Ashley Olano

Santorini, Greece

Milestone moments deserve more than just a trip—they deserve to feel deeply personal, well-thought-out, and seamless from start to finish. I specialize in planning celebration travel that’s elevated but never overdone, whether it’s a birthday in wine country, an anniversary in Italy, or a babymoon by the beach.These are the trips clients remember forever—not because they were the most extravagant, but because they were thoughtfully designed around the people and the moment.

What I Help Plan

Celebration travel comes in many forms, and no two trips look the same. I’ve designed itineraries for:

• 30th to 70th-birthday trips with friends in Europe and the U.S.
• Anniversary escapes for couples—from Paris to the Amalfi Coast
• Babymoons with just the right balance of comfort and pampering
• Graduation and retirement trips across Africa and South America
• Multi-generational milestone gatherings (often tied to a bucket-list destination)

Whether it’s a couple looking for rest and reconnection, or a group navigating different ages, needs, and travel styles—I take care of the logistics so you can focus on the experience.

The Right Stays for the Right Moments

Choosing the right hotel or villa is key to a successful celebration trip. I work with a global network of vetted luxury properties and preferred partners, allowing me to secure:

• Complimentary upgrades and perks
• Welcome amenities tailored to the occasion
• Special experiences like private dinners, spa credits, or in-room celebrations
• Flexible accommodations for families and groups

From boutique romantic stays to five-bedroom villas, I help match you with the ideal space to make the trip feel personal and elevated.

Special Touches & Experiences

Every celebration deserves something extra. Depending on the destination and occasion, I can include:

• Private chef dinners
• Photographer sessions for milestone memories
• Private boat days or vineyard picnics
• Custom excursions (cooking classes, helicopter tours, horseback rides, etc.)
• Planning support for onsite dinners, toasts, or surprises

And if you’re short on time or inspiration, I’ll bring the ideas to you—grounded in what works, what’s worth the spend, and what fits your group.

Where I Recommend for Celebration Travel

Some destinations naturally lend themselves to celebration trips. A few of my client favorites:

• Italy: Romantic escapes, multi-gen trips, and wine lovers' dream destinations
• France: Special occasion dining, châteaux stays, and culture-rich cities
• South Africa: Safari + wine country combos that feel once-in-a-lifetime
• Greece: Island-hopping celebrations with sun, sea, and style
• Patagonia: Bucket-list adventure and privacy for a special milestone
• Caribbean & Mexico: Relaxed, easy-to-reach getaways with top-notch service

Why Work With Me?

Celebration trips often come with pressure to “get it right.” Whether you’re planning for yourself or organizing for a group, I act as your partner in pulling it all together. I’ve helped clients:

• Plan trips as a surprise for a loved one
• Balance the needs of groups with different interests
• Add special experiences they’d never have found on their own
• Navigate timing, pacing, and budget trade-offs with clarity

As a travel advisor, I handle the research, reservations, communication with hotels and suppliers, and offer ongoing support before and during the trip. The result: a travel experience that’s effortless on your end, but rich in meaning and detail.