Alan is a Navy officer who will soon be stationed in Hawaii. His Highlander will be making the journey to the new post, but he is looking to supplement the family hauler with something a bit more fun. What car should he buy?

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Here is the scenario -

I’m a Navy officer with orders to Oahu, Hawaii. My family of five, a wife, three kids under 10 and a dog, is moving from Washington, D.C. to Hawaii. We have been a single-car family since I have relied on public transportation or my own two feet to get to and from work. We will ship our family 2010 Toyota Highlander, but need a second car that will act as my daily driver for approximately 30 miles. The Highlander has been a reliable but boring family hauler, and we’re looking for something that could be a little more fun for us to enjoy on the island.

Cool, unique and island-appropriate is how I would describe the car. Manual transmission is preferred. A convertible would be great, or something with a soft top that can be removed. Not a Jeep. A Jeep Wrangler seems like the obvious answer but I’ve already had one. Reliable or something that is easy to work on, that doesn’t have a ton of specialty parts that would be difficult to source in Hawaii. It should be able to take in all of Hawaii’s open ocean breezes.

I am looking to spend up to $20,000

Quick Facts:

Up to $20,000

Yes

Oahu, Hawaii

Fun, convertible, manual

A Jeep Wrangler

Expert 1: Tom McParland — Aloha!

Alan, congratulations on your transfer. Hawaii is a wonderful place. I’ve visited the state a few times, and it’s one of my favorite places. Of course, as a surfer kid from New Jersey, I found the surf conditions to be on another level. But you don’t need to be a pro to enjoy the water sports. Since Hawaii is all about enjoying the outdoors, I’m going to suggest something that’s not quite what you asked for. You need a TDI Sportwagen. The Sportwagen has enough room for the family. The kiddos might be tight in the back, but with a good set of roof racks, there’s plenty of space for whatever gear you are going to bring, whether it be surfboards, kayaks or mountain bikes.

Since fuel is bonkers expensive on the islands, you will appreciate the almost 40 mpg on the highway, and of course the Sportwagen can be had with a manual transmission. Well-equipped wagons come with a panoramic sunroof, which isn’t quite a convertible top but will provide a nice open-air experience. Now it goes without saying that you want to avoid buying a car on the island (since the prices are sky-high), especially if Uncle Sam is going to pay for the transport.

In an ideal world, you’d buy a convertible that has room for all your kids and your dog. That’s a tall order, though, since very few convertibles have both a rear bench and a large rear cargo area. As you noted, the Wrangler (four-door) is among the few that fit the bill, though there’s also the old 4Runner, the old K10 Blazer, the Bronco and a few others.

As you’ll be living in Hawaii, I hesitate to stray away from convertibles, but I think instead of buying those old 4x4s the play is to get something old with thin pillars, big windows that let in lots of light and maybe a sunroof. That way you can enjoy the sunshine, even in a non-convertible.

I recommend the VW Type III Squareback (the one above doesn’t have the optional sunroof), a vehicle that just looks like the perfect beach cruiser. It’s not four-wheel drive, but if your Highlander is, that should do a decent enough job for when you want to hit some light trails.

Seriously, just look at that wagon. Imagine surfboards up top, the pup in the rear, the kids in the back seat watching you shift through those four gears and staring out of those big windows at their amazing new home. It just seems right — well, to me at least. If it feels right to you, too, then call the seller and try to get him to to your budget of 20 large.

Then prepare for your children (and especially your dog) to have the sound of that air-cooled wonder (situated beneath the rear floor) forever imprinted in their minds.

Expert 3: Mercedes Streeter — Top Down Vintage Fun!

Congratulations on your move! Tom’s choice is a fantastic car. I own one of those Jetta Sportwagen TDIs and I would trust it to take me anywhere. However, I feel that even with a sunroof, there just isn’t enough air and sun to truly enjoy the outdoor beauty of where you’re going to live. You’re already importing an SUV for the family, so let’s get you something cool and fun. I wanted to recommend a Volkswagen Beetle TDI Convertible with a manual but those are both expensive and incredible unicorns, so here’s the next best thing.

This is a 1968 Volkswagen Beetle convertible with a manual transmission and only 7,612 miles! It’s in Texas, so rust probably won’t be an issue. It appears to be in good shape all around in the pictures. The seller notes the chrome and interior to be original, too. As a bonus, this car comes with a hidden bluetooth headunit, so at least you have some modern tech for your vintage auto. These aren’t fast but you’ll feel awesome driving along the shoreline, top down with your tunes turned up to 11.

It comes in , but since Uncle Sam is footing the shipping bill, you can go ahead and pocket the savings!

Expert 4: José Rodríguez Jr. — Be a good island Sport!

Boy, oh, boy! My fellow Jalops do love a beach-going VW, and I’m starting to get an idea of what counts as a cool Island ride around here. I am, however, going to go against the grain and call your attention to the underrated Isuzu Rodeo Sport. Get a two-door model, with a hardtop and a five-speed, Alan. That oughta save you some gas and buy you some sun.

The rear seat will likely be a tight fit for the kiddos and your dog, but they may not mind as you cruise down to the water with the hardtop off and the ocean breeze swirling about. You can jam everyone in and make memories as you row your gears at a leisurely pace. The 2.2-liter four-cylinder under the hood makes a modest 130 HP, but who’s in a hurry in a place like Hawaii?

Of course, there is a recall you want to look out for, so I’d inquire if a particular Rodeo was affected and whether steps were taken to address the issues. Depending on the Rodeo’s condition at the time of the recall, Isuzu would apply anticorrosion coating to the rust-prone mounting brackets.

A quick search didn’t bring up any manuals, but ersey hasn’t even hit its stride yet with just over 90,000 miles on the odometer. It’s not a stick, but it kicks up the displacement with a six-cylinder mill good for 215 HP. Oh, and it’s less than half of your budget! That ought to make up for the thirstier engine. Godspeed and aloha, Alan.

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