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While one of the typical things to do is a canal cruise, there is a different way to see the same sights.
To start the night in a different way and still "do the tourist thing" is to take an evening Canal Cruise. Most leave from near the Train Station and cruise up and down the major canals of the city. Amsterdam by night is much different from the day and the lighting on the houses and buildings make for a relaxing start to the evening. Most cruises include a bottle of wine (more for the buying if you like the bottle), some bread and cheese and a tour guide who is fluent in several languages.
Its kind of like a United Nations meeting where instead of simultaneous languages in your headphones, you might get to hear the basic story in English, French, German, Spanish, Dutch and even sometimes Japanese or Chinese (Mandarin or Cantonese). It gets somewhat hectic for the guide at times but the wine makes it easier to endure if you are not into learning a new language or revisiting high school French.
Boom Chicago offers small, open-air boats which are a refreshing alternative to the big boys and go down smaller canals like those in the red light district. Tours there in English only.
After the cruise, head for the shore and a "Brown Cafe", the Red Light District, your special place or your domicile for the rest of the evening.
If you really want to canal cruise like a local, there are multiple companies that will rent you a sloep by the hour (usually 2-3 hours min). A Dutch sloep is a small, usually electric, boat for 6-8 people. Pick up some snacks and some drinks and have a floating picnic you will always remember. Not giving preference to any one company, a few reputable offerings can be found at Sloepdelen (power up the boat from a smartphone), Boaty or Mokumboot (all sites in Dutch and English). Or, you could search online for terms like Amsterdam sloep, sloep verhuur (sloep for hire). If the weather is good, you'll really enjoy this off beat approach.
Flower Auction ( http://www.floraholland.com/en/) : This is an early morning trip (most everything is over by 9am): out close to the airport. You can get a local bus (172) from several points in the city. Almost ALL of the cut flowers in the WORLD go through this HUGE auction house. It is a self guided tour of the warehouse and auction rooms where millions of fresh cut flowers are auctioned.
More off-beat ideas in Amsterdam:
Get in touch with a concierge service for an extra special itinerary including 'best-kept-secrets' and hidden bars! (hint: a secret code is sometimes needed for these 'behind-the-scenes' location, and only a local's network can help you get in)
www.spottedbylocals.com/amsterdam = insiders' tips. The website is free. There is also a (paid) app.
Wander around Prinseneiland, tourists somehow cannot find this amazing, historical area in the centre!
Wander around Java-eiland, KNSM-eiland for modern architecture and nice cafes (east)
Pllek city beach / outdoor cafe with great views over the IJ water (NDSM in north, take the free ferry from behind Central Station)
Noorderlicht cafe (NDSM), mellow crowd, bonfire in the evenings
Wander around on Linnaeushof, a village-like pretty square in the east with flowers growing in the front yards and up the walls, and a church
Take a walk on De Nieuwe Ooster beautiful cemetery (east)
Distillery 't Nieuwe Diep, home brewed jenever (sort of gin) and liquors in 30 flavours, outdoor terrace overlooking a lake, indoor seating too, check opening hours beforehand, Flevopark http://www.nwediep.nl/ (east)
lounge on bean bags at Westergasterras in Westerpark (west)
roof terrace of Double Tree hotel, just take the elevator up to 11th floor (next to Central Station), it's pricey though, but great views
roof terrace of "Canvas op de 7e" (east), studenty atmosphere, live music some evenings
clubbing or a concert at Trouw (east)
De Nieuwe Anita squat cafe / cool parties (west)
OT301 squat bar / cool parties (west / south)
Maloe Melo underground rough bar in the centre with live music, but watch out for coat thieves (there is no guarded cloakroom)
Huis Marseille photography museum in a beautiful historical building, don't miss the photos in the garden house. (centre)
Verzetsmuseum / Museum of National Resistance (east / centre near Artis Zoo)
IJhallen monthly huge flea market (north)
Get delicious 'roti' (Surinamese dish) at Roopram and eat it in a park. The queues are there for a reason! (east)