Milestone Birthday Trips

Turning 40, 50, 60, or 80 is worth celebrating your way.

Maybe that means a weekend of rooftop dinners and ocean views. A luxury resort filled with family and friends. A private villa with a chef. Or a destination where everyone can find something they love.

Whatever the occasion, we help turn your celebration into a thoughtfully planned group travel experience.

Plan Your Celebration

Your Group

One celebration. Different travel styles.

Your group may include couples, solo travelers, children, grandparents, and friends with completely different ideas of the perfect vacation.

Some want golf and spa appointments. Others want the beach, excursions, great restaurants, or absolutely nothing on the schedule.

We help find destinations and accommodations that make room for everyone without losing sight of the person being celebrated.

Group Coordination

We coordinate the moving parts.

Group travel involves more than booking multiple rooms.

We help navigate accommodation options, group booking arrangements, individual reservations, payment timelines, airport transfers, and available experiences.

You remain the host of the celebration, not the person answering everyone’s travel questions.

A Repeat Client

From her sister’s party in Jamaica to her brother’s 50th.

“This was not my first time working with Chericka. I was introduced to her 3 years ago when she planned my sister’s party in Jamaica. So, she was my first thought when planning my brother’s 50th. She gets the vision at the first conversation. She is prompt when returning emails or phone calls. She is always pleasant and never too busy. She is a true professional and I appreciate her. I look forward to continuing my relationship with Chericka and Love & Leisure!” Gwendolyn · San Antonio, TX

Celebrate the way you want.

Milestone Birthdays

From a fabulous 40th to an unforgettable 80th, celebrate with a destination that fits the occasion.

Family Celebrations

Bring generations together with thoughtful accommodations and experiences for different ages and interests.

Friends’ Getaways

Reconnect somewhere extraordinary, whether that means poolside relaxation, nightlife, adventure, or a little of everything.

Private Group Escapes

Create a personalized getaway around your group’s shared interests, from wellness to culinary experiences.

Planning a larger group trip? See our group travel planning, or read our journal guide to planning a milestone trip worth celebrating.

The best part of bringing everyone together? Actually getting to enjoy them.

Tell us what you are celebrating and who is coming. We will help you plan the travel around it.

Start Planning Your Group Trip

Big Milestones Deserve More Than an Ordinary Trip.