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Sunshine Daydream: Boat Days are the Best Days!

Some of my favorite days are spent on the water. I know you have a lot of options when booking a boat trip, so, today, I’d like to introduce you to one of the top-rated companies in St. John – Sunshine Daydream Boat Charters.

Sunshine Daydream Boat Charters has been operating on St. John for the past nine years. It has more than 400 five-star reviews on Google, more than 800 five-star reviews on TripAdvisor, and they’ve received TripAdvisor’s coveted Travellers’ Choice Award eight times. It’s a solid choice for a US-based boat charter or a fun day exploring the British Virgin Islands.

Sunshine Daydream Boat Charters is owned and operated by Rob Woodworth, a former ski bum who chose the sun over snow (and we’re happy he did!). Rob spent several years living in Steamboat and Telluride, Colorado where he was living the life of a professional ski bum – his words, not mine! 🙂 He lived in Maui prior to that where he captained a 58-foot catamaran while also teaching guests how to scuba dive. Rob launched Sunshine Daydream Boat Charters back in 2015 and never looked back!

The Fleet

Sunshine Daydream charters three, newer model 32-foot World Cats. This is ultimate boat for exploring our waters as it is spacious and stable, allowing it to handle our sometimes-choppy waters very well. Sunshine Daydream has spacious and comfortable bow seating with cushioned backs for six adults, as well as a double-wide forward console seating complete with armrests. Each of its three boats can take up to 12 guests per boat. With three boats, Sunshine Daydream can accommodate groups up to 36.

Captains Nicole, Joel & Lee fueling up the fleet before a day out on the water.

Prefer the shade? Sunshine Daydream’s fleet includes a dual captain’s chair, plus comfortably-cushioned Yeti coolers, complete with backrests, which allows for plenty of seating in the shade once you’ve had enough fun in the sun. Lastly, the boats all have a sturdy, three-step ladder with handrails, which makes getting in and out of the water a snap.

Easy to get in & out of the water

Meet Your Captains

You’ve already met Rob. Now let’s meet the three other captains.

Captain Lee (left) with Captain Joel (right)

Captain Lee is a 100-ton Master Captain who’s been working on sailboats and power boats in the Virgin Islands for more than 10 years. He is also a PADI-certified scuba instructor. His knowledge of the our waters coupled with his passion for the ocean and the underwater world make him an excellent host for what’s sure to be the best day of your vacation.

Captain Nicole

Captain Nicole is a 100-ton Master Captain who was born and raised in St. John. Nicole is a former competitive surfer and sailor with many years experience as a surf and ocean safety instructor. She loves to share her vast knowledge of the ocean with her guests and spread the joy it gives us all. Hop on board with Nicole for a local’s guide through the idyllic Virgin Island waters that she grew up in.

Captain Rob (left) and Captain Joel (right)

Captain Joel has lived on St. John for the past 27 years. He started out his captain career daysailing and racing monohulls and catamarans around the USVI and BVI. After eight years of daysailing, he moved into the powerboat industry where he captained a 46-foot Sea Ray around the USVI and BVI. After that, Joel worked in the yachting industry for a bit too. He’s worked on several yachts ranging in size from 112 to 191 feet. Joel knows boats and he knows our waters. He is a great choice for your next boat day.

How to Spend Your Boat Day 

There are so many great places you can visit during your boat day. If you prefer to stay in US waters, you can circumnavigate St. John and all of the outlying cays and islands, making snorkel stops at some beautiful offshore reefs only that are only accessible by boat. You can enjoy world-class snorkeling, cliff jumping, and, of course, a whole lot of sightseeing. Looking to grab a bite to eat or perhaps a frosty beverage? You can always stop at Lime Out, St. John’s floating taco bar, Pizza Pi, the floating pizza boat, or even Dinghy’s Beach Bar on Water Island. The possibilities are endless.

Visit Lime Out, St. John’s floating taco bar
Or hang out at Pizza Pi, one of my favorite spots!

For those of you who prefer to check out the BVI, you can visit the world famous Soggy Dollar Bar and grab an original Painkiller. You can jump off of the Willy T over in Norman Island, or perhaps check out the Baths up in Virgin Gorda. The BVI opens a world of possibilities, including beach hopping, bar hopping, snorkeling, sightseeing and more.

Spend the day in White Bay.
Visit Leon at he Soggy Dollar Bar & try a Painkiller!
Jump off the Willy T at Norman Island!
Check out the Baths in Virgin Gorda.

What Will the Day Cost 

  • Full Day USVI Trip: $1,050 plus fuel
  • Four-Hour USVI Trip: $800 plus fuel
  • Afternoon Snorkel & Sunset: $550 plus fuel
  • Full Day British Virgin Islands (BVI) Trip: $1,350 plus fuel and customs
  • Best of Jose Van Dyke BVI Trip: $1,095 plus fuel and customs
  • Extended Day BVI Trip: $1,595 plus fuel and customs

Ready to Book?

If you would like to book a boat charter with Sunshine Daydream Boat Charters, just visit their website at Click the “Book Now” button to see real-time availability. Have a question? You can also email Captain Rob at or call/text 340-776-0928.

Click here to read Sunshine Daydream Boat Charters’ reviews.



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