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Miles on Milestones: Extending Your Travel Plans Past the Celebration
Discover how travelers are getting more out of a destination wedding or reunion by extending the milestone trip—and how you can do the same.
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April 07, 2026
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Lately, milestone travel is becoming more than a quick celebratory visit; it’s evolving into something bigger. While destination weddings, family reunions, and birthday getaways are on the rise, travelers are increasingly finding ways to stretch these special occasion-centered trips beyond the main event.
Enter Miles on Milestones, one of Amex Travel's 2026 Global Travel Trends that’s defined by savvy planning and intentional extensions. According to our survey1 insights from travelers worldwide, sixty-six percent plan to take a trip this year to celebrate someone else’s milestone, and nearly half say they plan to add extra days—either staying longer in the same destination or branching out nearby.
The motivation is clear: more time with loved ones, deeper exploration, and the chance to experience the destination on your own terms. Clever planners are extending their stays and maximizing their rewards, turning a single significant event into a full-blown getaway.
If milestone travel is on your calendar for 2026, chances are you’re traveling as part of a group, which makes a vacation rental a natural choice. When you book American Express Select Homes + Retreats™* with your Platinum Card® through AmexTravel.com, you earn 5X Membership Rewards® points for your booking. Or, you can choose to use Membership Rewards Pay with Points* for all or part of your booking. In addition, you have the flexibility to cancel for free within 48 hours after booking, if you booked at least 10 calendar days in advance of your stay.
Plus, you can rest easy knowing that your hosts are professional vacation rental management companies, and Card Members have around-the-clock phone support from American Express Travel® as needed.
Explore the following Select Homes + Retreats short-term rentals in popular U.S. destinations—plus a standout cruise option—when you want to get more mileage out of life’s milestones.
Asheville, North Carolina
Set on five acres in the Blue Ridge Mountains, Bridlewood Farm offers plenty of space to connect with friends and family—and to unwind on your own. Sleeping up to 10 guests, the property features four bedrooms, three bathrooms, and a spacious barn-style entertainment lounge packed with games that keep the fun going without leaving the grounds. It’s a natural fit for extended stays where relaxation is just as important as the occasion, be it a mountain wedding or a reunion of college friends.
Hosted by: Yonder Luxury Vacation Rentals
Charleston, South Carolina
With sweeping views and refined interiors, 207 High Dunes turns a group trip into a private island escape. Accommodating up to 10 people with five bedrooms and six bathrooms, the Kiawah home offers a resort-like feel that encourages you to recharge and reset after a long weekend. The idyllic setting makes it easy to balance quality time together with quiet, personal downtime.
Hosted by: ESPM Vacation Rentals
Telluride, Colorado
Located along the slopes at Telluride Ski Resort, Hang Glider Hideout blends alpine charm with ski-in, ski-out convenience. Accommodating up to 12 people across a four-bedroom main lodge and a one-bedroom guest house, this mountain retreat is ideal for group getaways or a multi-generational family stay. High ceilings, rustic wood beams, and intricate stonework create a cozy mountain feel, with walls of windows looking out to the woods. Enjoy multiple wood-burning fireplaces, spacious living areas, and an open-layout kitchen and dining space designed for entertaining. After a day on the slopes or trails, unwind in the hot tub, by the fire pit, or in the stone soaking tub.
Hosted by: InvitedHome
Designed for large groups of up to 16, the aptly named Entertainer’s Paradise is built around the idea of fun and togetherness. From pickleball and basketball to a putting green and resort-style pool with a hot tub, there’s no shortage of activities to keep everyone entertained. With eight bedrooms and seven bathrooms, the expansive Scottsdale estate makes it easy to celebrate in style while giving guests plenty of space to relax, play, connect, and create lasting memories.
Hosted by: Revana Realty / Holiday Rental
Explore more American Express Select Homes + Retreats™ properties across the country, available to Platinum Card Members.
Set Sail with Virgin Voyages
For groups looking to keep the energy and vibes high, adults-only sailings with Virgin Voyages feel tailor-made for milestone moments. With an extensive array of entertainment, dining, activities, and relaxation all built in, travelers can extend the festivities without worrying about logistics. From a sun-soaked pool deck scene by day to electric DJ sets by night, Virgin Voyages brings the party as it plies the Mediterranean and Caribbean Seas.
When you use your Platinum Card® to book with the Cruise Privileges Program* through AmexTravel.com, you’ll enjoy special benefits† on eligible sailings of 5 nights or more with 15+ participating cruise lines, including up to $300 onboard credit, and one unique amenity per stateroom. Plus, receive 2X Membership Rewards® Points on each eligible booking with your Platinum Card®.*
Ships' Registry: The Bahamas
†Ship and stateroom exclusions apply, please see full terms and conditions.
Explore Amex Travel's 2026 Global Travel Trends
Traveling for the Lore: When the Story Shapes Your Journey
Sight-Doing: Get to Know a Place Through Local Experiences
Snackpacking: Savor the Journey, One Bite at a Time
Get more out of your getaway with American Express
Enjoy savings on select premium tickets with Delta Air Lines on designated international flights with Platinum Member Airfares™*. Platinum Card and Centurion Members receive reduced fares compared to fares available for other American Express Card Members through Amex Travel™. As a Platinum Card Member, enjoy access to savings for up to 8 passengers per itinerary on select tickets in first class, business class, and premium economy with participating airlines on designated international flights. Eligible Card Member must be traveling on the itinerary.
Get more out of your getaway with American Express
With the American Express Global Lounge Collection® get access to 1,550+ airport lounges in over 500 airports around the world, including The Centurion® Lounge. Enjoy exclusive Centurion Member perks like priority check-in, complimentary premium drinks, and dedicated seating at select Centurion Lounges.
Get more out of your getaway with American Express
As an American Express Card Member, make your trip unforgettable with 10% off tours and activities booked at gyg.me/amex from 03/01/26 to 08/31/26. Terms apply.
Get more out of your getaway with American Express
Global Dining Access by Resy gives you special access to sought-after restaurants across the globe when you add your eligible Card to your Resy profile. Access to exclusive reservations, premium dining experiences, Priority Notify, and more, all from the Resy app. Terms apply.
Get more out of your getaway with American Express
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1Survey Methodology: This Morning Consult poll was conducted between December 30, 2025- January 14, 2026 among the following sample of global respondents: 2025 US Adults, 1001 Australia Adults, 1019 Canada Adults, 1005 UK Adults, 1021 Japan Adults, 1010 Mexico Adults and,1021 India Adults who all have at least a $50k+ income equivalent and typically travel at least once a year. The interviews were conducted online. Results from the full survey have a margin of error of plus or minus 2-3 percentage points. Some geographies may be weighted with fewer variables depending on local census data availability.
