Travel Advisor
Simon Fletcher
He/Him
Expertise
- California,
- Tropical,
- Outdoors & Nature,
- Couples Travel
Based in
Santa Cruz, California
Profile details
About
Hey, I'm Simon, a Santa Cruz, California native, math and science educator, surfer, husband, dad, and lifelong travel lover. With a passion for outdoor adventure, world exploration, and natural beauty, I specialize in cutting through the stress of travel planning to streamline your dream trip.
Travel style
I love designing trips that blend exhilarating outdoor adventure and deep relaxation, and strategizing how to get the best possible experiences with your time and budget. Specializing in California, the Mediterranean, and tropical regions, I create custom itineraries for solo travelers, couples, groups, and families, that weave together popular tourist spots and hidden gems.
I’m focused on finding accommodations that not only pair well with your itinerary, but that feel beautiful, comfortable and well-matched for your travel style. Whether you want to be out exploring or stay in and recharge, my intention is to design a trip that feels like your dreams have come true.
Ready for a beautiful adventure? Let's plan it together.
Simon's travel guides & trip reports
Lomani Island Resort: Romantic Adults-Only Luxury in Fiji
Mentawai Surf Retreat: A Playground Surf Adventure in Paradise
Epic Croatia Road Trip: Split, Dubrovnik, Peljesac, Hvar, Vis and Plitvice
10 Days in Bali: Uluwatu, Nusa Penida and Ubud
Two-Week Family Adventure in Costa Rica: Samara, Manuel Antonio and Monteverde
Sayulita, Mexico: A Family Friendly Surf and Beach Adventure
Explore the Beaches of the Big Island of Hawai'i
Beaches and Redwoods: 10 Spectacular State Parks to Visit in Santa Cruz, California
Favorite hotels
Simon's travel photos
Simon's reviews
Simon was great to work with. His communication was solid and gave many great suggestions based on our budget and interests. He kept asking if there was anything we needed and if he could help in any way. Our trip was pretty simple and straightforward. There was only one hiccup, not asking if we want to get trip insurance. We hardly ever book trips like this and trip insurance isn't something we get for smaller domestic trips. Unfortunately, a tropical storm came through right when we were departing for Belize and we had to arrive 2 days later than planned. Simon did everything he could to mitigate any financial loss and was able to get us one night credit at the resort. He was very apologetic and took it as a good learning lesson, as did I. I highly recommend Simon if you need assistance in booking travel!
- Alison R.
Booked travel to Belize
- November 2024
Worked hard on our itinerary.
- Danielle W.
Booked travel to Florida
- November 2024
Great. Very informative and was easily reachable for questions.
- Danielle W.
Booked travel by cruise
- November 2024
Very informative and worked hard on our itinerary.
- Danielle W.
Booked travel to Miami
- November 2024
Get in touch with Simon
Reach out to customize and book your own experience. Or, just to chat about travel in general.
You can normally expect a response from Simon within a business day or so. You’ll also be subscribed to our travel newsletter (you can unsubscribe at any time).
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