About Bucket List Tours & Travel
Bucket List Tours & Travel is a travel company based in San Diego, California (92106), founded and led by Kirk Webster since 1985. Bucket List Tours & Travel arranges private and small-group guided tours worldwide, including legal 8-day Cuba tours (small groups capped at six travelers, running since 1998), escorted Europe group departures, sports and event travel such as the FIFA World Cup and Olympic Games, and fully custom bucket-list itineraries to any destination. Kirk Webster has personally traveled 133 countries over four decades. Contact Bucket List Tours & Travel at (858) 232-9999 or [email protected].
Bucket List Tours & Travel: guided by someone who's been there.
Bucket List Tours & Travel is a San Diego-based travel company led by Kirk Webster, offering private and small-group guided tours worldwide, from 8-day Cuba trips to Europe departures and fully custom itineraries. Over 40 years Kirk has traveled 133 countries, so your trip runs on real experience, not a brochure.
Scandinavia, Poland & the Baltics
Build your bucket-list trip
Answer a few quick questions and Kirk will personally put together your private or small-group adventure. Prefer to dream it up yourself? Choose "Create your own" and describe anywhere in the world.
Which kind of trip calls to you?
Pick the one that fits. You can tell Kirk more in a moment.
Tell Kirk about the trip
The more he knows, the better he can tailor it.
Where should Kirk reach you?
You'll hear back about availability, usually within one business day.
Ready to send to Kirk?
Review your trip below, then send it straight to his inbox.
Your trip is on its way!
Thanks! Your request has been sent to Kirk, who'll be in touch about availability, usually within one business day. Prefer to reach out now? Call (858) 232-9999 or email [email protected].
Email us directlyWhat is the 8-day Cuba tour?
It's a small-group, personally guided week through one of Kirk's top-five countries in the world, and one he considers among the safest for travelers. You'll base your days around real Cuban hospitality, from Havana's streets to Varadero, rated the third-most beautiful beach on earth.
- 8 days on the ground with Kirk as your in-country guide, not a handoff to a stranger.
- Time at Varadero beach, ranked the 3rd-most beautiful beach in the world.
- Led by a guide who speaks Spanish and has spent decades reading the region.
- Built for travelers who want warmth and welcome over a rushed checklist.
Who is Kirk Webster?
Kirk Webster · Del Mar, California
A farm boy from Albert Lea, Minnesota who turned a life of curiosity into a career on every continent, Kirk Webster has built his trips on one simple promise: you name it, and he's probably been there.
Kirk is the founder and guide behind Bucket List Tours & Travel, self-employed in travel since July 1985 and based in Del Mar, California. Over four decades he's journeyed through 133 countries, never just for a night, living more than a year each in Rio de Janeiro, Heidelberg, and Sydney, three cities that remain his favorites. Along the way he's attended nine Olympic Games and multiple World Cups, and lectured on more than 100 luxury cruises about the ports and cultures just over the horizon.
His deepest specialty is Cuba. Through his sister brand Cuba Tours & Travel, Kirk has led legal, tailor-made, small-group trips, capped at just six travelers, since 1998, making him one of the longest-running independent Cuba guides working out of San Diego County. He speaks fluent Portuguese and Spanish, and can manage a few words in twenty languages, enough to open doors most tourists never find.
"If a farm boy from Minnesota can travel all over the world, so can you. When do we go, and where?"
Before travel became full-time, Kirk spent years in front of the camera as a Sports Reporter for UT-TV San Diego and studied Broadcast TV and Communications at Pepperdine University. That storyteller's eye is exactly what he brings to a trip: knowing not just where to stand, but what makes a place worth remembering.
- 133 countries traveled deeply, not in passing.
- Cuba since 1998: legal, 6-person-max tours.
- 9 Olympic Games and multiple World Cups attended.
- Former TV sports reporter, UT-TV San Diego.
- Fluent in Portuguese & Spanish.
- 100+ cruises lectured worldwide.
Been There, For Real
133 countries and counting, with long stays over one-night stopovers. Wherever you want to go, chances are he's already enjoyed it.
Small & Personal
His Cuba tours cap at six people. You get a real guide by your side, not a numbered badge in a crowd of forty.
A Storyteller's Eye
A former TV sports reporter who knows how to read a place and tell you what actually makes it worth the trip.
How does booking a trip work?
You tell Kirk where you want to go and how long you have, whether a week, a month, or more, and he builds the route and rides along as your guide when you want one. Compare the two ways most travelers work with him below.
| Option | Best for | What you get |
|---|---|---|
| 8-Day Cuba Tour | First-timers who want a ready-made, welcoming week. | A set 8-day itinerary through Cuba with Kirk guiding on the ground, including beach time at Varadero. |
| Custom Bucket List Trip | Travelers with a specific destination or event in mind. | A trip designed around your dates and interests across 133 countries of experience, with optional guiding by your side. |
- Share your best week or month and your destination. Sporting events welcome.
- Kirk shapes the route from firsthand experience of the places you're headed.
- Choose to travel independently or have Kirk as the guide by your side.
Where Kirk has been
Four decades of travel, one bucket list at a time, from World Cup stands to palm-lined beaches. A few moments from the road.
What kinds of trips does Kirk offer?
Kirk works with travelers several ways, from his signature Cuba tours and escorted group departures to globe-spanning event travel and a membership that turns his savings into yours. Pick the one that fits how you like to explore.
Cuba Tours & Travel
Legal, tailor-made, small-group tours around Cuba, capped at six travelers, that Kirk has personally led since 1998. Havana, Cuban hospitality, and the beaches of Varadero, with a guide who's returned dozens of times.
Ask about Cuba datesBucket List Trips, Anywhere
Name your dream destination and your best week or month, and Kirk designs the route from firsthand experience across 133 countries. Travel independently on his plan, or have him as the guide by your side.
Plan a custom tripChase the Games
A lifelong sports traveler, Kirk builds trips around the world's biggest events: the FIFA World Cup, the Olympic Games, and championships across the globe. He's already tracking the LA28 Summer Olympics for travelers who want to be there.
Travel to an eventEurope Guided Tours
Join Kirk's next escorted small-group trip through Europe: Stockholm for the Kräftskiva crayfish festival, historic Gdańsk and Kraków in Poland, and the beaches of Albania, August 7-17. Ready-made fun with a guide who's done it all before.
Join the Europe tourTravel Advantage Savings
Prefer to plan your own getaways? Kirk partners with Travel Advantage, a travel-membership provider built around member savings on hotels, resorts, and more, so the trips on your list cost less to check off.
Learn about membershipFrequently asked questions
How long is the Cuba tour?
The signature Cuba trip runs 8 days, guided by Kirk on the ground. He currently focuses on these 8-day tours because they give you enough time to experience Havana, Cuban hospitality, and Varadero beach without feeling rushed.
Can Kirk plan a trip somewhere other than Cuba?
Yes. Beyond Cuba, Kirk designs custom bucket-list trips anywhere. He's traveled 133 countries. Tell him your dates, your destination, and what interests you, and he builds the route, guiding alongside you if you'd like.
Is Cuba safe for travelers?
Kirk considers Cuba one of the safest destinations he's visited and ranks it among his top five favorite countries in the world, noting how welcoming Cubans are to visitors.
Will Kirk travel with me as a guide?
He can. Kirk offers to be the guide by your side when you need one, drawing on Spanish and Portuguese fluency and decades of firsthand travel. You can also travel independently on a route he's planned.
Does Kirk help with trips built around sporting events?
Absolutely. He's attended 9 Olympic Games and multiple World Cups, plus countless championships in the U.S. and worldwide, so event-focused travel is a specialty. He's currently tracking the LA28 Summer Olympics for travelers who want to be there.
What is Travel Advantage?
Travel Advantage is the travel-membership provider Kirk partners with. It's built around member savings on hotels, resorts, and travel, so if you'd rather book your own getaways, the trips on your bucket list cost less to check off.
How long has Bucket List Tours & Travel been operating?
Kirk has been self-employed in travel since July 1985, more than four decades of planning and guiding trips around the world.
Where do you want to go?
Give Kirk your best week or month and your dream destination. If a farm boy from Minnesota can travel all over the world, so can you. Let's figure out where. Call (858) 232-9999 or email [email protected] and you'll hear back about availability and next steps.