Luxury Caribbean Travel Agent

Your Luxury Expert

I’m Aleyah Simmons, the founder and visionary behind this boutique travel service. As a passionate traveler with a love for tropical escapes, I believe that everyone deserves the opportunity to experience the world's finest luxuries. The Caribbean, with its stunning landscapes, vibrant culture, and tranquil ambiance, has always been my inspiration—a place where relaxation, adventure, and unforgettable moments blend seamlessly.

Through my curated partnerships, I unlocked unpublished perks - villa upgrades, private chef access, jet charters for every client & much more.

  • Expertly Curated Luxury Getaways

    Aleyah specializes in crafting upscale, tailor-made experiences—from 5-star resorts to private villas—ensuring every detail meets your elite travel standards.

  • VIP Access & Exclusive Perks

    Enjoy priority upgrades, complimentary amenities, and behind-the-scenes access not available to the general public, thanks to Aleyah’s premium travel network.

  • Personalized 24/7 Concierge Service

    From pre-departure planning to in-destination support, Aleyah provides white-glove concierge assistance around the clock—so you never have to lift a finger.

  • Signature Experiences

    You receive world-class service, custom itineraries, and dedicated travel planning without waisting a beat.

  • Trusted by High-End Travelers

    Discerning clients rely on Aleyah for vacations over $10K, private jet bookings, and milestone celebrations, knowing their experience will exceed expectations every time.

Jazmine S

“Absolutely wonderful! I am super busy in my day to day life and I needed a break for my birthday. Aleyah planned my entire vacation from an upgraded room category to my dinners & activities. The resort customer service was not the best but Aleyah was able to retrieve a credit for the lack of professionalism on their part.”

KJ

“Aleyah has never let me down. She understands that my work load can be hectic so any time I need a last minute escape she is there ready to assist me and/or my family. Barts here we come”

FAQs

  • At Aleyah Travels, we require a planning fee to begin curating your luxury getaway. This deposit will be credited toward the total cost of your reservation. Visit our process page for more details.

    Please note, if you decide to cancel your trip after the booking process has begun, the deposit will no longer be refundable. We encourage you to reach out to us with any questions or concerns before confirming your reservation to ensure a smooth and enjoyable experience.

    Additional last minute booking fees & large group fees are subject to apply.

  • Aleyah Travels specializes in bespoke escapes to the world’s most exquisite tropical locations:

    Caribbean & West Indies

    • St. Barts

    • St. Martin

    • Virgin Islands (U.S. & British)

    • Anguilla

    • Antigua

    • Barbados

    • St. Lucia

    • Jamaica

    • Dominican Republic

    • Bahamas

    Mexico & Central America

    • Riviera Maya

    • Tulum

    • Cabo San Lucas

    • Puerto Vallarta

    • Punta Mita

    United States & Islands

    • Hawaii (Maui, Oahu, Big Island)

    Additional destinations are available.

  • At Aleyah Travels, every journey begins with intention, precision, and exclusivity.

    1. Private Consultation
    We begin with a personalized consultation to understand your vision, preferences, and lifestyle. This ensures that every element of your experience is tailored to you from the very start.

    2. Holding Deposit
    To proceed with itinerary design and secure your place in our planning calendar, we require a non-refundable holding deposit. This deposit confirms your commitment and is applied toward your final travel cost.

    3. Curated Itinerary Design
    Our team crafts a bespoke itinerary, curated with exclusive accommodations, premium upgrades, and VIP touches. This detailed plan is presented for your review, refinement, and approval.

    4. Finalization & Reservations
    Once approved, we finalize all arrangements—flights, villas, private chefs, spa appointments, childcare, and more. Every detail is booked and confirmed, leaving you to simply arrive and indulge.

  • At Aleyah Travels, we are dedicated to curating a truly exceptional and bespoke luxury experience.

    Some of the exclusive luxury experiences you can expect include:

    • VIP Services: Enjoy private drivers, villas, chefs, and designated babysitters,

    • Private Activities: Indulge in personalized excursions and activities, tailored to your interests and preferences.

    • Yacht Charter Experiences: Set sail in style with private yacht charters, offering a unique and luxurious way to explore the waters.

    • Club-Level Rooms with Personal Butlers: Stay in premium accommodations with the added luxury of a personal butler to cater to your every need.

    • Complimentary Room Upgrades: Experience the highest level of comfort with complimentary upgrades when available.

    • And Much More: From exclusive dining experiences to special access to events and attractions, we strive to deliver Aleyah Travels’ luxury at its finest.

    With Aleyah Travels, your journey is designed to be nothing short of extraordinary, offering you a luxurious and unforgettable experience at every turn.