The Ultimate Month-by-Month Events & Booking Guide
Want to know the secret to seamless, stress-free travel? It’s all about timing.
The world’s best events and experiences sell out fast, but with the right planning, you can skip the stress and lock in the trips that matter most to you. That’s where we (and this guide) come in.
We’ve put together a month-by-month breakdown of major global events, peak travel seasons, and key booking windows so you’ll never have FOMO again. If you want to score tickets to a once-in-a-lifetime event or snag the best hotel suite during peak season, consider this your go-to playbook for planning with confidence.
Ready to make it happen?
Reach out to us, and we’ll take care of the details - hotels, tickets, VIP experiences, transfers and everything in between - so all you have to do is make some memories!
This Year’s Hottest Events
Did you know we can get you tickets to the below events?! Booking six months to a year out is always ideal, but we can make last-minute plans work too!
Keep reading for a monthly breakdown of 2025 & early 2026’s can’t-miss events.
April & May, 2025
Masters - Augusta National Golf Club, Augusta, GA: Apr 7 - 13, 2025
F1 Miami Grand Prix - Miami, FL: May 2 - 4, 2025
Cannes Film Festival - Cannes, France: May 14 - 21, 2025
F1 Monaco Grand Prix - Monte Carlo: May 23 - 25, 2025
June & July, 2025
Aspen Food & Wine Classic - Aspen, CO: June 20-22, 2025
Wimbledon - All England Lawn Tennis Club, London, England: Jun 30 - Jul 13, 2025
August & September, 2025
Ryder Cup - Bethpage Black Course, Farmingdale, NY: Sep 26–28, 2025
US Open - Tennis National Tennis Center, Flushing Meadows, NY: Aug 25 - Sep 7, 2025
October & November 2025
F1 US Grand Prix - Circuit of the Americas, Austin, Texas: Oct 17 - 19, 2025
World Series - Location TBA: Oct 27 - Nov 1, 2025
F1 Las Vegas Grand Prix - Las Vegas Street Circuit: Las Vegas, NV: Nov 20 - 22, 2025
December 2025 & January 2026
Art Basel - Miami Beach, Florida: Dec 4th–7th, 2025
Sundance Film Festival - Park City, UT: January 22–February 1
February & March 2026
Super Bowl - Levi’s Stadium, Santa Clara, CA: Feb 8, 2026
Winter Olympic Games - Milan and Cortina, Italy: Feb 6 - 22, 2026
Mardi Gras - New Orleans, LA: Feb 17 2026
Peak Travel
Already know your vacation days? Hotels fill-up fast and we want to make sure that you get exactly what you want when booking travel with us. If the above was the “WHAT” guide, below is the “WHEN” guide to help ensure you stay ahead of the game and secure your spot at the best destinations!
Book the following trips in - April & May
Summer Vacation Plans - Especially if you’re traveling with a large group or aiming for popular destinations like the Mediterranean.
Holiday Travel - Thanksgiving & Christmas spots fill up quicker than you’d think. Book this in early Q2 for the best chance of getting the room you want.
Graduation Trips - Check out our ideas in Conde Nast Traveler!
2026 Bucket-List Destinations - Hello, White Lotus vibes in Thailand!
Book the following trips in - June & July
Leaf Peeping & Cozy Weekend Getaways - Slow down and soak in the autumn charm with these domestic ideas.
Europe’s Shoulder Season - fewer crowds and better rates in destinations like Italy, Spain or Portugal.
Book the following trips in - August & September
Ski Season & Tropical Winter Escapes - Book early for ski season in Aspen, Jackson Hole, and the Alps. Or, plan a beach vacation to destinations like Cabo for winter sun.
Book the following trips in - October & November
Spontaneous Fall Getaways - We get it! Sometimes a last-minute weekend trip is just what you need.
Last-Minute Holiday Travel Plans - Don’t stress. Planning ahead is best, but we can work our magic!
Book the following trips in - December 2025 & January 2026
Plan Ahead for 2026 - Start thinking about next year’s bucket-list destinations now. Be the early bird that gets the best spots for 2026.
Wellness Travel - Need a reset? Now’s the time to book a wellness trip to SHA Mexico or someplace similar!
Book the following trips in - February & March 2026
Memorial Day & 4th of July Getaways - Plan now to snag the best spots for summer's biggest holidays.
Spring & Summer Vacations - Check out our previous Summer Hot List to get the ideas flowing!
Cruises - Wave Season is here! It’s the best time to book your next cruise with special rates and perks.