13 Of The Most Iconic Harley-Davidson Models For Two Riders

If you're thinking about the passenger experience, Harley-Davidson motorcycles have a lot to offer. Many of the best Harleys ever made come with the legendary "2-UP" seating, a system that basically puts the pillion passenger above the rider, making for an extra-comfortable ride. Other stylish Harley-Davidson bikes are more typical two-seaters, but they're still massively comfortable, in addition to being powerful. 

We've sorted through years of Harley-Davidson history to bring you these striking two-seater models, most of which are still available to purchase brand new today — only one isn't available new 2025. Countless aftermarket modifications and custom shops can convert single-seat motorcycles into two-person machines, but we're focusing only and solely on bikes that rolled off Harley's production line with the ability to seat a pillion passenger. These gorgeous machines show Harley's understanding that some of life's best rides are meant to be shared. So, with that in mind, here are the most iconic Harley-Davidson motorcycles that came from the factory ready for two.

We start off strong with the 2025 Harley-Davidson Street Glide, which comes in with a base price of $27,749 (not including fees), with monthly payments starting from $408. It has a standard two-person seat, with the passenger being slightly raised above the rider, and also comes with the now-legendary batwing front-fairing with an integrated LED. Power comes from a massive Milwaukee-Eight V-twin 117 unit that churns out 105 hp and 130 lb-ft of torque. This beauty of a powerplant features liquid-cooling, specifically on the cylinder heads – which is where the actual combustion happens, so it's important these stay cool, as well as a radiator mounted in between the "valley" of the V-twin, helping it stay cool on any tour. 

Tech wise, it also has an 12.3-inch touchscreen infotainment-navigation system that can connect to your phone and provide AM/FM radio, USB audio, and Apple CarPlay. All these convenience features when coupled with the estimated 44 mpg fuel economy, make for a brilliant riding experience. For the 2025 model year, the Street Glide comes with a standard color scheme of billiard gray, with eight other options available for an additional cost – between $600 and $2,200. As usual, the bike is also available in two main trims: chrome, which is the standard option; and black, which, for an extra $1,350 removes all the shiny chrome and makes the Street Glide look a lot more menacing.

Next up, we have the 2025 Harley Street Glide Ultra, which can do everything that the Street Glide from above does, but better. In Harley's own words, the Ultra is basically just a Street Glide that has a few extra features that make ultra-long touring even more enjoyable, and this really shows. More storage, a passenger backrest, passenger shoulder rest, rear passenger floorboards, a two-up comfort seat, a bigger windshield, and heated handles, are just a few among many upgrades that the Ultra boasts over the regular Street Glide — if any Street Glide can be called regular. 

It isn't much more expensive than the regular model, coming in with a base price of $30,749 (excluding fees) and monthly payments from $452. The Ultra has exactly the same performance specifications as the base Street Glide: Milwaukee-Eight 117 engine, 105 hp, 130 lb-ft of torque, and a 44 mpg estimated economy — which is quite impressive. Additionally, the Ultra also has upgraded storage, with a total available space of 4.9 cubic feet – double that of the pedestrian Street Glide. To put it simply, the 2025 Street Glide Ultra is the ultimate touring machine for the "I have no budget restrictions" buyer, whether that's for solo touring, or with a passenger.

Harley fans have spent plenty of time comparing the Road glide to the Street Glide, and it's easy to see why. Both are extremely powerful, comfortable, and have a road presence unlike any other. They're priced similarly too, with the 2025 Road Glide having a base price just a little higher than the Street Glide, at $27,999 versus the Street Glide's $27,749 (before fees). Also, a special, high-performance vehicle of this bike is also available for purchase currently, in the form of the 2025 Harley-Davidson CVO Road Glide RR, though it does command a premium MSRP, starting at $110,000 and is a single seater. 

For the standard 2025 Road Glide, power is provided by the same Milwaukee-Eight 117 V-twin engine as the two Street Glide models we just covered above. The Road Glide's power output is a little higher – 107 hp versus 105 hp on the Street Glide – though torque is 1 lb-ft lower, at 129 lb-ft. It also has the same 12.3 inch touchscreen infotainment system with Skyline OS as the Street Glide. It would honestly be easier to mention the main difference between the two motorcycles – which is the fairing design and placement. This design difference causes the two bikes to handle very differently, with the Road Glide being known for its stability and aerodynamics, and the Street Glide being the more maneuverable sibling.

On Harley-Davidson motorcycles, CVO is an acronym for Custom Vehicle Operations, and the tag is given to only a few bikes each year. Each CVO motorcycle will have custom paint options not available on the regular variant – for each CVO bike is based off an existing platform – and will also usually be shipped with higher-quality components and (sometimes) premium features. The 2025 CVO Street Glide is one such option, being a two-seater bagger motorcycle that was built for the open road. The premium-ness of this model is clearly reflected in the price, which starts at an eye-watering $45,999, with monthly payments from $677 (not including fees). 

It comes with the VVT 121 engine that makes 117 hp and 139 lb-ft of torque, which is plenty, even for this massive batwing bagger. Also, unlike the basic Street Glide, the 2025 CVO Street Glide is only available in two chrome trims: there's the regular chrome finish, and a slightly duller one that Harley is calling "scorched chrome." Scorched chrome is the standard option on this model, with only two colorways available: purple, which is being called "Poison Berry" and black, which is named "Raven Fade." However, do note that if you opt for the regular chrome finish, the only colorway available on the CVO Street Glide is Blue Streak – which adds an unavoidable $5,000 markup – that's Harley for you.

The 2025 Heritage Softail Classic is a two-seater cruiser that's been about since 1984. Pricing for the 2025 model year hasn't been released at the time of writing; but we don't expect it to be too far off the 2024 base price of $22,499 (before fees). Standout features on the 2025 Heritage Softail Classic are the lockable, weather proof twin saddle bags, an all-new LED lighting system with auxiliary illumination, new circular air intake, new and retuned adjustable rear suspension and selectable ride modes. The different ride modes can be selected without much fuss via a selector switch that has been added to the left handle of the bike, alongside a traction control switch and cruise control button. 

Furthermore, the brake lever gets a quick-control knob that lets you adjust it, and the bike finally gets USB-C charging to keep your devices juiced up on every ride. The engine is the trusty Milwaukee-Eight 117 V-twin unit that makes 91 hp and 115 lb-ft of torque on the Heritage Softail Classic, which is lower than the Street Glide and Road Glide models, even though it is the same engine. However, there is no reason to fret, for the HSC has a lower weight of 718 pounds, meaning that it won't feel underpowered at all; and remains a fantastic choice of bike for two riders.

There is no question that this one is the undisputed king of whichever road it travels on. The 2025 Road King is an absolutely gorgeous two-seater unit, with the pillion rider being placed above the primary rider, as two-seater Harleys usually are. As with some other models this year, the standard color option is Billiard Gray, with a $500 upgrade to Vivid Black, and a $700 upgrade to Whiskey Fire; however, the only trim option for this model year is black, with the chrome option being omitted. Pricing for the 2025 Road King Special starts at $24,999, with monthly payments starting from just $379 (not including delivery fees). 

The Road King Special gets the slightly older Milwaukee-Eight 114 V-twin engine instead of the 117, but it still manages a respectable power output of 96 hp, 122 lb-ft of torque, and an impressive 43 mpg estimated fuel economy. The extended saddle bags offer ample storage, and are paint-matched to the body, the exhausts are menacingly blacked out, and perhaps most importantly, cruise control is a standard feature. In addition, the Brembo brakes that come as a standard option will ensure that the entire hulk and bulk of this monstrous motorcycle will easily come to a safe stop. All in all, it's a fantastic motorcycle for any rider who wishes to make an impression on the road – whether with a passenger or without.

A bit of a departure from the two-seater Harley-Davidson bikes we've been covering is this next one – the 2025 Trike Freewheeler. It is one of the most iconic Harley models ever, and has been around since 2014. Pricing for this unit starts at $31,999 (before fees), which works out to monthly payments starting at $471 – which is not horrible value, all things considered. Power for the Trike Freewheeler comes from the Milwaukee-Eight 114 V-twin, producing 90 hp and 119 lb-ft of torque at 2,750 RPM, and it is available in the same color options as the Road King Special that we just covered – Billiard Gray, Vivid Black, and Whiskey Fire respectively. 

Additionally, just like the Road King, there is no chrome trim available on the 2025 Trike Freewheeler, meaning that the blacked out look is the only one available. The bike features mini-ape handlebars, bobtail fenders, passenger grab-handles, and a massive lockable rear trunk that can fit in two helmets and still have room to spare. It's a very unique motorcycle that is guaranteed to turn heads wherever you go, and because it is a three-wheeler, it is, by definition, a lot more stable than a regular two-wheeled Harley.

The next two-seater Harley on our list is the 2025 Trike Tri-Glide Ultra, which has a number of subtle differences to the Trike Freewheeler, with a front end evoking Electra Glide Ultra Classic and storage space, among other things. Also, fun fact: The Trike Tri-Glide Ultra was the lead vehicle of the motorcade that inaugurated President Barack Obama's term in office back in 2009. Today's model has a base price of $ $37,999 (before fees), with monthly payments starting from a not-insignificant $559. For that price you get a full dresser, three-wheel behemoth that has a full 6.8 cubic-feet of space available, thanks to the included King-Pak luggage storage system. 

It also gets a premium audio system with four speaker units, and a 6.5-inch touchscreen display that controls virtually every function on the bike. The engine is the same Milwaukee-Eight 114 V-twin that's to be found on the Trike Freewheeler and on the 2025 Road King, producing 93 hp and 120 lb-ft of torque. Thanks to the signature batwing fairings at the front and other aero bits and bobs, this colossal 1,237 pound motorcycle can still average 42 mph – a feat that is nothing short of extraordinary. For those who want to go the distance with both a passenger and paraphernalia, the 2025 Trike Tri-Glide Ultra is undoubtedly the way to go.

The 2025 Street Bob comes from a nameplate that has been in use for more than two decades, introduced way back in 2005 for the 2006 model year. However, the most avid Harley fans will know that the legacy of the Street Bob goes back much further than 2006, as it was born from the legendary Dyna series of motorcycles, which started production 15 years prior, in 1991. Fast forward to today, and you'll find that the 2025 Street Bob costs a cool $15,999 (not including fees), which works out to a per-month payment of $267 – making it one of the most accessible two-seater Harleys on our list. 

It only comes in the chrome trim, with six color options to choose from, and buyers also get to upgrade to laced wheels for a $800 premium. The 2025 Street Bob draws its power from the Milwaukee-Eight 117 V-twin rumbler, which, in this model makes 98 hp, 120 lb-ft of torque, and averages 47 miles to the gallon – the most fuel efficient Harley we've covered so far. There are a number of aesthetic changes to the 2025 Street Bob, the most prominent of which is the new Harley-Davidson logo medallion mounted on each side of the gas tank – it directly resembles the original design made by W.G. Davidson back in '66. Other aesthetic changes include a new 5.75-inch LED headlight, annihilator wheels, and a bobber-style rear fender.

Arguably the most "Harley Davidson" Harley Davidson to ever exist, the 2025 Fat Boy is the next two-seater motorcycle on our list. It comes in with a base MSRP of $22,599 (not including fees), which equates to a monthly payment schedule beginning at $350. The engine on this beauty is a custom variant of the trusty Milwaukee-Eight 117, that, on the Fat Boy, makes 104 hp and 126 lb-ft of torque. Put together as a ride-ready unit, it weighs a significant 694 pounds, which is why it's a bit unbelievable that the Fat Boy gets an estimated 47 mpg economy. 

Updated for the 2025 model year is the digital-analog gauge, which consists of a large 5-inch analog gauge for speed mounted on the fuel tank, at the bottom of which sits an LCD-screen. On the LCD screen, you can see your gear, access your trip computer, as well as note the time, range, and tachometer readouts. Just as with the Heritage Softail Classic that we covered above, the Fat Boy gets a ride-control switch on the left handle that allows the rider to set the mode to road, rain, or sport. The same handle also has a control switch for cruise control, and a button for turning traction control on and off.

Next up, we have one of the newest Harley-Davidson motorcycles in the roster. The 2025 Breakout is a vintage-inspired cruiser priced at $23,099 (before fees), with monthly payment plans starting from $358 per month. Like many of the other models that we have included on this list, it is only available in one trim – chrome – but that can be forgiven because it looks stunning in chrome. In terms of features, it has all the modern ones you'd expect on a contemporary ride, such as USB-C charging, Dynamic ABS, 4-inch digital-analog display, drag-torque slip control, an adjustable brake lever, and advanced traction control. 

It, like the Gray Ghost from earlier, draws its power from a custom version of the Milwaukee-Eight 117 V-twin that, in this model, pushes out 104 hp and 126 lb-ft of torque. In addition, the 2025 Harley-Davidson Breakout has an estimated economy of 49 mpg. Given that the Breakout has a 5-gallon fuel tank, riders will be able to enjoy about 245 miles of uninterrupted cruising between fill ups – and that's just straight up fantastic.

The 2025 Nightster Special also gets a place on our list, being (arguably) one of the coolest-looking two-seater Harley-Davidson motorcycles on sale at the moment. Pricing for the Nightster Special starts with a base MSRP of $12,999 (excluding fees), which equates to a monthly payment starting from just $194 – making it the most accessible Harley on our list. For that price, you get a gorgeous sportster-style bike with a massive two-into-one matte-black exhaust, and absolutely no chrome whatsoever – barring the wheels and front fork. 

It is powered by a Revolution Max 975T that outputs 91hp and 72 lb-ft of torque, but given its relatively low weight of 483 pounds, this engine can extract a fuel economy of 52 mpg from the bike – nothing short of stellar. The chrome trim is absent on the Nightster – and we dare say it isn't missed – but four colorways are available, which are Billiard Gray (+$0), Black Denim (+$650), Whiskey Fire (+$750), and Blue Burst (+$750). Aside from the extortionate paint pricing, the Nightster is actually an amazing motorcycle – both in the looks and the performance department, and it's impossible to go wrong when choosing it as your ride.

Lastly, we have the only non-2025 model of our list of two-seater Harley-Davidson motorbikes. The 2014 Electra Glide is, by far, one of the most iconic and legendary Harleys ever made, and it's easy to see why. Power came from a high output twin-cam 103 cubic-inch engine that produced 76 hp and 96 lb-ft of torque that was mated to the tried and tested Harley six-speed transmission. It has one of the most comfortable seating positions for the pillion rider, with a plush backrest, shoulder support, and loads more comfort features. 

Not a lot more is there to be said about this motorcycle: it looks amazing, was decently performant for the time (more than a decade ago now), and was comfortable for both the primary and pillion riders. Today, a decent used example would run you between $9,500 and $14,000, making it an amazing deal for people who want the Harley-Davidson Grand-America touring lifestyle without paying the Milwaukee-House tax.