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Q: Would a MacBook Pro 13” fit in it ?

Google gives the MacBook Pro 13" dimensions as Dimensions 11.97 x 8.36 x 0.59 inches. I'm able to fit a MicroSoft Surface Book 2, @ 12.3 inches (31 cm)(length) 9.4 inches (24 cm)(width) 0.51 to 0.90 inches (1.3 to 2.3 cm)(depth), inside a Tumi Tablet or small laptop Sleve (for extra bump protection) in the bag. FWIW, the Tumi "sleve" itself is @ 12.75 to 13" long x 9" tall x 1" + 2 side pockets thick. They all fit well with space left over, even without the extra expansion zipper undone. HTH

Q: How do we request a monogram?

Just take your bag to nearest Tumi store and they will do it for you.

Q: Does a couple of shares of Apple stock come with this bag?

I wish. It is an awesome bag however. Fits a surface perfectly. Won’t work with anything larger though.

Q: Anyone know where i can buy a similar less expensive bag. don’t want to spend 300 bucks on a tote i may one 3 times a year since i have plenty of bags

Tumi is like Rolex they control pricing for their merchandise across the market. You may be able to find a knockoff cheaper but I don't know where.

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Would a MacBook Pro 13” fit in it ?

How do we request a monogram?

Does a couple of shares of Apple stock come with this bag?

Anyone know where i can buy a similar less expensive bag. don’t want to spend 300 bucks on a tote i may one 3 times a year since i have plenty of bags