04/17/2026
Massimo’s-Portsmouth
For the birthday dinner finale, we went to Massimo’s and started strong with cocktails. I had the Venetian Mai Tai ($16), made with Woodford and whatever other sorcery they’re using, and it was excellent. Hubby went with the Grey Goose dirty martini ($16), which arrived exactly as a dirty martini should: cold, briny, and confidently unbothered.
We kicked things off with the char-grilled octopus te****le with Calabrian chili, crusty bread, pickled fennel, citrus vin cotto, and smoked cured egg yolk ($19). It was genuinely delicious. The sauces and accompaniments played so well with the octopus that every bite felt a little fancy without trying too hard. That said, I’d seen a photo my son sent me of this same dish last year, and this version was… let’s say not in its peak octopus era visually. (I’ll drop a pic of his in the comments, you can decide for yourself) Still impressive in flavor, just not quite the showstopper I had built up in my head.
For dinner, we both ordered the grilled filet mignon with rosemary baby potatoes, rapini, Parmigiano Reggiano, and demi-glace. The steak was cooked perfectly and had great flavor, no notes there. But why, Massimo’s, why are we pre-slicing a filet into medallions? I wanted the full steak experience. I wanted to saw into a glorious hunk of beef like the carnivorous queen I am. Instead, it came pre-cut, which looked nice but stole a little of the drama. The potatoes were tasty, but buried under a thick layer of Parmesan that hardened up enough to make things more high-maintenance than necessary. Presentation? Beautiful. Ease of eating? Slightly less beautiful. The demi-glace was also saltier than I wanted, though the birthday boy was perfectly happy with it, so I guess I’ll allow it on his special day.
And then there was the asparagus. Listen to me carefully: this may have been the best asparagus of my life. Large, grilled, tender, flavorful, and somehow still had dignity. Not limp, not stringy, not an afterthought. Just elite asparagus behavior. Which reminds me…we didn’t get any rapini the asparagus must have been a game time substitution and what a good one it was.
Bonus points for bringing out a little birthday surprise cannoli, which was a sweet touch and exactly the kind of thing that makes a dinner feel special.
