Trips
Lifestyle resorts, cruises and takeovers, in one place.
Every upcoming lifestyle resort week, cruise and hotel takeover we track, grouped by month and destination. We list, you book direct: Your Open Season does not sell travel, and every booking is made with the host.
Some links on this page are affiliate links: if you book through them, we may earn a commission at no extra cost to you. We have no other business relationship with the resorts, cruise lines or hosts listed, and details can change, so always confirm dates and prices with the host. Affiliate disclosure
October 2026
Negril, Jamaica 7 trips
Glenview, United States 2 trips
Miami, United States 2 trips
New Orleans, United States 2 trips
Cancun, Mexico 1 trip
Los Angeles, United States 1 trip
Niagara Falls, Canada 1 trip
November 2026
Negril, Jamaica 10 trips
Miami, United States 3 trips
Whistler, Canada 2 trips
Bangkok, Thailand 1 trip
Puerto Morelos, Mexico 1 trip
Destination on listing 1 trip
December 2026
Negril, Jamaica 7 trips
Indianapolis, United States 1 trip
Sydney, Australia 1 trip
January 2027
Negril, Jamaica 7 trips
Fort Lauderdale, United States 1 trip
Las Vegas, United States 1 trip
Miami, United States 1 trip
Destination on listing 1 trip
February 2027
Negril, Jamaica 11 trips
Cancun, Mexico 1 trip
Fort Lauderdale, United States 1 trip
Glenview, United States 1 trip
Puerto Morelos, Mexico 1 trip
San Juan, United States 1 trip
Tampa, United States 1 trip
March 2027
Negril, Jamaica 9 trips
Tampa, United States 1 trip
April 2027
Negril, Jamaica 10 trips
Fort Lauderdale, United States 1 trip
Indianapolis, United States 1 trip
May 2027
Negril, Jamaica 5 trips
Franklin, United States 1 trip
Puerto Morelos, Mexico 1 trip
June 2027
Negril, Jamaica 7 trips
Cancun, Mexico 1 trip
Lexington, United States 1 trip
Tampa, United States 1 trip
Destination on listing 1 trip
July 2027
Negril, Jamaica 6 trips
New Orleans, United States 1 trip
August 2027
Franklin, United States 1 trip
Lexington, United States 1 trip
Destination on listing 1 trip
September 2027
Lisbon, Portugal 1 trip
Livonia, United States 1 trip
Destination on listing 1 trip
October 2027
Charlotte, United States 2 trips
Miami, United States 1 trip
November 2027
Miami, United States 1 trip
Interest list
YOS Trip #1: a founding group trip (planned for 2027)
We are gauging interest in a small founding group trip in 2027. It is an idea, not a product: there are no dates, prices or deposits yet, nothing is booked and nothing is guaranteed. Tell us where you would want to go and roughly what you would spend. If it firms up, you will hear about it first.
Planned for 2027, not yet available: YOS Pass, a membership with trip alerts, a trip planner and member pricing and presale on YOS trips. Reserving a founding member spot is free.