Let’s clear something up: we don’t do boat rentals.
Carefree Boat Club is a membership — boats you reserve, walk down the dock to, and take out like they’re yours, as often as you like. There’s no hourly meter running. That’s the whole point.
But people ask us about rentals all the time — a birthday on the water, family visiting from out of town, a sunset cruise with no commitment. And we’d rather send you to someone great than watch you roll the dice on a random dock. So here’s our answer: our friends at R&R.
Who R&R is
R&R is simply the best in the bay for that. They’re a separate rental outfit — not part of the club — and we recommend them because they’re genuinely the best at what they do: well-kept boats, honest briefings, and a crew that takes care of first-timers.
They operate in two spots on San Diego Bay:
R&R Electric Boat Rentals — 1450 Harbor Island Drive, San Diego
Electric boats, rented by the hour. Two boats — Cloud Nine and Pretty in Pink — quiet, zero-emission, and easy enough that no boating experience is needed. Take up to 9 passengers for 1, 2, or 3 hours, bring the dog, bring a cooler, and putter around the bay at your own pace. It’s the most relaxed way to get on the water in San Diego — dates, family outings, birthdays. Reservations: (619) 651-3088.
R&R Surf Rentals — 606 Marina Parkway, Chula Vista (Safe Harbor Marina)
The full watersports menu on the south bay: self-drive Sea-Doo Switch boat rentals, captained luxury pontoon charters for up to 12 guests (the Sea La Vie — birthdays, bachelorettes, sunset cruises), crystal-clear kayaks, eFoil and jet board lessons, guided kayak tours, and dock-and-dine experiences. Same number: (619) 651-3088. Online at sdrandrsurf.com.
The company is run by Artiss and Arlyn Redmond — Navy veterans with 46 years of combined time on the water. That background shows in how they brief first-timers: every rental comes with safety walkthroughs, life jacket fittings, and route guidance. You don’t need to know what you’re doing; they’ll make sure you do.
Why we send people there
Honestly? Because it’s the right tool for the job. Their business is built to capture casual renter demand — one afternoon, one celebration, one “let’s just get on the water.” Ours is structured for the regular boat user — the person who wants to be out there every other weekend without thinking about hourly rates.
They’re different businesses solving different problems, and we’d rather be straight about which one you need.
Rent or join? The honest line
Here’s the rule of thumb we give people at the dock:
- On the water a few times a year? Rent. Call R&R, have a perfect day, go home. No membership on earth beats that deal at that frequency.
- On the water every month — or you want to be? That’s when the club starts making sense. The per-outing math flips, and more importantly, the experience changes: reserved boats, no hourly clock, training that makes you confident at the helm, and a fleet you get to know.
We’ve done the full cost comparison before — boat club vs. renting in San Diego, with real 2026 numbers — if you want the spreadsheet version.
Either way, you’re on the water. That’s the part that matters.
Ready to stop watching the hourly clock? Our boats are maintained, fueled, and waiting at Point Loma and Newport Beach. Call (619) 488-6630 and we’ll show you what the club life feels like.
Frequently Asked Questions
Does Carefree Boat Club offer boat rentals?
No — we’re a membership club, not a rental dock. For one-time rentals and charters, we recommend R&R. They’re a separate rental company — simply the best in the bay at it.
Where can I rent a boat in San Diego for the day?
Our recommendation is R&R: electric boat rentals on Harbor Island (1450 Harbor Island Dr — up to 9 passengers, no experience needed, dog-friendly) and the full watersports lineup at Safe Harbor Marina in Chula Vista (606 Marina Pkwy — self-drive boats, captained pontoon charters, kayaks, eFoil lessons). Call them at (619) 651-3088.
Do I need boating experience to rent from R&R?
No. The electric boats are designed for complete beginners, and every rental includes a safety briefing, life jacket fitting, and route guidance. If you’d rather not drive at all, their captained pontoon charters come with a licensed captain.
Can I bring my dog on a rental boat?
Yes — R&R’s electric boats are dog-friendly. It’s one of the more popular ways locals do a low-key day on the bay with the whole crew.
How do I know whether to rent or join a boat club?
Frequency. A few outings a year: rent, and R&R is our pick. Monthly (or aspiring to it): look at the club — the math and the experience both change. Our boat club vs. rental comparison walks through the numbers.