The Best 2-Week Greece Itinerary for 2026

Dec 28, 2025

Lindsey has worked with me for nearly a decade. She’s seen the best (and worst) of the Greek islands across six major trips. I finally got her to put together her personal 14-day shortlist for a trip to Greece. It covers Athens, Santorini, Milos, Crete, and Rhodes - including her handpicked favorites and the spots she thinks you should skip. If you’re planning for next summer, this is a great place to start. Enjoy!

Check out Lindsey’s favorites and her full 2-week itinerary here.

Two Weeks in Japan

A November trip to Tokyo, Hakone, Kyoto, Osaka, Himeji, and Hiroshima.

Nov 25, 2025

My wife and I just got back from a two-week trip around Japan. We started and finished in Tokyo, and in between visited Hakone, Kyoto, Osaka, Hiroshima, and Himeji. It was my 6th trip to Japan and as usual, absolutely fantastic.

Now home and back to updating Greece for 2026.

The Highlights

The Seimon-Ishibashi, the stone bridge that serves as the main entrance to the Tokyo Imperial Palace.

A yokocho is a narrow street or alleyway packed with small izakaya (beer + grilled/fried food), bars, and food stalls. While the word can refer to any side street, it usually describes these cramped, atmospheric drinking districts. Yurakucho Yokocho sits below the JR tracks one stop south of Tokyo Station. I got this photo just before the stalls opened for the evening.

Sake barrel offerings at Meiji Jingu in Tokyo, donated by breweries across Japan as an offering to the shrine, a tradition that’s more than a century old.

Shibuya Crossing, one of Tokyo’s most famous and busiest intersections.

The Oak Bar at the marvelous Tokyo Station Hotel (maybe my favorite hotel in Tokyo).

Yayoi Kusama’s signature polka dots and bright colors at her museum in Tokyo.

The **Hakone Loop** is a sightseeing circuit that requires you to switch between five distinct modes of transportation - including a switchback mountain train, aerial ropeway, and cable car - to move between the mountain villages, views, and attractions.

Having a foot bath at our ryokan (traditional Japanese inn).

Walking to the Hakone station to grab a train to Kyoto (via Odawara).

Lanterns and stone guardians at a small Kyoto shrine.

Built in the early 1600s, the stone walls and corner turrets of Nijō Castle, once the Kyoto residence of the Tokugawa shoguns.

The Umeda Sky Building in Osaka, twin towers linked by a skybridge and a rooftop observatory. The V-shape in the middle are the escalators up to the viewing platform.

The neon-lit canal and packed walkways of Osaka’s Dotonbori district. Fun and chaotic.

The first exhibit as you enter Hiroshima’s Peace Memorial Museum.

The remains of the Atomic Bomb Dome mark the hypocenter of the 1945 blast.

Himeji Castle - Japan’s best-preserved samurai fortress.

Street art in one of Himeji’s open-air shopping arcades.

The Food

Charcoal-grilled yakitori (chicken) and yakiton (pork) in a Tokyo izakaya:

Ramen from a shop in “Ramen Street” in Tokyo Station.

I’m Donut - a trendy and very popular donut shop in Tokyo.

Tuna sushi from an all-tuna restaurant in Shibuya, Tokyo.

Yakitori and yakiton at a yokocho in Shinjuku - simple, smoky, and delicious.

Wagyu rib steak from the Gora Brewery & Grill in Hakone.

Traditional Japanese breakfast at our ryokan in Hakone.

Seared salmon covered with mayo and onions at a restaurant in Osaka.

At an Osaka teppanyaki counter, the chef cooks wagyu and fresh vegetables on the steel grill just in front of our plates.

Japanese curry with chicken at one of our favorite chains, Coco Curry.

Yakinuku (meaning you grill it yourself) in Himeji.

Getting Around

We took 5 Shinkansen, 3 regular trains, 1 mountain train, 1 ropeway, 1 funicular cable car, 1 aerial gondola, 12 subways, 1 taxi, and 1 boat during our two week trip.

Buying tickets from the electronic kiosks is quick and easy. (Ok, maybe not the first time, but you get the hang of it pretty quickly.)

Subways are clean, fast, and the best way to get around the big cities. (Osaka in this case.)

Getting a Suica card is essential for easy travel. The cards can be used on all subways and commuter trains (plus vending machines and convenience stores). Here we’re adding credits to the card.

Or get the app through Apple Wallet and scan your phone to enter the subway. ICOCA is for Osaka. Pasmo and Suica for Tokyo, but all 3 cards can be used in any system or city so it doesn’t really matter which you get.

Bikes are popular for getting around Kyoto, Osaka, and Hiroshima (pictured here). Less so in Tokyo but you’ll still see plenty there too.

Where We Stayed

Happy travels,
Santorini Dave

Greek Island Hopping

Our trip through the Cycladic Islands

Oct 03, 2025

My recent trip report has 91 photos, maps, and screenshots (too many for email), so you’ll have to read it here: Island Hopping Trip through the Greek Islands.

As always, questions and feedback are welcome.

Happy travels,
Santorini Dave

Best Time to Visit Santorini

Weather, wine, swimming, sun ...

Jul 12, 2025

Almost everyone (95% ++) will visit Santorini between May and October so that’s what I’ll focus on. Short answer: June and September are my two favorite months to visit.

Article: **Santorini in May**. Photo: Santo Wines on May 25th.

Article: **Santorini in June**. Photo: Oia on June 25th.

Article: **Santorini in July**. Photo: Pyrgos on July 2nd.

Article: **Santorini in August**. Photo: Imerovigli on August 7th.

Article: **Santorini in September**. Photo: Megalochori on September 1st.

Article: **Santorini in October**. Photo: Oia on October 4th.

Also:
• Mykonos in June
• Mykonos in July
• Mykonos in August
• Mykonos in September

Happy travels,
Santorini Dave

More Greek Islands/Croatia/Slovenia

New stuff ...

Jun 20, 2025

Corfu sits on the opposite side of Greece from the Cyclades. It has a very different vibe with its lush, green landscapes and distinct Venetian architecture, reflecting its close historical ties (and ferry connections) with Italy.

Magical Corfu Town is one of my favorite spots in Greece.

Here are some updates for several less-visited Greek islands, a bit removed from the superstar destinations like Santorini and Mykonos.

• Corfu - where to stay
• Corfu - best beaches
• Kefalonia - where to stay
• Kefalonia - best beaches
• Zakynthos - where to stay
• Zakynthos - best beaches
• Skopelos - where to stay
• Skopelos - best beaches
• Skiathos - where to stay
• Skiathos - best beaches
• Andros - where to stay
• Andros - best beaches
• Tinos - where to stay
• Tinos - best beaches
• Rhodes - where to stay

Nearby Destinations (Recently Updated)
• Adriatic Coast of Slovenia - where to stay
• Ljubljana - where to stay
• Dubrovnik - where to stay
• Split - where to stay
• Zagreb - where to stay
• Korčula Island (Croatia) - where to stay
• Istria (Croatia) - where to stay
• Hvar Island (Croatia) - where to stay
• Trieste - where to stay