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So you are more or less going to be limited to repeater use anyway. What I'd do is invest in a UHF HT capable of running 430-512 MHz (or something in that range). I say that because NYPD, NYFD and some of the city comms are still running on an analog T-band system (470-512 MHz). UHF tends to outperform VHF in an urban environment so I wouldn't worry too much about not having VHF. If interested in amateur radio, its also not that uncommon for small city wide coverage UHF repeaters to be tied into larger coverage VHF repeaters though I can't really speak for NYC. There are also some digital options that come into play if one is interested in that as well.

the 355's are good for the group users FRS and or GMRS but if you are operating the tour and want good repeater contact , for Emergency and or activity coordination, I would recommend a good 4 watt UHF radio with an enhanced whip antenna to reach distance repeaters. the blister pack radios do not have removable antennas, many UHF radios and some part 95 have removable antennas allowing you to add a nice 3db + of gain over the stock dummy load. Your outdoor activity sounds great, Beat of luck!