DAY 01 09:30
Walk like a Venetian
Strolling through the maze-like alleys of Rethymno’s Old Town, Crete’s most well-preserved medieval settlement, is a fascinating journey through time. Its charming lanes are punctuated by beautiful ancient doorways; look, too, for the wooden balconies, or sachnisia, of former Ottoman residences.
 
Makry Steno (“Long Alley”), also known as Nikiforou Foka Street, bisects the Old Town; the lanes off it, including Arabatzoglou, Minoos and Radamanthous, are all full of surprises. With great views, the 16th-century Venetian Fortezza is worth the €4 entrance fee.
The Archaeological Museum of Rethymno presents exhibits from Neolithic to Roman times and from the region’s most significant archaeological sites.
For more recent treasures, the Historical and Folk Museum depicts life in rural Rethymno in the 17th century. The nearby picture-perfect Venetian Harbor is the ideal place for a stroll.
Info
Archaeological Museum of Rethymno – 4 Aghiou Fragiskou, Tel. (+30) 28310.275.06, open: Wed-Mon 10:00-18:00
Historical and Folk Museum – 28-30 Vernardou, Tel. (+30) 28310.233.98, open: Mon-Sat 10:00-15:00
 
Venetian Fortezza – open daily 08:00-20:30
DAY 01 12:00
Rimondi Fountain
There’s no better spot to take your bearings than at the ancient fountain with the three lions’ heads at the Old Town’s “crossroads”. Under a bower of lavender-blue wisteria, Café Galero makes an ideal rest-and-rendezvous point. From here, the old quarter’s many delights are close at hand.
 
The impressive 16th-century Loggia, once a meeting-place for Venetian nobility, is now the gift shop of the Archaeological Museum. For delicious Cretan favorites with a twist, head to rustic Raki Ba Raki. Sit inside for a retro deli experience, or outside in the charming lanes, under the vines.
Next to the fountain is a very cool locals’ favorite. Meli serves the best ice cream in Crete, homemade from goat’s milk. Once you taste it, you’ll never forget it.
Info
Raki Ba Raki – 17 Arabatzoglou, Tel. (+30) 28310.582.50
DAY 01 13:00
Artisans and artists
Rethymniots are known for their creativity – mixing the old ways with contemporary flair. At Spantis in the Old Town, Yiannis Spantidakis uses raw unprocessed leather to create bags, belts and wallets. Vibrant colors and great designs make his leatherworks irresistible.
 
A few streets away at 30 Vernardou is the bakery workshop of Yiorgos Hatziparaschos – one of the last traditional filo pastry makers in Greece. His son Paraskevas is continuing the tradition, and you can watch as they whirl the dough into a giant bubble before stretching it by hand over the worktop. Taste the results by sampling their baklava or kataifi.
Such artisanal excellence is bound to raise a thirst, so head down the tunnel that takes you to the bar-restaurant Ali Vafi’s Garden for a beer in an ancient courtyard with citrus trees.
Info
Spantis – 9 Panou Koroneou
Ali Vafi’s Garden – 65 Tzane Bouniali, Tel. (+30) 28310.232.38
DAY 01 19:00
Dining out
Rethymno’s Old Town is blessed with great restaurants, of which one in particular stands out – Avli (22 Xanthoudidou. In its enchanting flower-filled courtyard, owner Katerina Xekalou serves exquisite Cretan-inspired dishes. Using the freshest ingredients in time-honored recipes and modern creative fusions, Avli’s award-winning alchemy creates a dining experience second to none.
 
For something lighter, head for bustling Vernardou Street and its traditional tavernas and mezedopoleia – eateries serving tasty tapas-style dishes. Rakodikeio and Asikiko are favorites. Light and airy Alana offers good value.
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Info
Avli – 22 Xanthoudidou, Tel. (+30) 28310.582.50
Rakodikeio – 7 Vernardou, Tel. (+30) 28310.544.37
 
Asikiko – 13 Vernardou, Tel. (+30) 28310.424.96
Alana – (15 Salaminos, Tel. (+30) 28310.277.37)
DAY 01 23:00
Nests for night owls
The palm-lined promenade between the Venetian Harbor and the marina is home to some of Rethymno’s most popular bars and cafés. Watching the passersby from here while sipping a colorful cocktail is part of the Rethymno experience.
 
The elegant Livingroom is a slice of Manhattan – all lush velvets, mirrored walls, video screens and top-notch service. Fraoules, with its neon and chandeliers, is cool and has a nice vibe.
Info
Livingroom – 5 Eleftheriou Venizelou, Tel. (+30) 28310.213.86
Fraoules – 62 Eleftheriou Venizelou, Tel. (+30) 28310.245.25
DAY 02 09:30
Breakfast and Beach
Near the ancient Guora Gate, the café-bakery Gaias Gefseis is a cozy breakfast spot on the Old Town’s main street; it makes some of the best traditional cakes and cookies in Rethymno. Across Tesseris Martyres Square, Sweet Cup is a gorgeous tea/coffee shop that serves beautiful cakes to match its charming decor. In the shaded Municipal Garden, nice for a morning stroll, is Kipos Café, a child-friendly destination.
 
No trip to Rethymno is complete without whiling away at least a few hours on its seemingly endless fine sand beach. Over two kilometers in length, this stretch of seafront is the perfect place for lying back and losing yourself in a good book. You won’t find it difficult to find a sun lounger, either; there are more than a thousand to choose from! Popeye Watersports has plenty of them; for its more energetic customers, it also offers water sport activities such as aqua paragliding and jet skiing.
Info
Gaias Gefseis – 15 Ethnikis Antistaseos
Sweet Cup – 6 Dimokratias
DAY 02 13:00
Lunch with the locals
Away from the main tourist spots but close to the beach, the suburb of Kallithea – east of the center – offers a glimpse into everyday Rethymniot life. Grocery stores, bakeries and butchers’ shops, along with a handful of cafés, line Markou Portaliou Street as it leads out of town towards Perivolia.
 
The locals’ favorite restaurant is here, too – To Katsarolaki, with its great traditional Cretan dishes. Further east, Zisis Taverna is popular and offers good value.
Info
To Katsarolaki – 19 Emmanouil Portaliou, Tel. (+30) 28310.513.98
Zisis Taverna – 63 Machis Kritis, Missiria, Tel. (+30) 28310.288.14
DAY 02 16:00
A Time for Gifts
Back in the Old Town, two main streets, Ethnikis Antistaseos and Arkadiou, and the tiny alleyway Souliou that connects them, all offer great shopping opportunities. Whether it’s quality embroidery, woodcrafts or an interesting memento, there’s something for everyone.
 
Chrissi Galerou has jewelry to die for – from designer pieces to unique handmade creations. There’s a delightful diversity to the retail experience in these streets. At 41 Ethnikis Antistaseos, don’t let the sign that reads koureio, or barbershop, confuse you. This tiny unassuming shop is the place for an authentic Cretan macheri (knife), sariki (headscarf) or komboloi (worry beads).
Good local cheese, honey, raki and olive oil can be found at Stylianos Koutakis’ shop at 86 Ethnikis Antistaseos. The quaint Biblioscopio has books for all the family in English and Greek, as well as great stationery items and captivating toys for little ones. If you want a truly tuneful Cretan souvenir, Stagakis’ Lyra Workshop is the place for handcrafted Cretan lyras.
Info
Chrissi Galerou – 277 Arkadiou
Stylianos Koutakis – 86 Ethnikis Antistaseos
 
Biblioscopio – 38 Agnostou Stratioti Square
Stagakis’ Lyra Workshop – 45 Hatzimichali Giannari
DAY 02 19:00
Right on the water
Head for a superlative last-night supper at a seafront table on the edge of town. Prima Plora prides itself on great organic dishes and has fresh seafood to match its dreamy location. The menu at nearby 7 Thalasses (89 Stamathioudaki, is excellent – this is another fine-dining option where you can almost dip your toes into the sea.
 
Climb the steps to an idyllic perch on Fortezza Rock to reach Thalassographia for amazing views and perfect sunset drinks.
Info
Prima Plora – 4 Akrotiriou, Tel. (+30) 28310.569.90
7 Thalasses – 89 Stamathioudaki, Tel. (+30) 28310.580.00
 
Thalassographia – 33 Kefalogiannidon, Tel. (+30) 28310.525.69
DAY 02 21:00
Summer nights
A gentle breeze, a cool drink, and stars above and on the big screen in front of you: open-air movies are the quintessential Greek summer experience. Round off your stay in style at the open-air cinema Asteria. Nightly screenings at 21:00 and 23:00. Entry €5.
 
And what could be better than one last celebratory stop? For full-blown late-night revelry, head to hip Nafpigio, with a nice crowd and the best dance music in town. The Rewine Bar, open until 02:00, has fine selections from across the globe – it’s a wonderful spot to “wine down.”
Info
Asteria Cinema – 21 Ioannou Melissinou, Tel. +30 28310.228.30
Nafpigio – 254 Arkadiou
 
Rewine Bar – 25-27 Tsagari, Tel. (+30) 28310.500.03