Living in Tokyo means I’m spoiled for choice with quick getaways. Ask me my go-to short trips for first-timers to Tokyo and without hesitation I’d say Hakone for hot springs or Enoshima/Kamakura for the ocean breeze.
But here’s my guilty confession: I haven’t been back in ages. Well… we know that it is because they’ve both become mainstream. Translation: the kind of crowd that makes you accidentally photobomb 17 strangers’ selfies in one walk.
Still, I get asked all the time for recommendations, and truth is — these places are popular for a reason, because… they are awesome. Simple as that.
You are in luck today, because this blog post will detail how you can navigate Hakone and Enoshima/Kamakura seamlessly, skip the ticket stress, and actually enjoy while saving you some yen! That’s where the digital Freepasses come in.
Also, I have a few hidden spots up my sleeve, so read till the end!
HAKONE FREEPASS

I always recommend starting your Hakone trip with the Romancecar from Shinjuku — a comfy, panoramic ride that feels like your holiday has already begun the moment the train pulls out of the station..

When you arrive at Hakone-Yumoto Station, do yourself a favor: drop your luggage at the baggage delivery service conveniently right by the platform. Your bags will magically find their way to your hotel while you wander hands-free.
What the Hakone Freepass Covers (aka Why It’s Magic)

The pass is basically an all-you-can-ride buffet of moving about. You get unlimited rides on 8 different Hakone-area transportation modes:
-
Round trip travel on the Odakyu Line between Shinjuku and Odawara (please note that you have to reserve the Limited Express Romancecar separately with a surcharge. Good news: it can be booked on the same website along with your ticket!)
-
Hakone Tozan Train (slow but scenic mountain climb)
-
Hakone Tozan Cable Car
-
Hakone Ropeway (with Mt. Fuji views on a clear day… or cloud appreciation if not)
-
Hakone Sightseeing Cruise (yes, the pirate ship on Lake Ashi!)
-
Local Hakone buses
On this trip, I did a quick calculation: my transportation cost came to just 8,400 yen (Hakone Freepass + Romancecar Express). Without the freepass, it would have been 12,460 yen. That’s a solid 4,060 yen saved per person — and if you’re traveling as a family, the savings really add up!

This is perfect for doing the classic Hakone loop: cable car up, ropeway over to Owakudani’s black eggs, pirate ship across Lake Ashi, and a bus ride back. Instead of panicking at each ticket gate (espeically if you have a mom-brain that makes you lose your paper ticket all the damn time), you just flash your pass and hop on.


Cheesie’s Recommended Spot:
But let’s be real. You can find a hundred guides to Hakone’s famous spots with one Google search. So let me skip the obvious and share my favorite tucked-away experiences:
Lunch Option: Gyunabe Ukon

Before you get whisked away by cable cars and ropeways, fuel up here. Since it’s tucked away from the busy Hakone-Yumoto shopping street, you can either take a short taxi ride or walked about 15-20 minutes from Hakone-Yumoto Station. The best part is its kawadoko (川床) riverside terrace, where you can dine right above the flowing stream with the lush greenery unfolding like a living painting around you. Their sukiyaki-style wagyu beef hotpot is hearty, slightly sweet, and exactly what you need for mountain wandering.
Lunch Option: cafe KOMON

If you are taking the Hakone Sightseeing Cruise and alight at Hakonemachi-ko, here’s the perfect spot to have lunch right across the cruise dock. Cafe KOMON is the kind of place where your meal comes with front-row seats to Lake Ashi and even Mount Fuji on a clear day. They offer a good variety of dishes, and I went for the “odashi gohan” featuring salmon raised in the pure water of Mt Fuji, topped with ikura. Not only does cafe KOMON serve absolutely delicious dishes made with local ingredients, but the menu also adds a playful twist. Here, you get to make your own meal: whisk a bowl of matcha into a frothy latte, hand-grill colorful dango over charcoal, or even assemble your own fruity daifuku.
Visit: Fukazawa Zeniarai Benzaiten

Instead of following the crowd straight to Lake Ashi, take the Tozan Cable Car (yes, included in the pass!) and hop off for this shrine. It’s tiny, quiet, and you can “wash” your coins for good fortune. Think of it as laundering money—but the good,spiritual kind, hahaha.
Stay: Hakone Hatsuhana




Hakone Hatsuhana is perfect if you want your very own private onsen in every room—just step out to the terrace and soak with the sounds of the river and greenery as your backdrop. And when you’re not in the bath, you’ll be indulging in beautifully crafted kaiseki dinners and a breakfast served on exquisite yosegi-zaiku woodcraft, a traditional Hakone artistry.
A Bit of History: Hakone’s Tokaido Route
Back in the Edo period, the Tokaido was Japan’s most important highway, linking Edo (now Tokyo) with Kyoto. Of its 53 post towns,Hakone was one of its toughest and most famous checkpoints–travelers had to pass through here under strict inspection, especially women leaving Edo (to prevent daimyo families from fleeing).

The route through Hakone was no easy stroll. Winding mountain paths, cedar forests, and steep climbs made it a challenge, but also a place of stunning natural beauty. Even today, stretches of the original stone-paved road remain, shaded by towering cedars. Walking it feels like stepping back in time, imagining merchants, pilgrims, and samurai making the same journey centuries ago.
Sadly, since the development of highways and the world’s most amazing Shinkansen, this once-bustling path has slowly lost its footprints as fewer people travel on foot. Which is exactly why you should come — to savor this precious piece of living history and help make it lively again.

Start at Hatajuku – This quiet little village was once a rest stop on the old Edo–Kyoto highway. Today it’s famous for Hakone yosegi-zaiku (traditional wood marquetry). It feels like stepping back in time, with craft shops and a slower pace

Hatajuku Yosegi Kaikan – Pop into this workshop/museum to see how artisans piece together tiny bits of wood into mesmerizing geometric patterns. You’ll leave with a whole new appreciation for Hakone’s craft heritage (and probably a puzzle box or two).


Amasakechaya – From Hatajuku, walk about an hour along cedar-lined paths of the old Tokaido until you reach Amasakechaya. This thatched-roof teahouse has been serving travelers for over 400 years with sweet amazake (a non-alcoholic fermented rice drink) and shaved ice in summer time. It’s the kind of spot where you can almost imagine a samurai tying up his horse outside.
These little detours are why I still love Hakone—yes, it’s mainstream, but with the Freepass and a willingness to step off the beaten path, you’ll find pockets of peace (and great food) everywhere.
ENOSHIMA-KAMAKURA FREEPASS

If Hakone is all about mountains and hot springs, then Enoshima and Kamakura are Tokyo’s salty-haired seaside escape. Think: beach breeze, temples, and the freshest seafood bowls.

The ENOSHIMA-KAMAKURA FREEPASS covers:
-
A roundtrip on the Odakyu Line from Shinjuku to Fujisawa.
-
Unlimited rides on the Odakyu Line (Between Fujisawa and Katase-Enoshima) and Enoden Line (the adorable seaside tram that slides between backyards, beaches, and temples like an anime daydream)
The Classic Spots in Kamakura
These are the “can’t miss” places if it is your first time to Kamakura:
Houkokuji Temple (報国寺)
Famous for its serene bamboo grove, Houkokuji is often called Kamakura’s “little Kyoto.” The narrow forest path and tea house overlooking the lush bamboo make it an absolute tourist magnet.
Nearest station: Kamakura Station (Enoden Line or JR Yokosuka Line), then take the Keikyu Bus from Kamakura Station East Exit, Platform 4 and get off at Jomyoji (12 minutes), or a 25-minute walk. It is not directly on the Enoden line, so the Freepass won’t cover the bus fare — but it’s absolutely worth the detour.
Zeniarai Benzaiten Ugafuku Shrine (銭洗弁財天宇賀福神社)

One of Kamakura’s most unique spots, this cave-like shrine is where you wash your money in sacred spring water. The legend says rinsed coins will multiply, making it a must-visit for fortune seekers. The entrance tunnel carved into the rock feels like stepping into a hidden world.

Nearest station: About a 20-minute walk from Kamakura Station (JR / Enoden).
Enoshima Island (江の島)
Connected to the mainland by a bridge, Enoshima is a small island packed with shrines, caves, food stalls, and viewpoints.
Hidden within the island are three separate shrines that together make up Enoshima Shrine, each tucked away along forested paths, inviting visitors on a small spiritual pilgrimage.

At the summit stands the Enoshima Sea Candle lighthouse, where you can look out over Sagami Bay. The island is especially magical at sunset, when the sky glows pink and orange behind Mt. Fuji on the horizon — a view that feels like it belongs on a postcard.

Beautiful sunset at Chigogafuchi Abyss (稚児ヶ淵).
Nearest station to Enoshima Island: Enoshima Station (Enoden Line) or Katase-Enoshima Station (Odakyu Line), about 10–15 minutes on foot across the bridge.
Bonus Foodie Stops
Mushinan Kamakura (無心庵)

A nostalgic teahouse literally hugging the Enoden track.Housed in a century-old traditional home, it’s one of Kamakura’s oldest cafés and carries a warm, nostalgic charm that has earned it many loyal fans.

Here you can sip matcha or enjoy classic Japanese sweets such as shiruko, anmitsu while the tram rattles by just outside the window. It’s atmospheric, cozy, and feels like stepping back into a slower Japan.
Nearest station: Right besides Wadazuka Station (Enoden Line).
Shirasu-ya (しらすや)

Kamakura and Enoshima are famous for shirasu (whitebait), and Shirasu-ya is one of the best places to try it fresh. Their shirasu-don (whitebait rice bowl) comes raw, boiled, or mixed with other seafood. Enjoy this rather off-the-radar eatery for max local flavors!
Nearest station: Koshigoe Station (Enoden Line), about 5 minutes on foot.
Enoden Monaka Ogiya (扇屋)

This long-standing confectionery shop has been around for over a century, and its retro wooden storefront and quiet atmosphere ooze old-school Kamakura charm. The shop is extra special because right outside, you’ll spot an old Enoden train car that remained in active service until 1990.
Nearest station: Enoshima Station (Enoden Line), about 3 minutes on foot.

Fun tip: Right opposite Ogiya, there’s now a new food stall, (Asahi Honten Enoshima Maruyaki Tako Senbei Enoden Shonan store ) shaped like a classic Enoden car. It sells tako senbei (octopus rice crackers) and other street snacks — the perfect quirky contrast to Ogiya’s traditional sweets.
To End Your Trip

After a day of temples, seaside snacks, and Enoden rides, I like to end my trip at Katase-Enoshima Station. The station itself looks like a fairytale dragon palace, making it a charming finale. For extra comfort, hop on the Romancecar back to Shinjuku — you’ll be gliding home in style, with your camera roll full and your stomach happily full too.
Enoshima and Kamakura are mainstream, no denying that. But the Freepass makes it painless: hop on and off the Enoden as much as you want, wander a bit off the main roads, and you’ll discover quiet temples, nostalgic tram crossings, and locals hanging laundry against a backdrop of ocean. It’s those little slices of everyday seaside life that keep me coming back.
Here’s where you can find out more about these two freepasses:
HAKONE FREEPASS
ENOSHIMA-KAMAKURA FREEPASS
PS: If you enjoy this article or find it helpful, it would mean the world if you could help me support Japan by buying a daikon!





