Caribbean, ship edition

Our first group cruise - San Juan round trip through the islands we called home, on a ship we'd sail ourselves.

WINTER 2028 · DATES SET WITH THE GROUP 7 NIGHTS RUNS AT 5 FAMILIES EST. $1,400-2,100 / PERSON KIDS CLUB ONBOARD WE SAIL WITH YOU

Unpack once. See five islands.

This is the lowest-logistics group trip we run: one cabin, one unpacking, five islands. I handle the part cruises get wrong - cabin strategy, dining times, and which shore days are worth an excursion versus a beach cab - and the kids' club handles the part parents get wrong (never scheduling a night off). We sail with you: shared dinner table, shore days together for whoever wants them, and the sail-away deck party is mandatory in spirit only.

FROM THE BLOG Ten Days on the Norwegian EscapeOur own first Caribbean cruise - everything this trip does right, we learned there. READ →

WHAT YOUR FAMILY GETS

→Cabin strategy + group booking

→Dining times + a shared table

→A shore plan for every port

→Kids'-club signup handled

→Our family sailing with yours

NOT INCLUDED (HONESTLY)

-The cruise fare itself (booked at direct price)

-Flights to San Juan

-Excursions you choose to add

YOU TRAVEL WITH ALL OF US

Jen plans and leads · Cody keeps logistics and tech running · Skye is your kids' built-in trip ambassador. Meet the family →

How the trip flows.

BROAD ON PURPOSE - EXACT DATES + ORDER SET WITH THE GROUP

EMBARKATION

Fly into San Juan a day early (I'll tell you why). Board in the afternoon window, not the morning line.

SEA DAY

Ship day - kids' club for them, an actual book for you. Group dinner, same table, every night.

ISLAND CALLS

St. Thomas, Dominica, Barbados and more - exact ports depend on the sailing the group picks.

SHORE DAYS, TWO SPEEDS

Join our excursion plan, or take the beach-cab option I map for every port. No wrong answers.

LAST SEA DAY

The go-kart / waterslide / hot-tub victory lap. Packing can wait until 9pm; I'll show you how.

DISEMBARK

Walk off in San Juan - add beach days after if you're smart about it (I can plan those too).

Hold your family's spot.

$250 per family · fully refunded if the trip doesn't run · exact dates picked together.

Venmo to reserve · $250 Questions first?