A Pirate Looks at 50
Seven Seas, a white sailing catamaran, seen from above in brilliant blue water

July 23-31, 2027 · British Virgin Islands

A Pirate
Looks at 50.

Drew’s birthday week aboard Seven Seas

Ten of us. A 55-foot catamaran. Our own captain and chef. Seven nights in the BVI. Nobody cooks, nobody sails, nobody sets an alarm.

Add trip to calendar
7nights
5couples
55′Lagoon
3crew

Meet the boat

Your home on the water.

A new Lagoon 55 built for exactly this: five couples, each with their own queen cabin and bathroom, and enough room to disappear for an afternoon.

Captain. Chef. Mate.They handle the sailing, three meals a day, drinks, the dinghy, the water toys and the daily decision of which ridiculous blue cove we wake up in next.
The shaded outdoor dining and lounge deck aboard Seven Seas
Lunch tastes better out here.
A calm, modern queen cabin aboard the Lagoon 55
One ensuite cabin per couple.

Sample itinerary · Not our final route

Wake up somewhere new.

This is a sample of what a great BVI week could look like. We’ll develop our own itinerary in Q1 2027, custom-tailored to our group and what we want to do. These stops and days aren’t locked in; the final route will also depend on weather and the captain’s guidance.

01

Sat 24

Norman Island

First sail, snorkel the caves, sunset at anchor.
02

Sun 25

Cooper Island

A slow morning, paddleboards and rum tasting ashore.
03

Mon 26

Virgin Gorda

The Baths before the crowds: granite boulders and sea pools.
04

Tue 27

Anegada

Miles of empty sand and lobster on the beach.
05

Wed 28

Marina Cay

A long sail back and Drew’s birthday dinner aboard.
06

Thu 29

Jost Van Dyke

White Bay, Soggy Dollar and the Painkiller.
07

Fri 30

Cane Garden Bay

One more swim. One more sunset.
08

Sat 31

West End

Off at noon with one last look back.

Our crew. Our wish list. A week made for us.

What we’re getting into

Seven days.
Plenty of trouble.

This isn’t a week of doing nothing. It’s a week of doing exactly the right things, with a swim and a Painkiller in between.

Hundreds of boats and partygoers gathered in turquoise water for Christmas in July in the BVI
The big one

Christmas in July

Hundreds of boats raft up at Virgin Gorda for the BVI’s huge annual party: music, dancing, food and one gloriously ridiculous day on the water.

We’ll confirm the 2027 event day before the captain locks our route.Photo: Caribbean Journal
A scuba diver exploring the coral-covered RMS Rhone wreck in the British Virgin Islands
Below the surface

Scuba dive

Rendezvous with a local dive operator for the RMS Rhone or another captain-approved site, with snorkeling nearby for the rest of the crew.

Photo: All Star Liveaboards
A school of yellowtail fish underwater in clear blue water
Lines out

Fish the crossings

Troll between islands and see what bites. We’ll arrange the right BVI fishing permit and gear before departure.

Photo: Drew’s pick
The colorful Soggy Dollar beach bar on White Bay, Jost Van Dyke
White Bay

Soggy Dollar

Swim ashore, order the original Painkiller and settle in for one of the best beach-bar afternoons anywhere.

Photo: Epic Yacht Charters
Also worth keeping in the captain’s back pocketThe Indians + Norman Island cavesThe Baths at first lightAnegada lobster dinnerJost Van Dyke’s Bubbly Pool

Getting there

Book these flights.

Please book within 2 weeks

Choose whichever airline cabin or fare class you prefer - just match these flights and times so we can travel together.

Friday, July 23

LAX10:25 AM
MIA6:46 PM

American AA1480 · Nonstop · Overnight in Miami

Saturday, July 24

MIA9:11 AM
EIS12:11 PM

American AA3861 · Nonstop · Operated by Envoy Air

Saturday, July 31

EIS12:51 PM
LAX7:58 PM

AA3861 + AA2290 · 1 stop in Miami · 10h 7m

Friday night in Miami: Mayfair House, dinner at MILA, then the Saturday morning flight to Tortola together. See our Miami plans.

Friday, July 23, 2027 · Miami

One night.
A proper send-off.

Before the bare feet and boat life: a lush Coconut Grove hideaway at Mayfair House and dinner together at MILA. Our vacation starts in Miami.

Lush gardens and distinctive architecture at Mayfair House Hotel & Garden in Coconut GroveGolden-hour view of the rooftop pool and colorful Sipsip terrace at Mayfair House Hotel & Garden

Stay · Coconut Grove

Mayfair House
Hotel & Garden

Lush gardens, wonderfully eclectic design and a rooftop pool tucked above the Grove. A little tropical escape before our island escape—and our home base for the first night together.

Check in
Friday, July 23, 2027
Check out
Saturday, July 24, 2027

3000 Florida Avenue, Coconut Grove, Miami

View hotel & check rates

Each couple books its own room for one night. Rates and availability are confirmed by the hotel; no group room block is reserved.

Photos: Mayfair House Hotel & Garden
MILA’s atmospheric rooftop dining terrace in Miami Beach

Dinner · Miami Beach

MILA

A rooftop night out with Mediterranean-meets-Japanese food, cocktails and plenty of atmosphere. Ten friends, one table, and a toast to the week ahead.

The plan
Friday, July 23 · Dinner together
Reservation
Time & group booking to come

1636 Meridian Avenue, rooftop, Miami Beach

Explore MILA & the menu

We’ll arrange the dinner reservation as a group. MILA is across the bay from our hotel, so plan on a ride to dinner.

Photo: MILA Restaurant

The money, without the boring part

What your $9,400 gets you.

Included

  • The whole boat and all five ensuite cabins
  • Captain, chef and mate for seven days
  • Every meal cooked aboard
  • Open bar: beer, wine, house spirits and mixers
  • Fuel, mooring balls, cruising permits and customs fees
  • Snorkel gear, paddleboards, floats and water toys
  • Air conditioning, day and night

What’s additional

  • Crew gratuity: 20% standard, $1,880 per couple
  • Scuba diving and certification
  • Top-shelf liquor, champagne and special wine requests
  • Beach bar tabs and dinners ashore
  • Airport taxis and the Miami hotel night
  • Flights and whatever trouble we find on land
All in per couple, including 20% crew gratuity$11,280

September 12, 2026$4,700 depositDue to secure the boat

May 24, 2027$4,700 balanceThen you’re set

End of the week$1,880 gratuityPaid aboard

Protect your share

Invoice it.
Insure it. Relax.

Each couple gets their own invoice from the boat manager for the $4,700 deposit and $4,700 final payment. That paper trail lets you document your non-refundable trip cost when you buy your own Faye travel protection plan.

Deposit due September 12, 2026. Each couple must submit their $4,700 deposit payment by this date to secure the boat.

Standard trip cancellationUp to 100%

Faye says eligible non-refundable trip costs can be reimbursed when you cancel for a covered reason, up to the trip cost entered in your plan.

Cancel For Any Reason add-onUp to 75%

Buy within 14 days after your first trip deposit. Faye’s purchase window starts with your first trip payment, which may be a flight or hotel booked before the boat deposit.

You must cancel at least 48 hours before departure. Enter the full non-refundable trip cost you want covered and check your plan’s terms.

Check Faye’s CFAR purchase deadline

Why the separate invoices matter: the boat keeps the non-refundable payments; an approved claim reimburses the insured couple under their policy, so their cancellation doesn’t leave the rest of the group trying to cover an undocumented share.

Coverage, availability and reimbursement depend on your state, plan documents and approved claim. Enter the full non-refundable trip cost you want covered and review the policy before buying.

Five couples. Five cabins. That’s it.

Tell us you’re in.

Choose your couple and tap “We’re in.” Everyone will see the shared roll call update, and the boat manager will invoice each confirmed couple separately.

RSVP roll call0 of 5 couples in
KatonasWaiting on RSVP
ZarillisWaiting on RSVP
BachmansWaiting on RSVP
ChappiesWaiting on RSVP
LaylandsWaiting on RSVP

RSVP first, then check off your deposit, flights and Miami hotel as you book them. These shared checkmarks are updated by each couple; they don’t make a payment or reservation.

Ready for the deposit invoice? Copy this note and send it to Drew.

Download Drew’s 50th brochure Add the trip to your calendar