Welcome to Jeffsetter Travel
Curating Customized Travel Experiences
Travel Planning Services
Customized mystery trip based on your budget. Place a bet, pack your bags, and collect your jackpot trip!
Customized trip based on your travel style.
You know all the details before you pack your bags.
Giving you the most value by saving you time.
A la carte services for research, planning, and booking.
America’s first travel portfolio planning service .
Create your list, budget, save, enjoy your travel dreams!
America’s first-ever travel family planning service.
Create life experiences for your family across generations!
Wild Card Adventures
Tired of thinking about planning trips and vacations?
Just "place your bet" with us.
We do all the work, and deal you a Wild Card Adventure.
Let us create a Safe Bet Adventure for you.
A Safe Bet adventure is a custom-tailored holiday.
We do all the work. You spend your time exploring the world, not the internet.
With a Safe Bet Adventure, the vacation of your dreams becomes a reality.
High Roller Host
We offer an a la carte personal High Roller Host service to save you time.
The High Roller Host service is designed to help you with your one off travel wants. We provide our time to be your personal travel assistant.
From research and recommendations for unique accommodations (Airbnb, VRBO, bed and breakfasts) to a day by day guide for your trip to the best value for your point balances, we use our knowledge and network to help you create your own unique experiences.
Explore the world not the internet...
The average traveler spends 40 hours planning a vacation. We can give you back your time, plus a vacation.
Recent Blog Posts by Island Miler and the rest of the Jeffsetter Crew
Top Contributors to the Jeffsetter Travel Blog
Kyle lives on the island of Oahu in Hawaii and shares a unique perspective on Hawaiian travel and foodie-ism. Don't view on an empty stomach!
Charlotte is currently living full time in an RV around the United States. If you want to see the world through a new pair of eyes, pay attention to what Charlotte is doing!
Amanda left the corporate world to design epic travel adventures. Then the Pandemic hit... Currently making dreams come true for those brave enough to travel!
The "OG" (i.e. Obsessive Geoff) of this blog. Jeff started this blog in 2012 as a way to share travels with family and friends. Currently (mostly) stationary with Mrs. Jeffsetter and Baby J.