Itinerary
Five nights, two basecamps: live aboard a crewed catamaran for the first three nights, then move to a St. John villa for the finale. Times are targets — the boat runs on island time. draft
Arrival & cast off
- All crews land at STT (see Flight Guide), taxi to Red Hook Marina — ATL crew lands 12:40 PM and holds the boat
- Board 1:30 PM · cast off 2:00 PM — provisioning & cabin assignments
- First stop: snorkel Hawksnest Bay, sunset swim, welcome dinner aboard
- Championship opens — first events scored tonight
Cliff jumping & snorkeling — along the sail
- Snorkel stops working down the cays
- Cliff jumping stop on the sailing route — Championship style points on the line
- Sail on — sunset swim & dinner aboard
Bordeaux summit — from the anchorage
- Anchor off St. John — tender in & hike Bordeaux Mountain (1,277 ft)
- Swim call off the back of the boat after the descent
- Last night at anchor — cards & rum after dark
Marlin day — the charter finale
- Transfer at sea — the sportfisher comes alongside the catamaran, gear over the rail
- Full day offshore — blue marlin & mahi; First Fish & Biggest Catch scored
- Drop-off at the marina — transfer to the villa near Cruz Bay, grill the catch & dominoes
Cruz Bay crawl & the crowning
- Morning guided spearfishing on the reef, then beach recovery & final scored events
- Cruz Bay bar crawl — Woody's → Quiet Mon Pub → Skinny Legs
- Champion crowned — trophy presented, loser put on notice
Wheels up
- Villa checkout, transfers to STT
- Reverse the flight plan home — safe travels, gentlemen
Vendors
Who we're booking with for each piece. Names/contacts marked tbd still need to be locked — fill these in as deposits go down.
Catamaran charter tbd
Crewed catamaran, 3 nights (Oct 2–5), sleeps 10 + crew. Includes captain & chef.
Contact: _______ · Deposit: _______
Marlin fishing charter tbd
Full-day offshore sportfishing (Oct 5). Pick-up at sea from the catamaran, drop-off at the marina — confirm the at-sea transfer with both captains. Rods, bait, mate included.
Contact: _______ · Deposit: _______
Spearfishing guide tbd
Guided spearfishing / free-dive (Oct 6, morning). Gear rental for non-divers.
Contact: _______ · Deposit: _______
St. John villa tbd
2 nights (Oct 5–7), 5BR+ with pool, near Cruz Bay.
Contact: _______ · Deposit: _______
Ground & ferry transport tbd
Airport taxis, STT→STJ ferry, island safaris on St. John.
Contact: _______
Provisioning tbd
Grocery + alcohol delivery to the boat at the marina (see alcohol duty in Packing).
Contact: _______
Budget
Target of ~$1,495 per person (10 guys), covering shared trip costs. Excludes your flights to STT and personal spending. estimate
| Line item | Per person | Group (×10) |
|---|---|---|
| Catamaran charter — 3 nights, crewed | $550 | $5,500 |
| St. John villa — 2 nights | $200 | $2,000 |
| Marlin fishing charter | $200 | $2,000 |
| Spearfishing guide & gear | $100 | $1,000 |
| Food & provisioning | $180 | $1,800 |
| Alcohol | $80 | $800 |
| Ground transport & ferries | $70 | $700 |
| Activities & misc (hike, bar crawl kitty) | $65 | $650 |
| Crew tips | $50 | $500 |
| Total per person | $1,495 | $14,950 |
Booking Timeline
What needs to happen, and when, to keep the trip on the rails. draft
Lock the roster & deposits
Confirm all 10 in. Everyone sends the $500 deposit (Venmo @jonesy_88). Book flights while award seats last — fares only climb.
Secure the big items
Catamaran deposit down and dates held. Marlin charter reserved (Oct 5, with at-sea pick-up). Villa held for Oct 5–7.
Activities & balances
Book spearfishing guide. Pay villa balance. Confirm ground transport & STT→STJ ferry plan.
Final payments & provisioning
Collect remaining ~$995/person. Place grocery + alcohol provisioning order. Finalize alcohol duty assignments. Send packing list reminder.
Sicily & Guam depart
Long-haul crews start travel — overnight routing via ATL (see Flight Guide).
Cast off
Everyone on-island, board the catamaran. The Last Cast begins.
The Last Cast Championship
14 scored events across the week. Points tallied daily; the Champion is crowned on Oct 6. draft scoring
The stakes: The overall winner takes the trophy and eternal glory. The overall loser buys the first round at the wedding. No exemptions, no appeals. The groom plays but cannot lose (it's his party).
The 14 events
First Fish
First man to land a fish on the marlin charter.
Biggest Catch
Largest fish by weight over the trip.
The Marlin Bonus
Land a billfish — automatic bounty.
Spearfishing Haul
Most fish speared in the dive session.
Cliff Jump — Style
Judged on the panel's 1–10 scorecard.
Bordeaux Summit
First man to the top of the mountain.
Snorkel Scavenger Hunt
Most items off the reef checklist.
Knot & First-Mate Challenge
Fastest correct cleat hitch & bowline aboard.
Painkiller Chug
Head-to-head bracket, island cocktail edition.
Dominoes Tournament
Villa-night bones bracket, island rules.
Cornhole / Cards
Running scoreboard across the week.
Best Dressed — Pirate Hat
Daily fit check; commitment to the bit rewarded.
Bar Crawl Survivor
Last man standing on the Cruz Bay crawl.
Sunrise Club
Up and on deck for sunrise — points each morning.
Packing List
Tap to check items off — your progress saves on this device. Soft duffel only — hard luggage doesn't fit on the catamaran.
The non-negotiables
Documents & money
Apparel
Water & activity
Toiletries & misc
Alcohol duty
Flight Guide
Two routings to get all 10 to St. Thomas (STT) by Oct 2. confirm seats
Group A — NoVA · Indiana · Mississippi
Routing: American Airlines via Miami, arriving Oct 2 at 1:03 PM.
| Flight | Route | Notes |
|---|---|---|
| AA 1232 | DCA → MIA | Connect in Miami |
| AA 419 | MIA → STT | Departs 10:16 AM · lands STT 1:03 PM |
Indiana & Mississippi crews position to DCA (or join the same MIA connection) to ride AA 419 together into STT.
Group B — Sicily & Guam
Routing: Long-haul via Atlanta (ATL), departing Oct 1 with an overnight, arriving Oct 2.
- Depart home stations Oct 1 (Guam is a full day ahead — leave accordingly)
- Overnight transit / layover routed through ATL
- Delta ATL → STT departs 8:05 AM, lands 12:40 PM — board first at Red Hook & hold the boat
No bottles to haul — alcohol gets sorted on island with everyone else.