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Bailey L.

Bailey L.

Sabbatical & Extended Travel Designer | 6 Years Nomadic, 40+ Countries

As a Top Travel Planner on the Upwork Platform, I’m excited to assist you with all your travel planning needs! Thanks to my last six years (and counting) on the road as a full-time traveler (aka world-traveling digital nomad), I have an increasing library of knowledge and information all things travel related. With my on-ground experience traveling to 40+ countries combined with 4 years of travel planning experience ($1m+), backed by a highly regarded travel agent network (certified PRO at Fora Travel), I am highly organized, detailed, and passionate about putting together full itineraries and solving other travel-related tasks. Additionally, I received my CTA (Certified Travel Associate) certification from The Travel Institute in July 2025, so I am not just a "certified travel agent" as many claim, but I'm truly Certified through a highly respected travel educator. I love to mix genuine cultural experiences with fun and exciting adventure, while always attempting to avoid over-tourism and promote sustainability. If you’re looking for a personal travel planner for your around-the-world adventure, that is exactly what I specialize in! Just ask about my LLC! Types of Travel I specialize in: 🧳 Leisure vacations 🗿 Cultural experiences 🪂 Adventures & Excursions 🧑‍🤝‍🧑 Group Trips 👩‍💼 Business Travel 🌍 Around-the-World trips 🚐 Road trips (especially #VanLife/Camper) 💍 Honeymoons 🤓 Simple Travel Research 🏡 Home and Villa rental 💎 Luxury Travel 👩🏻‍💻 Sabbatical Travel The services I provide: 🗺️ Mapped routes 📍 Google Map pins lists for every destination 🛩️ Flights 🛌 Accommodation 🚞 Transportation 👟 Activities, excursions, and tours 🕰️ Scheduled free time & rest, and flexibility to allow for spontaneous detours and in-the-moment choices 💳 Booking services 📞 Concierge services: on-call assistance at all times 😎 VIP treatment, free upgrades, and resort credits at many of the best hotels in the world Why hire me? ⌚️ Maximize your time spent adventuring rather 🔋 Optimize your travels with thoughtfully curated schedules, avoiding common novice mistakes 🕶️ Benefit from my extensive travel agent network and local connections (including VIP perks) 🏔️ Gain access to hidden gems, authentic cultural encounters, and adventurous expeditions 🙆🏻‍♀️ Get actual human advice and 24/7 on-call support from a professional that you know and trust

🇺🇸Aurora, United States$55/hr100% JSS4.96 (45)Since Sep 2019

Earnings and projects

MRR
$139

Last 6 months ÷ 6

World#125,869 / 412k
🇺🇸Country#17,279 / 62.1k
Revenue, last 30 days
$0

Last 6 months: $831

Total earnings
$21k

Billed in all: $22k

World#135,659 / 412k
🇺🇸Country#22,617 / 62.1k
Per project
$257

$416 in the last 6 months

World#244,693 / 412k
🇺🇸Country#39,363 / 62.1k
Projects, last 6 months
2

Across 5 contracts

60% fixed40% hourly
World#88,918 / 412k
🇺🇸Country#11,762 / 62.1k
Projects in all
83

Across 89 contracts

56% fixed44% hourly
World#35,166 / 412k
🇺🇸Country#5,507 / 62.1k

Earnings, last 30 days

$21.7kNothing earned in the last 30 daysBilled in all, before Upwork's fee · drag across the chart to see what was earned in any stretch
$21,250$21,500$21,750$22,000Oct 8Oct 23Nov 7

Skill rankings: Top 22% in Lifestyle & Travel

Ranked by MRR among everyone on Upwork with the skill.

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  8. #3,777Writing16,517 freelancers · 🇺🇸 #1,181Top 23%