Know where you want to go.
I know how to get you there.
SmartFlyer Affiliate · Virtuoso Member · Nashville, TN
How I connect you.
I do not book travel. I connect people to the right place, the right experience, and the right support: before, during, and after every trip.
01 Connection to Place
Authentic local experiences. Insider access. VIP treatment from real relationships, not a booking engine.
02 Connection to People
Relationships built one trip at a time, recognized by the Nashville Business Journal as a Power 100 Connector four years running.
03 Peace of Mind
One person handles everything. Reachable before, during, and after your trip.
04 Connection to Luxury
SmartFlyer affiliate and Virtuoso member. Breakfast, upgrades, credits, priority reservations.
05 Connection to Values
LGBT-inclusive travel. When I say a property is welcoming, I am speaking from experience: not a checklist.
06 The SmartFlyer Flight Team
Most advisors handle hotels and let you figure out flights yourself. I do not. The SmartFlyer flight team manages complex air routing, premium cabin strategy, and real-time changes. When something breaks, you have a team on it, not a hold queue.
07 Less Information. Better Decisions.
Top 10 lists are written for everyone. They serve no one particularly well. I know what is worth your money, your time, and your attention right now. And I know what to skip.
08 Your Budget Goes Further
Planning fees are offset by what I recover through negotiated rates, Virtuoso amenity value, and the fact that you are not overpaying for the wrong room. I direct spend toward what is commissionable and meaningful.
09 I Learn How You Travel
Over time, I need less from you to deliver more. I learn your preferences, your pace, your standards. That compounds into better trips, faster planning, and a working relationship that gets easier every year.
The right trip for the right traveler.
I focus on experiences that match who you are.
Luxury Hotels & Resorts
Virtuoso amenities at thousands of properties worldwide, including complimentary breakfast, room upgrades, resort credits, and priority reservations. I match travelers to the right property, then unlock perks direct booking cannot offer.
Ocean & River Cruises
From expedition ships to ultra-luxury lines, I know which vessels, itineraries, and cabin categories deliver value worth the investment. Seven personal sailings across Royal Caribbean, Celebrity, Virgin, Ponant, and Explora. Certified Virtuoso Voyages Host.
Honeymoons & Celebrations
Milestone travel demands more than a good deal. It demands a perfect experience. I create trips people talk about for years.
Custom FIT Itineraries
Fully independent travel built around your preferences. Not a package. Not a template. Your trip, designed from scratch.
Group Travel
Family reunions, friend groups, corporate retreats. Managing the logistics so everyone can actually enjoy the trip.
Ski & Outdoor
A lifelong skier and outdoorsman. I started skiing at two, became a ski patroller at 15, and grew up hunting, rafting, and hiking in Idaho. I plan outdoor trips the way I'd want them planned for myself.
Safari
Safari rewards expertise, not guesswork. I connect clients to a vetted network of DMC partners and on-the-ground providers who know the camps, the routes, and the season.
History & Culture
Cultural immersion and heritage travel, planned with the same attention to detail as any luxury itinerary.
Inclusive & LGBT Travel
Safe, affirming destinations and properties where every traveler is genuinely welcomed. I travel within this community and know the difference.
Explore by Trip Type
Custom Itineraries | Luxury Cruise Bookings | LGBTQ+ Travel Advisor
Simple from the start.
You tell me where you want to go. I handle everything else.
01
Tell Me Where
Fill out a quick inquiry form. Tell me your travel style, budget, and what matters most.
02
I Build It With You
I design options based on your preferences. I refine until it is exactly right.
03
I Handle Everything
Bookings, confirmations, and real support before, during, and after your trip.
ABOUT JOE
I am a connector.
Joe Woolley is the founder of joe.travel, a luxury travel advisory affiliated with SmartFlyer and Virtuoso. Named to the Nashville Business Journal Power 100 list as a Connector for four consecutive years, Joe built his career moving journalists through conflict zones at CBS News, moving students across the globe as Communications Director at the Cooperative Center for Study Abroad, and building a statewide business community as CEO of the Nashville LGBT Chamber. He founded joe.travel to bring that same connector approach to travel advising. Joe is a certified Virtuoso Voyages Host, an experienced cruiser who has sailed on seven voyages across the world’s leading lines, and a lifelong outdoorsman who has skied since age two. He plans trips the way he travels with his husband Jim: looking for the best experience, the right hotel, and the story worth telling. He handles every detail so his clients can focus on the trip.
Trusted Affiliations
Access you cannot book yourself.
My SmartFlyer and Virtuoso affiliations unlock exclusive amenities at thousands of properties worldwide, including complimentary breakfast, room upgrades, resort credits, and priority reservations.
Certified Virtuoso Voyages HostYour connection to extraordinary.
Ready to go?
Tell me where you want to go. I will take it from there.
© 2026 Woolley Travel dba joe.travel · All rights reserved
