon — 3 passengers missing passport data
DL 902 delayed +35m — 4 pax on 11:30 transfer affected
Manifest not yet sent for tomorrow (deadline 4:00 PM)
Sea Dancer — service due in 12 days
Fleet status
Lady Lina
Cap.24 · Shared
Active
Sea Dancer
Cap.30 · Dual
Active
Blue Horizon
Cap.22 · Shared
Active
Miss Anguilla
Cap.12 · Private
Active
Calypso I
Cap.10 · Fishing
Active
Island Star
Cap.14 · Dual
In Repair
Calypso II
Cap.24 · Shared
Active
Sandy Point
Cap.16 · Private
Retired
The Platform — Module 03

Calendar — Google-style daily list view

Module 03 — Calendar

Every booking in a clean daily list.

Colour-coded by service type — exactly like the Google Calendar list view your team already knows. Blue = Shared · Green = Excursion · Red = Private · Amber = Fishing.

  • Familiar date + time + event layout — identical to Google Calendar list view
  • Colour dot per service type — immediately scannable
  • Vessel, PAX count, and flight number visible per row
  • Filter by vessel, service type, or date range
  • Click any entry to open full booking detail
app.calypso.vc/calendar
CC
Dashboard
Bookings
Calendar
Manifest
Passengers
Fleet
Reports
March – April 2026‹ ›
● Shared ● Excursion ● Private ● Fishing All vessels ▾
25
MAR, WED
08:30 – 10:00am
Sea Dancer · Shared Transfer
18 pax · AXA → SXM · AA204 · Johnson, R.
10:00 – 11:30am
Miss Anguilla · Private Transfer
Clarke, M. · 6 pax · AXA → SXM
11:30am – 1:00pm
Lady Lina · Shared Transfer
19 pax · AXA → SXM · B6384 · Rousseau, C.
26
MAR, THU
7:00am – 1:00pm
Calypso I · Fishing Charter
Webb, M. · 8 pax
09:00 – 10:30am
Blue Horizon · Shared Transfer
18 pax · AXA → SXM · DL902 · Benson, T.
2:00 – 6:00pm
Sea Dancer · Excursion PM
Martínez, S. · 24 pax
27
MAR, FRI
08:30 – 10:00am
Calypso II · Shared Transfer
Baptiste, C. · 30 pax · AXA → SXM · UA521
11:00am – 12:30pm
Miss Anguilla · Private Transfer
O'Brien, J. · 4 pax
28
MAR, SAT
9:00am – 1:00pm
Sea Dancer · Excursion AM
Chen, D. · 22 pax
7:00am – 1:00pm
Calypso I · Fishing Charter
Martinez, J. · 6 pax
2:00 – 3:30pm
Lady Lina · Shared Transfer
14 pax · SXM → AXA
The Platform — Module 04

Auto-Generated Manifest

Module 04 — Manifest Engine

45 minutes of daily work becomes one press.

Built from existing booking data. Formatted per recipient. Sent to captains, clerks, and immigration by the configured deadline. Full audit trail included.

  • One-click generation from all confirmed bookings
  • Role-scoped outputs — captains see crew info, immigration sees passport data
  • Scheduled auto-send with configurable deadline (default 4PM)
  • Export to Excel or PDF for existing recipients
  • Full audit trail — who received what and when
app.calypso.vc/manifest
CC
Dashboard
Bookings
Calendar
Manifest
Passengers
Fleet
Reports
Manifest — 27 March 20267 departures · 123 passengers total
⏰ Not sent — due 4:00 PM Send all ⬇ Export
⚠ 3 bookings still pending — review passport data before sending
Time Lead Name Vessel Captain Pax Service Route Flight Status
08:30 Johnson, R. Sea Dancer Capt. Andre 18 Shared AXA→SXM AA204 Ready
09:00 Benson, T. Blue Horizon Capt. Marcus 18 Shared AXA→SXM DL902 Pending
10:00 Clarke, M. Miss Anguilla Capt. James 6 Private AXA→SXM Ready
11:30 Rousseau, C. Lady Lina Capt. Pierre 19 Shared AXA→SXM B6384 Check-in
14:00 Webb, M. Calypso I Capt. Roy 8 Fishing AXA Ready
15:00 Martínez, S. Sea Dancer Capt. Andre 24 Excursion AXA Pending
Captains (5)
✓ Sent 15:42
Desk Clerks AXA
✓ Sent 15:42
Desk Clerks SXM
Pending
AXA Immigration
Pending
SXM Immigration
Pending

Vendor Portal

SXM and AXA hotel vendors get their own login. Live availability, direct booking, own manifests. No phone calls needed.

Captain Mobile View

Assigned trips, passenger list, souls-on-board count. Marks vessel departed — creates the auditable safety record.

Immigration Export

Passport data collected at booking auto-populated into the immigration export. 30+ minutes saved per departure day.

Access Control

The right information, for the right people.

Six user roles, each precisely scoped. Agents never see each other's data. Captains never see financials. Immigration sees all passenger movements and nothing about revenue.

Super Admin
Admin
Full access. Calypso management only.
Everything
Pricing + rates
All reports
User management
System config
Reservations
Reservations Clerk
Office-based. Creates all bookings.
Create / edit bookings
Add passengers + docs
Send confirmations
Build + send manifest
No pricing config
Desk Clerk
Desk Clerk
Terminal-based. Check-in passengers.
View day's bookings
Check in passengers
Add walk-ons
Update SOB count
No booking creation
Vendor
Vendor
SXM / AXA hotels. Own portal.
Live availability
Create own bookings
View own manifest
Add passengers
No other vendors' data
Captain
Captain
Own trips only. Mobile view.
Own schedule
Passenger list
SOB count
Mark departed
No financials
Immigration
Immigration / Police
Full manifest. Both ports. Read only.
All daily manifests
All passenger data
Passport + nationality
Both AXA and SXM
No financials
Permission Matrix

Who can do what.

Three hard rules enforced from day one: vendor data isolation, port-scoped immigration access, and cancellations requiring admin approval at all times.

Feature Admin Res. Clerk Desk Clerk Vendor Captain Immigration
Bookings
Create booking Full Full Full
Edit booking Full Full Own only
Cancel booking Full Request only Request only
View all bookings Full Full View Own only
Send confirmation Full Full Own bookings
Passengers
Add / edit passengers Full Full Check-in only Own bookings
Upload documents Full Full Full Own bookings
View passenger data Full Full Full Own bookings Assigned trip Full view
Manifest & Departure
Generate & send manifest Full Full
View daily manifest Full Full View Own bookings Assigned trip Full view
Check in passengers Full Full
Update SOB headcount Full Full Full
Mark vessel departed Full Full Full
Fleet & System
Manage vessels Full
Flight arrival feed Full Full View View View
Financials & Reports
Revenue & payments Full
Monthly reports Full View
User & role management Full

Three hard rules built into the database: (1) Vendors are fully siloed — they cannot see another vendor's bookings or Calypso's revenue. (2) Cancellations always require admin approval — automatic audit trail. (3) Immigration access is complete on passenger movements, zero on financials.

Project Timeline

Live in 12 weeks.

A focused 12-week delivery structured into four phases, covering frontend design, backend development, testing, and go-live training. The final week runs parallel to your existing process to ensure a smooth handover.

Weeks 1–2

Discovery & Frontend Design

Finalise requirements, confirm boat list and manifest format. Design all UI screens — dashboard, booking flow, calendar, manifest, passenger views. Client review and sign-off on designs before development begins.

UI/UX designScreen layoutsClient reviewRequirements confirmed
Weeks 3–4

Frontend Development

Build all frontend screens from approved designs — dashboard, booking form, calendar list view, manifest view, passenger management, fleet registry, and vendor portal interface.

All UI screens builtBooking flow (all types)Calendar list viewPassenger managementVessel availability view
Weeks 5–6

Backend Development — Core

Core database, authentication, user roles, vessel registry, booking engine, and approval workflow. Shared transfer payment flow (online card). Excursion and private transfer request and approval flow.

Database + authBooking engineApproval workflowOnline paymentConfirmation emails
Weeks 7–8

Backend Development — Operations

Auto-manifest generation and distribution, live dashboard, SXM flight API, vendor portal with data isolation, immigration export, captain mobile view, and WhatsApp notification integration.

Manifest engineDashboard + alertsFlight feed (SXM)Vendor portalImmigration export WhatsApp integration
Weeks 9–10

Notifications, Reports & Full QA

Email and WhatsApp automated notification system, monthly reporting suite, SOB tracking, vessel movements view, and comprehensive quality assurance testing across all six user roles.

Email notificationsWhatsApp alertsDaily summary reportMonthly reportsFull QA all roles
Weeks 11–12

Go-Live & Training

Data migration from existing tools. Role-based team training sessions (admin, reservations, desk clerks, captains, vendors). Parallel running alongside existing process during Week 11. Go-live Week 12 with live support throughout. Full handover documentation and video guides delivered.

Investment

Two ways to get started.

Choose the model that fits your business — a one-time build you own outright, or a lower upfront option with frontend ownership and a monthly backend subscription. Both plans deliver the complete platform in 12 weeks.

Plan A
Full Ownership
One-time build fee. You own the frontend and backend code outright.
FRONTEND DEVELOPMENT
$5,500
Website + operations UI · owned outright
BACKEND DEVELOPMENT
$11,000
Full system + integrations · owned outright
Payment schedule
On contract signing$6,600 (40%)
Midpoint — Week 4$4,950 (30%)
On go-live — Week 12$4,950 (30%)
  • Full source code transferred on delivery
  • Hosting $150/mo billed separately
  • Modify or extend with any developer
  • Best long-term value
  • New features quoted separately
Lower upfront
Plan B
Frontend + Subscription
Own your frontend. Subscribe to the backend, hosting, and everything that runs it.
ONE-TIME — FRONTEND DEVELOPMENT
$5,500
Frontend code owned by Calypso on delivery
MONTHLY — BACKEND + HOSTING, ALL-IN
$450/mo
12-month minimum · then month-to-month
Monthly subscription includes
Backend system + operations engine
Unlimited users across all roles
Unlimited vessels / fleet size
Secure cloud hosting + daily backups
Platform updates + bug fixes
SXM flight API subscription
  • Frontend code owned outright after $5,500
  • Full platform from day one — nothing removed
  • Backend stays with Evoluut — access only
  • New features quoted separately

Side-by-side comparison

Plan A — Full Ownership Plan B — Frontend + Subscription
Frontend development (one-time) $5,500 $5,500
Backend development (one-time) $11,000 Included in subscription
Total upfront $16,500 $5,500
Monthly ongoing $150/mo hosting $450/mo all-in
Year 1 total cost ~$18,300 ~$10,900
Year 2 total cost ~$1,800 (hosting only) ~$5,400
Frontend code ownership ✓ Owned outright ✓ Owned outright
Backend code ownership ✓ Owned outright ✗ Evoluut retains IP
Unlimited users + fleet ✓ Included ✓ Included
Hosting + updates + flight API $150/mo separately ✓ All included
New features Quoted separately Quoted separately
Minimum commitment None after delivery 12 months
Delivery timeline 12 weeks 12 weeks

Both plans include the same complete platform

✓ All 6 modules
✓ All 6 user roles
✓ Unlimited users + fleet
✓ Data migration
✓ Email + WhatsApp setup
✓ Role training sessions
✓ 30-day post-launch support
✓ 12-week delivery
✗ New features not included
Why Evoluut

We built this proposal around your operation.

01
We mapped your workflow before writing a line of this proposal
This document is built on a detailed operational analysis of how Calypso actually runs — not a generic template. Every module solves a specific problem we identified in your process.
02
Fixed price. Fixed timeline. No surprises.
12 weeks, complete delivery. The scope is defined, the price is fixed, and the timeline is binding. You go live with a complete system — not a partial build with a roadmap of features coming eventually.
03
You own everything on delivery (Plan A)
The source code, the data, the platform — all transferred to Calypso Charters at go-live. No vendor lock-in, no dependency on Evoluut to keep operating. Build on it, modify it, or hand it to any developer.

Ready to run Calypso the way it should be run?

The next step is a 60-minute discovery session to confirm the final requirements — boat list, manifest format, and a few operational decisions. We begin immediately after sign-off.

EVOLUUT
evoluut.co