
Simon Fletcher
He/HimBased in Santa Cruz, California
Simon Fletcher
Ask me about
My Story
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.
My 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.
My reviews (10)
Amy T.
5 months ago
Very responsive, good communication and made this trip possible since we were not up to planning a trip ourselves and were overwhelmed by the prospect
Adam L.
8 months ago
Simon is amazing. He makes everything so easy. This is the second trip I've used him for and will definitely be using his services in the future.
Alison R.
a year ago
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!
Danielle W.
a year ago
Worked hard on our itinerary.
Danielle W.
a year ago
Great. Very informative and was easily reachable for questions.
Amy T.
5 months ago
Very responsive, good communication and made this trip possible since we were not up to planning a trip ourselves and were overwhelmed by the prospect
Adam L.
8 months ago
Simon is amazing. He makes everything so easy. This is the second trip I've used him for and will definitely be using his services in the future.
Alison R.
a year ago
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!
Danielle W.
a year ago
Worked hard on our itinerary.
My travel ideas (8)

Lomani Island Resort: Romantic Adults-Only Luxury in Fiji
Lomani Island Resort is a small, adults-only resort with a private beach and a shallow, crystal-clear tropical lagoon, located on the island of Malolo Lailai in Fiji. This is an ideal destination for those seeking spectacular natural beauty, a quiet, peaceful setting for relaxation and easy opportunities for playful adventures. We loved that all of their accommodations, amenities and activities blended luxury and authenticity, with laid-back vibes and gorgeous, rustic island character at the core of it all. With its intimate size, dreamy tropical beauty and genuinely friendly staff who even remembered our names and food orders all throughout our stay, Lomani Island Resort holds a special place in our hearts and is one of our most favorite destinations on the planet.

Lomani Island Resort: Romantic Adults-Only Luxury in Fiji
Lomani Island Resort is a small, adults-only resort with a private beach and a shallow, crystal-clear tropical lagoon, located on the island of Malolo Lailai in Fiji. This is an ideal destination for those seeking spectacular natural beauty, a quiet, peaceful setting for relaxation and easy opportunities for playful adventures. We loved that all of their accommodations, amenities and activities blended luxury and authenticity, with laid-back vibes and gorgeous, rustic island character at the core of it all. With its intimate size, dreamy tropical beauty and genuinely friendly staff who even remembered our names and food orders all throughout our stay, Lomani Island Resort holds a special place in our hearts and is one of our most favorite destinations on the planet.

Mentawai Surf Retreat: A Playground Surf Adventure in Paradise
If you are a serious surfer, you have either traveled to the Mentawai Islands of Indonesia or dreamt of surfing there. The Mentawai Surf Retreat offers a perfect setting to soak up the beauty of the islands while having access to all of the iconic surf breaks of the Playgrounds area. Situated right on the beach in front of Pit Stops, you can paddle out in minutes or explore other waves like Hideaways, Rifles and Burgerworld using the resort's speedboats. The food is fresh, healthy and plentiful and the vibe is relaxed. This truly is a retreat for the mind, body and soul.

Mentawai Surf Retreat: A Playground Surf Adventure in Paradise
If you are a serious surfer, you have either traveled to the Mentawai Islands of Indonesia or dreamt of surfing there. The Mentawai Surf Retreat offers a perfect setting to soak up the beauty of the islands while having access to all of the iconic surf breaks of the Playgrounds area. Situated right on the beach in front of Pit Stops, you can paddle out in minutes or explore other waves like Hideaways, Rifles and Burgerworld using the resort's speedboats. The food is fresh, healthy and plentiful and the vibe is relaxed. This truly is a retreat for the mind, body and soul.

Epic Croatia Road Trip: Split, Dubrovnik, Peljesac, Hvar, Vis and Plitvice
Croatia has so much to explore — islands, beaches, oceans as clear as a swimming pool, endless vineyards, mountains and rivers. You will find ancient structures thousands of years old reflecting the deep history of this bridge between European and Mediterranean cultures. Both the wine and the food are outstanding, with interesting variations as you move between geographic regions. One could easily spend months meandering through coastal villages and mountain hamlets — not to mention the more than 1,000 islands scattered throughout the Adriatic Sea. This itinerary covers a nice variety of what Croatia has to offer and will definitely leave you ready to plan your next Croatia adventure.

Epic Croatia Road Trip: Split, Dubrovnik, Peljesac, Hvar, Vis and Plitvice
Croatia has so much to explore — islands, beaches, oceans as clear as a swimming pool, endless vineyards, mountains and rivers. You will find ancient structures thousands of years old reflecting the deep history of this bridge between European and Mediterranean cultures. Both the wine and the food are outstanding, with interesting variations as you move between geographic regions. One could easily spend months meandering through coastal villages and mountain hamlets — not to mention the more than 1,000 islands scattered throughout the Adriatic Sea. This itinerary covers a nice variety of what Croatia has to offer and will definitely leave you ready to plan your next Croatia adventure.

10 Days in Bali: Uluwatu, Nusa Penida and Ubud
Bali is a magical place with so much to explore. This ten-day itinerary takes you to some of our favorite places, including beaches, waterfalls and temples. Along the way, be sure to sample the local food at some amazing warungs, and take some time to get off the beaten path to discover some hidden gems away from the crowds. You will likely discover what we did: there is so much beauty to take in you will wish you had more than ten days to take it all in.

10 Days in Bali: Uluwatu, Nusa Penida and Ubud
Bali is a magical place with so much to explore. This ten-day itinerary takes you to some of our favorite places, including beaches, waterfalls and temples. Along the way, be sure to sample the local food at some amazing warungs, and take some time to get off the beaten path to discover some hidden gems away from the crowds. You will likely discover what we did: there is so much beauty to take in you will wish you had more than ten days to take it all in.

Two-Week Family Adventure in Costa Rica: Samara, Manuel Antonio and Monteverde
Costa Rica is one of the most popular travel destinations in the world, and for good reason. You can experience stunning tropical beaches, dense mountain jungles, volcanic hot springs and an incredible diversity of wildlife all in a small, safe country with friendly welcoming people. Tourism is well established, making it a great destination for families looking for adventure and fun. You could easily spend months here and still not see it all. This guide highlights some of our favorite places to visit if you only have a few weeks.

Two-Week Family Adventure in Costa Rica: Samara, Manuel Antonio and Monteverde
Costa Rica is one of the most popular travel destinations in the world, and for good reason. You can experience stunning tropical beaches, dense mountain jungles, volcanic hot springs and an incredible diversity of wildlife all in a small, safe country with friendly welcoming people. Tourism is well established, making it a great destination for families looking for adventure and fun. You could easily spend months here and still not see it all. This guide highlights some of our favorite places to visit if you only have a few weeks.

Sayulita, Mexico: A Family Friendly Surf and Beach Adventure
Sayulita, once a small, sleepy fishing village, is now a lively beach town attracting travelers looking for the laid back vibe it is famous for. Even though it has grown over the years, we love coming back to Sayulita because it has retained that small, laid back vibe. You can immerse yourself in the bustling beach and town center, and also easily find peace and solitude. The food is fantastic, the beaches are beautiful, and there are plenty of things to do for families as well as couples.

Sayulita, Mexico: A Family Friendly Surf and Beach Adventure
Sayulita, once a small, sleepy fishing village, is now a lively beach town attracting travelers looking for the laid back vibe it is famous for. Even though it has grown over the years, we love coming back to Sayulita because it has retained that small, laid back vibe. You can immerse yourself in the bustling beach and town center, and also easily find peace and solitude. The food is fantastic, the beaches are beautiful, and there are plenty of things to do for families as well as couples.

Explore the Beaches of the Big Island of Hawai'i
The Big Island is exactly what the name implies - big! There is so much variety and plenty of opportunities to chill or explore. You can spend the day relaxing by the pool, swimming in the warm water on some of the most beautiful beaches in the world, or hiking into lush tropical valleys. As with all of the Hawai'ian Islands, the Big Island has its own unique charms and you could easily spend weeks discovering new places and still feel like there is so much more to uncover.

Explore the Beaches of the Big Island of Hawai'i
The Big Island is exactly what the name implies - big! There is so much variety and plenty of opportunities to chill or explore. You can spend the day relaxing by the pool, swimming in the warm water on some of the most beautiful beaches in the world, or hiking into lush tropical valleys. As with all of the Hawai'ian Islands, the Big Island has its own unique charms and you could easily spend weeks discovering new places and still feel like there is so much more to uncover.

Beaches and Redwoods: 10 Spectacular State Parks to Visit in Santa Cruz, California
I have lived in Santa Cruz all of my life and I am still amazed to find new places to explore. Santa Cruz is home to amazing beaches and Redwood forests literally minutes apart. People who live here tend to be very active, taking advantage of the variety of outdoor resources available. Whether you are looking for surfing, hiking, mountain biking, wine tasting, or relaxing on the beach, you will find plenty of fun to fill your days in Santa Cruz.

Beaches and Redwoods: 10 Spectacular State Parks to Visit in Santa Cruz, California
I have lived in Santa Cruz all of my life and I am still amazed to find new places to explore. Santa Cruz is home to amazing beaches and Redwood forests literally minutes apart. People who live here tend to be very active, taking advantage of the variety of outdoor resources available. Whether you are looking for surfing, hiking, mountain biking, wine tasting, or relaxing on the beach, you will find plenty of fun to fill your days in Santa Cruz.

Lomani Island Resort: Romantic Adults-Only Luxury in Fiji
Lomani Island Resort is a small, adults-only resort with a private beach and a shallow, crystal-clear tropical lagoon, located on the island of Malolo Lailai in Fiji. This is an ideal destination for those seeking spectacular natural beauty, a quiet, peaceful setting for relaxation and easy opportunities for playful adventures. We loved that all of their accommodations, amenities and activities blended luxury and authenticity, with laid-back vibes and gorgeous, rustic island character at the core of it all. With its intimate size, dreamy tropical beauty and genuinely friendly staff who even remembered our names and food orders all throughout our stay, Lomani Island Resort holds a special place in our hearts and is one of our most favorite destinations on the planet.

Lomani Island Resort: Romantic Adults-Only Luxury in Fiji
Lomani Island Resort is a small, adults-only resort with a private beach and a shallow, crystal-clear tropical lagoon, located on the island of Malolo Lailai in Fiji. This is an ideal destination for those seeking spectacular natural beauty, a quiet, peaceful setting for relaxation and easy opportunities for playful adventures. We loved that all of their accommodations, amenities and activities blended luxury and authenticity, with laid-back vibes and gorgeous, rustic island character at the core of it all. With its intimate size, dreamy tropical beauty and genuinely friendly staff who even remembered our names and food orders all throughout our stay, Lomani Island Resort holds a special place in our hearts and is one of our most favorite destinations on the planet.

Mentawai Surf Retreat: A Playground Surf Adventure in Paradise
If you are a serious surfer, you have either traveled to the Mentawai Islands of Indonesia or dreamt of surfing there. The Mentawai Surf Retreat offers a perfect setting to soak up the beauty of the islands while having access to all of the iconic surf breaks of the Playgrounds area. Situated right on the beach in front of Pit Stops, you can paddle out in minutes or explore other waves like Hideaways, Rifles and Burgerworld using the resort's speedboats. The food is fresh, healthy and plentiful and the vibe is relaxed. This truly is a retreat for the mind, body and soul.

Mentawai Surf Retreat: A Playground Surf Adventure in Paradise
If you are a serious surfer, you have either traveled to the Mentawai Islands of Indonesia or dreamt of surfing there. The Mentawai Surf Retreat offers a perfect setting to soak up the beauty of the islands while having access to all of the iconic surf breaks of the Playgrounds area. Situated right on the beach in front of Pit Stops, you can paddle out in minutes or explore other waves like Hideaways, Rifles and Burgerworld using the resort's speedboats. The food is fresh, healthy and plentiful and the vibe is relaxed. This truly is a retreat for the mind, body and soul.

Epic Croatia Road Trip: Split, Dubrovnik, Peljesac, Hvar, Vis and Plitvice
Croatia has so much to explore — islands, beaches, oceans as clear as a swimming pool, endless vineyards, mountains and rivers. You will find ancient structures thousands of years old reflecting the deep history of this bridge between European and Mediterranean cultures. Both the wine and the food are outstanding, with interesting variations as you move between geographic regions. One could easily spend months meandering through coastal villages and mountain hamlets — not to mention the more than 1,000 islands scattered throughout the Adriatic Sea. This itinerary covers a nice variety of what Croatia has to offer and will definitely leave you ready to plan your next Croatia adventure.

Epic Croatia Road Trip: Split, Dubrovnik, Peljesac, Hvar, Vis and Plitvice
Croatia has so much to explore — islands, beaches, oceans as clear as a swimming pool, endless vineyards, mountains and rivers. You will find ancient structures thousands of years old reflecting the deep history of this bridge between European and Mediterranean cultures. Both the wine and the food are outstanding, with interesting variations as you move between geographic regions. One could easily spend months meandering through coastal villages and mountain hamlets — not to mention the more than 1,000 islands scattered throughout the Adriatic Sea. This itinerary covers a nice variety of what Croatia has to offer and will definitely leave you ready to plan your next Croatia adventure.
My travel photos





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