Travel Advisor Kristen Bailey

About Me

With over 10 years of experience in the travel industry, I truly love what I do—helping turn my clients' travel dreams into unforgettable memories. Whether you're planning a relaxing Caribbean escape, an adventure in Costa Rica, a breathtaking Hawaiian vacation, or exploring destinations across the USA, I'm here to make every step of the planning process easy and exciting. My favorite trip will always be my wedding and honeymoon on the beautiful island of Anguilla, followed closely by an unforgettable Hawaiian adventure with my mom and brother. Those personal experiences fuel my passion for creating meaningful vacations for others. My #1 packing tip? Leave room for souvenirs! The best trips always come with treasures and memories worth bringing home. When you're ready to plan your next getaway, book with me and let's make your dream vacation a reality!

My Recommended Destinations

Hawaii

Costa Rica

Caribbean

Colorful buildings line the waterfront of Willemstad, the vibrant capital of Curacao, showcasing Dutch colonial architecture

Places I've Been

Alaska, Anguilla, Arizona, Aruba, Bahamas, Bermuda, Boston, California, Chicago, Colorado, Connecticut, Costa Rica, Delaware, District of Columbia, Dominican Republic, Florida, Fort Lauderdale, Georgia, Hawaii, Illinois, Jamaica, Las Vegas, Los Angeles, Louisiana, Maryland, Massachusetts, Maui, Mexico, Miami, Nashville, Nevada, New Jersey, New Orleans, New York, New York City, Oahu, Ohio, Pennsylvania, Philadelphia, Puerto Rico, Rhode Island, San Diego, South Carolina, St. Barths, St. Maarten-St. Martin, Tennessee, Texas, Turks & Caicos, United States, Vermont, Walt Disney World® Resort, Washington D.C., West Virginia

Recent Customer Reviews

My Recommended Travel Blogs

5 Best U.S. Beaches for Catching Some Summer Rays

Top 5 U.S. Beaches for a Perfect Summer Vacation

Looking for the best beaches in the U.S. for your summer vacation?

Globe TrotterMay 31, 2026

The Edit Getaway Edition travel collage featuring turquoise waters, relaxed poolside moments and all-inclusive beach resorts

The Getaway Edition: Short Stays, Big Moments

You know that feeling when wanderlust hits but your calendar laughs back? When you crave something beyond the everyday but can't carve out two full weeks? That's exactly what The Getaway Edition is all about.

Globe TrotterMarch 2, 2026

Pay Over Time with Affirm

Envoyage has partnered with Affirm to offer flexible payment options, allowing you to book now and pay over time with no late or hidden fees. When you're ready to book, connect with an advisor and request Affirm as your payment method. Pick the payment plan that works best for you with fixed monthly installments from three, six, 12 or 18 months*. Subject to eligibility.