There is no royal road to geometry, and philosophy is no different. There is no such book, I am afraid, even if you did focus just on Western philosophy, or even on philosophy of mathematics only. Also, philosophy is not mathematics or science, surveys and commentary are not enough to get the "gist". It is as much in the original context as it is in the summarizable content, reading the sources, at least a bit, is indispensable. Here are some partial suggestions.
Philosophy of Mathematics
Colyvan's Introduction to Philosophy of Mathematics is fairly accessible,
"including such topics as the realism/anti-realism debate in mathematics, mathematical explanation, the limits of mathematics, the significance of mathematical notation, inconsistent mathematics and the applications of mathematics. Each chapter has a number of discussion questions and recommended further reading from both the contemporary literature and older sources".
You can supplement it with readings from Jacquette's Philosophy of Mathematics: an Anthology:
"Many of Jacquette's selections are important for understanding current debates, and he provides helpful introductory discussions"; "The featured papers are organized thematically, rather than chronologically, to provide the best overview of philosophical issues connected with mathematics and the development of mathematical knowledge. Coverage ranges from general topics in mathematical explanation and the concept of number, to specialized investigations of the ontology of mathematical entities and the nature of mathematical truth, models and methods of mathematical proof, intuitionistic mathematics, and philosophical foundations of set theory."
Western Philosophy
On Western (not only analytic) philosophy generally Kenny's four volume New History of Western Philosophy is fairly good:
"Kenny tells the story of philosophy chronologically, his lively narrative bringing the great philosophers to life and filling in the historical and intellectual background to their work. Kenny also looks closely at each of the main areas of philosophical exploration: knowledge and understanding; science; metaphysics; mind and soul; the nature and content of morality; political philosophy; and God."
Supplemental reading can be from Cottingham's Western Philosophy: An Anthology:
"Readings are introduced and linked together by a lucid philosophical commentary which guides the reader through the key arguments
Embraces all the major subfields of philosophy: theory of knowledge and metaphysics, philosophy of mind, religion and science, moral philosophy (theoretical and applied), political theory, and aesthetics."
Non-Western Philosophy
Try Companion to World Philosophies:
"The text is organized around a series of central topics concerning conceptions of reality and divinity, of causality, of truth, of the nature of rationality, of selfhood, of humankind and nature, of the good, of aesthetic values, and of social and political ideals. Outstanding scholars present essays that articulate the distinctive ways in which these specific problems have been formulated and addressed in the non-Western traditions against the background of their varied historical and cultural presuppositions."
Supplement by readings from Bonevac's World Philosophy anthology:
"The editors have arranged these topics according to their increasing complexity--from the most concrete (ethics) to the most theoretical (philosophical theology)--making the material as accessible as possible for students. Organized both chronologically and geographically, the anthology's five parts include readings from Indian, Chinese, Greek, Christian, Jewish, Islamic, Spanish, Latin-American, and African traditions, as well as selections from early modern, Kantian, and post-Kantian philosophy... Chapters are divided into 93 sections, each of which opens with a detailed introduction that prepares students for the readings that follow."
